fix (controller) : update DevWorkspace status with different message for debug start

When DevWorkspace contains 'controller.devfile.io/debug-start' annotation,
set a different message for DevWorkspace Starting phase to give user indication
that debug start mode is activated and they need to monitor DevWorkspace pod's
logs or exec into it for debugging.

Signed-off-by: Rohan Kumar <rohaan@redhat.com>

Author: rohanKanojia

controllers/workspace/devworkspace_controller.go

@@ -324,7 +324,10 @@ func (r *DevWorkspaceReconciler) Reconcile(ctx context.Context, req ctrl.Request
 	}
 
 	postStartDebugTrapSleepDuration := ""
+	deploymentReadyConditionMessage := "Waiting for workspace deployment"
 	if workspace.Annotations[constants.DevWorkspaceDebugStartAnnotation] == "true" {
+		deploymentReadyConditionMessage = "Debug mode: failed postStart commands will be trapped; inspect logs/exec to debug"
+		reconcileStatus.setConditionTrue(conditions.Started, "DevWorkspace is starting in debug mode")
 		postStartDebugTrapSleepDuration = workspace.Config.Workspace.ProgressTimeout
 	}
 	devfilePodAdditions, err := containerlib.GetKubeContainersFromDevfile(
@@ -494,7 +497,7 @@ func (r *DevWorkspaceReconciler) Reconcile(ctx context.Context, req ctrl.Request
 	if err := wsprovision.SyncDeploymentToCluster(workspace, allPodAdditions, serviceAcctName, clusterAPI); err != nil {
 		if shouldReturn, reconcileResult, reconcileErr := r.checkDWError(workspace, err, "Error creating DevWorkspace deployment", metrics.DetermineProvisioningFailureReason(err.Error()), reqLogger, &reconcileStatus); shouldReturn {
 			reqLogger.Info("Waiting on deployment to be ready")
-			reconcileStatus.setConditionFalse(conditions.DeploymentReady, "Waiting for workspace deployment")
+			reconcileStatus.setConditionFalse(conditions.DeploymentReady, deploymentReadyConditionMessage)
 			return reconcileResult, reconcileErr
 		}
 	}

test/e2e/pkg/tests/devworkspace_debug_poststart_tests.go

@@ -0,0 +1,78 @@
+// Copyright (c) 2019-2025 Red Hat, Inc.
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package tests
+
+import (
+	"fmt"
+	"strings"
+
+	dw "github.com/devfile/api/v2/pkg/apis/workspaces/v1alpha2"
+	"github.com/devfile/devworkspace-operator/test/e2e/pkg/config"
+	"github.com/onsi/ginkgo/v2"
+)
+
+var _ = ginkgo.Describe("[DevWorkspace Debug Start Mode]", func() {
+	defer ginkgo.GinkgoRecover()
+
+	ginkgo.It("Wait DevWorkspace Webhook Server Pod", func() {
+		controllerLabel := "app.kubernetes.io/name=devworkspace-webhook-server"
+
+		deploy, err := config.AdminK8sClient.WaitForPodRunningByLabel(config.OperatorNamespace, controllerLabel)
+		if err != nil {
+			ginkgo.Fail(fmt.Sprintf("cannot get the DevWorkspace Webhook Server Pod status with label %s: %s", controllerLabel, err.Error()))
+			return
+		}
+
+		if !deploy {
+			ginkgo.Fail("Devworkspace webhook didn't start properly")
+		}
+	})
+
+	ginkgo.It("Add Debug DevWorkspace to cluster and wait starting status", func() {
+		commandResult, err := config.DevK8sClient.OcApplyWorkspace(config.DevWorkspaceNamespace, "test/resources/simple-devworkspace-debug-start-annotation.yaml")
+		if err != nil {
+			ginkgo.Fail(fmt.Sprintf("Failed to create DevWorkspace: %s %s", err.Error(), commandResult))
+			return
+		}
+
+		deploy, err := config.DevK8sClient.WaitDevWsStatus("code-latest-with-debug-start", config.DevWorkspaceNamespace, dw.DevWorkspaceStatusStarting)
+		if !deploy {
+			ginkgo.Fail(fmt.Sprintf("DevWorkspace didn't start properly. Error: %s", err))
+		}
+	})
+
+	ginkgo.It("Check DevWorkspace Conditions for Debug Start message", func() {
+		devWorkspaceStatus, err := config.DevK8sClient.GetDevWsStatus("code-latest-with-debug-start", config.DevWorkspaceNamespace)
+		if err != nil {
+			ginkgo.Fail(fmt.Sprintf("Failure in fetching DevWorkspace status. Error: %s", err))
+		}
+
+		expectedSubstring := "Debug mode: failed postStart commands will be trapped; inspect logs/exec to debug"
+
+		found := false
+		for _, cond := range devWorkspaceStatus.Conditions {
+			if cond.Message != "" && strings.Contains(cond.Message, expectedSubstring) {
+				found = true
+				break
+			}
+		}
+
+		if !found {
+			ginkgo.Fail(fmt.Sprintf(
+				"DevWorkspace status does not contain expected debug message.\nExpected substring: %q\nGot conditions: %+v",
+				expectedSubstring, devWorkspaceStatus.Conditions,
+			))
+		}
+	})
+})

test/resources/simple-devworkspace-debug-start-annotation.yaml

@@ -0,0 +1,19 @@
+kind: DevWorkspace
+apiVersion: workspace.devfile.io/v1alpha2
+metadata:
+  name: code-latest-with-debug-start
+  annotations:
+    controller.devfile.io/debug-start: "true"
+spec:
+  started: true
+  template:
+    projects:
+      - name: web-nodejs-sample
+        git:
+          remotes:
+            origin: "https://github.com/che-samples/web-nodejs-sample.git"
+    components:
+      - name: dev
+        container:
+          image: quay.io/wto/web-terminal-tooling:latest
+          args: ["tail", "-f", "/dev/null"]