diff --git a/.changeset/slow-trees-compare.md b/.changeset/slow-trees-compare.md
new file mode 100644
index 0000000000..18e1a82ff9
--- /dev/null
+++ b/.changeset/slow-trees-compare.md
@@ -0,0 +1,8 @@
+---
+'@backstage/plugin-scaffolder-backend': patch
+'@backstage/plugin-scaffolder-react': patch
+'@backstage/plugin-scaffolder-node': patch
+'@backstage/plugin-scaffolder': patch
+---
+
+Make it possible to manually retry the scaffolder template from the step it failed
diff --git a/plugins/scaffolder-backend/report.api.md b/plugins/scaffolder-backend/report.api.md
index 112d58046b..9ea60fcfdd 100644
--- a/plugins/scaffolder-backend/report.api.md
+++ b/plugins/scaffolder-backend/report.api.md
@@ -398,7 +398,6 @@ export interface CurrentClaimedTask {
   spec: TaskSpec;
   state?: JsonObject;
   taskId: string;
-  // (undocumented)
   workspace?: Promise<Buffer>;
 }
 
@@ -488,6 +487,8 @@ export class DatabaseTaskStore implements TaskStore {
     targetPath: string;
   }): Promise<void>;
   // (undocumented)
+  retryTask?(options: { taskId: string }): Promise<void>;
+  // (undocumented)
   saveTaskState(options: { taskId: string; state?: JsonObject }): Promise<void>;
   // (undocumented)
   serializeWorkspace(options: { path: string; taskId: string }): Promise<void>;
@@ -740,6 +741,8 @@ export interface TaskStore {
     targetPath: string;
   }): Promise<void>;
   // (undocumented)
+  retryTask?(options: { taskId: string }): Promise<void>;
+  // (undocumented)
   saveTaskState?(options: {
     taskId: string;
     state?: JsonObject;
@@ -776,6 +779,7 @@ export type TaskStoreEmitOptions<TBody = JsonObject> = {
 
 // @public
 export type TaskStoreListEventsOptions = {
+  isTaskRecoverable?: boolean;
   taskId: string;
   after?: number | undefined;
 };
@@ -884,7 +888,8 @@ export type TemplatePermissionRuleInput<
 // src/scaffolder/tasks/DatabaseTaskStore.d.ts:104:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
 // src/scaffolder/tasks/DatabaseTaskStore.d.ts:107:5 - (ae-undocumented) Missing documentation for "serializeWorkspace".
 // src/scaffolder/tasks/DatabaseTaskStore.d.ts:111:5 - (ae-undocumented) Missing documentation for "cancelTask".
-// src/scaffolder/tasks/DatabaseTaskStore.d.ts:114:5 - (ae-undocumented) Missing documentation for "recoverTasks".
+// src/scaffolder/tasks/DatabaseTaskStore.d.ts:114:5 - (ae-undocumented) Missing documentation for "retryTask".
+// src/scaffolder/tasks/DatabaseTaskStore.d.ts:117:5 - (ae-undocumented) Missing documentation for "recoverTasks".
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:24:5 - (ae-undocumented) Missing documentation for "create".
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:26:5 - (ae-undocumented) Missing documentation for "spec".
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:27:5 - (ae-undocumented) Missing documentation for "cancelSignal".
@@ -900,31 +905,31 @@ export type TemplatePermissionRuleInput<
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:52:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:53:5 - (ae-undocumented) Missing documentation for "complete".
 // src/scaffolder/tasks/StorageTaskBroker.d.ts:55:5 - (ae-undocumented) Missing documentation for "getInitiatorCredentials".
-// src/scaffolder/tasks/StorageTaskBroker.d.ts:83:5 - (ae-undocumented) Missing documentation for "workspace".
 // src/scaffolder/tasks/TaskWorker.d.ts:60:5 - (ae-undocumented) Missing documentation for "create".
 // src/scaffolder/tasks/TaskWorker.d.ts:61:5 - (ae-undocumented) Missing documentation for "recoverTasks".
 // src/scaffolder/tasks/TaskWorker.d.ts:62:5 - (ae-undocumented) Missing documentation for "start".
 // src/scaffolder/tasks/TaskWorker.d.ts:63:5 - (ae-undocumented) Missing documentation for "stop".
