diff --git a/.mockery.yaml b/.mockery.yaml
index c2445f42811..ea5df1eebbe 100644
--- a/.mockery.yaml
+++ b/.mockery.yaml
@@ -29,3 +29,11 @@ packages:
   github.com/elastic/elastic-agent/internal/pkg/agent/application/info:
     interfaces:
       Agent:
+  github.com/elastic/elastic-agent/internal/pkg/agent/cmd:
+    interfaces:
+      agentWatcher:
+        config:
+          mockname: "AgentWatcher"
+      installationModifier:
+        config:
+          mockname: "InstallationModifier"
diff --git a/NOTICE-fips.txt b/NOTICE-fips.txt
index 1a7297d3477..4237a9151c6 100644
--- a/NOTICE-fips.txt
+++ b/NOTICE-fips.txt
@@ -1254,11 +1254,11 @@ SOFTWARE
 
 --------------------------------------------------------------------------------
 Dependency : github.com/elastic/elastic-agent-libs
-Version: v0.20.1
+Version: v0.21.0
 Licence type (autodetected): Apache-2.0
 --------------------------------------------------------------------------------
 
-Contents of probable licence file $GOMODCACHE/github.com/elastic/elastic-agent-libs@v0.20.1/LICENSE:
+Contents of probable licence file $GOMODCACHE/github.com/elastic/elastic-agent-libs@v0.21.0/LICENSE:
 
                                  Apache License
                            Version 2.0, January 2004
diff --git a/NOTICE.txt b/NOTICE.txt
index 836e0a89058..512d23728e2 100644
--- a/NOTICE.txt
+++ b/NOTICE.txt
@@ -1254,11 +1254,11 @@ SOFTWARE
 
 --------------------------------------------------------------------------------
 Dependency : github.com/elastic/elastic-agent-libs
-Version: v0.20.1
+Version: v0.21.0
 Licence type (autodetected): Apache-2.0
 --------------------------------------------------------------------------------
 
-Contents of probable licence file $GOMODCACHE/github.com/elastic/elastic-agent-libs@v0.20.1/LICENSE:
+Contents of probable licence file $GOMODCACHE/github.com/elastic/elastic-agent-libs@v0.21.0/LICENSE:
 
                                  Apache License
                            Version 2.0, January 2004
diff --git a/changelog/fragments/1751024454-preserve-upgrade-marker-and-add-rollback-reason.yaml b/changelog/fragments/1751024454-preserve-upgrade-marker-and-add-rollback-reason.yaml
new file mode 100644
index 00000000000..08b69f468a4
--- /dev/null
+++ b/changelog/fragments/1751024454-preserve-upgrade-marker-and-add-rollback-reason.yaml
@@ -0,0 +1,34 @@
+# Kind can be one of:
+# - breaking-change: a change to previously-documented behavior
+# - deprecation: functionality that is being removed in a later release
+# - bug-fix: fixes a problem in a previous version
+# - enhancement: extends functionality but does not break or fix existing behavior
+# - feature: new functionality
+# - known-issue: problems that we are aware of in a given version
+# - security: impacts on the security of a product or a user’s deployment.
+# - upgrade: important information for someone upgrading from a prior version
+# - other: does not fit into any of the other categories
+kind: feature
+
+# Change summary; a 80ish characters long description of the change.
+summary: Preserve upgrade marker when rolling back upgrade and add rollback reason
+
+# Long description; in case the summary is not enough to describe the change
+# this field accommodate a description without length limits.
+# NOTE: This field will be rendered only for breaking-change and known-issue kinds at the moment.
+description: Upgrade marker is now preserved by the watcher when performing a rollback and a new `reason`
+  field is added to the upgrade details structure. The reason for keeping the upgrade marker when rolling back is
+  to allow the rolled back agent to read the rollback reason and communicate that to user/Fleet.
+
+# Affected component; usually one of "elastic-agent", "fleet-server", "filebeat", "metricbeat", "auditbeat", "all", etc.
+component: elastic-agent
+
+# PR URL; optional; the PR number that added the changeset.
+# If not present is automatically filled by the tooling finding the PR where this changelog fragment has been added.
+# NOTE: the tooling supports backports, so it's able to fill the original PR number instead of the backport PR number.
+# Please provide it if you are adding a fragment for a different PR.
+pr: https://github.com/elastic/elastic-agent/8407
+
+# Issue URL; optional; the GitHub issue related to this changeset (either closes or is part of).
+# If not present is automatically filled by the tooling with the issue linked to the PR number.
+#issue: https://github.com/owner/repo/1234
diff --git a/control_v2.proto b/control_v2.proto
index 0bfd98e8580..55a988a37ff 100644
--- a/control_v2.proto
+++ b/control_v2.proto
@@ -265,6 +265,10 @@ message UpgradeDetailsMetadata {
   // The deadline until when a retryable upgrade step, e.g. the download
   // step, will be retried.
   string retry_until = 6;
+
+  // Reason is a string that may give out more information about transitioning to the current state.
+  // It has been introduced initially to distinguish between manual and automatic rollbacks
+  string reason = 7;
 }
 
 // DiagnosticFileResult is a file result from a diagnostic result.
diff --git a/go.mod b/go.mod
index 53e299a4dc9..5f29c31e6b8 100644
--- a/go.mod
+++ b/go.mod
@@ -18,7 +18,7 @@ require (
 	github.com/elastic/cloud-on-k8s/v2 v2.0.0-20250327073047-b624240832ae
 	github.com/elastic/elastic-agent-autodiscover v0.9.2
 	github.com/elastic/elastic-agent-client/v7 v7.17.2
-	github.com/elastic/elastic-agent-libs v0.20.1
+	github.com/elastic/elastic-agent-libs v0.21.0
 	github.com/elastic/elastic-agent-system-metrics v0.11.16
 	github.com/elastic/elastic-transport-go/v8 v8.7.0
 	github.com/elastic/go-elasticsearch/v8 v8.18.1
diff --git a/go.sum b/go.sum
index 6091f7cb1b3..b9eef4089ae 100644
--- a/go.sum
+++ b/go.sum
@@ -522,8 +522,8 @@ github.com/elastic/elastic-agent-autodiscover v0.9.2 h1:eBmru2v66HRRHOFf89rDl9OZ
 github.com/elastic/elastic-agent-autodiscover v0.9.2/go.mod h1:RNaHnOTYfNptSTQUyZYnjypxmrR5AaE6BIap/175F5c=
 github.com/elastic/elastic-agent-client/v7 v7.17.2 h1:Cl2TeABqWZgW40t5fchGWT/sRk4MDDLWA0d8iHHOxLA=
 github.com/elastic/elastic-agent-client/v7 v7.17.2/go.mod h1:5irRFqp6HLqtu1S+OeY0jg8x7K6PLL+DW+PwVk1vJnk=
-github.com/elastic/elastic-agent-libs v0.20.1 h1:M7ZME7yctVhI9349OiG0VQ8a+RsuParA/ZUgCuctwBE=
-github.com/elastic/elastic-agent-libs v0.20.1/go.mod h1:xSeIP3NtOIT4N2pPS4EyURmS1Q8mK0lWZ8Wd1Du6q3w=
+github.com/elastic/elastic-agent-libs v0.21.0 h1:lt2Xc87Si0mea0BgRKZGZA30j8LEx57k7GAyiKmZP/8=
+github.com/elastic/elastic-agent-libs v0.21.0/go.mod h1:xSeIP3NtOIT4N2pPS4EyURmS1Q8mK0lWZ8Wd1Du6q3w=
 github.com/elastic/elastic-agent-system-metrics v0.11.16 h1:cLjuO8pE5cUwPGWUHmy1VOERmJVDaep8gY+U4YRQ5vs=
 github.com/elastic/elastic-agent-system-metrics v0.11.16/go.mod h1:qiZC5p1hd8te4XVnhh7FkXdcYhxFnl5i9GJpROtf6zo=
 github.com/elastic/elastic-transport-go/v8 v8.7.0 h1:OgTneVuXP2uip4BA658Xi6Hfw+PeIOod2rY3GVMGoVE=
diff --git a/internal/pkg/agent/application/upgrade/details/details.go b/internal/pkg/agent/application/upgrade/details/details.go
index 835cb8900bc..cd83c61855d 100644
--- a/internal/pkg/agent/application/upgrade/details/details.go
+++ b/internal/pkg/agent/application/upgrade/details/details.go
@@ -55,6 +55,10 @@ type Metadata struct {
 	// the Fail() method of UpgradeDetails to correctly record details when
 	// an upgrade fails.
 	ErrorMsg string `json:"error_msg,omitempty" yaml:"error_msg,omitempty"`
+
+	// Reason is a string that may give out more information about transitioning to the current state. It has been
+	// introduced initially to distinguish between manual and automatic rollbacks
+	Reason string `json:"reason,omitempty" yaml:"reason,omitempty"`
 }
 
 func NewDetails(targetVersion string, initialState State, actionID string) *Details {
@@ -87,6 +91,27 @@ func (d *Details) SetState(s State) {
 	d.notifyObservers()
 }
 
+// SetStateWithReason is a convenience method to set the state of the upgrade, the metadata.reason and
+// notify all observers.
+// Do NOT call SetStateWithReason with StateFailed; call the Fail method instead.
+func (d *Details) SetStateWithReason(s State, reason string) {
+	d.mu.Lock()
+	defer d.mu.Unlock()
+
+	d.State = s
+	d.Metadata.Reason = reason
+
+	// If State is something other than StateFailed, make sure to clear
+	// Metadata.FailedState and Metadata.ErrorMsg as those two fields
+	// should be set when State is set to StateFailed. See the Fail method.
+	if s != StateFailed {
+		d.Metadata.ErrorMsg = ""
+		d.Metadata.FailedState = ""
+	}
+
+	d.notifyObservers()
+}
+
 // SetDownloadProgress is a convenience method to set the download percent
 // and download rate when the upgrade is in UPG_DOWNLOADING state.
 func (d *Details) SetDownloadProgress(percent, rateBytesPerSecond float64) {
diff --git a/internal/pkg/agent/application/upgrade/details/details_test.go b/internal/pkg/agent/application/upgrade/details/details_test.go
index 7e10cd8916d..a3e7b5803c7 100644
--- a/internal/pkg/agent/application/upgrade/details/details_test.go
+++ b/internal/pkg/agent/application/upgrade/details/details_test.go
@@ -11,6 +11,7 @@ import (
 	"testing"
 	"time"
 
+	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
@@ -30,6 +31,15 @@ func TestDetailsSetState(t *testing.T) {
 	require.Equal(t, StateDownloading, det.State)
 }
 
+func TestDetailsSetStateWithReason(t *testing.T) {
+	det := NewDetails("99.999.9999", StateWatching, "test_action_id")
+	require.Equal(t, StateWatching, det.State)
+
+	det.SetStateWithReason(StateRollback, ReasonWatchFailed)
+	assert.Equal(t, StateRollback, det.State)
+	assert.Equal(t, ReasonWatchFailed, det.Metadata.Reason)
+}
+
 func TestDetailsFail(t *testing.T) {
 	det := NewDetails("99.999.9999", StateRequested, "test_action_id")
 	require.Equal(t, StateRequested, det.State)
diff --git a/internal/pkg/agent/application/upgrade/details/state.go b/internal/pkg/agent/application/upgrade/details/state.go
index d02c3fa4d3d..41a04698cdb 100644
--- a/internal/pkg/agent/application/upgrade/details/state.go
+++ b/internal/pkg/agent/application/upgrade/details/state.go
@@ -6,9 +6,9 @@ package details
 
 type State string
 
-// The values of these State* constants should match those enumerated for
-// upgrade_details.state in https://github.com/elastic/fleet-server/blob/main/model/openapi.yml
 const (
+	// The values of these State* constants should match those enumerated for
+	// upgrade_details.state in https://github.com/elastic/fleet-server/blob/main/model/openapi.yml
 	StateRequested   State = "UPG_REQUESTED"
 	StateScheduled   State = "UPG_SCHEDULED"
 	StateDownloading State = "UPG_DOWNLOADING"
@@ -19,4 +19,7 @@ const (
 	StateRollback    State = "UPG_ROLLBACK"
 	StateCompleted   State = "UPG_COMPLETED"
 	StateFailed      State = "UPG_FAILED"
+
+	// List of well-known reasons for state transitions
+	ReasonWatchFailed = "watch failed"
 )
diff --git a/internal/pkg/agent/application/upgrade/marker_watcher.go b/internal/pkg/agent/application/upgrade/marker_watcher.go
index c34043722bc..f4a1b33d849 100644
--- a/internal/pkg/agent/application/upgrade/marker_watcher.go
+++ b/internal/pkg/agent/application/upgrade/marker_watcher.go
@@ -146,7 +146,7 @@ func (mfw *MarkerFileWatcher) processMarker(currentVersion string, commit string
 		if marker.Details == nil {
 			marker.Details = details.NewDetails("unknown", details.StateRollback, marker.GetActionID())
 		} else if marker.Details.State == "" {
-			marker.Details.SetState(details.StateRollback)
+			marker.Details.SetStateWithReason(details.StateRollback, details.ReasonWatchFailed)
 		}
 	}
 
diff --git a/internal/pkg/agent/application/upgrade/rollback.go b/internal/pkg/agent/application/upgrade/rollback.go
index b562ab323b6..90be1bbe2df 100644
--- a/internal/pkg/agent/application/upgrade/rollback.go
+++ b/internal/pkg/agent/application/upgrade/rollback.go
@@ -63,7 +63,7 @@ func Rollback(ctx context.Context, log *logger.Logger, c client.Client, topDirPa
 	}
 
 	// cleanup everything except version we're rolling back into
-	return Cleanup(log, topDirPath, prevVersionedHome, prevHash, true, true)
+	return Cleanup(log, topDirPath, prevVersionedHome, prevHash, false, true)
 }
 
 // Cleanup removes all artifacts and files related to a specified version.
diff --git a/internal/pkg/agent/application/upgrade/rollback_test.go b/internal/pkg/agent/application/upgrade/rollback_test.go
index 664eb72978b..3f9cc0a33ab 100644
--- a/internal/pkg/agent/application/upgrade/rollback_test.go
+++ b/internal/pkg/agent/application/upgrade/rollback_test.go
@@ -390,7 +390,7 @@ func checkFilesAfterRollback(t *testing.T, topDir, oldAgentHome, newAgentHome st
 		assert.Equal(t, []byte("Placeholder for agent 1.2.3-SNAPSHOT"), elasticAgentBytes, "reading elastic-agent content through symbolic link should point to the old version")
 	}
 
-	assert.NoFileExists(t, filepath.Join(topDir, "data", markerFilename), "update marker should have been cleaned up")
+	assert.FileExists(t, filepath.Join(topDir, "data", markerFilename), "update marker should survive cleanup in case of rollback")
 }
 
