diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts
index 20e9672f04..abf8ae7f41 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts
@@ -484,7 +484,7 @@ export class DatabaseTaskStore implements TaskStore {
   async listEvents(
     options: TaskStoreListEventsOptions,
   ): Promise<{ events: SerializedTaskEvent[] }> {
-    const { taskId, after } = options;
+    const { isTaskRecoverable, taskId, after } = options;
     const rawEvents = await this.db<RawDbTaskEventRow>('task_events')
       .where({
         task_id: taskId,
@@ -502,6 +502,7 @@ export class DatabaseTaskStore implements TaskStore {
         const body = JSON.parse(event.body) as JsonObject;
         return {
           id: Number(event.id),
+          isTaskRecoverable,
           taskId,
           body,
           type: event.event_type,
@@ -602,6 +603,38 @@ export class DatabaseTaskStore implements TaskStore {
     });
   }
 
+  async retryTask?(options: { taskId: string }): Promise<void> {
+    await this.db.transaction(async tx => {
+      const result = await tx<RawDbTaskRow>('tasks')
+        .where('id', options.taskId)
+        .update(
+          {
+            status: 'open',
+            last_heartbeat_at: this.db.fn.now(),
+          },
+          ['id', 'spec'],
+        );
+
+      for (const { id, spec } of result) {
+        const taskSpec = JSON.parse(spec as string) as TaskSpec;
+
+        await tx<RawDbTaskEventRow>('task_events')
+          .where('task_id', id)
+          .andWhere(q => q.whereIn('event_type', ['cancelled', 'completion']))
+          .del();
+
+        await tx<RawDbTaskEventRow>('task_events').insert({
+          task_id: id,
+          event_type: 'recovered',
+          body: JSON.stringify({
+            recoverStrategy:
+              taskSpec.EXPERIMENTAL_recovery?.EXPERIMENTAL_strategy ?? 'none',
+          }),
+        });
+      }
+    });
+  }
+
   async recoverTasks(
     options: TaskStoreRecoverTaskOptions,
   ): Promise<{ ids: string[] }> {
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
index 3960228529..1da2b4b349 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
@@ -254,7 +254,9 @@ export interface CurrentClaimedTask {
    * The creator of the task.
    */
   createdBy?: string;
-
+  /**
+   * The workspace of the task.
+   */
   workspace?: Promise<Buffer>;
 }
 
@@ -317,7 +319,7 @@ export class StorageTaskBroker implements TaskBroker {
             shouldUnsubscribe = true;
           }
 
-          if (event.type === 'completion') {
+          if (event.type === 'completion' && !event.isTaskRecoverable) {
             shouldUnsubscribe = true;
           }
         }
@@ -416,8 +418,17 @@ export class StorageTaskBroker implements TaskBroker {
       let cancelled = false;
 
       (async () => {
+        const task = await this.storage.getTask(taskId);
+        const isTaskRecoverable =
+          task.spec.EXPERIMENTAL_recovery?.EXPERIMENTAL_strategy ===
+          'startOver';
+
         while (!cancelled) {
-          const result = await this.storage.listEvents({ taskId, after });
+          const result = await this.storage.listEvents({
+            isTaskRecoverable,
+            taskId,
+            after,
+          });
           const { events } = result;
           if (events.length) {
             after = events[events.length - 1].id;
@@ -485,4 +496,9 @@ export class StorageTaskBroker implements TaskBroker {
       },
     });
   }
+
+  async retry?(taskId: string): Promise<void> {
+    await this.storage.retryTask?.({ taskId });
+    this.signalDispatch();
+  }
 }
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/WorkspaceService.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/WorkspaceService.ts
index ab424806bf..bb3ce448fc 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/WorkspaceService.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/WorkspaceService.ts
@@ -19,6 +19,7 @@ import { CurrentClaimedTask } from './StorageTaskBroker';
 import { WorkspaceProvider } from '@backstage/plugin-scaffolder-node/alpha';
 import { DatabaseWorkspaceProvider } from './DatabaseWorkspaceProvider';
 import { TaskStore } from './types';
+import fs from 'fs-extra';
 
