diff --git a/.changelog/4099.txt b/.changelog/4099.txt
new file mode 100644
index 00000000000..dd593194614
--- /dev/null
+++ b/.changelog/4099.txt
@@ -0,0 +1,4 @@
+```release-note:improvement
+core: Auto run a status report after a deployment or release operation rather
+than only if `waypoint deploy` or `waypoint release` CLI is run.
+```
diff --git a/internal/cli/deployment_create.go b/internal/cli/deployment_create.go
index ed2cca27245..defb27afa0f 100644
--- a/internal/cli/deployment_create.go
+++ b/internal/cli/deployment_create.go
@@ -70,18 +70,6 @@ func (c *DeploymentCreateCommand) Run(args []string) int {
 			hostname = hostnamesResp.Hostnames[0]
 		}
 
-		// Status Report
-		app.UI.Output("")
-		_, err = app.StatusReport(ctx, &pb.Job_StatusReportOp{
-			Target: &pb.Job_StatusReportOp_Deployment{
-				Deployment: deployment,
-			},
-		})
-		if err != nil {
-			app.UI.Output(clierrors.Humanize(err), terminal.WithErrorStyle())
-			return ErrSentinel
-		}
-
 		// Release if we're releasing
 		var releaseUrl string
 		if c.flagRelease {
diff --git a/internal/cli/release_create.go b/internal/cli/release_create.go
index 3e124b35820..f2def906c24 100644
--- a/internal/cli/release_create.go
+++ b/internal/cli/release_create.go
@@ -182,18 +182,6 @@ func (c *ReleaseCreateCommand) Run(args []string) int {
 		tbl := fmtVariablesOutput(resp.VariableFinalValues)
 		c.ui.Table(tbl)
 
-		// Status Report
-		app.UI.Output("")
-		_, err = app.StatusReport(ctx, &pb.Job_StatusReportOp{
-			Target: &pb.Job_StatusReportOp_Release{
-				Release: result.Release,
-			},
-		})
-		if err != nil {
-			app.UI.Output(clierrors.Humanize(err), terminal.WithErrorStyle())
-			return ErrSentinel
-		}
-
 		if result.Release.Url == "" {
 			app.UI.Output("\n"+strings.TrimSpace(releaseNoUrl),
 				deploy.Id,
diff --git a/internal/runner/operation_deploy.go b/internal/runner/operation_deploy.go
index f1af4323a72..324ab24285b 100644
--- a/internal/runner/operation_deploy.go
+++ b/internal/runner/operation_deploy.go
@@ -52,6 +52,12 @@ func (r *Runner) executeDeployOp(
 		return nil, err
 	}
 
+	// Run a status report on the recent deployment
+	_, err = app.DeploymentStatusReport(ctx, deployment)
+	if err != nil {
+		return nil, err
+	}
+
 	return &pb.Job_Result{
 		Deploy: &pb.Job_DeployResult{
 			Deployment: deployment,
diff --git a/internal/runner/operation_release.go b/internal/runner/operation_release.go
index af06517321e..fcaf6cff2df 100644
--- a/internal/runner/operation_release.go
+++ b/internal/runner/operation_release.go
@@ -211,5 +211,11 @@ func (r *Runner) executeReleaseOp(
 		}
 	}
 
+	// Run a status report operation on the recent release
+	_, err = app.ReleaseStatusReport(ctx, release)
+	if err != nil {
+		return nil, err
+	}
+
 	return result, nil
 }