diff --git a/components/dashboard/src/prebuilds/detail/PrebuildDetailPage.tsx b/components/dashboard/src/prebuilds/detail/PrebuildDetailPage.tsx
index f1636ee2b96298..cbc4349abaebac 100644
--- a/components/dashboard/src/prebuilds/detail/PrebuildDetailPage.tsx
+++ b/components/dashboard/src/prebuilds/detail/PrebuildDetailPage.tsx
@@ -296,7 +296,7 @@ export const PrebuildDetailPage: FC = () => {
                                 <div className="py-4 px-6 flex flex-col gap-1">
                                     <PrebuildStatus prebuild={prebuild} />
                                     {prebuild?.status?.message && (
-                                        <div className="text-pk-content-secondary truncate">
+                                        <div className="text-pk-content-secondary line-clamp-2">
                                             {prebuild?.status.message}
                                         </div>
                                     )}
diff --git a/components/dashboard/src/start/StartWorkspace.tsx b/components/dashboard/src/start/StartWorkspace.tsx
index 505216670f8f54..633f5bd694ce13 100644
--- a/components/dashboard/src/start/StartWorkspace.tsx
+++ b/components/dashboard/src/start/StartWorkspace.tsx
@@ -822,7 +822,7 @@ function ImageBuildView(props: ImageBuildViewProps) {
                             💡 You can use the <code>gp validate</code> command to validate the workspace configuration
                             from the editor terminal. &nbsp;
                             <a
-                                href="https://www.gitpod.io/docs/configure/workspaces/workspace-image#trying-out-changes-to-your-dockerfile"
+                                href="https://www.gitpod.io/docs/configure/workspaces#validate-your-gitpod-configuration"
                                 target="_blank"
                                 rel="noopener noreferrer"
                                 className="gp-link"
diff --git a/components/server/src/workspace/workspace-starter.ts b/components/server/src/workspace/workspace-starter.ts
index c3f1916c822d1c..5d41e278e28a86 100644
--- a/components/server/src/workspace/workspace-starter.ts
+++ b/components/server/src/workspace/workspace-starter.ts
@@ -843,7 +843,7 @@ export class WorkspaceStarter {
 
     /**
      * failInstanceStart properly fails a workspace instance if something goes wrong before the instance ever reaches
-     * workspace manager. In this case we need to make sure we also fulfil the tasks of the bridge (e.g. for prebulds).
+     * workspace manager. In this case we need to make sure we also fulfil the tasks of the bridge (e.g. for prebuilds).
      */
     private async failInstanceStart(ctx: TraceContext, err: any, workspace: Workspace, instance: WorkspaceInstance) {
         if (ctxIsAborted()) {
@@ -1344,7 +1344,10 @@ export class WorkspaceStarter {
                     `workspace image build failed: ${message}`,
                     { looksLikeUserError: true },
                 );
-                err = new StartInstanceError("imageBuildFailedUser", err);
+                err = new StartInstanceError(
+                    "imageBuildFailedUser",
+                    `workspace image build failed: ${message}. For further logs, try executing \`gp validate\` inside of a workspace`,
+                );
                 // Don't report this as "failed" to our metrics as it would trigger an alert
             } else {
                 log.error(
diff --git a/components/supervisor/pkg/supervisor/config.go b/components/supervisor/pkg/supervisor/config.go
index 86ec6476d027ac..ef31fd25799c2a 100644
--- a/components/supervisor/pkg/supervisor/config.go
+++ b/components/supervisor/pkg/supervisor/config.go
@@ -309,6 +309,9 @@ type WorkspaceConfig struct {
 	// GitpodHeadless controls whether the workspace is running headless
 	GitpodHeadless string `env:"GITPOD_HEADLESS"`
 
+	// BobDockerfilePath is the path to the Dockerfile image builder will attempt to build
+	BobDockerfilePath string `env:"BOB_DOCKERFILE_PATH"`
+
 	// DebugEnabled controls whether the supervisor debugging facilities (pprof, grpc tracing) should be enabled
 	DebugEnable bool `env:"SUPERVISOR_DEBUG_ENABLE"`
 
@@ -468,6 +471,11 @@ func (c WorkspaceConfig) isDebugWorkspace() bool {
 	return c.DebugWorkspaceType != api.DebugWorkspaceType_noDebug
 }
 
+// isImageBuild returns true if the workspace is an image build.
+func (c WorkspaceConfig) isImageBuild() bool {
+	return c.BobDockerfilePath != ""
+}
+
 var contentSources = map[api.ContentSource]csapi.WorkspaceInitSource{
 	api.ContentSource_from_other:    csapi.WorkspaceInitFromOther,
 	api.ContentSource_from_backup:   csapi.WorkspaceInitFromBackup,
diff --git a/components/supervisor/pkg/supervisor/supervisor.go b/components/supervisor/pkg/supervisor/supervisor.go
index 77320943313f92..569289c04fa9f7 100644
--- a/components/supervisor/pkg/supervisor/supervisor.go
+++ b/components/supervisor/pkg/supervisor/supervisor.go
@@ -465,7 +465,7 @@ func Run(options ...RunOption) {
 
 	if cfg.isHeadless() {
 		wg.Add(1)
-		go stopWhenTasksAreDone(ctx, &wg, shutdown, tasksSuccessChan)
+		go stopWhenTasksAreDone(&wg, cfg, shutdown, tasksSuccessChan)
 	} else if !opts.RunGP {
 		wg.Add(1)
 		go portMgmt.Run(ctx, &wg)
@@ -1593,15 +1593,20 @@ func tunnelOverSSH(ctx context.Context, tunneled *ports.TunneledPortsService, ne
 	<-ctx.Done()
 }
 
-func stopWhenTasksAreDone(ctx context.Context, wg *sync.WaitGroup, shutdown chan ShutdownReason, successChan <-chan taskSuccess) {
+func stopWhenTasksAreDone(wg *sync.WaitGroup, cfg *Config, shutdown chan ShutdownReason, successChan <-chan taskSuccess) {
 	defer wg.Done()
 	defer close(shutdown)
 
 	success := <-successChan
 	if success.Failed() {
+		var msg []byte
+		if cfg.isImageBuild() {
+			msg = []byte("image build failed (" + string(success) + "). This is likely due to a misconfiguration in your Dockerfile. Debug this using `gp validate` (visit https://www.gitpod.io/docs/configure/workspaces#validate-your-gitpod-configuration) to learn more")
+		} else {
+			msg = []byte("headless task failed: " + string(success))
+		}
 		// we signal task failure via kubernetes termination log
-		msg := []byte("headless task failed: " + string(success))
-		err := ioutil.WriteFile("/dev/termination-log", msg, 0o644)
+		err := os.WriteFile("/dev/termination-log", msg, 0o644)
 		if err != nil {
 			log.WithError(err).Error("err while writing termination log")
 		}