diff --git a/CHANGELOG.md b/CHANGELOG.md
index dcfb8b9..9e91605 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -31,8 +31,11 @@
 - Add configuration option to allow Tailscale clients to use a random WireGuard port. [kb/1181/firewalls](https://tailscale.com/kb/1181/firewalls) [#624](https://github.com/juanfont/headscale/pull/624)
 - Improve obtuse UX regarding missing configuration (`ephemeral_node_inactivity_timeout` not set) [#639](https://github.com/juanfont/headscale/pull/639)
 - Fix nodes being shown as 'offline' in `tailscale status` [648](https://github.com/juanfont/headscale/pull/648)
+- Fix nodes being shown as 'offline' in `tailscale status` [#648](https://github.com/juanfont/headscale/pull/648)
+- Improve shutdown behaviour [#651](https://github.com/juanfont/headscale/pull/651)
 - Drop Gin as web framework in Headscale [648](https://github.com/juanfont/headscale/pull/648)
 
+
 ## 0.15.0 (2022-03-20)
 
 **Note:** Take a backup of your database before upgrading.
diff --git a/app.go b/app.go
index e6a5121..952a180 100644
--- a/app.go
+++ b/app.go
@@ -55,12 +55,13 @@ const (
 )
 
 const (
-	AuthPrefix         = "Bearer "
-	Postgres           = "postgres"
-	Sqlite             = "sqlite3"
-	updateInterval     = 5000
-	HTTPReadTimeout    = 30 * time.Second
-	privateKeyFileMode = 0o600
+	AuthPrefix          = "Bearer "
+	Postgres            = "postgres"
+	Sqlite              = "sqlite3"
+	updateInterval      = 5000
+	HTTPReadTimeout     = 30 * time.Second
+	HTTPShutdownTimeout = 3 * time.Second
+	privateKeyFileMode  = 0o600
 
 	registerCacheExpiration = time.Minute * 15
 	registerCacheCleanup    = time.Minute * 20
@@ -685,8 +686,13 @@ func (h *Headscale) Serve() error {
 				h.shutdownChan <- struct{}{}
 
 				// Gracefully shut down servers
-				promHTTPServer.Shutdown(ctx)
-				httpServer.Shutdown(ctx)
+				ctx, cancel := context.WithTimeout(context.Background(), HTTPShutdownTimeout)
+				if err := promHTTPServer.Shutdown(ctx); err != nil {
+					log.Error().Err(err).Msg("Failed to shutdown prometheus http")
+				}
+				if err := httpServer.Shutdown(ctx); err != nil {
+					log.Error().Err(err).Msg("Failed to shutdown http")
+				}
 				grpcSocket.GracefulStop()
 
 				// Close network listeners
@@ -697,7 +703,21 @@ func (h *Headscale) Serve() error {
 				// Stop listening (and unlink the socket if unix type):
 				socketListener.Close()
 
+				// Close db connections
+				db, err := h.db.DB()
+				if err != nil {
+					log.Error().Err(err).Msg("Failed to get db handle")
+				}
+				err = db.Close()
+				if err != nil {
+					log.Error().Err(err).Msg("Failed to close db")
+				}
+
+				log.Info().
+					Msg("Headscale stopped")
+
 				// And we're done:
+				cancel()
 				os.Exit(0)
 			}
 		}
diff --git a/cmd/headscale/cli/utils.go b/cmd/headscale/cli/utils.go
index 327c8c1..c07e3a2 100644
--- a/cmd/headscale/cli/utils.go
+++ b/cmd/headscale/cli/utils.go
@@ -55,6 +55,7 @@ func getHeadscaleCLIClient() (context.Context, v1.HeadscaleServiceClient, *grpc.
 			Err(err).
 			Caller().
 			Msgf("Failed to load configuration")
+		os.Exit(-1) // we get here if logging is suppressed (i.e., json output)
 	}
 
 	log.Debug().
@@ -116,6 +117,7 @@ func getHeadscaleCLIClient() (context.Context, v1.HeadscaleServiceClient, *grpc.
 	conn, err := grpc.DialContext(ctx, address, grpcOptions...)
 	if err != nil {
 		log.Fatal().Caller().Err(err).Msgf("Could not connect: %v", err)
+		os.Exit(-1) // we get here if logging is suppressed (i.e., json output)
 	}
 
 	client := v1.NewHeadscaleServiceClient(conn)