diff --git a/client/allocrunner/taskrunner/plugin_supervisor_hook.go b/client/allocrunner/taskrunner/plugin_supervisor_hook.go
index 21491cf77c..6c246c74cb 100644
--- a/client/allocrunner/taskrunner/plugin_supervisor_hook.go
+++ b/client/allocrunner/taskrunner/plugin_supervisor_hook.go
@@ -38,6 +38,7 @@ type csiPluginSupervisorHook struct {
 
 	// eventEmitter is used to emit events to the task
 	eventEmitter ti.EventEmitter
+	lifecycle    ti.TaskLifecycle
 
 	shutdownCtx      context.Context
 	shutdownCancelFn context.CancelFunc
@@ -54,6 +55,7 @@ type csiPluginSupervisorHookConfig struct {
 	clientStateDirPath string
 	events             ti.EventEmitter
 	runner             *TaskRunner
+	lifecycle          ti.TaskLifecycle
 	capabilities       *drivers.Capabilities
 	logger             hclog.Logger
 }
@@ -90,6 +92,7 @@ func newCSIPluginSupervisorHook(config *csiPluginSupervisorHookConfig) *csiPlugi
 	hook := &csiPluginSupervisorHook{
 		alloc:            config.runner.Alloc(),
 		runner:           config.runner,
+		lifecycle:        config.lifecycle,
 		logger:           config.logger,
 		task:             task,
 		mountPoint:       pluginRoot,
@@ -209,20 +212,27 @@ func (h *csiPluginSupervisorHook) ensureSupervisorLoop(ctx context.Context) {
 
 	t := time.NewTimer(0)
 
+	// We're in Poststart at this point, so if we can't connect within
+	// this deadline, assume it's broken so we can restart the task
+	startCtx, startCancelFn := context.WithTimeout(ctx, 30*time.Second)
+	defer startCancelFn()
+
+	var err error
+	var pluginHealthy bool
+
 	// Step 1: Wait for the plugin to initially become available.
 WAITFORREADY:
 	for {
 		select {
-		case <-ctx.Done():
+		case <-startCtx.Done():
+			h.kill(ctx, fmt.Errorf("CSI plugin failed probe: %v", err))
 			return
 		case <-t.C:
-			pluginHealthy, err := h.supervisorLoopOnce(ctx, client)
+			pluginHealthy, err = h.supervisorLoopOnce(startCtx, client)
 			if err != nil || !pluginHealthy {
-				h.logger.Debug("CSI Plugin not ready", "error", err)
-
-				// Plugin is not yet returning healthy, because we want to optimise for
-				// quickly bringing a plugin online, we use a short timeout here.
-				// TODO(dani): Test with more plugins and adjust.
+				h.logger.Debug("CSI plugin not ready", "error", err)
+				// Use only a short delay here to optimize for quickly
+				// bringing up a plugin
 				t.Reset(5 * time.Second)
 				continue
 			}
@@ -240,13 +250,11 @@ WAITFORREADY:
 	// Step 2: Register the plugin with the catalog.
 	deregisterPluginFn, err := h.registerPlugin(client, socketPath)
 	if err != nil {
-		h.logger.Error("CSI plugin registration failed", "error", err)
-		event := structs.NewTaskEvent(structs.TaskPluginUnhealthy)
-		event.SetMessage(fmt.Sprintf("failed to register plugin: %s, reason: %v", h.task.CSIPluginConfig.ID, err))
-		h.eventEmitter.EmitEvent(event)
+		h.kill(ctx, fmt.Errorf("CSI plugin failed to register: %v", err))
 	}
 
-	// Step 3: Start the lightweight supervisor loop.
+	// Step 3: Start the lightweight supervisor loop. At this point, failures
+	// don't cause the task to restart
 	t.Reset(0)
 	for {
 		select {
@@ -271,7 +279,7 @@ WAITFORREADY:
 			if h.previousHealthState && !pluginHealthy {
 				event := structs.NewTaskEvent(structs.TaskPluginUnhealthy)
 				if err != nil {
-					event.SetMessage(fmt.Sprintf("error: %v", err))
+					event.SetMessage(fmt.Sprintf("Error: %v", err))
 				} else {
 					event.SetMessage("Unknown Reason")
 				}
@@ -359,7 +367,7 @@ func (h *csiPluginSupervisorHook) supervisorLoopOnce(ctx context.Context, client
 
 	healthy, err := client.PluginProbe(probeCtx)
 	if err != nil {
-		return false, fmt.Errorf("failed to probe plugin: %v", err)
+		return false, err
 	}
 
 	return healthy, nil
@@ -378,6 +386,21 @@ func (h *csiPluginSupervisorHook) Stop(_ context.Context, req *interfaces.TaskSt
 	return nil
 }
 
+func (h *csiPluginSupervisorHook) kill(ctx context.Context, reason error) {
+	h.logger.Error("killing task because plugin failed", "error", reason)
+	event := structs.NewTaskEvent(structs.TaskPluginUnhealthy)
+	event.SetMessage(fmt.Sprintf("Error: %v", reason.Error()))
+	h.eventEmitter.EmitEvent(event)
+
+	if err := h.lifecycle.Kill(ctx,
+		structs.NewTaskEvent(structs.TaskKilling).
+			SetFailsTask().
+			SetDisplayMessage("CSI plugin did not become healthy before timeout"),
+	); err != nil {
+		h.logger.Error("failed to kill task", "kill_reason", reason, "error", err)
+	}
+}
+
 func ensureMountpointInserted(mounts []*drivers.MountConfig, mount *drivers.MountConfig) []*drivers.MountConfig {
 	for _, mnt := range mounts {
 		if mnt.IsEqual(mount) {
diff --git a/client/allocrunner/taskrunner/task_runner_hooks.go b/client/allocrunner/taskrunner/task_runner_hooks.go
index b3f44a8b98..62ff26c4b6 100644
--- a/client/allocrunner/taskrunner/task_runner_hooks.go
+++ b/client/allocrunner/taskrunner/task_runner_hooks.go
@@ -76,6 +76,7 @@ func (tr *TaskRunner) initHooks() {
 				clientStateDirPath: tr.clientConfig.StateDir,
 				events:             tr,
 				runner:             tr,
+				lifecycle:          tr,
 				capabilities:       tr.driverCapabilities,
 				logger:             hookLogger,
 			}))