 // setupAgents create fake agent installs, update marker file and symlink pointing to one of the installations' elastic-agent placeholder
diff --git a/internal/pkg/agent/application/upgrade/step_mark.go b/internal/pkg/agent/application/upgrade/step_mark.go
index c9dd6862bd5..6e270ee7d24 100644
--- a/internal/pkg/agent/application/upgrade/step_mark.go
+++ b/internal/pkg/agent/application/upgrade/step_mark.go
@@ -313,8 +313,8 @@ func loadMarker(markerFile string) (*UpdateMarker, error) {
 // SaveMarker serializes and persists the given upgrade marker to disk.
 // For critical upgrade transitions, pass shouldFsync as true so the marker
 // file is immediately flushed to persistent storage.
-func SaveMarker(marker *UpdateMarker, shouldFsync bool) error {
-	return saveMarkerToPath(marker, markerFilePath(paths.Data()), shouldFsync)
+func SaveMarker(dataDirPath string, marker *UpdateMarker, shouldFsync bool) error {
+	return saveMarkerToPath(marker, markerFilePath(dataDirPath), shouldFsync)
 }
 
 func saveMarkerToPath(marker *UpdateMarker, markerFile string, shouldFsync bool) error {
diff --git a/internal/pkg/agent/application/upgrade/upgrade.go b/internal/pkg/agent/application/upgrade/upgrade.go
index 1738cfe0170..19d3b67cb2b 100644
--- a/internal/pkg/agent/application/upgrade/upgrade.go
+++ b/internal/pkg/agent/application/upgrade/upgrade.go
@@ -417,7 +417,7 @@ func waitForWatcherWithTimeoutCreationFunc(ctx context.Context, log *logger.Logg
 			}
 
 		case <-watcherContext.Done():
-			log.Error("upgrade watcher did not start watching within %s or context has expired", waitTime)
+			log.Errorf("upgrade watcher did not start watching within %s or context has expired", waitTime)
 			return goerrors.Join(ErrWatcherNotStarted, watcherContext.Err())
 		}
 	}
@@ -449,7 +449,7 @@ func (u *Upgrader) Ack(ctx context.Context, acker acker.Acker) error {
 
 	marker.Acked = true
 
-	return SaveMarker(marker, false)
+	return SaveMarker(paths.Data(), marker, false)
 }
 
 func (u *Upgrader) AckAction(ctx context.Context, acker acker.Acker, action fleetapi.Action) error {
diff --git a/internal/pkg/agent/cmd/status.go b/internal/pkg/agent/cmd/status.go
index d9c82359462..bdffc8e3420 100644
--- a/internal/pkg/agent/cmd/status.go
+++ b/internal/pkg/agent/cmd/status.go
@@ -230,6 +230,9 @@ func listUpgradeDetails(l list.Writer, upgradeDetails *cproto.UpgradeDetails) {
 		if upgradeDetails.Metadata.RetryErrorMsg != "" {
 			l.AppendItem("retry_error_msg: " + upgradeDetails.Metadata.RetryErrorMsg)
 		}
+		if upgradeDetails.Metadata.Reason != "" {
+			l.AppendItem("reason: " + upgradeDetails.Metadata.Reason)
+		}
 		l.UnIndent()
 	}
 
diff --git a/internal/pkg/agent/cmd/watch.go b/internal/pkg/agent/cmd/watch.go
index 037c01a91d0..f203c1814f7 100644
--- a/internal/pkg/agent/cmd/watch.go
+++ b/internal/pkg/agent/cmd/watch.go
@@ -53,7 +53,7 @@ func newWatchCommandWithArgs(_ []string, streams *cli.IOStreams) *cobra.Command
 			// Make sure to flush any buffered logs before we're done.
 			defer log.Sync() //nolint:errcheck // flushing buffered logs is best effort.
 
-			if err := watchCmd(log, cfg); err != nil {
+			if err := watchCmd(log, paths.Top(), cfg.Settings.Upgrade.Watcher, new(upgradeAgentWatcher), new(upgradeInstallationModifier)); err != nil {
 				log.Errorw("Watch command failed", "error.message", err)
 				fmt.Fprintf(streams.Err, "Watch command failed: %v\n%s\n", err, troubleshootMessage())
 				os.Exit(4)
@@ -64,21 +64,30 @@ func newWatchCommandWithArgs(_ []string, streams *cli.IOStreams) *cobra.Command
 	return cmd
 }
 
-func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
-	log.Infow("Upgrade Watcher started", "process.pid", os.Getpid(), "agent.version", version.GetAgentPackageVersion())
-	marker, err := upgrade.LoadMarker(paths.Data())
+type agentWatcher interface {
+	Watch(ctx context.Context, tilGrace, errorCheckInterval time.Duration, log *logp.Logger) error
+}
+
+type installationModifier interface {
+	Cleanup(log *logger.Logger, topDirPath, currentVersionedHome, currentHash string, removeMarker, keepLogs bool) error
+	Rollback(ctx context.Context, log *logger.Logger, c client.Client, topDirPath, prevVersionedHome, prevHash string) error
+}
+
+func watchCmd(log *logp.Logger, topDir string, cfg *configuration.UpgradeWatcherConfig, watcher agentWatcher, installModifier installationModifier) error {
+	log.Infow("Upgrade Watcher started", "process.pid", os.Getpid(), "agent.version", version.GetAgentPackageVersion(), "config", cfg)
+	dataDir := paths.DataFrom(topDir)
+	marker, err := upgrade.LoadMarker(dataDir)
 	if err != nil {
 		log.Error("failed to load marker", err)
 		return err
 	}
 	if marker == nil {
 		// no marker found we're not in upgrade process
-		log.Infof("update marker not present at '%s'", paths.Data())
+		log.Infof("update marker not present at '%s'", dataDir)
 		return nil
 	}
 
-	log.Infof("Loaded update marker %+v", marker)
-
+	log.With("marker", marker, "details", marker.Details).Info("Loaded update marker")
 	locker := filelock.NewAppLocker(paths.Top(), watcherLockFile)
 	if err := locker.TryLock(); err != nil {
 		if errors.Is(err, filelock.ErrAppAlreadyRunning) {
@@ -93,14 +102,18 @@ func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
 		_ = locker.Unlock()
 	}()
 
-	isWithinGrace, tilGrace := gracePeriod(marker, cfg.Settings.Upgrade.Watcher.GracePeriod)
-	if !isWithinGrace {
-		log.Infof("not within grace [updatedOn %v] %v", marker.UpdatedOn.String(), time.Since(marker.UpdatedOn).String())
+	isWithinGrace, tilGrace := gracePeriod(marker, cfg.GracePeriod)
+	if isTerminalState(marker) || !isWithinGrace {
+		stateString := ""
+		if marker.Details != nil {
+			stateString = string(marker.Details.State)
+		}
+		log.Infof("not within grace [updatedOn %v] %v or agent have been rolled back [state: %s]", marker.UpdatedOn.String(), time.Since(marker.UpdatedOn).String(), stateString)
 		// if it is started outside of upgrade loop
 		// if we're not within grace and marker is still there it might mean
 		// that cleanup was not performed ok, cleanup everything except current version
 		// hash is the same as hash of agent which initiated watcher.
-		if err := upgrade.Cleanup(log, paths.Top(), paths.VersionedHome(paths.Top()), release.ShortCommit(), true, false); err != nil {
+		if err := installModifier.Cleanup(log, paths.Top(), paths.VersionedHome(topDir), release.ShortCommit(), true, false); err != nil {
 			log.Error("clean up of prior watcher run failed", err)
 		}
 		// exit nicely
@@ -109,15 +122,18 @@ func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
 
 	// About to start watching the upgrade. Initialize upgrade details and save them in the
 	// upgrade marker.
-	upgradeDetails := initUpgradeDetails(marker, upgrade.SaveMarker, log)
+	saveMarkerFunc := func(marker *upgrade.UpdateMarker, b bool) error {
+		return upgrade.SaveMarker(dataDir, marker, b)
+	}
+	upgradeDetails := initUpgradeDetails(marker, saveMarkerFunc, log)
 
-	errorCheckInterval := cfg.Settings.Upgrade.Watcher.ErrorCheck.Interval
+	errorCheckInterval := cfg.ErrorCheck.Interval
 	ctx := context.Background()
-	if err := watch(ctx, tilGrace, errorCheckInterval, log); err != nil {
+	if err := watcher.Watch(ctx, tilGrace, errorCheckInterval, log); err != nil {
 		log.Error("Error detected, proceeding to rollback: %v", err)
 
-		upgradeDetails.SetState(details.StateRollback)
-		err = upgrade.Rollback(ctx, log, client.New(), paths.Top(), marker.PrevVersionedHome, marker.PrevHash)
+		upgradeDetails.SetStateWithReason(details.StateRollback, details.ReasonWatchFailed)
+		err = installModifier.Rollback(ctx, log, client.New(), paths.Top(), marker.PrevVersionedHome, marker.PrevHash)
 		if err != nil {
 			log.Error("rollback failed", err)
 			upgradeDetails.Fail(err)
@@ -135,13 +151,31 @@ func watchCmd(log *logp.Logger, cfg *configuration.Configuration) error {
 	// Why is this being skipped on Windows? The comment above is not clear.
 	// issue: https://github.com/elastic/elastic-agent/issues/3027
 	removeMarker := !isWindows()
-	err = upgrade.Cleanup(log, paths.Top(), marker.VersionedHome, marker.Hash, removeMarker, false)
+	err = installModifier.Cleanup(log, topDir, marker.VersionedHome, marker.Hash, removeMarker, false)
 	if err != nil {
 		log.Error("cleanup after successful watch failed", err)
 	}
 	return err
 }
 
+// isTerminalState returns true if the state in the upgrade marker contains details and the upgrade details state is a
+// terminal one: UPG_COMPLETE, UPG_ROLLBACK and UPG_FAILED
+// If the upgrade marker or the upgrade marker details are nil the function will return false: as
+// no state is specified, having simply a marker without details would mean that some upgrade operation is ongoing
+// (probably initiated by an older agent).
+func isTerminalState(marker *upgrade.UpdateMarker) bool {
+	if marker.Details == nil {
+		return false
+	}
+
+	switch marker.Details.State {
+	case details.StateCompleted, details.StateRollback, details.StateFailed:
+		return true
+	default:
+		return false
+	}
+}
+
 func isWindows() bool {
 	return runtime.GOOS == "windows"
 }
diff --git a/internal/pkg/agent/cmd/watch_impl.go b/internal/pkg/agent/cmd/watch_impl.go
new file mode 100644
index 00000000000..92e3118435c
--- /dev/null
+++ b/internal/pkg/agent/cmd/watch_impl.go
@@ -0,0 +1,31 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License 2.0;
+// you may not use this file except in compliance with the Elastic License 2.0.
+
+package cmd
+
+import (
+	"context"
+	"time"
+
+	"github.com/elastic/elastic-agent-libs/logp"
+	"github.com/elastic/elastic-agent/internal/pkg/agent/application/upgrade"
+	"github.com/elastic/elastic-agent/pkg/control/v2/client"
+	"github.com/elastic/elastic-agent/pkg/core/logger"
+)
+
+type upgradeAgentWatcher struct{}
+
+func (a upgradeAgentWatcher) Watch(ctx context.Context, tilGrace, errorCheckInterval time.Duration, log *logp.Logger) error {
+	return watch(ctx, tilGrace, errorCheckInterval, log)
+}
+
+type upgradeInstallationModifier struct{}
+
+func (a upgradeInstallationModifier) Cleanup(log *logger.Logger, topDirPath, currentVersionedHome, currentHash string, removeMarker, keepLogs bool) error {
+	return upgrade.Cleanup(log, topDirPath, currentVersionedHome, currentHash, removeMarker, keepLogs)
+}
+
+func (a upgradeInstallationModifier) Rollback(ctx context.Context, log *logger.Logger, c client.Client, topDirPath, prevVersionedHome, prevHash string) error {
+	return upgrade.Rollback(ctx, log, c, topDirPath, prevVersionedHome, prevHash)
+}
diff --git a/internal/pkg/agent/cmd/watch_test.go b/internal/pkg/agent/cmd/watch_test.go
index e1f6524c012..9451c476543 100644
--- a/internal/pkg/agent/cmd/watch_test.go
+++ b/internal/pkg/agent/cmd/watch_test.go
@@ -5,18 +5,28 @@
 package cmd
 
 import (
+	"fmt"
+	"os"
+	"runtime"
 	"testing"
+	"time"
 
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/mock"
 	"go.uber.org/zap/zapcore"
 
+	"github.com/stretchr/testify/require"
+
+	"github.com/elastic/elastic-agent/internal/pkg/agent/application/paths"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/upgrade/details"
+	"github.com/elastic/elastic-agent/internal/pkg/agent/configuration"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/errors"
 	"github.com/elastic/elastic-agent/internal/pkg/fleetapi"
+	"github.com/elastic/elastic-agent/internal/pkg/release"
 	"github.com/elastic/elastic-agent/pkg/core/logger/loggertest"
 