 export interface WorkspaceService {
   serializeWorkspace(options: { path: string }): Promise<void>;
@@ -74,6 +75,7 @@ export class DefaultWorkspaceService implements WorkspaceService {
     targetPath: string;
   }): Promise<void> {
     if (this.isWorkspaceSerializationEnabled()) {
+      await fs.mkdirp(options.targetPath);
       await this.workspaceProvider.rehydrateWorkspace(options);
     }
   }
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/types.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/types.ts
index b87e0c4b9b..874793922f 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/types.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/types.ts
@@ -119,6 +119,7 @@ export type TaskStoreEmitOptions<TBody = JsonObject> = {
  * @public
  */
 export type TaskStoreListEventsOptions = {
+  isTaskRecoverable?: boolean;
   taskId: string;
   after?: number | undefined;
 };
@@ -170,6 +171,8 @@ export interface TaskStore {
     options: TaskStoreCreateTaskOptions,
   ): Promise<TaskStoreCreateTaskResult>;
 
+  retryTask?(options: { taskId: string }): Promise<void>;
+
   recoverTasks?(
     options: TaskStoreRecoverTaskOptions,
   ): Promise<{ ids: string[] }>;
diff --git a/plugins/scaffolder-backend/src/service/router.ts b/plugins/scaffolder-backend/src/service/router.ts
index 4584d64257..80406496d2 100644
--- a/plugins/scaffolder-backend/src/service/router.ts
+++ b/plugins/scaffolder-backend/src/service/router.ts
@@ -652,6 +652,19 @@ export async function createRouter(
       await taskBroker.cancel?.(taskId);
       res.status(200).json({ status: 'cancelled' });
     })
+    .post('/v2/tasks/:taskId/retry', async (req, res) => {
+      const credentials = await httpAuth.credentials(req);
+      // Requires both read and cancel permissions
+      await checkPermission({
+        credentials,
+        permissions: [taskCreatePermission, taskReadPermission],
+        permissionService: permissions,
+      });
+
+      const { taskId } = req.params;
+      await taskBroker.retry?.(taskId);
+      res.status(201).json({ id: taskId });
+    })
     .get('/v2/tasks/:taskId/eventstream', async (req, res) => {
       const credentials = await httpAuth.credentials(req);
       await checkPermission({
@@ -687,7 +700,7 @@ export async function createRouter(
             res.write(
               `event: ${event.type}\ndata: ${JSON.stringify(event)}\n\n`,
             );
-            if (event.type === 'completion') {
+            if (event.type === 'completion' && !event.isTaskRecoverable) {
               shouldUnsubscribe = true;
             }
           }
diff --git a/plugins/scaffolder-node/src/tasks/types.ts b/plugins/scaffolder-node/src/tasks/types.ts
index 27a131c513..b830c0633a 100644
--- a/plugins/scaffolder-node/src/tasks/types.ts
+++ b/plugins/scaffolder-node/src/tasks/types.ts
@@ -76,6 +76,7 @@ export type TaskEventType = 'completion' | 'log' | 'cancelled' | 'recovered';
  */
 export type SerializedTaskEvent = {
   id: number;
+  isTaskRecoverable?: boolean;
   taskId: string;
   body: JsonObject;
   type: TaskEventType;
@@ -163,6 +164,8 @@ export interface TaskContext {
 export interface TaskBroker {
   cancel?(taskId: string): Promise<void>;
 
+  retry?(taskId: string): Promise<void>;
+
   claim(): Promise<TaskContext>;
 
   recoverTasks?(): Promise<void>;
diff --git a/plugins/scaffolder-react/src/api/types.ts b/plugins/scaffolder-react/src/api/types.ts
index eaef54ff1b..3816c4bcbf 100644
--- a/plugins/scaffolder-react/src/api/types.ts
+++ b/plugins/scaffolder-react/src/api/types.ts
@@ -161,6 +161,7 @@ export interface ScaffolderGetIntegrationsListResponse {
  * @public
  */
 export interface ScaffolderStreamLogsOptions {
+  isTaskRecoverable?: boolean;
   taskId: string;
   after?: number;
 }
@@ -213,6 +214,13 @@ export interface ScaffolderApi {
    */
   cancelTask(taskId: string): Promise<void>;
 