 // src/scaffolder/tasks/TaskWorker.d.ts:64:5 - (ae-undocumented) Missing documentation for "onReadyToClaimTask".
 // src/scaffolder/tasks/TaskWorker.d.ts:65:5 - (ae-undocumented) Missing documentation for "runOneTask".
-// src/scaffolder/tasks/types.d.ts:123:5 - (ae-undocumented) Missing documentation for "cancelTask".
-// src/scaffolder/tasks/types.d.ts:124:5 - (ae-undocumented) Missing documentation for "createTask".
-// src/scaffolder/tasks/types.d.ts:125:5 - (ae-undocumented) Missing documentation for "recoverTasks".
-// src/scaffolder/tasks/types.d.ts:128:5 - (ae-undocumented) Missing documentation for "getTask".
-// src/scaffolder/tasks/types.d.ts:129:5 - (ae-undocumented) Missing documentation for "claimTask".
-// src/scaffolder/tasks/types.d.ts:130:5 - (ae-undocumented) Missing documentation for "completeTask".
-// src/scaffolder/tasks/types.d.ts:135:5 - (ae-undocumented) Missing documentation for "heartbeatTask".
-// src/scaffolder/tasks/types.d.ts:136:5 - (ae-undocumented) Missing documentation for "listStaleTasks".
-// src/scaffolder/tasks/types.d.ts:143:5 - (ae-undocumented) Missing documentation for "list".
-// src/scaffolder/tasks/types.d.ts:163:5 - (ae-undocumented) Missing documentation for "list".
-// src/scaffolder/tasks/types.d.ts:182:5 - (ae-undocumented) Missing documentation for "emitLogEvent".
-// src/scaffolder/tasks/types.d.ts:183:5 - (ae-undocumented) Missing documentation for "getTaskState".
-// src/scaffolder/tasks/types.d.ts:188:5 - (ae-undocumented) Missing documentation for "saveTaskState".
-// src/scaffolder/tasks/types.d.ts:192:5 - (ae-undocumented) Missing documentation for "listEvents".
-// src/scaffolder/tasks/types.d.ts:195:5 - (ae-undocumented) Missing documentation for "shutdownTask".
-// src/scaffolder/tasks/types.d.ts:196:5 - (ae-undocumented) Missing documentation for "rehydrateWorkspace".
-// src/scaffolder/tasks/types.d.ts:200:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
-// src/scaffolder/tasks/types.d.ts:203:5 - (ae-undocumented) Missing documentation for "serializeWorkspace".
+// src/scaffolder/tasks/types.d.ts:124:5 - (ae-undocumented) Missing documentation for "cancelTask".
+// src/scaffolder/tasks/types.d.ts:125:5 - (ae-undocumented) Missing documentation for "createTask".
+// src/scaffolder/tasks/types.d.ts:126:5 - (ae-undocumented) Missing documentation for "retryTask".
+// src/scaffolder/tasks/types.d.ts:129:5 - (ae-undocumented) Missing documentation for "recoverTasks".
+// src/scaffolder/tasks/types.d.ts:132:5 - (ae-undocumented) Missing documentation for "getTask".
+// src/scaffolder/tasks/types.d.ts:133:5 - (ae-undocumented) Missing documentation for "claimTask".
+// src/scaffolder/tasks/types.d.ts:134:5 - (ae-undocumented) Missing documentation for "completeTask".
+// src/scaffolder/tasks/types.d.ts:139:5 - (ae-undocumented) Missing documentation for "heartbeatTask".
+// src/scaffolder/tasks/types.d.ts:140:5 - (ae-undocumented) Missing documentation for "listStaleTasks".
+// src/scaffolder/tasks/types.d.ts:147:5 - (ae-undocumented) Missing documentation for "list".
+// src/scaffolder/tasks/types.d.ts:167:5 - (ae-undocumented) Missing documentation for "list".
+// src/scaffolder/tasks/types.d.ts:186:5 - (ae-undocumented) Missing documentation for "emitLogEvent".
+// src/scaffolder/tasks/types.d.ts:187:5 - (ae-undocumented) Missing documentation for "getTaskState".
