diff --git a/go.mod b/go.mod
index eed02b301..b3164431e 100644
--- a/go.mod
+++ b/go.mod
@@ -92,7 +92,7 @@ require github.com/hashicorp/go-dbw v0.0.0-20220412153211-c470aec9369f // this i
 require (
 	github.com/DATA-DOG/go-sqlmock v1.5.0
 	github.com/hashicorp/go-kms-wrapping/extras/kms/v2 v2.0.0-20220515130442-cac0b5ac133b
-	github.com/hashicorp/nodeenrollment v0.0.0-20220607152131-4f253e6da747
+	github.com/hashicorp/nodeenrollment v0.0.0-20220609044242-598c08a89c45
 )
 
 require (
diff --git a/go.sum b/go.sum
index 31a89704a..61ee52032 100644
--- a/go.sum
+++ b/go.sum
@@ -740,8 +740,8 @@ github.com/hashicorp/golang-lru v0.5.4 h1:YDjusn29QI/Das2iO9M0BHnIbxPeyuCHsjMW+l
 github.com/hashicorp/golang-lru v0.5.4/go.mod h1:iADmTwqILo4mZ8BN3D2Q6+9jd8WM5uGBxy+E8yxSoD4=
 github.com/hashicorp/hcl v1.0.0 h1:0Anlzjpi4vEasTeNFn2mLJgTSwt0+6sfsiTG8qcWGx4=
 github.com/hashicorp/hcl v1.0.0/go.mod h1:E5yfLk+7swimpb2L/Alb/PJmXilQ/rhwaUYs4T20WEQ=
-github.com/hashicorp/nodeenrollment v0.0.0-20220607152131-4f253e6da747 h1:/S1ePrvxgLI3jgL6XLVVQAOm3Ua0wS4PvRhmiTgG6hQ=
-github.com/hashicorp/nodeenrollment v0.0.0-20220607152131-4f253e6da747/go.mod h1:8l3RSuZJAibZKnqX6tvLaeoFzPhDf4oCRVsyFjU5Soc=
+github.com/hashicorp/nodeenrollment v0.0.0-20220609044242-598c08a89c45 h1:vnRJfKOMBoan6+PFw5P5CItnl3Z6lJJI1JaBM1tlLCo=
+github.com/hashicorp/nodeenrollment v0.0.0-20220609044242-598c08a89c45/go.mod h1:8l3RSuZJAibZKnqX6tvLaeoFzPhDf4oCRVsyFjU5Soc=
 github.com/hashicorp/vault/api v1.3.1 h1:pkDkcgTh47PRjY1NEFeofqR4W/HkNUi9qIakESO2aRM=
 github.com/hashicorp/vault/api v1.3.1/go.mod h1:QeJoWxMFt+MsuWcYhmwRLwKEXrjwAFFywzhptMsTIUw=
 github.com/hashicorp/vault/sdk v0.1.13/go.mod h1:B+hVj7TpuQY1Y/GPbCpffmgd+tSEwvhkWnjtSYCaS2M=
diff --git a/internal/daemon/worker/controller_connection.go b/internal/daemon/worker/controller_connection.go
index 1851536dd..e75ac8a62 100644
--- a/internal/daemon/worker/controller_connection.go
+++ b/internal/daemon/worker/controller_connection.go
@@ -71,6 +71,7 @@ func (w *Worker) StartControllerConnections() error {
 }
 
 func (w *Worker) controllerDialerFunc() func(context.Context, string) (net.Conn, error) {
+	const op = "worker.(Worker).controllerDialerFunc"
 	return func(ctx context.Context, addr string) (net.Conn, error) {
 		var conn net.Conn
 		var err error
@@ -89,9 +90,20 @@ func (w *Worker) controllerDialerFunc() func(context.Context, string) (net.Conn,
 				}
 			}
 		}
+		switch err {
+		case nil:
+		case nodeenrollment.ErrNotAuthorized:
+			// We don't event in this case, because the function retries often
+			// and will spam the logs. The status function will event indicating
+			// that it can't send status because it's not authorized, so that
+			// will be a fine hint to the user as to the issue.
+		default:
+			event.WriteError(ctx, op, err)
+		}
 
 		if !w.everAuthenticated.Load() && err == nil && conn != nil {
 			w.everAuthenticated.Store(true)
+			event.WriteSysEvent(ctx, op, "worker has successfully authenticated")
 		}
 
 		return conn, err
diff --git a/internal/daemon/worker/status.go b/internal/daemon/worker/status.go
index 728e0fe63..8890ef111 100644
--- a/internal/daemon/worker/status.go
+++ b/internal/daemon/worker/status.go
@@ -95,6 +95,7 @@ func (w *Worker) sendWorkerStatus(cancelCtx context.Context) {
 	// any session information anyways and this will produce a ton of noise in
 	// observability, so suppress it
 	if !w.everAuthenticated.Load() {
+		event.WriteSysEvent(cancelCtx, op, "worker is not authenticated to an upstream, not sending status")
 		return
 	}