-	"github.com/stretchr/testify/require"
-
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/upgrade"
+	cmdmocks "github.com/elastic/elastic-agent/testing/mocks/internal_/pkg/agent/cmd"
 )
 
 func TestInitUpgradeDetails(t *testing.T) {
@@ -74,3 +84,200 @@ func TestInitUpgradeDetails(t *testing.T) {
 	require.Equal(t, zapcore.ErrorLevel, logs[0].Level)
 	require.Equal(t, `unable to save upgrade marker after clearing upgrade details: some error`, logs[0].Message)
 }
+
+func Test_watchCmd(t *testing.T) {
+	type args struct {
+		cfg *configuration.UpgradeWatcherConfig
+	}
+	tests := []struct {
+		name               string
+		setupUpgradeMarker func(t *testing.T, tmpDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier)
+		args               args
+		wantErr            assert.ErrorAssertionFunc
+	}{
+		{
+			name: "no upgrade marker, no party",
+			setupUpgradeMarker: func(t *testing.T, topDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier) {
+				dataDirPath := paths.DataFrom(topDir)
+				err := os.MkdirAll(dataDirPath, 0755)
+				require.NoError(t, err)
+			},
+			args: args{
+				cfg: configuration.DefaultUpgradeConfig().Watcher,
+			},
+			wantErr: assert.NoError,
+		},
+		{
+			name: "happy path: no error watching, cleanup prev install",
+			setupUpgradeMarker: func(t *testing.T, topDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier) {
+				dataDirPath := paths.DataFrom(topDir)
+				err := os.MkdirAll(dataDirPath, 0755)
+				require.NoError(t, err)
+				err = upgrade.SaveMarker(
+					dataDirPath,
+					&upgrade.UpdateMarker{
+						Version:           "4.5.6",
+						Hash:              "newver",
+						VersionedHome:     "elastic-agent-4.5.6-newver",
+						UpdatedOn:         time.Now(),
+						PrevVersion:       "1.2.3",
+						PrevHash:          "prvver",
+						PrevVersionedHome: "elastic-agent-prvver",
+						Acked:             false,
+						Action:            nil,
+						Details:           nil, //details.NewDetails("4.5.6", details.StateReplacing, ""),
+						DesiredOutcome:    upgrade.OUTCOME_UPGRADE,
+					},
+					true,
+				)
+				require.NoError(t, err)
+
+				watcher.EXPECT().
+					Watch(mock.Anything, mock.Anything, mock.Anything, mock.Anything).
+					Return(nil)
+
+				// on windows the marker is not removed immediately to allow for cleanup on restart
+				expectedRemoveMarkerFlag := runtime.GOOS != "windows"
+
+				installModifier.EXPECT().
+					Cleanup(mock.Anything, topDir, "elastic-agent-4.5.6-newver", "newver", expectedRemoveMarkerFlag, false).
+					Return(nil)
+			},
+			args: args{
+				cfg: configuration.DefaultUpgradeConfig().Watcher,
+			},
+			wantErr: assert.NoError,
+		},
+		{
+			name: "unhappy path: error watching, rollback to previous install",
+			setupUpgradeMarker: func(t *testing.T, topDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier) {
+				dataDirPath := paths.DataFrom(topDir)
+				err := os.MkdirAll(dataDirPath, 0755)
+				require.NoError(t, err)
+				err = upgrade.SaveMarker(
+					dataDirPath,
+					&upgrade.UpdateMarker{
+						Version:           "4.5.6",
+						Hash:              "newver",
+						VersionedHome:     "elastic-agent-4.5.6-newver",
+						UpdatedOn:         time.Now(),
+						PrevVersion:       "1.2.3",
+						PrevHash:          "prvver",
+						PrevVersionedHome: "elastic-agent-prvver",
+						Acked:             false,
+						Action:            nil,
+						Details:           nil, //details.NewDetails("4.5.6", details.StateReplacing, ""),
+						DesiredOutcome:    upgrade.OUTCOME_UPGRADE,
+					},
+					true,
+				)
+				require.NoError(t, err)
+
+				watcher.EXPECT().
+					Watch(mock.Anything, mock.Anything, mock.Anything, mock.Anything).
+					Return(errors.New("some watch error due to agent misbehaving"))
+				installModifier.EXPECT().
+					Rollback(mock.Anything, mock.Anything, mock.Anything, paths.Top(), "elastic-agent-prvver", "prvver").
+					Return(nil)
+			},
+			args: args{
+				cfg: configuration.DefaultUpgradeConfig().Watcher,
+			},
+			wantErr: assert.NoError,
+		},
+		{
+			name: "upgrade rolled back: no watching, cleanup must be called",
+			setupUpgradeMarker: func(t *testing.T, topDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier) {
+				dataDirPath := paths.DataFrom(topDir)
+				err := os.MkdirAll(dataDirPath, 0755)
+				require.NoError(t, err)
+				err = upgrade.SaveMarker(
+					dataDirPath,
+					&upgrade.UpdateMarker{
+						Version:           "4.5.6",
+						Hash:              "newver",
+						VersionedHome:     "elastic-agent-4.5.6-newver",
+						UpdatedOn:         time.Now(),
+						PrevVersion:       "1.2.3",
+						PrevHash:          "prvver",
+						PrevVersionedHome: "elastic-agent-prvver",
+						Acked:             false,
+						Action:            nil,
+						Details: &details.Details{
+							TargetVersion: "4.5.6",
+							State:         details.StateRollback,
+							Metadata: details.Metadata{
+								Reason: details.ReasonWatchFailed,
+							},
+						},
+						DesiredOutcome: upgrade.OUTCOME_UPGRADE,
+					},
+					true,
+				)
+				require.NoError(t, err)
+				// topdir, prevVersionedHome and prevHash are not taken from the upgrade marker, otherwise they would be
+				// <topDir, "topDir/data/elastic-agent-prvver", "prvver">
+				installModifier.EXPECT().
+					Cleanup(mock.Anything, paths.Top(), paths.VersionedHome(topDir), release.ShortCommit(), true, false).
+					Return(nil)
+			},
+			args: args{
+				cfg: configuration.DefaultUpgradeConfig().Watcher,
+			},
+			wantErr: assert.NoError,
+		},
+		{
+			name: "after grace period: no watching, cleanup must be called",
+			setupUpgradeMarker: func(t *testing.T, topDir string, watcher *cmdmocks.AgentWatcher, installModifier *cmdmocks.InstallationModifier) {
+				dataDirPath := paths.DataFrom(topDir)
+				err := os.MkdirAll(dataDirPath, 0755)
+				require.NoError(t, err)
+				updatedOn := time.Now().Add(-5 * time.Minute)
+				err = upgrade.SaveMarker(
+					dataDirPath,
+					&upgrade.UpdateMarker{
+						Version:           "4.5.6",
+						Hash:              "newver",
+						VersionedHome:     "elastic-agent-4.5.6-newver",
+						UpdatedOn:         updatedOn,
+						PrevVersion:       "1.2.3",
+						PrevHash:          "prvver",
+						PrevVersionedHome: "elastic-agent-prvver",
+						Acked:             false,
+						Action:            nil,
+						Details:           nil,
+						DesiredOutcome:    upgrade.OUTCOME_UPGRADE,
+					},
+					true,
+				)
+				require.NoError(t, err)
+
+				// topdir, prevVersionedHome and prevHash are not taken from the upgrade marker, otherwise they would be
+				// <topDir, "topDir/data/elastic-agent-prvver", "prvver">
+				installModifier.EXPECT().
+					Cleanup(mock.Anything, paths.Top(), paths.VersionedHome(topDir), release.ShortCommit(), true, false).
+					Return(nil)
+			},
+			args: args{
+				cfg: &configuration.UpgradeWatcherConfig{
+					GracePeriod: 2 * time.Minute,
+					ErrorCheck: configuration.UpgradeWatcherCheckConfig{
+						Interval: time.Second,
+					},
+				},
+			},
+			wantErr: assert.NoError,
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			log, obs := loggertest.New(t.Name())
+			tmpDir := t.TempDir()
+			mockWatcher := cmdmocks.NewAgentWatcher(t)
+			mockInstallModifier := cmdmocks.NewInstallationModifier(t)
+			tt.setupUpgradeMarker(t, tmpDir, mockWatcher, mockInstallModifier)
+			tt.wantErr(t, watchCmd(log, tmpDir, tt.args.cfg, mockWatcher, mockInstallModifier), fmt.Sprintf("watchCmd(%v, ...)", tt.args.cfg))
+			t.Logf("watchCmd logs:\n%v", obs.All())
+		})
+	}
+}
diff --git a/pkg/control/v2/cproto/control_v2.pb.go b/pkg/control/v2/cproto/control_v2.pb.go
index e3df292cc67..674529fdbad 100644
--- a/pkg/control/v2/cproto/control_v2.pb.go
+++ b/pkg/control/v2/cproto/control_v2.pb.go
@@ -423,7 +423,7 @@ type VersionResponse struct {
 	BuildTime string `protobuf:"bytes,3,opt,name=buildTime,proto3" json:"buildTime,omitempty"`
 	// Current running version is a snapshot.
 	Snapshot bool `protobuf:"varint,4,opt,name=snapshot,proto3" json:"snapshot,omitempty"`
-	// Current running version is FIPS-capable.
+	// Current running version is FIPS-compliant.
 	Fips bool `protobuf:"varint,5,opt,name=fips,proto3" json:"fips,omitempty"`
 }
 
@@ -1353,6 +1353,9 @@ type UpgradeDetailsMetadata struct {
 	// The deadline until when a retryable upgrade step, e.g. the download
 	// step, will be retried.
 	RetryUntil string `protobuf:"bytes,6,opt,name=retry_until,json=retryUntil,proto3" json:"retry_until,omitempty"`
+	// Reason is a string that may give out more information about transitioning to the current state.
+	// It has been introduced initially to distinguish between manual and automatic rollbacks
+	Reason string `protobuf:"bytes,7,opt,name=reason,proto3" json:"reason,omitempty"`
 }
 
 func (x *UpgradeDetailsMetadata) Reset() {
@@ -1429,6 +1432,13 @@ func (x *UpgradeDetailsMetadata) GetRetryUntil() string {
 	return ""
 }
 
+func (x *UpgradeDetailsMetadata) GetReason() string {
+	if x != nil {
+		return x.Reason
+	}
+	return ""
+}
+
 // DiagnosticFileResult is a file result from a diagnostic result.
 type DiagnosticFileResult struct {
 	state         protoimpl.MessageState
@@ -2236,7 +2246,7 @@ var file_control_v2_proto_rawDesc = []byte{
 	0x64, 0x12, 0x3a, 0x0a, 0x08, 0x6d, 0x65, 0x74, 0x61, 0x64, 0x61, 0x74, 0x61, 0x18, 0x04, 0x20,
 	0x01, 0x28, 0x0b, 0x32, 0x1e, 0x2e, 0x63, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x2e, 0x55, 0x70, 0x67,
 	0x72, 0x61, 0x64, 0x65, 0x44, 0x65, 0x74, 0x61, 0x69, 0x6c, 0x73, 0x4d, 0x65, 0x74, 0x61, 0x64,
-	0x61, 0x74, 0x61, 0x52, 0x08, 0x6d, 0x65, 0x74, 0x61, 0x64, 0x61, 0x74, 0x61, 0x22, 0xef, 0x01,
+	0x61, 0x74, 0x61, 0x52, 0x08, 0x6d, 0x65, 0x74, 0x61, 0x64, 0x61, 0x74, 0x61, 0x22, 0x87, 0x02,
 	0x0a, 0x16, 0x55, 0x70, 0x67, 0x72, 0x61, 0x64, 0x65, 0x44, 0x65, 0x74, 0x61, 0x69, 0x6c, 0x73,
 	0x4d, 0x65, 0x74, 0x61, 0x64, 0x61, 0x74, 0x61, 0x12, 0x21, 0x0a, 0x0c, 0x73, 0x63, 0x68, 0x65,
 	0x64, 0x75, 0x6c, 0x65, 0x64, 0x5f, 0x61, 0x74, 0x18, 0x01, 0x20, 0x01, 0x28, 0x09, 0x52, 0x0b,
@@ -2251,170 +2261,172 @@ var file_control_v2_proto_rawDesc = []byte{
 	0x65, 0x72, 0x72, 0x6f, 0x72, 0x5f, 0x6d, 0x73, 0x67, 0x18, 0x05, 0x20, 0x01, 0x28, 0x09, 0x52,
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-	0xdf, 0x01, 0x0a, 0x14, 0x44, 0x69, 0x61, 0x67, 0x6e, 0x6f, 0x73, 0x74, 0x69, 0x63, 0x46, 0x69,
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+	0x62, 0x06, 0x70, 0x72, 0x6f, 0x74, 0x6f, 0x33,
 }
 
 var (
diff --git a/pkg/control/v2/server/server.go b/pkg/control/v2/server/server.go
index 2ea355ce92e..5ef757b064e 100644
--- a/pkg/control/v2/server/server.go
+++ b/pkg/control/v2/server/server.go
@@ -378,6 +378,7 @@ func stateToProto(state *coordinator.State, agentInfo info.Agent) (*cproto.State
 				FailedState:     string(state.UpgradeDetails.Metadata.FailedState),
 				ErrorMsg:        state.UpgradeDetails.Metadata.ErrorMsg,
 				RetryErrorMsg:   state.UpgradeDetails.Metadata.RetryErrorMsg,
+				Reason:          state.UpgradeDetails.Metadata.Reason,
 			},
 		}
 