+// src/scaffolder/tasks/types.d.ts:192:5 - (ae-undocumented) Missing documentation for "saveTaskState".
+// src/scaffolder/tasks/types.d.ts:196:5 - (ae-undocumented) Missing documentation for "listEvents".
+// src/scaffolder/tasks/types.d.ts:199:5 - (ae-undocumented) Missing documentation for "shutdownTask".
+// src/scaffolder/tasks/types.d.ts:200:5 - (ae-undocumented) Missing documentation for "rehydrateWorkspace".
+// src/scaffolder/tasks/types.d.ts:204:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
+// src/scaffolder/tasks/types.d.ts:207:5 - (ae-undocumented) Missing documentation for "serializeWorkspace".
 // src/service/router.d.ts:17:1 - (ae-undocumented) Missing documentation for "TemplatePermissionRuleInput".
 // src/service/router.d.ts:22:1 - (ae-undocumented) Missing documentation for "ActionPermissionRuleInput".
 // src/service/router.d.ts:30:5 - (ae-undocumented) Missing documentation for "logger".
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.test.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.test.ts
index a58c5cb863..fbd314cbbc 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.test.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.test.ts
@@ -16,7 +16,7 @@
 
 import { DatabaseManager } from '@backstage/backend-common';
 import { ConfigReader } from '@backstage/config';
-import { DatabaseTaskStore } from './DatabaseTaskStore';
+import { DatabaseTaskStore, RawDbTaskEventRow } from './DatabaseTaskStore';
 import { TaskSpec } from '@backstage/plugin-scaffolder-common';
 import { ConflictError } from '@backstage/errors';
 import { createMockDirectory } from '@backstage/backend-test-utils';
@@ -267,6 +267,48 @@ describe('DatabaseTaskStore', () => {
     expect(event.type).toBe('log');
   });
 
+  it('should be able to retied cancelled recoverable task', async () => {
+    const { store, manager } = await createStore();
+    const client = await manager.getClient();
+
+    const { taskId } = await store.createTask({
+      spec: {
+        EXPERIMENTAL_recovery: { EXPERIMENTAL_strategy: 'startOver' },
+      } as TaskSpec,
+      createdBy: 'me#too',
+    });
+    await store.completeTask({ taskId, status: 'cancelled', eventBody: {} });
+
+    await store.retryTask?.({ taskId });
+
+    const taskAfterRetry = await store.getTask(taskId);
+    expect(taskAfterRetry.status).toBe('open');
+
+    expect(
+      await client<RawDbTaskEventRow>('task_events')
+        .where({
+          task_id: taskId,
+          event_type: 'recovered',
+        })
+        .select(['body', 'event_type', 'task_id']),
+    ).toEqual([
+      {
+        body: JSON.stringify({ recoverStrategy: 'startOver' }),
+        event_type: 'recovered',
+        task_id: taskId,
+      },
+    ]);
+
+    expect(
+      await client<RawDbTaskEventRow>('task_events')
+        .where({
+          task_id: taskId,
+        })
+        .andWhere(q => q.whereIn('event_type', ['cancelled', 'completion']))
+        .select(['body', 'event_type', 'task_id']),
+    ).toEqual([]);
+  });
+
   it('should complete the task', async () => {
     const { store } = await createStore();
     const { taskId } = await store.createTask({
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/DatabaseTaskStore.ts
index 20e9672f04..65bafca619 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 +603,44 @@ 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;
+
+        /**
+         * Once task is picked up, all event types are replayed.
+         * We have to remove cancelled or completion event_type as these are as actions for frontend to perform.
+         * In contrary, we send 'recovered' event_type to reset the state on the frontend side.
+         *
+         */
+        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/report.api.md b/plugins/scaffolder-node/report.api.md
index ca48a25aa8..ed4f19c7d8 100644
--- a/plugins/scaffolder-node/report.api.md
+++ b/plugins/scaffolder-node/report.api.md
@@ -292,6 +292,7 @@ export type SerializedTask = {
 // @public
 export type SerializedTaskEvent = {
   id: number;
+  isTaskRecoverable?: boolean;
   taskId: string;
   body: JsonObject;
   type: TaskEventType;
@@ -340,6 +341,8 @@ export interface TaskBroker {
   // (undocumented)
   recoverTasks?(): Promise<void>;
   // (undocumented)
+  retry?(taskId: string): Promise<void>;
+  // (undocumented)
   vacuumTasks(options: { timeoutS: number }): Promise<void>;
 }
 
@@ -498,30 +501,31 @@ export type TemplateGlobal =
 // src/files/types.d.ts:7:5 - (ae-undocumented) Missing documentation for "content".
