diff --git a/components/local-app/pkg/common/ws.go b/components/local-app/pkg/common/ws.go
index 53da94ba7b93d0..b569e7147736cc 100644
--- a/components/local-app/pkg/common/ws.go
+++ b/components/local-app/pkg/common/ws.go
@@ -20,6 +20,7 @@ import (
 
 	"github.com/bufbuild/connect-go"
 	v1 "github.com/gitpod-io/gitpod/components/public-api/go/experimental/v1"
+	"github.com/sirupsen/logrus"
 )
 
 type WorkspaceDisplayData struct {
@@ -49,7 +50,6 @@ func GetWorkspaceRepo(ws *v1.Workspace) string {
 	return repository
 }
 
-// workspace.Msg.Result.Status.Instance.Status.Url
 func GetWorkspaceUrl(ws *v1.Workspace) string {
 	if ws == nil || ws.Status == nil ||
 		ws.Status.Instance == nil || ws.Status.Instance.Status == nil {
@@ -224,41 +224,53 @@ func ObserveWsUntilStarted(ctx context.Context, workspaceId string) error {
 		return fmt.Errorf("Workspace already running")
 	}
 
-	stream, err := gitpod.Workspaces.StreamWorkspaceStatus(ctx, connect.NewRequest(&v1.StreamWorkspaceStatusRequest{WorkspaceId: workspaceId}))
-
-	if err != nil {
-		return err
-	}
-
 	fmt.Println("Waiting for workspace to start...")
-
 	fmt.Println("Workspace " + HumanizeWorkspacePhase(wsInfo.Msg.GetResult()))
 
-	previousStatus := ""
-
-	for stream.Receive() {
-		msg := stream.Msg()
-		if msg == nil {
-			fmt.Println("No message received")
+	maxRetries := 4
+	retries := 0
+	for {
+		stream, err := gitpod.Workspaces.StreamWorkspaceStatus(ctx, connect.NewRequest(&v1.StreamWorkspaceStatusRequest{WorkspaceId: workspaceId}))
+		if err != nil {
+			if retries >= maxRetries {
+				return fmt.Errorf("Failed to stream workspace status after %d retries: %w", maxRetries, err)
+			}
+			retries++
+			logrus.WithFields(logrus.Fields{
+				"retry":      retries,
+				"maxRetries": maxRetries,
+			}).Warn("Streaming failed, retrying")
 			continue
 		}
 
-		if msg.GetResult().Instance.Status.Phase == v1.WorkspaceInstanceStatus_PHASE_RUNNING {
-			fmt.Println("Workspace running")
-			return nil
-		}
+		previousStatus := ""
+		for stream.Receive() {
+			msg := stream.Msg()
+			if msg == nil {
+				fmt.Println("No message received")
+				continue
+			}
 
-		currentStatus := HumanizeWorkspacePhase(wsInfo.Msg.GetResult())
+			if msg.GetResult().Instance.Status.Phase == v1.WorkspaceInstanceStatus_PHASE_RUNNING {
+				fmt.Println("Workspace running")
+				return nil
+			}
 
-		if currentStatus != previousStatus {
-			fmt.Println("Workspace " + currentStatus)
-			previousStatus = currentStatus
+			currentStatus := HumanizeWorkspacePhase(wsInfo.Msg.GetResult())
+			if currentStatus != previousStatus {
+				fmt.Println("Workspace " + currentStatus)
+				previousStatus = currentStatus
+			}
 		}
-	}
 
-	if err := stream.Err(); err != nil {
-		return err
+		if err := stream.Err(); err != nil {
+			if retries >= maxRetries {
+				return fmt.Errorf("Workspace stream ended unexpectedly after %d retries: %w", maxRetries, err)
+			}
+			retries++
+			fmt.Printf("Stream ended unexpectedly, retrying %d/%d\n", retries, maxRetries)
+		} else {
+			return fmt.Errorf("Workspace stream ended unexpectedly")
+		}
 	}
-
-	return fmt.Errorf("Workspace stream ended unexpectedly")
 }