diff --git a/testing/integration/ess/repackage.go b/testing/integration/ess/repackage.go
new file mode 100644
index 00000000000..3e21c36f8f7
--- /dev/null
+++ b/testing/integration/ess/repackage.go
@@ -0,0 +1,297 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License 2.0;
+// you may not use this file except in compliance with the Elastic License 2.0.
+
+//go:build integration
+
+package ess
+
+import (
+	"archive/tar"
+	"archive/zip"
+	"bytes"
+	"compress/gzip"
+	"context"
+	"errors"
+	"io"
+	"os"
+	"path"
+	"path/filepath"
+	"strings"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/elastic/elastic-agent/dev-tools/mage"
+	v1 "github.com/elastic/elastic-agent/pkg/api/v1"
+	atesting "github.com/elastic/elastic-agent/pkg/testing"
+	"github.com/elastic/elastic-agent/pkg/version"
+	agtversion "github.com/elastic/elastic-agent/version"
+)
+
+func repackageArchive(ctx context.Context, t *testing.T, startFixture *atesting.Fixture, newVersionBuildMetadata string, currentVersion *version.ParsedSemVer, newPackageContainingDir string, parsedNewVersion *version.ParsedSemVer) (*version.ParsedSemVer, error) {
+	err := startFixture.EnsurePrepared(ctx)
+	require.NoErrorf(t, err, "fixture should be prepared")
+
+	// retrieve the compressed package file location
+	srcPackage, err := startFixture.SrcPackage(ctx)
+	require.NoErrorf(t, err, "error retrieving start fixture source package")
+
+	originalPackageFileName := filepath.Base(srcPackage)
+
+	// integration test fixtures and package names treat the version as a string including the "-SNAPSHOT" suffix
+	// while the repackage functions below separate version from the snapshot flag.
+	// Normally the early release versions are not snapshots but this test runs on PRs and main branch when we test
+	// starting from SNAPSHOT packages, so we have to work around the fact that we cannot simply re-generate the packages
+	// by defining versions in 2 separate ways for repackage hack and for fixtures
+	buildMetadataForAgentFixture := newVersionBuildMetadata
+	if currentVersion.IsSnapshot() {
+		buildMetadataForAgentFixture += "-SNAPSHOT"
+	}
+	versionForFixture := version.NewParsedSemVer(currentVersion.Major(), currentVersion.Minor(), currentVersion.Patch(), "", buildMetadataForAgentFixture)
+
+	// calculate the new package name
+	newPackageFileName := strings.Replace(originalPackageFileName, currentVersion.String(), versionForFixture.String(), 1)
+	t.Logf("originalPackageName: %q newPackageFileName: %q", originalPackageFileName, newPackageFileName)
+
+	newPackageAbsPath := filepath.Join(newPackageContainingDir, newPackageFileName)
+
+	// hack the package based on type
+	ext := filepath.Ext(originalPackageFileName)
+	if ext == ".gz" {
+		// fetch the next extension
+		ext = filepath.Ext(strings.TrimRight(originalPackageFileName, ext)) + ext
+	}
+	switch ext {
+	case ".zip":
+		t.Logf("file %q is a .zip package", originalPackageFileName)
+		repackageZipArchive(t, srcPackage, newPackageAbsPath, parsedNewVersion)
+	case ".tar.gz":
+		t.Logf("file %q is a .tar.gz package", originalPackageFileName)
+		repackageTarArchive(t, srcPackage, newPackageAbsPath, parsedNewVersion)
+	default:
+		t.Logf("unknown extension %q for package file %q ", ext, originalPackageFileName)
+		t.FailNow()
+	}
+
+	// Create hash file for the new package
+	err = mage.CreateSHA512File(newPackageAbsPath)
+	require.NoErrorf(t, err, "error creating .sha512 for file %q", newPackageAbsPath)
+	return versionForFixture, err
+}
+
+func repackageTarArchive(t *testing.T, srcPackagePath string, newPackagePath string, newVersion *version.ParsedSemVer) {
+	oldTopDirectoryName := strings.TrimRight(filepath.Base(srcPackagePath), ".tar.gz")
+	newTopDirectoryName := strings.TrimRight(filepath.Base(newPackagePath), ".tar.gz")
+
+	// Open the source package and create readers
+	srcPackageFile, err := os.Open(srcPackagePath)
+	require.NoErrorf(t, err, "error opening source file %q", srcPackagePath)
+	defer func(srcPackageFile *os.File) {
+		err := srcPackageFile.Close()
+		if err != nil {
+			assert.Failf(t, "error closing source file %q: %v", srcPackagePath, err)
+		}
+	}(srcPackageFile)
+
+	gzReader, err := gzip.NewReader(srcPackageFile)
+	require.NoErrorf(t, err, "error creating gzip reader for file %q", srcPackagePath)
+	defer func(gzReader *gzip.Reader) {
+		err := gzReader.Close()
+		if err != nil {
+			assert.Failf(t, "error closing gzip reader for source file %q: %v", srcPackagePath, err)
+		}
+	}(gzReader)
+
+	tarReader := tar.NewReader(gzReader)
+
+	// Create the output file and its writers
+	newPackageFile, err := os.OpenFile(newPackagePath, os.O_CREATE|os.O_RDWR|os.O_TRUNC, 0o750)
+	require.NoErrorf(t, err, "error opening output file %q", newPackagePath)
+	defer func(newPackageFile *os.File) {
+		err := newPackageFile.Close()
+		if err != nil {
+			assert.Failf(t, "error closing output file %q: %v", newPackagePath, err)
+		}
+	}(newPackageFile)
+
+	gzWriter := gzip.NewWriter(newPackageFile)
+	defer func(gzWriter *gzip.Writer) {
+		err := gzWriter.Close()
+		if err != nil {
+			assert.Failf(t, "error closing gzip writer for file %q: %v", newPackagePath, err)
+		}
+	}(gzWriter)
+
+	tarWriter := tar.NewWriter(gzWriter)
+	defer func(tarWriter *tar.Writer) {
+		err := tarWriter.Close()
+		if err != nil {
+			assert.Failf(t, "error closing tar writer for file %q: %v", newPackagePath, err)
+		}
+	}(tarWriter)
+
+	hackTarGzPackage(t, tarReader, tarWriter, oldTopDirectoryName, newTopDirectoryName, newVersion)
+}
+
+func hackTarGzPackage(t *testing.T, reader *tar.Reader, writer *tar.Writer, oldTopDirName string, newTopDirName string, newVersion *version.ParsedSemVer) {
+
+	for {
+		f, err := reader.Next()
+		if errors.Is(err, io.EOF) {
+			break
+		}
+		require.NoError(t, err, "error reading source package")
+
+		// tar format uses forward slash as path separator, make sure we use only "path" package for checking and manipulation
+		switch path.Base(f.Name) {
+		case v1.ManifestFileName:
+			// read old content and generate the new manifest based on that
+			newManifest := generateNewManifestContent(t, reader, newVersion)
+			newManifestBytes := []byte(newManifest)
+
+			// fix file length in header
+			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, int64(len(newManifestBytes)))
+
+			// write the new manifest body
+			_, err = writer.Write(newManifestBytes)
+			require.NoError(t, err, "error writing out modified manifest")
+
+		case agtversion.PackageVersionFileName:
+
+			t.Logf("writing new package version: %q", newVersion.String())
+
+			// new package version file contents
+			newPackageVersionBytes := []byte(newVersion.String())
+			// write new header
+			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, int64(len(newPackageVersionBytes)))
+			// write content
+			_, err := writer.Write(newPackageVersionBytes)
+			require.NoError(t, err, "error writing out modified package version")
+		default:
+			// write entry header with the size untouched
+			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, f.Size)
+
+			// copy body
+			_, err := io.Copy(writer, reader)
+			require.NoErrorf(t, err, "error writing file content for %+v", f)
+		}
+
+	}
+
+}
+
+func writeModifiedTarHeader(t *testing.T, writer *tar.Writer, header *tar.Header, oldTopDirName, newTopDirName string, size int64) {
+	// replace top dir in the path
+	header.Name = strings.Replace(header.Name, oldTopDirName, newTopDirName, 1)
+	header.Size = size
+
+	err := writer.WriteHeader(header)
+	require.NoErrorf(t, err, "error writing tar header %+v", header)
+}
+
+func repackageZipArchive(t *testing.T, srcPackagePath string, newPackagePath string, newVersion *version.ParsedSemVer) {
+	oldTopDirectoryName := strings.TrimRight(filepath.Base(srcPackagePath), ".zip")
+	newTopDirectoryName := strings.TrimRight(filepath.Base(newPackagePath), ".zip")
+
+	// Open the source package and create readers
+	zipReader, err := zip.OpenReader(srcPackagePath)
+	require.NoErrorf(t, err, "error opening source file %q", srcPackagePath)
+	defer func(zipReader *zip.ReadCloser) {
+		err := zipReader.Close()
+		if err != nil {
+			assert.Failf(t, "error closing source file %q: %v", srcPackagePath, err)
+		}
+	}(zipReader)
+
+	// Create the output file and its writers
+	newPackageFile, err := os.OpenFile(newPackagePath, os.O_CREATE|os.O_RDWR|os.O_TRUNC, 0o750)
+	require.NoErrorf(t, err, "error opening output file %q", newPackagePath)
+	defer func(newPackageFile *os.File) {
+		err := newPackageFile.Close()
+		if err != nil {
+			assert.Failf(t, "error closing output file %q: %v", newPackagePath, err)
+		}
+	}(newPackageFile)
+
+	zipWriter := zip.NewWriter(newPackageFile)
+	defer func(zipWriter *zip.Writer) {
+		err := zipWriter.Close()
+		if err != nil {
+			assert.Failf(t, "error closing zip writer for output file %q: %v", newPackagePath, err)
+		}
+	}(zipWriter)
+
+	hackZipPackage(t, zipReader, zipWriter, oldTopDirectoryName, newTopDirectoryName, newVersion)
+}
+
+func hackZipPackage(t *testing.T, reader *zip.ReadCloser, writer *zip.Writer, oldTopDirName string, newTopDirName string, newVersion *version.ParsedSemVer) {
+	for _, zippedFile := range reader.File {
+		zippedFileHeader := zippedFile.FileHeader
+
+		// zip format uses forward slash as path separator, make sure we use only "path" package for checking and manipulation
+		switch path.Base(zippedFile.Name) {
+		case v1.ManifestFileName:
+			// read old content
+			manifestReader, err := zippedFile.Open()
+			require.NoError(t, err, "error opening manifest file in zipped package")
+
+			// generate new manifest based on the old manifest and the new version
+			newManifest := generateNewManifestContent(t, manifestReader, newVersion)
+
+			// we need to close the file content reader
+			err = manifestReader.Close()
+			require.NoError(t, err, "error closing manifest file in zipped package")
+
+			newManifestBytes := []byte(newManifest)
+			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, uint64(len(newManifest)))
+
+			_, err = io.Copy(fileContentWriter, bytes.NewReader(newManifestBytes))
+			require.NoError(t, err, "error writing out modified manifest")
+
+		case agtversion.PackageVersionFileName:
+			t.Logf("writing new package version: %q", newVersion.String())
+			// new package version file contents
+			newPackageVersionBytes := []byte(newVersion.String())
+			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, uint64(len(newPackageVersionBytes)))
+
+			_, err := io.Copy(fileContentWriter, bytes.NewReader(newPackageVersionBytes))
+			require.NoError(t, err, "error writing out modified package version")
+		default:
+			// write entry header with the size untouched
+			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, zippedFile.UncompressedSize64)
+			fileContentReader, err := zippedFile.Open()
+			require.NoErrorf(t, err, "error opening zip file content reader for %+v", zippedFileHeader)
+			// copy body
+			_, err = io.Copy(fileContentWriter, fileContentReader)
+			require.NoErrorf(t, err, "error writing file content for %+v", zippedFileHeader)
+
+			// we need to close the file content reader
+			err = fileContentReader.Close()
+			require.NoError(t, err, "error closing zipped file writer for %+v", zippedFileHeader)
+		}
+	}
+}
+
+func writeModifiedZipFileHeader(t *testing.T, writer *zip.Writer, header zip.FileHeader, oldTopDirName, newTopDirName string, size uint64) io.Writer {
+	header.Name = strings.Replace(header.Name, oldTopDirName, newTopDirName, 1)
+	header.UncompressedSize64 = size
+	fileContentWriter, err := writer.CreateHeader(&header)
+	require.NoErrorf(t, err, "error creating header for %+v", header)
+	return fileContentWriter
+}
+
+func generateNewManifestContent(t *testing.T, manifestReader io.Reader, newVersion *version.ParsedSemVer) string {
+	oldManifest, err := v1.ParseManifest(manifestReader)
+	require.NoError(t, err, "reading manifest content from tar source archive")
+
+	t.Logf("read old manifest: %+v", oldManifest)
+
+	// replace manifest content
+	newManifest, err := mage.GeneratePackageManifest("elastic-agent", newVersion.String(), oldManifest.Package.Snapshot, oldManifest.Package.Hash, oldManifest.Package.Hash[:6], oldManifest.Package.Fips, nil)
+	require.NoErrorf(t, err, "GeneratePackageManifest(%v, %v, %v, %v, %v) failed", newVersion.String(), oldManifest.Package.Snapshot, oldManifest.Package.Hash, oldManifest.Package.Hash[:6], nil)
+
+	t.Logf("generated new manifest:\n%s", newManifest)
+	return newManifest
+}
diff --git a/testing/integration/ess/upgrade_fleet_test.go b/testing/integration/ess/upgrade_fleet_test.go
index 23dc5d447c5..d77aa72a15a 100644
--- a/testing/integration/ess/upgrade_fleet_test.go
+++ b/testing/integration/ess/upgrade_fleet_test.go
@@ -24,8 +24,8 @@ import (
 	"testing"
 	"time"
 
+	"github.com/cenkalti/backoff/v5"
 	"github.com/gofrs/uuid/v5"
-	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
 	"github.com/elastic/elastic-agent-libs/kibana"
@@ -393,7 +393,19 @@ func testUpgradeFleetManagedElasticAgent(
 	unprivileged bool,
 	opts ...upgradetest.UpgradeOpt,
 ) {
+	require.NoError(t, PerformManagedUpgrade(ctx, t, info, startFixture, endFixture, policy, unprivileged, opts...))
+}
 
+func PerformManagedUpgrade(
+	ctx context.Context,
+	t *testing.T,
+	info *define.Info,
+	startFixture *atesting.Fixture,
+	endFixture *atesting.Fixture,
+	policy kibana.AgentPolicy,
+	unprivileged bool,
+	opts ...upgradetest.UpgradeOpt,
+) error {
 	// use the passed in options to perform the upgrade
 	var upgradeOpts upgradetest.UpgradeOpts
 	for _, o := range opts {
@@ -403,13 +415,21 @@ func testUpgradeFleetManagedElasticAgent(
 	kibClient := info.KibanaClient
 
 	startVersionInfo, err := startFixture.ExecVersion(ctx)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("exec version on startFixture: %w", err)
+	}
 	startParsedVersion, err := version.ParseVersion(startVersionInfo.Binary.String())
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("parsing version on startVersionInfo: %w", err)
+	}
 	endVersionInfo, err := endFixture.ExecVersion(ctx)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("exec version on endFixture: %w", err)
+	}
 	endParsedVersion, err := version.ParseVersion(endVersionInfo.Binary.String())
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("parsing version on endVersionInfo: %w", err)
+	}
 
 	if unprivileged {
 		if !upgradetest.SupportsUnprivileged(startParsedVersion, endParsedVersion) {
@@ -419,24 +439,29 @@ func testUpgradeFleetManagedElasticAgent(
 
 	if startVersionInfo.Binary.Commit == endVersionInfo.Binary.Commit {
 		t.Skipf("target version has the same commit hash %q", endVersionInfo.Binary.Commit)
-		return
 	}
 
 	t.Log("Creating Agent policy...")
 	policyResp, err := kibClient.CreatePolicy(ctx, policy)
-	require.NoError(t, err, "failed creating policy")
-	policy = policyResp.AgentPolicy
+	if err != nil {
+		return fmt.Errorf("failed creating policy: %w", err)
+	}
 