+  /**
+   * Starts the task again from the point where it failed.
+   *
+   * @param taskId - the id of the task
+   */
+  retry?(taskId: string): Promise<void>;
+
   listTasks?(options: {
     filterByOwnership: 'owned' | 'all';
   }): Promise<{ tasks: ScaffolderTask[] }>;
diff --git a/plugins/scaffolder-react/src/hooks/useEventStream.ts b/plugins/scaffolder-react/src/hooks/useEventStream.ts
index f63f6024e6..7c5ce09ab7 100644
--- a/plugins/scaffolder-react/src/hooks/useEventStream.ts
+++ b/plugins/scaffolder-react/src/hooks/useEventStream.ts
@@ -143,6 +143,11 @@ function reducer(draft: TaskStream, action: ReducerAction) {
     }
 
     case 'RECOVERED': {
+      draft.cancelled = false;
+      draft.completed = false;
+      draft.output = undefined;
+      draft.error = undefined;
+
       for (const stepId in draft.steps) {
         if (draft.steps.hasOwnProperty(stepId)) {
           draft.steps[stepId].startedAt = undefined;
@@ -185,12 +190,16 @@ export const useTaskEventStream = (taskId: string): TaskStream => {
     let subscription: Subscription | undefined;
     let logPusher: NodeJS.Timeout | undefined;
     let retryCount = 1;
+    let isTaskRecoverable = false;
     const startStreamLogProcess = () =>
       scaffolderApi.getTask(taskId).then(
         task => {
           if (didCancel) {
             return;
           }
+          isTaskRecoverable =
+            task.spec.EXPERIMENTAL_recovery?.EXPERIMENTAL_strategy ===
+            'startOver';
           dispatch({ type: 'INIT', data: task });
 
           // TODO(blam): Use a normal fetch to fetch the current log for the event stream
@@ -199,7 +208,10 @@ export const useTaskEventStream = (taskId: string): TaskStream => {
           // stream logs. Without this, if you have a lot of logs, it can look like the
           // task is being rebuilt on load as it progresses through the steps at a slower
           // rate whilst it builds the status from the event logs
-          const observable = scaffolderApi.streamLogs({ taskId });
+          const observable = scaffolderApi.streamLogs({
+            isTaskRecoverable,
+            taskId,
+          });
 
           const collectedLogEvents = new Array<LogEvent>();
 
@@ -270,12 +282,14 @@ export const useTaskEventStream = (taskId: string): TaskStream => {
       );
     void startStreamLogProcess();
     return () => {
-      didCancel = true;
-      if (subscription) {
-        subscription.unsubscribe();
-      }
-      if (logPusher) {
-        clearInterval(logPusher);
+      if (!isTaskRecoverable) {
+        didCancel = true;
+        if (subscription) {
+          subscription.unsubscribe();
+        }
+        if (logPusher) {
+          clearInterval(logPusher);
+        }
       }
     };
   }, [scaffolderApi, dispatch, taskId]);
diff --git a/plugins/scaffolder/src/api.ts b/plugins/scaffolder/src/api.ts
index 1809ed4c15..93db7386f3 100644
--- a/plugins/scaffolder/src/api.ts
+++ b/plugins/scaffolder/src/api.ts
@@ -217,12 +217,10 @@ export class ScaffolderClient implements ScaffolderApi {
   }
 
   private streamLogsEventStream({
+    isTaskRecoverable,
     taskId,
     after,
-  }: {
-    taskId: string;
-    after?: number;
-  }): Observable<LogEvent> {
+  }: ScaffolderStreamLogsOptions): Observable<LogEvent> {
     return new ObservableImpl(subscriber => {
       const params = new URLSearchParams();
       if (after !== undefined) {
@@ -246,14 +244,14 @@ export class ScaffolderClient implements ScaffolderApi {
           };
 
           const ctrl = new AbortController();
-          fetchEventSource(url, {
+          void fetchEventSource(url, {
             fetch: this.fetchApi.fetch,
             signal: ctrl.signal,
             onmessage(e: EventSourceMessage) {
               if (e.event === 'log') {
                 processEvent(e);
                 return;
-              } else if (e.event === 'completion') {
+              } else if (e.event === 'completion' && !isTaskRecoverable) {
                 processEvent(e);
                 subscriber.complete();
                 ctrl.abort();
@@ -338,6 +336,21 @@ export class ScaffolderClient implements ScaffolderApi {
     return await response.json();
   }
 
