diff --git a/changelog/fragments/1692141038-upgrade-watcher-logging.yaml b/changelog/fragments/1692141038-upgrade-watcher-logging.yaml
new file mode 100644
index 00000000000..3212098077c
--- /dev/null
+++ b/changelog/fragments/1692141038-upgrade-watcher-logging.yaml
@@ -0,0 +1,32 @@
+# 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: enhancement
+
+# Change summary; a 80ish characters long description of the change.
+summary: Adds more logging to the rollback process
+
+# 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:
+
+# 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/pull/3245
+
+# 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/internal/pkg/agent/application/upgrade/rollback.go b/internal/pkg/agent/application/upgrade/rollback.go
index f2ba0dee309..84d15e37a81 100644
--- a/internal/pkg/agent/application/upgrade/rollback.go
+++ b/internal/pkg/agent/application/upgrade/rollback.go
@@ -45,7 +45,7 @@ func Rollback(ctx context.Context, log *logger.Logger, prevHash string, currentH
 
 	// Restart
 	log.Info("Restarting the agent after rollback")
-	if err := restartAgent(ctx); err != nil {
+	if err := restartAgent(ctx, log); err != nil {
 		return err
 	}
 
@@ -127,7 +127,7 @@ func InvokeWatcher(log *logger.Logger) error {
 	return cmd.Start()
 }
 
-func restartAgent(ctx context.Context) error {
+func restartAgent(ctx context.Context, log *logger.Logger) error {
 	restartFn := func(ctx context.Context) error {
 		c := client.New()
 		err := c.Connect(ctx)
@@ -147,16 +147,21 @@ func restartAgent(ctx context.Context) error {
 	signal := make(chan struct{})
 	backExp := backoff.NewExpBackoff(signal, restartBackoffInit, restartBackoffMax)
 
-	for i := maxRestartCount; i >= 1; i-- {
+	for restartAttempt := 1; restartAttempt <= maxRestartCount; restartAttempt++ {
 		backExp.Wait()
+		log.Infof("Restarting Agent via control protocol; attempt %d of %d", restartAttempt, maxRestartCount)
+
 		err := restartFn(ctx)
 		if err == nil {
 			break
 		}
 
-		if i == 1 {
+		if restartAttempt == maxRestartCount {
+			log.Error("Failed to restart agent via control protocol after final attempt")
 			return err
 		}
+
+		log.Warnf("Failed to restart agent via control protocol: %s; will try again in %v", err.Error(), backExp.NextWait())
 	}
 
 	close(signal)
diff --git a/internal/pkg/agent/cmd/run.go b/internal/pkg/agent/cmd/run.go
index 01b24a48b02..bc5d6a0be9b 100644
--- a/internal/pkg/agent/cmd/run.go
+++ b/internal/pkg/agent/cmd/run.go
@@ -144,6 +144,9 @@ func run(override cfgOverrider, testingMode bool, fleetInitTimeout time.Duration
 		return err
 	}
 
+	// Make sure to flush any buffered logs before we're done.
+	defer baseLogger.Sync() //nolint:errcheck // flushing buffered logs is best effort.
+
 	l := baseLogger.With("log", map[string]interface{}{
 		"source": agentName,
 	})
diff --git a/internal/pkg/agent/cmd/watch.go b/internal/pkg/agent/cmd/watch.go
index b3c29509471..83e31d38366 100644
--- a/internal/pkg/agent/cmd/watch.go
+++ b/internal/pkg/agent/cmd/watch.go
@@ -47,6 +47,9 @@ func newWatchCommandWithArgs(_ []string, streams *cli.IOStreams) *cobra.Command
 				os.Exit(3)
 			}
 
+			// 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 {
 				log.Errorw("Watch command failed", "error.message", err)
 				fmt.Fprintf(streams.Err, "Watch command failed: %v\n%s\n", err, troubleshootMessage())