+	policy = policyResp.AgentPolicy
 	t.Log("Creating Agent enrollment API key...")
 	createEnrollmentApiKeyReq := kibana.CreateEnrollmentAPIKeyRequest{
 		PolicyID: policyResp.ID,
 	}
 	enrollmentToken, err := kibClient.CreateEnrollmentAPIKey(ctx, createEnrollmentApiKeyReq)
-	require.NoError(t, err, "failed creating enrollment API key")
+	if err != nil {
+		return fmt.Errorf("failed creating enrollment token: %w", err)
+	}
 
 	t.Log("Getting default Fleet Server URL...")
 	fleetServerURL, err := fleettools.DefaultURL(ctx, kibClient)
-	require.NoError(t, err, "failed getting Fleet Server URL")
+	if err != nil {
+		return fmt.Errorf("failed getting default Fleet Server URL: %w", err)
+	}
 
 	t.Logf("Installing Elastic Agent (unprivileged: %t)...", unprivileged)
 	var nonInteractiveFlag bool
@@ -453,78 +478,135 @@ func testUpgradeFleetManagedElasticAgent(
 		Privileged: !unprivileged,
 	}
 	output, err := startFixture.Install(ctx, &installOpts)
-	require.NoError(t, err, "failed to install start agent [output: %s]", string(output))
+	t.Logf("install start agent output:\n%s", string(output))
+	if err != nil {
+		return fmt.Errorf("failed to install start agent: %w", err)
+	}
+
+	// start fixture gets the agent configured to use a faster watcher
+	// THIS IS A HACK: we are modifying elastic-agent.yaml after enrollment because the watcher reads only that file to
+	// configure itself. This is obviously not fit for production code or even guaranteed to be stable.
+	if upgradeOpts.CustomWatcherCfg != "" {
+		t.Log("Setting custom watcher config")
+		err = startFixture.Configure(ctx, []byte("fleet.enabled: true\n"+upgradeOpts.CustomWatcherCfg))
+	}
 
 	t.Log("Waiting for Agent to be correct version and healthy...")
 	err = upgradetest.WaitHealthyAndVersion(ctx, startFixture, startVersionInfo.Binary, 2*time.Minute, 10*time.Second, t)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("waiting for agent to become healthy: %w", err)
+	}
 
 	agentID, err := startFixture.AgentID(ctx)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("retrieving agent ID: %w", err)
+	}
 	t.Logf("Agent ID: %q", agentID)
 
 	t.Log("Waiting for enrolled Agent status to be online...")
-	require.Eventually(t,
-		check.FleetAgentStatus(
-			ctx, t, kibClient, agentID, "online"),
-		2*time.Minute,
-		10*time.Second,
-		"Agent status is not online")
+	_, err = backoff.Retry(ctx, func() (bool, error) {
+		checkSuccessful := check.FleetAgentStatus(
+			ctx, t, kibClient, agentID, "online")()
+		if !checkSuccessful {
+			return checkSuccessful, fmt.Errorf("agent status is not online")
+		}
+		return checkSuccessful, nil
+	}, backoff.WithMaxElapsedTime(2*time.Minute), backoff.WithBackOff(backoff.NewConstantBackOff(10*time.Second)))
+	if err != nil {
+		return fmt.Errorf("waiting for upgraded agent to be online: %w", err)
+	}
 
 	t.Logf("Upgrading from version \"%s-%s\" to version \"%s-%s\"...",
 		startParsedVersion, startVersionInfo.Binary.Commit,
 		endVersionInfo.Binary.String(), endVersionInfo.Binary.Commit)
 	err = fleettools.UpgradeAgent(ctx, kibClient, agentID, endVersionInfo.Binary.String(), true)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("requesting agent upgrade: %w", err)
+	}
 
 	t.Log("Waiting from upgrade details to show up in Fleet")
-	var agent kibana.GetAgentResponse
-	require.Eventuallyf(t, func() bool {
-		agent, err = kibClient.GetAgent(ctx, kibana.GetAgentRequest{ID: agentID})
-		return err == nil && agent.UpgradeDetails != nil
-	},
-		5*time.Minute, time.Second,
-		"last error: %v. agent.UpgradeDetails: %s",
-		err, agentUpgradeDetailsString(agent))
+	_, err = backoff.Retry[kibana.GetAgentResponse](ctx, func() (kibana.GetAgentResponse, error) {
+		agent, getAgentErr := kibClient.GetAgent(ctx, kibana.GetAgentRequest{ID: agentID})
+		if getAgentErr != nil {
+			return agent, getAgentErr
+		}
+		if agent.UpgradeDetails == nil {
+			return agent, fmt.Errorf("agent upgrade details is empty")
+		}
+		return agent, nil
+	}, backoff.WithMaxElapsedTime(5*time.Minute), backoff.WithBackOff(backoff.NewConstantBackOff(time.Second)))
+	if err != nil {
+		return fmt.Errorf("waiting for upgrade details to show up in Fleet: %w", err)
+	}
 
 	// wait for the watcher to show up
 	t.Logf("Waiting for upgrade watcher to start...")
 	err = upgradetest.WaitForWatcher(ctx, 5*time.Minute, 10*time.Second)
-	require.NoError(t, err, "upgrade watcher did not start")
+	if err != nil {
+		return fmt.Errorf("waiting for upgrade watcher to start: %w", err)
+	}
 	t.Logf("Upgrade watcher started")
 
+	if upgradeOpts.PostUpgradeHook != nil {
+		if err := upgradeOpts.PostUpgradeHook(); err != nil {
+			return fmt.Errorf("post upgrade hook failed: %w", err)
+		}
+	}
+
 	// wait for the agent to be healthy and correct version
 	err = upgradetest.WaitHealthyAndVersion(ctx, startFixture, endVersionInfo.Binary, 2*time.Minute, 10*time.Second, t)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("waiting for agent to be healthy and version %s: %w", endVersionInfo.Binary.String(), err)
+	}
 
-	t.Log("Waiting for enrolled Agent status to be online...")
-	require.Eventually(t, check.FleetAgentStatus(ctx, t, kibClient, agentID, "online"), 10*time.Minute, 15*time.Second, "Agent status is not online")
+	t.Log("Waiting for upgraded Agent status to be online...")
+	_, err = backoff.Retry(ctx, func() (any, error) {
+		checkSuccessful := check.FleetAgentStatus(ctx, t, kibClient, agentID, "online")()
+		if !checkSuccessful {
+			return checkSuccessful, fmt.Errorf("agent status is not online")
+		}
+		return checkSuccessful, nil
+	}, backoff.WithMaxElapsedTime(10*time.Minute), backoff.WithBackOff(backoff.NewConstantBackOff(15*time.Second)))
+
+	if err != nil {
+		return fmt.Errorf("waiting for upgraded agent to be online: %w", err)
+	}
 
 	// wait for version
-	require.Eventually(t, func() bool {
+	_, err = backoff.Retry(ctx, func() (string, error) {
 		t.Log("Getting Agent version...")
 		newVersion, err := fleettools.GetAgentVersion(ctx, kibClient, agentID)
 		if err != nil {
 			t.Logf("error getting agent version: %v", err)
-			return false
+			return "", fmt.Errorf("getting agent information: %w", err)
 		}
-		return endVersionInfo.Binary.Version == newVersion
-	}, 5*time.Minute, time.Second)
+		if endVersionInfo.Binary.Version != newVersion {
+			return newVersion, fmt.Errorf("agent version mismatch: got %s, want %s", newVersion, endVersionInfo.Binary.Version)
+		}
+		return newVersion, nil
+	}, backoff.WithMaxElapsedTime(5*time.Minute), backoff.WithBackOff(backoff.NewConstantBackOff(time.Second)))
 
 	t.Logf("Waiting for upgrade watcher to finish...")
 	err = upgradetest.WaitForNoWatcher(ctx, 2*time.Minute, 10*time.Second, 1*time.Minute+15*time.Second)
-	require.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("waiting for upgrade watcher to finish: %w", err)
+	}
 	t.Logf("Upgrade watcher finished")
 
 	// now that the watcher has stopped lets ensure that it's still the expected
 	// version, otherwise it's possible that it was rolled back to the original version
 	err = upgradetest.CheckHealthyAndVersion(ctx, startFixture, endVersionInfo.Binary)
-	assert.NoError(t, err)
+	if err != nil {
+		return fmt.Errorf("checking agent has not been rolled back: %w", err)
+	}
 
 	if upgradeOpts.PostWatcherSuccessHook != nil {
 		err = upgradeOpts.PostWatcherSuccessHook(ctx, startFixture)
-		require.NoError(t, err)
+		if err != nil {
+			return fmt.Errorf("PostWatcherSuccessHook failed: %w", err)
+		}
 	}
+	return nil
 }
 
 func defaultPolicy() kibana.AgentPolicy {
diff --git a/testing/integration/ess/upgrade_rollback_test.go b/testing/integration/ess/upgrade_rollback_test.go
index 359d056a8ae..26ce4aa475b 100644
--- a/testing/integration/ess/upgrade_rollback_test.go
+++ b/testing/integration/ess/upgrade_rollback_test.go
@@ -15,10 +15,12 @@ import (
 	"testing"
 	"time"
 
+	"github.com/gofrs/uuid/v5"
 	"github.com/kardianos/service"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
+	"github.com/elastic/elastic-agent-libs/kibana"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/paths"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/application/upgrade/details"
 	"github.com/elastic/elastic-agent/internal/pkg/agent/install"
@@ -33,7 +35,7 @@ import (
 
 const reallyFastWatcherCfg = `
 agent.upgrade.watcher:
-  grace_period: 1m
+  grace_period: 2m
   error_check.interval: 5s
 `
 
@@ -140,7 +142,11 @@ inputs:
 			if state.UpgradeDetails == nil {
 				t.Fatal("upgrade details in the state cannot be nil")
 			}
-			require.Equal(t, details.StateRollback, details.State(state.UpgradeDetails.State))
+
+			assert.Equal(t, details.StateRollback, details.State(state.UpgradeDetails.State))
+			if !startVersion.Less(*upgradetest.Version_9_1_0_SNAPSHOT) {
+				assert.Equal(t, details.ReasonWatchFailed, state.UpgradeDetails.Metadata.Reason)
+			}
 		} else {
 			t.Logf("rollback finished, status is '%s', cannot check UpgradeDetails", state.State.String())
 		}
@@ -172,27 +178,241 @@ func TestStandaloneUpgradeRollbackOnRestarts(t *testing.T) {
 		t.Skip("This test is flaky on windows. See https://github.com/elastic/elastic-agent/issues/6733")
 	}
 
-	ctx, cancel := testcontext.WithDeadline(t, context.Background(), time.Now().Add(10*time.Minute))
-	defer cancel()
+	type fixturesSetupFunc func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture)
+	testcases := []struct {
+		name          string
+		fixturesSetup fixturesSetupFunc
+	}{
+		{
+			name: "upgrade from previous minor to current version",
+			fixturesSetup: func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture) {
+				// Upgrade from an old build because the new watcher from the new build will
+				// be ran. Otherwise the test will run the old watcher from the old build.
+				upgradeFromVersion, err := upgradetest.PreviousMinor()
+				require.NoError(t, err)
+				startFixture, err := atesting.NewFixture(
+					t,
+					upgradeFromVersion.String(),
+					atesting.WithFetcher(atesting.ArtifactFetcher()),
+				)
+				require.NoError(t, err)
+
+				// Upgrade to the build under test.
+				endFixture, err := define.NewFixtureFromLocalBuild(t, define.Version())
+				require.NoError(t, err)
+				return startFixture, endFixture
+			},
+		},
+		{
+			name: "downgrade from current version to previous minor",
+			fixturesSetup: func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture) {
+				// Upgrade from the current build to an older one. The new watcher will be run anyway, and we can check
+				// the postconditions on a rollback
+
+				// Start from the build under test.
+				fromFixture, err := define.NewFixtureFromLocalBuild(t, define.Version())
+				require.NoError(t, err)
+
+				// Downgrade to a previous version (doesn't really matter what)
+				upgradeToVersion, err := upgradetest.PreviousMinor()
+				require.NoError(t, err)
+				toFixture, err := atesting.NewFixture(
+					t,
+					upgradeToVersion.String(),
+					atesting.WithFetcher(atesting.ArtifactFetcher()),
+				)
+				require.NoError(t, err)
+
+				return fromFixture, toFixture
+			},
+		},
+		{
+			name: "upgrade to a repackaged agent built from the same commit",
+			fixturesSetup: func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture) {
+				// Upgrade from the current build to the same build as Independent Agent Release.
+
+				// Start from the build under test.
+				fromFixture, err := define.NewFixtureFromLocalBuild(t, define.Version())
+				require.NoError(t, err)
+
+				// Create a new package with a different version (IAR-style)
+				newPackageContainingDir := t.TempDir()
+
+				// modify the version with the "+buildYYYYMMDDHHMMSS"
+				currentVersion, err := version.ParseVersion(define.Version())
+				require.NoErrorf(t, err, "define.Version() %q is not parsable.", define.Version())
+
+				newVersionBuildMetadata := "build" + time.Now().Format("20060102150405")
+				parsedNewVersion := version.NewParsedSemVer(currentVersion.Major(), currentVersion.Minor(), currentVersion.Patch(), "", newVersionBuildMetadata)
+
+				versionForFixture, err := repackageArchive(t.Context(), t, fromFixture, newVersionBuildMetadata, currentVersion, newPackageContainingDir, parsedNewVersion)
+				require.NoError(t, err, "error repackaging the archive built from the same commit")
+
+				// I wish I could just pass the location of the package on disk to the whole upgrade tests/fixture/fetcher code
+				// but I would have to break too much code for that, when in Rome... add more code on top of inflexible code
+				repackagedLocalFetcher := atesting.LocalFetcher(newPackageContainingDir)
+				toFixture, err := atesting.NewFixture(
+					t,
+					versionForFixture.String(),
+					atesting.WithFetcher(repackagedLocalFetcher),
+				)
+				require.NoError(t, err)
+
+				return fromFixture, toFixture
+			},
+		},
+	}
 