+  async retry?(taskId: string): Promise<void> {
+    const baseUrl = await this.discoveryApi.getBaseUrl('scaffolder');
+    const url = `${baseUrl}/v2/tasks/${encodeURIComponent(taskId)}/retry`;
+
+    const response = await this.fetchApi.fetch(url, {
+      method: 'POST',
+    });
+
+    if (!response.ok) {
+      throw await ResponseError.fromResponse(response);
+    }
+
+    return await response.json();
+  }
+
   async autocomplete({
     token,
     resource,
diff --git a/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx b/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx
index e0ab01fc67..c3e9250d2b 100644
--- a/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx
+++ b/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx
@@ -41,8 +41,10 @@ import { scaffolderTranslationRef } from '../../translation';
 
 type ContextMenuProps = {
   cancelEnabled?: boolean;
+  canRetry: boolean;
   logsVisible?: boolean;
   buttonBarVisible?: boolean;
+  onRetry?: () => void;
   onStartOver?: () => void;
   onToggleLogs?: (state: boolean) => void;
   onToggleButtonBar?: (state: boolean) => void;
@@ -58,8 +60,10 @@ const useStyles = makeStyles<Theme, { fontColor: string }>(() => ({
 export const ContextMenu = (props: ContextMenuProps) => {
   const {
     cancelEnabled,
+    canRetry,
     logsVisible,
     buttonBarVisible,
+    onRetry,
     onStartOver,
     onToggleLogs,
     onToggleButtonBar,
@@ -151,6 +155,16 @@ export const ContextMenu = (props: ContextMenuProps) => {
             </ListItemIcon>
             <ListItemText primary={t('ongoingTask.contextMenu.startOver')} />
           </MenuItem>
+          <MenuItem
+            onClick={onRetry}
+            disabled={cancelEnabled || !canRetry}
+            data-testid="retry-task"
+          >
+            <ListItemIcon>
+              <Retry fontSize="small" />
+            </ListItemIcon>
+            <ListItemText primary="Retry" />
+          </MenuItem>
           <MenuItem
             onClick={cancel}
             disabled={
diff --git a/plugins/scaffolder/src/components/OngoingTask/OngoingTask.tsx b/plugins/scaffolder/src/components/OngoingTask/OngoingTask.tsx
index b956e27aca..1e2031ce1b 100644
--- a/plugins/scaffolder/src/components/OngoingTask/OngoingTask.tsx
+++ b/plugins/scaffolder/src/components/OngoingTask/OngoingTask.tsx
@@ -58,6 +58,9 @@ const useStyles = makeStyles(theme => ({
   cancelButton: {
     marginRight: theme.spacing(1),
   },
+  retryButton: {
+    marginRight: theme.spacing(1),
+  },
   logsVisibilityButton: {
     marginRight: theme.spacing(1),
   },
@@ -130,6 +133,12 @@ export const OngoingTask = (props: {
     return 0;
   }, [steps]);
 
+  const isRetryableTask =
+    taskStream.task?.spec.EXPERIMENTAL_recovery?.EXPERIMENTAL_strategy ===
+    'startOver';
+
+  const canRetry = canReadTask && canCreateTask && isRetryableTask;
+
   const startOver = useCallback(() => {
     const { namespace, name } =
       taskStream.task?.spec.templateInfo?.entity?.metadata ?? {};
@@ -157,6 +166,13 @@ export const OngoingTask = (props: {
     templateRouteRef,
   ]);
 
+  const [{ status: _ }, { execute: triggerRetry }] = useAsync(async () => {
+    if (taskId) {
+      analytics.captureEvent('retried', 'Template has been retried');
+      await scaffolderApi.retry?.(taskId);
+    }
+  });
+
   const [{ status: cancelStatus }, { execute: triggerCancel }] = useAsync(
     async () => {
       if (taskId) {
@@ -190,9 +206,11 @@ export const OngoingTask = (props: {
       >
         <ContextMenu
           cancelEnabled={cancelEnabled}
+          canRetry={canRetry}
           logsVisible={logsVisible}
           buttonBarVisible={buttonBarVisible}
           onStartOver={startOver}
+          onRetry={triggerRetry}
           onToggleLogs={setLogVisibleState}
           onToggleButtonBar={setButtonBarVisibleState}
           taskId={taskId}
@@ -237,6 +255,14 @@ export const OngoingTask = (props: {
                   >
                     {t('ongoingTask.cancelButtonTitle')}
                   </Button>
+                  <Button
+                    className={classes.retryButton}
+                    disabled={cancelEnabled || !canRetry}
+                    onClick={triggerRetry}
+                    data-testid="retry-button"
+                  >
+                    Retry
+                  </Button>
                   <Button
                     className={classes.logsVisibilityButton}
                     color="primary"