diff --git a/cmd/sst/ui/error.go b/cmd/sst/ui/error.go
index e8a7843ac..e42adfefb 100644
--- a/cmd/sst/ui/error.go
+++ b/cmd/sst/ui/error.go
@@ -17,11 +17,14 @@ func parseError(input string) []string {
 
 	if strings.Contains(input, "occurred:") {
 		lines := []string{}
-		for _, line := range strings.Split(input, "\n") {
+		sections := strings.Split(input, "*")
+		for _, line := range sections[1:] {
 			line = strings.TrimSpace(line)
-			if strings.HasPrefix(line, "*") {
-				splits := strings.Split(line, ":")
-				lines = append(lines, strings.TrimSpace(splits[len(splits)-1]))
+			splits := strings.Split(line, ":")
+			final := strings.TrimSpace(splits[len(splits)-1])
+
+			for _, split := range strings.Split(final, "\n") {
+				lines = append(lines, split)
 			}
 		}
 		return lines
diff --git a/cmd/sst/ui/ui.go b/cmd/sst/ui/ui.go
index a6bd20cfc..2b27dfebf 100644
--- a/cmd/sst/ui/ui.go
+++ b/cmd/sst/ui/ui.go
@@ -273,7 +273,7 @@ func (u *UI) Trigger(evt *project.StackEvent) {
 				Color:   color.FgRed,
 				Final:   true,
 				Label:   "Error",
-				Message: parseError(evt.DiagnosticEvent.Message)[0],
+				Message: parseError(evt.DiagnosticEvent.Message),
 			})
 		}
 
@@ -338,7 +338,7 @@ func (u *UI) Trigger(evt *project.StackEvent) {
 			if status.URN != "" {
 				color.New(color.FgRed, color.Bold).Println("   " + formatURN(status.URN))
 			}
-			color.New(color.FgWhite).Println(strings.Join(parseError(status.Message), "\n"))
+			color.New(color.FgWhite).Println("   " + strings.Join(parseError(status.Message), "\n   "))
 		}
 	}
 }
@@ -488,7 +488,7 @@ type Progress struct {
 	Label   string
 	URN     string
 	Final   bool
-	Message string
+	Message []string
 	time.Duration
 }
 
@@ -516,8 +516,12 @@ func (u *UI) printProgress(progress Progress) {
 	if progress.Duration != 0 {
 		color.New(color.FgHiBlack).Printf(" (%s)", progress.Duration)
 	}
-	if progress.Message != "" {
-		color.New(color.FgHiBlack).Print(progress.Message)
+	if len(progress.Message) > 0 {
+		for _, item := range progress.Message {
+			fmt.Println()
+			color.New(progress.Color, color.Bold).Print("|  ")
+			color.New(color.FgWhite).Print(item)
+		}
 	}
 	fmt.Println()
 	u.hasProgress = true
diff --git a/examples/test/sst.config.ts b/examples/test/sst.config.ts
index 4c769e70b..7cddb48fa 100644
--- a/examples/test/sst.config.ts
+++ b/examples/test/sst.config.ts
@@ -12,11 +12,9 @@ export default $config({
     };
   },
   async run() {
-    const fn = new sst.aws.Function("MyFunction", {
-      handler: "src/index.handler",
-    });
-    new aws.s3.Bucket("MyBucket", {
-      bucket: "my-bucket",
+    new aws.dynamodb.Table("Web", {
+      name: "/aweofih",
+      billingMode: "PAY_PER_REQUEST",
     });
     return {};
   },
diff --git a/pkg/project/stack.go b/pkg/project/stack.go
index f1d837a9a..482a9b9db 100644
--- a/pkg/project/stack.go
+++ b/pkg/project/stack.go
@@ -268,15 +268,19 @@ func (s *stack) Run(ctx context.Context, input *StackInput) error {
 				if !ok {
 					return
 				}
-				input.OnEvent(&StackEvent{EngineEvent: event})
 
 				if event.DiagnosticEvent != nil && event.DiagnosticEvent.Severity == "error" {
+					if strings.HasPrefix(event.DiagnosticEvent.Message, "update failed") {
+						break
+					}
 					complete.Errors = append(complete.Errors, Error{
 						Message: event.DiagnosticEvent.Message,
 						URN:     event.DiagnosticEvent.URN,
 					})
 				}
 
+				input.OnEvent(&StackEvent{EngineEvent: event})
+
 				if event.SummaryEvent != nil {
 					complete.Finished = true
 				}