-	// Upgrade from an old build because the new watcher from the new build will
-	// be ran. Otherwise the test will run the old watcher from the old build.
-	upgradeFromVersion, err := upgradetest.PreviousMinor()
-	require.NoError(t, err)
-	startFixture, err := atesting.NewFixture(
-		t,
-		upgradeFromVersion.String(),
-		atesting.WithFetcher(atesting.ArtifactFetcher()),
+	for _, tc := range testcases {
+		t.Run(tc.name, func(t *testing.T) {
+			ctx, cancel := testcontext.WithDeadline(t, t.Context(), time.Now().Add(10*time.Minute))
+			defer cancel()
+			from, to := tc.fixturesSetup(t)
+
+			standaloneRollbackRestartTest(ctx, t, from, to)
+		})
+	}
+
+}
+
+// TestFleetManagedUpgradeRollbackOnRestarts tests the scenario where upgrading to a new version
+// of Agent fails due to the new Agent binary not starting up. It checks that the Agent is
+// rolled back to the previous version and that Fleet reports the correct informations
+func TestFleetManagedUpgradeRollbackOnRestarts(t *testing.T) {
+	info := define.Require(t, define.Requirements{
+		Group: integration.Fleet,
+		Local: false, // requires Agent installation
+		Sudo:  true,  // requires Agent installation
+		Stack: &define.Stack{},
+	})
+
+	type fixturesSetupFunc func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture)
+	testcases := []struct {
+		name          string
+		fixturesSetup fixturesSetupFunc
+	}{
+		{
+			name: "downgrade from current version to previous minor",
+			fixturesSetup: func(t *testing.T) (from *atesting.Fixture, to *atesting.Fixture) {
+				// Upgrade from the current build to an older one. The new watcher will be run anyway, and we can check
+				// the postconditions on a rollback
+
+				// Start from the build under test.
+				fromFixture, err := define.NewFixtureFromLocalBuild(t, define.Version())
+				require.NoError(t, err)
+
+				// Downgrade to a previous version (doesn't really matter what)
+				upgradeToVersion, err := upgradetest.PreviousMinor()
+				require.NoError(t, err)
+				toFixture, err := atesting.NewFixture(
+					t,
+					upgradeToVersion.String(),
+					atesting.WithFetcher(atesting.ArtifactFetcher()),
+				)
+				require.NoError(t, err)
+
+				return fromFixture, toFixture
+			},
+		},
+	}
+
+	for _, tc := range testcases {
+		t.Run(tc.name, func(t *testing.T) {
+			ctx, cancel := testcontext.WithDeadline(t, t.Context(), time.Now().Add(10*time.Minute))
+			defer cancel()
+			from, to := tc.fixturesSetup(t)
+
+			managedRollbackRestartTest(ctx, t, info, from, to)
+		})
+	}
+}
+
+func managedRollbackRestartTest(ctx context.Context, t *testing.T, info *define.Info, from *atesting.Fixture, to *atesting.Fixture) {
+
+	startVersionInfo, err := from.ExecVersion(ctx)
+	require.NoError(t, err, "failed to get start agent build version info")
+
+	endVersionInfo, err := to.ExecVersion(ctx)
+	require.NoError(t, err, "failed to get end agent build version info")
+
+	t.Logf("Testing Elastic Agent upgrade from %s to %s...", from.Version(), endVersionInfo.Binary.String())
+
+	policyUUID := uuid.Must(uuid.NewV4()).String()
+
+	policy := kibana.AgentPolicy{
+		Name:        fmt.Sprintf("%s-policy-%s", t.Name(), policyUUID),
+		Namespace:   "default",
+		Description: fmt.Sprintf("Rollback test policy %s (%s)", t.Name(), policyUUID),
+		MonitoringEnabled: []kibana.MonitoringEnabledOption{
+			kibana.MonitoringEnabledLogs,
+			kibana.MonitoringEnabledMetrics,
+		},
+	}
+
+	// Use the post-upgrade hook to skip part of the PerformUpgrade (the checks during the grace period)
+	// because we want to do our own checks for the rollback.
+	var ErrSkipGrace = errors.New("skip grace period")
+	postUpgradeHook := func() error {
+		return ErrSkipGrace
+	}
+
+	err = PerformManagedUpgrade(ctx, t, info, from, to, policy, false,
+		upgradetest.WithPostUpgradeHook(postUpgradeHook),
+		upgradetest.WithDisableHashCheck(true),
+		upgradetest.WithCustomWatcherConfig(reallyFastWatcherCfg),
 	)
+
+	// we expect ErrSkipGrace at this point, meaning that we finished installing but didn't wait for agent to become healthy
+	require.ErrorIs(t, err, ErrSkipGrace, "managed upgrade failed with unexpected error")
+
+	// A few seconds after the upgrade, deliberately restart upgraded Agent a
+	// couple of times to simulate Agent crashing.
+	restartAgentNTimes(t, 3, 10*time.Second)
+
+	// wait for the agent to be healthy and correct version
+	err = upgradetest.WaitHealthyAndVersion(ctx, from, startVersionInfo.Binary, 2*time.Minute, 10*time.Second, t)
+	require.NoError(t, err, "agent never came online with version %s", startVersionInfo.Binary.String())
+
+	agentID, err := from.AgentID(ctx)
+	require.NoError(t, err, "error retrieving agent ID")
+
+	// ensure that upgrade details now show the state as UPG_ROLLBACK. This is only possible with Elastic
+	// Agent versions >= 8.12.0.
+	startVersion, err := version.ParseVersion(startVersionInfo.Binary.Version)
 	require.NoError(t, err)
+
+	if !startVersion.Less(*version.NewParsedSemVer(8, 12, 0, "", "")) {
+		fleetAgent, fleetAgentErr := info.KibanaClient.GetAgent(ctx, kibana.GetAgentRequest{ID: agentID})
+		require.NoError(t, fleetAgentErr, "error getting agent from Fleet")
+		require.NotNil(t, fleetAgent.UpgradeDetails, "upgrade details not set")
+		assert.Equal(t, details.StateRollback, details.State(fleetAgent.UpgradeDetails.State))
+		if !startVersion.Less(*upgradetest.Version_9_1_0_SNAPSHOT) {
+			assert.Equal(t, details.ReasonWatchFailed, fleetAgent.UpgradeDetails.Metadata.Reason)
+		}
+	}
+
+	// rollback should stop the watcher
+	// killTimeout is greater than timeout as the watcher should have been
+	// stopped on its own, and we don't want this test to hide that fact
+	err = upgradetest.WaitForNoWatcher(ctx, 2*time.Minute, 10*time.Second, 3*time.Minute)
+	require.NoError(t, err)
+
+	// now that the watcher has stopped lets ensure that it's still the expected
+	// version, otherwise it's possible that it was rolled back to the original version
+	err = upgradetest.CheckHealthyAndVersion(ctx, from, startVersionInfo.Binary)
+	assert.NoError(t, err)
+
+}
+
+func standaloneRollbackRestartTest(ctx context.Context, t *testing.T, startFixture *atesting.Fixture, endFixture *atesting.Fixture) {
+
 	startVersionInfo, err := startFixture.ExecVersion(ctx)
 	require.NoError(t, err, "failed to get start agent build version info")
 
-	// Upgrade to the build under test.
-	endFixture, err := define.NewFixtureFromLocalBuild(t, define.Version())
-	require.NoError(t, err)
+	endVersionInfo, err := startFixture.ExecVersion(ctx)
+	require.NoError(t, err, "failed to get end agent build version info")
 
-	t.Logf("Testing Elastic Agent upgrade from %s to %s...", upgradeFromVersion, define.Version())
+	t.Logf("Testing Elastic Agent upgrade from %s to %s...", startFixture.Version(), endVersionInfo.Binary.String())
 
 	// Use the post-upgrade hook to bypass the remainder of the PerformUpgrade
 	// because we want to do our own checks for the rollback.
@@ -204,57 +424,18 @@ func TestStandaloneUpgradeRollbackOnRestarts(t *testing.T) {
 	err = upgradetest.PerformUpgrade(
 		ctx, startFixture, endFixture, t,
 		upgradetest.WithPostUpgradeHook(postUpgradeHook),
-		upgradetest.WithCustomWatcherConfig(reallyFastWatcherCfg))
+		upgradetest.WithCustomWatcherConfig(reallyFastWatcherCfg),
+		upgradetest.WithDisableHashCheck(true))
 	if !errors.Is(err, ErrPostExit) {
 		require.NoError(t, err)
 	}
 
 	// A few seconds after the upgrade, deliberately restart upgraded Agent a
 	// couple of times to simulate Agent crashing.
-	for restartIdx := 0; restartIdx < 3; restartIdx++ {
-		time.Sleep(10 * time.Second)
-		topPath := paths.Top()
-
-		t.Logf("Stopping agent via service to simulate crashing")
-		err = install.StopService(topPath, install.DefaultStopTimeout, install.DefaultStopInterval)
-		if err != nil && runtime.GOOS == define.Windows && strings.Contains(err.Error(), "The service has not been started.") {
-			// Due to the quick restarts every 10 seconds its possible that this is faster than Windows
-			// can handle. Decrementing restartIdx means that the loop will occur again.
-			t.Logf("Got an allowed error on Windows: %s", err)
-			err = nil
-		}
-		require.NoError(t, err)
-
-		// ensure that it's stopped before starting it again
-		var status service.Status
-		var statusErr error
-		require.Eventuallyf(t, func() bool {
-			status, statusErr = install.StatusService(topPath)
-			if statusErr != nil {
-				return false
-			}
-			return status != service.StatusRunning
-		}, 2*time.Minute, 1*time.Second, "service never fully stopped (status: %v): %s", status, statusErr)
-		t.Logf("Stopped agent via service to simulate crashing")
-
-		// start it again
-		t.Logf("Starting agent via service to simulate crashing")
-		err = install.StartService(topPath)
-		require.NoError(t, err)
-
-		// ensure that it's started before next loop
-		require.Eventuallyf(t, func() bool {
-			status, statusErr = install.StatusService(topPath)
-			if statusErr != nil {
-				return false
-			}
-			return status == service.StatusRunning
-		}, 2*time.Minute, 1*time.Second, "service never fully started (status: %v): %s", status, statusErr)
-		t.Logf("Started agent via service to simulate crashing")
-	}
+	restartAgentNTimes(t, 3, 10*time.Second)
 
 	// wait for the agent to be healthy and back at the start version
-	err = upgradetest.WaitHealthyAndVersion(ctx, startFixture, startVersionInfo.Binary, 10*time.Minute, 10*time.Second, t)
+	err = upgradetest.WaitHealthyAndVersion(ctx, startFixture, startVersionInfo.Binary, 2*time.Minute, 10*time.Second, t)
 	if err != nil {
 		// agent never got healthy, but we need to ensure the watcher is stopped before continuing
 		// this kills the watcher instantly and waits for it to be gone before continuing
@@ -279,7 +460,10 @@ func TestStandaloneUpgradeRollbackOnRestarts(t *testing.T) {
 		require.NoError(t, err)
 
 		require.NotNil(t, state.UpgradeDetails)
-		require.Equal(t, details.StateRollback, details.State(state.UpgradeDetails.State))
+		assert.Equal(t, details.StateRollback, details.State(state.UpgradeDetails.State))
+		if !startVersion.Less(*upgradetest.Version_9_1_0_SNAPSHOT) {
+			assert.Equal(t, details.ReasonWatchFailed, state.UpgradeDetails.Metadata.Reason)
+		}
 	}
 
 	// rollback should stop the watcher
@@ -293,3 +477,48 @@ func TestStandaloneUpgradeRollbackOnRestarts(t *testing.T) {
 	err = upgradetest.CheckHealthyAndVersion(ctx, startFixture, startVersionInfo.Binary)
 	assert.NoError(t, err)
 }
+
+func restartAgentNTimes(t *testing.T, noOfRestarts int, sleepBetweenIterations time.Duration) {
+	topPath := paths.Top()
+
+	for restartIdx := 0; restartIdx < noOfRestarts; restartIdx++ {
+		time.Sleep(sleepBetweenIterations)
+
+		t.Logf("Stopping agent via service to simulate crashing")
+		err := install.StopService(topPath, install.DefaultStopTimeout, install.DefaultStopInterval)
+		if err != nil && runtime.GOOS == define.Windows && strings.Contains(err.Error(), "The service has not been started.") {
+			// Due to the quick restarts every 10 seconds its possible that this is faster than Windows
+			// can handle. Decrementing restartIdx means that the loop will occur again.
+			t.Logf("Got an allowed error on Windows: %s", err)
+			err = nil
+		}
+		require.NoError(t, err)
+
+		// ensure that it's stopped before starting it again
+		var status service.Status
+		var statusErr error
+		require.Eventuallyf(t, func() bool {
+			status, statusErr = install.StatusService(topPath)
+			if statusErr != nil {
+				return false
+			}
+			return status != service.StatusRunning
+		}, 5*time.Minute, 1*time.Second, "service never fully stopped (status: %v): %s", status, statusErr)
+		t.Logf("Stopped agent via service to simulate crashing")
+
+		// start it again
+		t.Logf("Starting agent via service to simulate crashing")
+		err = install.StartService(topPath)
+		require.NoError(t, err)
+
+		// ensure that it's started before next loop
+		require.Eventuallyf(t, func() bool {
+			status, statusErr = install.StatusService(topPath)
+			if statusErr != nil {
+				return false
+			}
+			return status == service.StatusRunning
+		}, 5*time.Minute, 1*time.Second, "service never fully started (status: %v): %s", status, statusErr)
+		t.Logf("Started agent via service to simulate crashing")
+	}
+}
diff --git a/testing/integration/ess/upgrade_standalone_same_commit_test.go b/testing/integration/ess/upgrade_standalone_same_commit_test.go
index b470a9c120b..48e6e5993f6 100644
--- a/testing/integration/ess/upgrade_standalone_same_commit_test.go
+++ b/testing/integration/ess/upgrade_standalone_same_commit_test.go
@@ -7,33 +7,20 @@
 package ess
 
 import (
-	"archive/tar"
-	"archive/zip"
-	"bytes"
-	"compress/gzip"
 	"context"
-	"errors"
 	"fmt"
-	"io"
-	"os"
-	"path"
-	"path/filepath"
-	"strings"
 	"testing"
 	"time"
 
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 
-	"github.com/elastic/elastic-agent/dev-tools/mage"
-	v1 "github.com/elastic/elastic-agent/pkg/api/v1"
 	atesting "github.com/elastic/elastic-agent/pkg/testing"
 	"github.com/elastic/elastic-agent/pkg/testing/define"
 	"github.com/elastic/elastic-agent/pkg/testing/tools/testcontext"
 	"github.com/elastic/elastic-agent/pkg/version"
 	"github.com/elastic/elastic-agent/testing/integration"
 	"github.com/elastic/elastic-agent/testing/upgradetest"
-	agtversion "github.com/elastic/elastic-agent/version"
 )
 
 func TestStandaloneUpgradeSameCommit(t *testing.T) {
@@ -44,8 +31,8 @@ func TestStandaloneUpgradeSameCommit(t *testing.T) {
 	})
 
 	// parse the version we are testing
-	currentVersion, err := version.ParseVersion(define.Version())
-	require.NoError(t, err)
+	currentVersion, parseVersionErr := version.ParseVersion(define.Version())
+	require.NoError(t, parseVersionErr)
 
 	// 8.13.0-SNAPSHOT is the minimum version we need for testing upgrading with the same hash
 	if currentVersion.Less(*upgradetest.Version_8_13_0_SNAPSHOT) {
@@ -82,7 +69,7 @@ func TestStandaloneUpgradeSameCommit(t *testing.T) {
 	})
 
 	t.Run(fmt.Sprintf("Upgrade on a repackaged version of agent %s (%s)", currentVersion, unPrivilegedString), func(t *testing.T) {
-		ctx, cancel := testcontext.WithDeadline(t, context.Background(), time.Now().Add(10*time.Minute))
+		ctx, cancel := context.WithDeadline(t.Context(), time.Now().Add(10*time.Minute))
 		defer cancel()
 
 		startFixture, err := define.NewFixtureFromLocalBuild(
@@ -95,54 +82,9 @@ func TestStandaloneUpgradeSameCommit(t *testing.T) {
 		newVersionBuildMetadata := "build" + time.Now().Format("20060102150405")
 		parsedNewVersion := version.NewParsedSemVer(currentVersion.Major(), currentVersion.Minor(), currentVersion.Patch(), "", newVersionBuildMetadata)
 
-		err = startFixture.EnsurePrepared(ctx)
-		require.NoErrorf(t, err, "fixture should be prepared")
-
-		// retrieve the compressed package file location
-		srcPackage, err := startFixture.SrcPackage(ctx)
-		require.NoErrorf(t, err, "error retrieving start fixture source package")
-
-		originalPackageFileName := filepath.Base(srcPackage)
-
-		// integration test fixtures and package names treat the version as a string including the "-SNAPSHOT" suffix
-		// while the repackage functions below separate version from the snapshot flag.
-		// Normally the early release versions are not snapshots but this test runs on PRs and main branch when we test
-		// starting from SNAPSHOT packages, so we have to work around the fact that we cannot simply re-generate the packages
-		// by defining versions in 2 separate ways for repackage hack and for fixtures
-		buildMetadataForAgentFixture := newVersionBuildMetadata
-		if currentVersion.IsSnapshot() {
-			buildMetadataForAgentFixture += "-SNAPSHOT"
-		}
-		versionForFixture := version.NewParsedSemVer(currentVersion.Major(), currentVersion.Minor(), currentVersion.Patch(), "", buildMetadataForAgentFixture)
-
-		// calculate the new package name
-		newPackageFileName := strings.Replace(originalPackageFileName, currentVersion.String(), versionForFixture.String(), 1)
-		t.Logf("originalPackageName: %q newPackageFileName: %q", originalPackageFileName, newPackageFileName)
-
 		newPackageContainingDir := t.TempDir()
-		newPackageAbsPath := filepath.Join(newPackageContainingDir, newPackageFileName)
-
-		// hack the package based on type
-		ext := filepath.Ext(originalPackageFileName)
-		if ext == ".gz" {
-			// fetch the next extension
-			ext = filepath.Ext(strings.TrimRight(originalPackageFileName, ext)) + ext
-		}
-		switch ext {
-		case ".zip":
-			t.Logf("file %q is a .zip package", originalPackageFileName)
-			repackageZipArchive(t, srcPackage, newPackageAbsPath, parsedNewVersion)
-		case ".tar.gz":
-			t.Logf("file %q is a .tar.gz package", originalPackageFileName)
-			repackageTarArchive(t, srcPackage, newPackageAbsPath, parsedNewVersion)
-		default:
-			t.Logf("unknown extension %q for package file %q ", ext, originalPackageFileName)
-			t.FailNow()
-		}
 
