diff --git a/airflow/docker.go b/airflow/docker.go
index 4be9e2987..acc091367 100644
--- a/airflow/docker.go
+++ b/airflow/docker.go
@@ -64,7 +64,6 @@ var (
 	errNoFile                = errors.New("file specified does not exist")
 	errSettingsPath          = "error looking for settings.yaml"
 	errComposeProjectRunning = errors.New("project is up and running")
-	errWebServerUnHealthy    = errors.New("webserver has not become healthy yet")
 
 	initSettings      = settings.ConfigSettings
 	exportSettings    = settings.Export
@@ -762,8 +761,8 @@ var checkWebserverHealth = func(settingsFile string, project *types.Project, com
 	})
 	if err != nil {
 		if errors.Is(err, context.DeadlineExceeded) {
-			fmt.Println("\nProject is not yet running. The project is still attempting to start up. Run 'astro dev logs --webserver | --scheduler' for details.")
-			return fmt.Errorf("%w: the health check timed out after %s. Use the --wait flag to increase the time out", errWebServerUnHealthy, timeout)
+			fmt.Printf("\n")
+			return fmt.Errorf("there might be a problem with your project starting up. The webserver health check timed out after %s but your project will continue trying to start. Run 'astro dev logs --webserver | --scheduler' for details.\n\nTry again or use the --wait flag to increase the time out", timeout) //nolint:goerr113
 		}
 		if !errors.Is(err, errComposeProjectRunning) {
 			return err
diff --git a/airflow/docker_test.go b/airflow/docker_test.go
index 141c6917c..07b5b9161 100644
--- a/airflow/docker_test.go
+++ b/airflow/docker_test.go
@@ -1426,8 +1426,7 @@ func TestCheckWebserverHealth(t *testing.T) {
 		isM1 = mockIsM1
 
 		err := checkWebserverHealth(settingsFile, &types.Project{Name: "test"}, composeMock, 2, false, 1*time.Second)
-		assert.ErrorIs(t, err, errWebServerUnHealthy)
-		assert.ErrorContains(t, err, "webserver has not become healthy yet: the health check timed out after 1s")
+		assert.ErrorContains(t, err, "The webserver health check timed out after 1s")
 	})
 	t.Run("timeout waiting for webserver to get to healthy with long timeout", func(t *testing.T) {
 		settingsFile := "./testfiles/test_dag_inegrity_file.py" // any file which exists
@@ -1455,8 +1454,7 @@ func TestCheckWebserverHealth(t *testing.T) {
 		isM1 = mockIsM1
 
 		err := checkWebserverHealth(settingsFile, &types.Project{Name: "test"}, composeMock, 2, false, 1*time.Second)
-		assert.ErrorIs(t, err, errWebServerUnHealthy)
-		assert.ErrorContains(t, err, "webserver has not become healthy yet: the health check timed out after 1s")
+		assert.ErrorContains(t, err, "The webserver health check timed out after 1s")
 	})
 }