diff --git a/agent/agent.go b/agent/agent.go
index 7f7e8cd64dff8..0d2326d2ab9d3 100644
--- a/agent/agent.go
+++ b/agent/agent.go
@@ -743,7 +743,7 @@ func (a *agent) run(ctx context.Context) error {
 				return script.RunOnStart
 			})
 			if err != nil {
-				a.logger.Warn(ctx, "startup script failed", slog.Error(err))
+				a.logger.Warn(ctx, "startup script(s) failed", slog.Error(err))
 				if errors.Is(err, agentscripts.ErrTimeout) {
 					a.setLifecycle(ctx, codersdk.WorkspaceAgentLifecycleStartTimeout)
 				} else {
@@ -1465,6 +1465,7 @@ func (a *agent) Close() error {
 		return script.RunOnStop
 	})
 	if err != nil {
+		a.logger.Warn(ctx, "shutdown script(s) failed", slog.Error(err))
 		if errors.Is(err, agentscripts.ErrTimeout) {
 			lifecycleState = codersdk.WorkspaceAgentLifecycleShutdownTimeout
 		} else {
diff --git a/agent/agentscripts/agentscripts.go b/agent/agentscripts/agentscripts.go
index c3bd525109ced..3acc48b0a140c 100644
--- a/agent/agentscripts/agentscripts.go
+++ b/agent/agentscripts/agentscripts.go
@@ -27,6 +27,14 @@ import (
 var (
 	// ErrTimeout is returned when a script times out.
 	ErrTimeout = xerrors.New("script timed out")
+	// ErrOutputPipesOpen is returned when a script exits leaving the output
+	// pipe(s) (stdout, stderr) open. This happens because we set WaitDelay on
+	// the command, which gives us two things:
+	//
+	// 1. The ability to ensure that a script exits (this is important for e.g.
+	//    blocking login, and avoiding doing so indefinitely)
+	// 2. Improved command cancellation on timeout
+	ErrOutputPipesOpen = xerrors.New("script exited without closing output pipes")
 
 	parser = cron.NewParser(cron.Second | cron.Minute | cron.Hour | cron.Dom | cron.Month | cron.DowOptional)
 )
@@ -248,7 +256,22 @@ func (r *Runner) run(ctx context.Context, script codersdk.WorkspaceAgentScript)
 		err = cmdCtx.Err()
 	case err = <-cmdDone:
 	}
-	if errors.Is(err, context.DeadlineExceeded) {
+	switch {
+	case errors.Is(err, exec.ErrWaitDelay):
+		err = ErrOutputPipesOpen
+		message := fmt.Sprintf("script exited successfully, but output pipes were not closed after %s", cmd.WaitDelay)
+		details := fmt.Sprint(
+			"This usually means a child process was started with references to stdout or stderr. As a result, this " +
+				"process may now have been terminated. Consider redirecting the output or using a separate " +
+				"\"coder_script\" for the process, see " +
+				"https://coder.com/docs/v2/latest/templates/troubleshooting#startup-script-issues for more information.",
+		)
+		// Inform the user by propagating the message via log writers.
+		_, _ = fmt.Fprintf(cmd.Stderr, "WARNING: %s. %s\n", message, details)
+		// Also log to agent logs for ease of debugging.
+		r.Logger.Warn(ctx, message, slog.F("details", details), slog.Error(err))
+
+	case errors.Is(err, context.DeadlineExceeded):
 		err = ErrTimeout
 	}
 	return err