-		// Create hash file for the new package
-		err = mage.CreateSHA512File(newPackageAbsPath)
-		require.NoErrorf(t, err, "error creating .sha512 for file %q", newPackageAbsPath)
+		versionForFixture, err := repackageArchive(ctx, t, startFixture, newVersionBuildMetadata, currentVersion, newPackageContainingDir, parsedNewVersion)
 
 		// I wish I could just pass the location of the package on disk to the whole upgrade tests/fixture/fetcher code
 		// but I would have to break too much code for that, when in Rome... add more code on top of inflexible code
@@ -160,218 +102,3 @@ func TestStandaloneUpgradeSameCommit(t *testing.T) {
 	})
 
 }
-
-func repackageTarArchive(t *testing.T, srcPackagePath string, newPackagePath string, newVersion *version.ParsedSemVer) {
-	oldTopDirectoryName := strings.TrimRight(filepath.Base(srcPackagePath), ".tar.gz")
-	newTopDirectoryName := strings.TrimRight(filepath.Base(newPackagePath), ".tar.gz")
-
-	// Open the source package and create readers
-	srcPackageFile, err := os.Open(srcPackagePath)
-	require.NoErrorf(t, err, "error opening source file %q", srcPackagePath)
-	defer func(srcPackageFile *os.File) {
-		err := srcPackageFile.Close()
-		if err != nil {
-			assert.Failf(t, "error closing source file %q: %v", srcPackagePath, err)
-		}
-	}(srcPackageFile)
-
-	gzReader, err := gzip.NewReader(srcPackageFile)
-	require.NoErrorf(t, err, "error creating gzip reader for file %q", srcPackagePath)
-	defer func(gzReader *gzip.Reader) {
-		err := gzReader.Close()
-		if err != nil {
-			assert.Failf(t, "error closing gzip reader for source file %q: %v", srcPackagePath, err)
-		}
-	}(gzReader)
-
-	tarReader := tar.NewReader(gzReader)
-
-	// Create the output file and its writers
-	newPackageFile, err := os.OpenFile(newPackagePath, os.O_CREATE|os.O_RDWR|os.O_TRUNC, 0o750)
-	require.NoErrorf(t, err, "error opening output file %q", newPackageFile)
-	defer func(newPackageFile *os.File) {
-		err := newPackageFile.Close()
-		if err != nil {
-			assert.Failf(t, "error closing output file %q: %v", newPackagePath, err)
-		}
-	}(newPackageFile)
-
-	gzWriter := gzip.NewWriter(newPackageFile)
-	defer func(gzWriter *gzip.Writer) {
-		err := gzWriter.Close()
-		if err != nil {
-			assert.Failf(t, "error closing gzip writer for file %q: %v", newPackagePath, err)
-		}
-	}(gzWriter)
-
-	tarWriter := tar.NewWriter(gzWriter)
-	defer func(tarWriter *tar.Writer) {
-		err := tarWriter.Close()
-		if err != nil {
-			assert.Failf(t, "error closing tar writer for file %q: %v", newPackagePath, err)
-		}
-	}(tarWriter)
-
-	hackTarGzPackage(t, tarReader, tarWriter, oldTopDirectoryName, newTopDirectoryName, newVersion)
-}
-
-func hackTarGzPackage(t *testing.T, reader *tar.Reader, writer *tar.Writer, oldTopDirName string, newTopDirName string, newVersion *version.ParsedSemVer) {
-
-	for {
-		f, err := reader.Next()
-		if errors.Is(err, io.EOF) {
-			break
-		}
-		require.NoError(t, err, "error reading source package")
-
-		// tar format uses forward slash as path separator, make sure we use only "path" package for checking and manipulation
-		switch path.Base(f.Name) {
-		case v1.ManifestFileName:
-			// read old content and generate the new manifest based on that
-			newManifest := generateNewManifestContent(t, reader, newVersion)
-			newManifestBytes := []byte(newManifest)
-
-			// fix file length in header
-			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, int64(len(newManifestBytes)))
-
-			// write the new manifest body
-			_, err = writer.Write(newManifestBytes)
-			require.NoError(t, err, "error writing out modified manifest")
-
-		case agtversion.PackageVersionFileName:
-
-			t.Logf("writing new package version: %q", newVersion.String())
-
-			// new package version file contents
-			newPackageVersionBytes := []byte(newVersion.String())
-			// write new header
-			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, int64(len(newPackageVersionBytes)))
-			// write content
-			_, err := writer.Write(newPackageVersionBytes)
-			require.NoError(t, err, "error writing out modified package version")
-		default:
-			// write entry header with the size untouched
-			writeModifiedTarHeader(t, writer, f, oldTopDirName, newTopDirName, f.Size)
-
-			// copy body
-			_, err := io.Copy(writer, reader)
-			require.NoErrorf(t, err, "error writing file content for %+v", f)
-		}
-
-	}
-
-}
-
-func writeModifiedTarHeader(t *testing.T, writer *tar.Writer, header *tar.Header, oldTopDirName, newTopDirName string, size int64) {
-	// replace top dir in the path
-	header.Name = strings.Replace(header.Name, oldTopDirName, newTopDirName, 1)
-	header.Size = size
-
-	err := writer.WriteHeader(header)
-	require.NoErrorf(t, err, "error writing tar header %+v", header)
-}
-
-func repackageZipArchive(t *testing.T, srcPackagePath string, newPackagePath string, newVersion *version.ParsedSemVer) {
-	oldTopDirectoryName := strings.TrimRight(filepath.Base(srcPackagePath), ".zip")
-	newTopDirectoryName := strings.TrimRight(filepath.Base(newPackagePath), ".zip")
-
-	// Open the source package and create readers
-	zipReader, err := zip.OpenReader(srcPackagePath)
-	require.NoErrorf(t, err, "error opening source file %q", srcPackagePath)
-	defer func(zipReader *zip.ReadCloser) {
-		err := zipReader.Close()
-		if err != nil {
-			assert.Failf(t, "error closing source file %q: %v", srcPackagePath, err)
-		}
-	}(zipReader)
-
-	// Create the output file and its writers
-	newPackageFile, err := os.OpenFile(newPackagePath, os.O_CREATE|os.O_RDWR|os.O_TRUNC, 0o750)
-	require.NoErrorf(t, err, "error opening output file %q", newPackageFile)
-	defer func(newPackageFile *os.File) {
-		err := newPackageFile.Close()
-		if err != nil {
-			assert.Failf(t, "error closing output file %q: %v", newPackagePath, err)
-		}
-	}(newPackageFile)
-
-	zipWriter := zip.NewWriter(newPackageFile)
-	defer func(zipWriter *zip.Writer) {
-		err := zipWriter.Close()
-		if err != nil {
-			assert.Failf(t, "error closing zip writer for output file %q: %v", newPackagePath, err)
-		}
-	}(zipWriter)
-
-	hackZipPackage(t, zipReader, zipWriter, oldTopDirectoryName, newTopDirectoryName, newVersion)
-}
-
-func hackZipPackage(t *testing.T, reader *zip.ReadCloser, writer *zip.Writer, oldTopDirName string, newTopDirName string, newVersion *version.ParsedSemVer) {
-	for _, zippedFile := range reader.File {
-		zippedFileHeader := zippedFile.FileHeader
-
-		// zip format uses forward slash as path separator, make sure we use only "path" package for checking and manipulation
-		switch path.Base(zippedFile.Name) {
-		case v1.ManifestFileName:
-			// read old content
-			manifestReader, err := zippedFile.Open()
-			require.NoError(t, err, "error opening manifest file in zipped package")
-
-			// generate new manifest based on the old manifest and the new version
-			newManifest := generateNewManifestContent(t, manifestReader, newVersion)
-
-			// we need to close the file content reader
-			err = manifestReader.Close()
-			require.NoError(t, err, "error closing manifest file in zipped package")
-
-			newManifestBytes := []byte(newManifest)
-			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, uint64(len(newManifest)))
-
-			_, err = io.Copy(fileContentWriter, bytes.NewReader(newManifestBytes))
-			require.NoError(t, err, "error writing out modified manifest")
-
-		case agtversion.PackageVersionFileName:
-			t.Logf("writing new package version: %q", newVersion.String())
-			// new package version file contents
-			newPackageVersionBytes := []byte(newVersion.String())
-			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, uint64(len(newPackageVersionBytes)))
-
-			_, err := io.Copy(fileContentWriter, bytes.NewReader(newPackageVersionBytes))
-			require.NoError(t, err, "error writing out modified package version")
-		default:
-			// write entry header with the size untouched
-			fileContentWriter := writeModifiedZipFileHeader(t, writer, zippedFileHeader, oldTopDirName, newTopDirName, zippedFile.UncompressedSize64)
-			fileContentReader, err := zippedFile.Open()
-			require.NoErrorf(t, err, "error opening zip file content reader for %+v", zippedFileHeader)
-			// copy body
-			_, err = io.Copy(fileContentWriter, fileContentReader)
-			require.NoErrorf(t, err, "error writing file content for %+v", zippedFileHeader)
-
-			// we need to close the file content reader
-			err = fileContentReader.Close()
-			require.NoError(t, err, "error closing zipped file writer for %+v", zippedFileHeader)
-		}
-	}
-}
-
-func writeModifiedZipFileHeader(t *testing.T, writer *zip.Writer, header zip.FileHeader, oldTopDirName, newTopDirName string, size uint64) io.Writer {
-	header.Name = strings.Replace(header.Name, oldTopDirName, newTopDirName, 1)
-	header.UncompressedSize64 = size
-	fileContentWriter, err := writer.CreateHeader(&header)
-	require.NoErrorf(t, err, "error creating header for %+v", header)
-	return fileContentWriter
-}
-
-func generateNewManifestContent(t *testing.T, manifestReader io.Reader, newVersion *version.ParsedSemVer) string {
-	oldManifest, err := v1.ParseManifest(manifestReader)
-	require.NoError(t, err, "reading manifest content from tar source archive")
-
-	t.Logf("read old manifest: %+v", oldManifest)
-
-	// replace manifest content
-	newManifest, err := mage.GeneratePackageManifest("elastic-agent", newVersion.String(), oldManifest.Package.Snapshot, oldManifest.Package.Hash, oldManifest.Package.Hash[:6], oldManifest.Package.Fips, nil)
-	require.NoErrorf(t, err, "GeneratePackageManifest(%v, %v, %v, %v, %v) failed", newVersion.String(), oldManifest.Package.Snapshot, oldManifest.Package.Hash, oldManifest.Package.Hash[:6], nil)
-
-	t.Logf("generated new manifest:\n%s", newManifest)
-	return newManifest
-}
diff --git a/testing/mocks/internal_/pkg/agent/application/actions/handlers/diagnostics_provider_mock.go b/testing/mocks/internal_/pkg/agent/application/actions/handlers/diagnostics_provider_mock.go
index 7a166506eaf..56409b31b2b 100644
--- a/testing/mocks/internal_/pkg/agent/application/actions/handlers/diagnostics_provider_mock.go
+++ b/testing/mocks/internal_/pkg/agent/application/actions/handlers/diagnostics_provider_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package handlers
 
diff --git a/testing/mocks/internal_/pkg/agent/application/actions/handlers/log_level_setter_mock.go b/testing/mocks/internal_/pkg/agent/application/actions/handlers/log_level_setter_mock.go
index c937315d8a0..1fa190652b2 100644
--- a/testing/mocks/internal_/pkg/agent/application/actions/handlers/log_level_setter_mock.go
+++ b/testing/mocks/internal_/pkg/agent/application/actions/handlers/log_level_setter_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package handlers
 
diff --git a/testing/mocks/internal_/pkg/agent/application/actions/handlers/uploader_mock.go b/testing/mocks/internal_/pkg/agent/application/actions/handlers/uploader_mock.go
index f89f8b85641..76b66ad5513 100644
--- a/testing/mocks/internal_/pkg/agent/application/actions/handlers/uploader_mock.go
+++ b/testing/mocks/internal_/pkg/agent/application/actions/handlers/uploader_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package handlers
 
diff --git a/testing/mocks/internal_/pkg/agent/application/info/agent_mock.go b/testing/mocks/internal_/pkg/agent/application/info/agent_mock.go
index 32d403a7d5c..3c69cd9095e 100644
--- a/testing/mocks/internal_/pkg/agent/application/info/agent_mock.go
+++ b/testing/mocks/internal_/pkg/agent/application/info/agent_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.53.0. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package info
 
