diff --git a/cli/server.go b/cli/server.go
index 9d07673fbd640..92e7f9bbc7d1b 100644
--- a/cli/server.go
+++ b/cli/server.go
@@ -532,6 +532,15 @@ func Server(vip *viper.Viper, newAPI func(context.Context, *coderd.Options) (*co
 					return xerrors.Errorf("dial postgres: %w", err)
 				}
 				defer sqlDB.Close()
+
+				pingCtx, pingCancel := context.WithTimeout(ctx, 15*time.Second)
+				defer pingCancel()
+
+				err = sqlDB.PingContext(pingCtx)
+				if err != nil {
+					return xerrors.Errorf("ping postgres: %w", err)
+				}
+
 				// Ensure the PostgreSQL version is >=13.0.0!
 				version, err := sqlDB.QueryContext(ctx, "SHOW server_version;")
 				if err != nil {
@@ -552,10 +561,6 @@ func Server(vip *viper.Viper, newAPI func(context.Context, *coderd.Options) (*co
 				}
 				logger.Debug(ctx, "connected to postgresql", slog.F("version", versionStr))
 
-				err = sqlDB.Ping()
-				if err != nil {
-					return xerrors.Errorf("ping postgres: %w", err)
-				}
 				err = migrations.Up(sqlDB)
 				if err != nil {
 					return xerrors.Errorf("migrate up: %w", err)
@@ -793,9 +798,10 @@ func Server(vip *viper.Viper, newAPI func(context.Context, *coderd.Options) (*co
 			}()
 
 			hasFirstUser, err := client.HasFirstUser(ctx)
-			if !hasFirstUser && err == nil {
-				cmd.Println()
-				cmd.Println("Get started by creating the first user (in a new terminal):")
+			if err != nil {
+				cmd.Println("\nFailed to check for the first user: " + err.Error())
+			} else if !hasFirstUser {
+				cmd.Println("\nGet started by creating the first user (in a new terminal):")
 				cmd.Println(cliui.Styles.Code.Render("coder login " + accessURLParsed.String()))
 			}