diff --git a/testing/mocks/internal_/pkg/agent/cmd/agent_watcher_mock.go b/testing/mocks/internal_/pkg/agent/cmd/agent_watcher_mock.go
new file mode 100644
index 00000000000..4541e5d9aa0
--- /dev/null
+++ b/testing/mocks/internal_/pkg/agent/cmd/agent_watcher_mock.go
@@ -0,0 +1,93 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License 2.0;
+// you may not use this file except in compliance with the Elastic License 2.0.
+
+// Code generated by mockery v2.53.4. DO NOT EDIT.
+
+package cmd
+
+import (
+	context "context"
+
+	mock "github.com/stretchr/testify/mock"
+
+	logp "github.com/elastic/elastic-agent-libs/logp"
+
+	time "time"
+)
+
+// AgentWatcher is an autogenerated mock type for the agentWatcher type
+type AgentWatcher struct {
+	mock.Mock
+}
+
+type AgentWatcher_Expecter struct {
+	mock *mock.Mock
+}
+
+func (_m *AgentWatcher) EXPECT() *AgentWatcher_Expecter {
+	return &AgentWatcher_Expecter{mock: &_m.Mock}
+}
+
+// Watch provides a mock function with given fields: ctx, tilGrace, errorCheckInterval, log
+func (_m *AgentWatcher) Watch(ctx context.Context, tilGrace time.Duration, errorCheckInterval time.Duration, log *logp.Logger) error {
+	ret := _m.Called(ctx, tilGrace, errorCheckInterval, log)
+
+	if len(ret) == 0 {
+		panic("no return value specified for Watch")
+	}
+
+	var r0 error
+	if rf, ok := ret.Get(0).(func(context.Context, time.Duration, time.Duration, *logp.Logger) error); ok {
+		r0 = rf(ctx, tilGrace, errorCheckInterval, log)
+	} else {
+		r0 = ret.Error(0)
+	}
+
+	return r0
+}
+
+// AgentWatcher_Watch_Call is a *mock.Call that shadows Run/Return methods with type explicit version for method 'Watch'
+type AgentWatcher_Watch_Call struct {
+	*mock.Call
+}
+
+// Watch is a helper method to define mock.On call
+//   - ctx context.Context
+//   - tilGrace time.Duration
+//   - errorCheckInterval time.Duration
+//   - log *logp.Logger
+func (_e *AgentWatcher_Expecter) Watch(ctx interface{}, tilGrace interface{}, errorCheckInterval interface{}, log interface{}) *AgentWatcher_Watch_Call {
+	return &AgentWatcher_Watch_Call{Call: _e.mock.On("Watch", ctx, tilGrace, errorCheckInterval, log)}
+}
+
+func (_c *AgentWatcher_Watch_Call) Run(run func(ctx context.Context, tilGrace time.Duration, errorCheckInterval time.Duration, log *logp.Logger)) *AgentWatcher_Watch_Call {
+	_c.Call.Run(func(args mock.Arguments) {
+		run(args[0].(context.Context), args[1].(time.Duration), args[2].(time.Duration), args[3].(*logp.Logger))
+	})
+	return _c
+}
+
+func (_c *AgentWatcher_Watch_Call) Return(_a0 error) *AgentWatcher_Watch_Call {
+	_c.Call.Return(_a0)
+	return _c
+}
+
+func (_c *AgentWatcher_Watch_Call) RunAndReturn(run func(context.Context, time.Duration, time.Duration, *logp.Logger) error) *AgentWatcher_Watch_Call {
+	_c.Call.Return(run)
+	return _c
+}
+
+// NewAgentWatcher creates a new instance of AgentWatcher. It also registers a testing interface on the mock and a cleanup function to assert the mocks expectations.
+// The first argument is typically a *testing.T value.
+func NewAgentWatcher(t interface {
+	mock.TestingT
+	Cleanup(func())
+}) *AgentWatcher {
+	mock := &AgentWatcher{}
+	mock.Mock.Test(t)
+
+	t.Cleanup(func() { mock.AssertExpectations(t) })
+
+	return mock
+}
diff --git a/testing/mocks/internal_/pkg/agent/cmd/installation_modifier_mock.go b/testing/mocks/internal_/pkg/agent/cmd/installation_modifier_mock.go
new file mode 100644
index 00000000000..14f73d912a8
--- /dev/null
+++ b/testing/mocks/internal_/pkg/agent/cmd/installation_modifier_mock.go
@@ -0,0 +1,146 @@
+// Copyright Elasticsearch B.V. and/or licensed to Elasticsearch B.V. under one
+// or more contributor license agreements. Licensed under the Elastic License 2.0;
+// you may not use this file except in compliance with the Elastic License 2.0.
+
+// Code generated by mockery v2.53.4. DO NOT EDIT.
+
+package cmd
+
+import (
+	client "github.com/elastic/elastic-agent/pkg/control/v2/client"
+
+	context "context"
+
+	logp "github.com/elastic/elastic-agent-libs/logp"
+
+	mock "github.com/stretchr/testify/mock"
+)
+
+// InstallationModifier is an autogenerated mock type for the installationModifier type
+type InstallationModifier struct {
+	mock.Mock
+}
+
+type InstallationModifier_Expecter struct {
+	mock *mock.Mock
+}
+
+func (_m *InstallationModifier) EXPECT() *InstallationModifier_Expecter {
+	return &InstallationModifier_Expecter{mock: &_m.Mock}
+}
+
+// Cleanup provides a mock function with given fields: log, topDirPath, currentVersionedHome, currentHash, removeMarker, keepLogs
+func (_m *InstallationModifier) Cleanup(log *logp.Logger, topDirPath string, currentVersionedHome string, currentHash string, removeMarker bool, keepLogs bool) error {
+	ret := _m.Called(log, topDirPath, currentVersionedHome, currentHash, removeMarker, keepLogs)
+
+	if len(ret) == 0 {
+		panic("no return value specified for Cleanup")
+	}
+
+	var r0 error
+	if rf, ok := ret.Get(0).(func(*logp.Logger, string, string, string, bool, bool) error); ok {
+		r0 = rf(log, topDirPath, currentVersionedHome, currentHash, removeMarker, keepLogs)
+	} else {
+		r0 = ret.Error(0)
+	}
+
+	return r0
+}
+
+// InstallationModifier_Cleanup_Call is a *mock.Call that shadows Run/Return methods with type explicit version for method 'Cleanup'
+type InstallationModifier_Cleanup_Call struct {
+	*mock.Call
+}
+
+// Cleanup is a helper method to define mock.On call
+//   - log *logp.Logger
+//   - topDirPath string
+//   - currentVersionedHome string
+//   - currentHash string
+//   - removeMarker bool
+//   - keepLogs bool
+func (_e *InstallationModifier_Expecter) Cleanup(log interface{}, topDirPath interface{}, currentVersionedHome interface{}, currentHash interface{}, removeMarker interface{}, keepLogs interface{}) *InstallationModifier_Cleanup_Call {
+	return &InstallationModifier_Cleanup_Call{Call: _e.mock.On("Cleanup", log, topDirPath, currentVersionedHome, currentHash, removeMarker, keepLogs)}
+}
+
+func (_c *InstallationModifier_Cleanup_Call) Run(run func(log *logp.Logger, topDirPath string, currentVersionedHome string, currentHash string, removeMarker bool, keepLogs bool)) *InstallationModifier_Cleanup_Call {
+	_c.Call.Run(func(args mock.Arguments) {
+		run(args[0].(*logp.Logger), args[1].(string), args[2].(string), args[3].(string), args[4].(bool), args[5].(bool))
+	})
+	return _c
+}
+
+func (_c *InstallationModifier_Cleanup_Call) Return(_a0 error) *InstallationModifier_Cleanup_Call {
+	_c.Call.Return(_a0)
+	return _c
+}
+
+func (_c *InstallationModifier_Cleanup_Call) RunAndReturn(run func(*logp.Logger, string, string, string, bool, bool) error) *InstallationModifier_Cleanup_Call {
+	_c.Call.Return(run)
+	return _c
+}
+
+// Rollback provides a mock function with given fields: ctx, log, c, topDirPath, prevVersionedHome, prevHash
+func (_m *InstallationModifier) Rollback(ctx context.Context, log *logp.Logger, c client.Client, topDirPath string, prevVersionedHome string, prevHash string) error {
+	ret := _m.Called(ctx, log, c, topDirPath, prevVersionedHome, prevHash)
+
+	if len(ret) == 0 {
+		panic("no return value specified for Rollback")
+	}
+
+	var r0 error
+	if rf, ok := ret.Get(0).(func(context.Context, *logp.Logger, client.Client, string, string, string) error); ok {
+		r0 = rf(ctx, log, c, topDirPath, prevVersionedHome, prevHash)
+	} else {
+		r0 = ret.Error(0)
+	}
+
+	return r0
+}
+
+// InstallationModifier_Rollback_Call is a *mock.Call that shadows Run/Return methods with type explicit version for method 'Rollback'
+type InstallationModifier_Rollback_Call struct {
+	*mock.Call
+}
+
+// Rollback is a helper method to define mock.On call
+//   - ctx context.Context
+//   - log *logp.Logger
+//   - c client.Client
+//   - topDirPath string
+//   - prevVersionedHome string
+//   - prevHash string
+func (_e *InstallationModifier_Expecter) Rollback(ctx interface{}, log interface{}, c interface{}, topDirPath interface{}, prevVersionedHome interface{}, prevHash interface{}) *InstallationModifier_Rollback_Call {
+	return &InstallationModifier_Rollback_Call{Call: _e.mock.On("Rollback", ctx, log, c, topDirPath, prevVersionedHome, prevHash)}
+}
+
+func (_c *InstallationModifier_Rollback_Call) Run(run func(ctx context.Context, log *logp.Logger, c client.Client, topDirPath string, prevVersionedHome string, prevHash string)) *InstallationModifier_Rollback_Call {
+	_c.Call.Run(func(args mock.Arguments) {
+		run(args[0].(context.Context), args[1].(*logp.Logger), args[2].(client.Client), args[3].(string), args[4].(string), args[5].(string))
+	})
+	return _c
+}
+
+func (_c *InstallationModifier_Rollback_Call) Return(_a0 error) *InstallationModifier_Rollback_Call {
+	_c.Call.Return(_a0)
+	return _c
+}
+
+func (_c *InstallationModifier_Rollback_Call) RunAndReturn(run func(context.Context, *logp.Logger, client.Client, string, string, string) error) *InstallationModifier_Rollback_Call {
+	_c.Call.Return(run)
+	return _c
+}
+
+// NewInstallationModifier creates a new instance of InstallationModifier. It also registers a testing interface on the mock and a cleanup function to assert the mocks expectations.
+// The first argument is typically a *testing.T value.
+func NewInstallationModifier(t interface {
+	mock.TestingT
+	Cleanup(func())
+}) *InstallationModifier {
+	mock := &InstallationModifier{}
+	mock.Mock.Test(t)
+
+	t.Cleanup(func() { mock.AssertExpectations(t) })
+
+	return mock
+}
diff --git a/testing/mocks/internal_/pkg/agent/storage/storage_mock.go b/testing/mocks/internal_/pkg/agent/storage/storage_mock.go
index 44f62085db7..2bec6c96cbb 100644
--- a/testing/mocks/internal_/pkg/agent/storage/storage_mock.go
+++ b/testing/mocks/internal_/pkg/agent/storage/storage_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package storage
 
diff --git a/testing/mocks/internal_/pkg/fleetapi/acker/acker_mock.go b/testing/mocks/internal_/pkg/fleetapi/acker/acker_mock.go
index 79446571246..cdeb18b9d57 100644
--- a/testing/mocks/internal_/pkg/fleetapi/acker/acker_mock.go
+++ b/testing/mocks/internal_/pkg/fleetapi/acker/acker_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package acker
 
diff --git a/testing/mocks/internal_/pkg/fleetapi/client/sender_mock.go b/testing/mocks/internal_/pkg/fleetapi/client/sender_mock.go
index ff40afa3ee1..68d4999a3a7 100644
--- a/testing/mocks/internal_/pkg/fleetapi/client/sender_mock.go
+++ b/testing/mocks/internal_/pkg/fleetapi/client/sender_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package client
 
diff --git a/testing/mocks/pkg/control/v2/client/client_mock.go b/testing/mocks/pkg/control/v2/client/client_mock.go
index 281086ad6f3..c408984634b 100644
--- a/testing/mocks/pkg/control/v2/client/client_mock.go
+++ b/testing/mocks/pkg/control/v2/client/client_mock.go
@@ -2,7 +2,7 @@
 // or more contributor license agreements. Licensed under the Elastic License 2.0;
 // you may not use this file except in compliance with the Elastic License 2.0.
 
-// Code generated by mockery v2.51.1. DO NOT EDIT.
+// Code generated by mockery v2.53.4. DO NOT EDIT.
 
 package client
 
diff --git a/testing/upgradetest/upgrader.go b/testing/upgradetest/upgrader.go
index 49573301591..1a1076370cc 100644
--- a/testing/upgradetest/upgrader.go
+++ b/testing/upgradetest/upgrader.go
@@ -41,7 +41,7 @@ type UpgradeOpts struct {
 	skipVerify       bool
 	skipDefaultPgp   bool
 	customPgp        *CustomPGP
-	customWatcherCfg string
+	CustomWatcherCfg string
 	installServers   bool
 
 	// Used to disable upgrade details checks for versions that don't support them, like 7.17.x.
@@ -54,7 +54,7 @@ type UpgradeOpts struct {
 	preInstallHook         func() error
 	postInstallHook        func() error
 	preUpgradeHook         func() error
-	postUpgradeHook        func() error
+	PostUpgradeHook        func() error
 	PostWatcherSuccessHook func(context.Context, *atesting.Fixture) error
 }
 
@@ -119,10 +119,10 @@ func WithPreUpgradeHook(hook func() error) UpgradeOpt {
 	}
 }
 
-// WithPostUpgradeHook sets a hook to be called before install.
+// WithPostUpgradeHook sets a hook to be called after install.
 func WithPostUpgradeHook(hook func() error) UpgradeOpt {
 	return func(opts *UpgradeOpts) {
-		opts.postUpgradeHook = hook
+		opts.PostUpgradeHook = hook
 	}
 }
 
@@ -137,7 +137,7 @@ func WithPostWatcherSuccessHook(hook func(context.Context, *atesting.Fixture) er
 // WithCustomWatcherConfig sets a custom watcher configuration to use.
 func WithCustomWatcherConfig(cfg string) UpgradeOpt {
 	return func(opts *UpgradeOpts) {
-		opts.customWatcherCfg = cfg
+		opts.CustomWatcherCfg = cfg
 	}
 }
 
@@ -193,8 +193,8 @@ func PerformUpgrade(
 	}
 
 	// start fixture gets the agent configured to use a faster watcher
-	if upgradeOpts.customWatcherCfg != "" {
-		err = startFixture.Configure(ctx, []byte(upgradeOpts.customWatcherCfg))
+	if upgradeOpts.CustomWatcherCfg != "" {
+		err = startFixture.Configure(ctx, []byte(upgradeOpts.CustomWatcherCfg))
 	} else {
 		err = ConfigureFastWatcher(ctx, startFixture)
 	}
@@ -387,8 +387,8 @@ func PerformUpgrade(
 		}
 	}
 
-	if upgradeOpts.postUpgradeHook != nil {
-		if err := upgradeOpts.postUpgradeHook(); err != nil {
+	if upgradeOpts.PostUpgradeHook != nil {
+		if err := upgradeOpts.PostUpgradeHook(); err != nil {
 			return fmt.Errorf("post upgrade hook failed: %w", err)
 		}
 	}
diff --git a/testing/upgradetest/versions.go b/testing/upgradetest/versions.go
index d8006108188..35a1189e737 100644
--- a/testing/upgradetest/versions.go
+++ b/testing/upgradetest/versions.go
@@ -46,6 +46,7 @@ var (
 	Version_8_19_0_SNAPSHOT = version.NewParsedSemVer(8, 19, 0, "SNAPSHOT", "")
 
 	// Version_9_1_0_SNAPSHOT is a FIPS-capable artifact.
+	// Version_9_1_0_SNAPSHOT is the minimum version for manual rollback and rollback reason
 	Version_9_1_0_SNAPSHOT = version.NewParsedSemVer(9, 1, 0, "SNAPSHOT", "")
 
 	// ErrNoSnapshot is returned when a requested snapshot is not on the version list.