 // src/files/types.d.ts:8:5 - (ae-undocumented) Missing documentation for "executable".
 // src/files/types.d.ts:9:5 - (ae-undocumented) Missing documentation for "symlink".
-// src/tasks/types.d.ts:82:5 - (ae-undocumented) Missing documentation for "cancelSignal".
-// src/tasks/types.d.ts:83:5 - (ae-undocumented) Missing documentation for "spec".
-// src/tasks/types.d.ts:84:5 - (ae-undocumented) Missing documentation for "secrets".
-// src/tasks/types.d.ts:85:5 - (ae-undocumented) Missing documentation for "createdBy".
-// src/tasks/types.d.ts:86:5 - (ae-undocumented) Missing documentation for "done".
-// src/tasks/types.d.ts:87:5 - (ae-undocumented) Missing documentation for "isDryRun".
-// src/tasks/types.d.ts:88:5 - (ae-undocumented) Missing documentation for "complete".
-// src/tasks/types.d.ts:89:5 - (ae-undocumented) Missing documentation for "emitLog".
-// src/tasks/types.d.ts:90:5 - (ae-undocumented) Missing documentation for "getTaskState".
-// src/tasks/types.d.ts:93:5 - (ae-undocumented) Missing documentation for "updateCheckpoint".
-// src/tasks/types.d.ts:102:5 - (ae-undocumented) Missing documentation for "serializeWorkspace".
-// src/tasks/types.d.ts:105:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
-// src/tasks/types.d.ts:106:5 - (ae-undocumented) Missing documentation for "rehydrateWorkspace".
-// src/tasks/types.d.ts:110:5 - (ae-undocumented) Missing documentation for "getWorkspaceName".
-// src/tasks/types.d.ts:111:5 - (ae-undocumented) Missing documentation for "getInitiatorCredentials".
-// src/tasks/types.d.ts:119:5 - (ae-undocumented) Missing documentation for "cancel".
-// src/tasks/types.d.ts:120:5 - (ae-undocumented) Missing documentation for "claim".
-// src/tasks/types.d.ts:121:5 - (ae-undocumented) Missing documentation for "recoverTasks".
-// src/tasks/types.d.ts:122:5 - (ae-undocumented) Missing documentation for "dispatch".
-// src/tasks/types.d.ts:123:5 - (ae-undocumented) Missing documentation for "vacuumTasks".
-// src/tasks/types.d.ts:126:5 - (ae-undocumented) Missing documentation for "event$".
-// src/tasks/types.d.ts:132:5 - (ae-undocumented) Missing documentation for "get".
-// src/tasks/types.d.ts:133:5 - (ae-undocumented) Missing documentation for "list".
-// src/tasks/types.d.ts:153:5 - (ae-undocumented) Missing documentation for "list".
+// src/tasks/types.d.ts:83:5 - (ae-undocumented) Missing documentation for "cancelSignal".
+// src/tasks/types.d.ts:84:5 - (ae-undocumented) Missing documentation for "spec".
+// src/tasks/types.d.ts:85:5 - (ae-undocumented) Missing documentation for "secrets".
+// src/tasks/types.d.ts:86:5 - (ae-undocumented) Missing documentation for "createdBy".
+// src/tasks/types.d.ts:87:5 - (ae-undocumented) Missing documentation for "done".
+// src/tasks/types.d.ts:88:5 - (ae-undocumented) Missing documentation for "isDryRun".
+// src/tasks/types.d.ts:89:5 - (ae-undocumented) Missing documentation for "complete".
+// src/tasks/types.d.ts:90:5 - (ae-undocumented) Missing documentation for "emitLog".
+// src/tasks/types.d.ts:91:5 - (ae-undocumented) Missing documentation for "getTaskState".
+// src/tasks/types.d.ts:94:5 - (ae-undocumented) Missing documentation for "updateCheckpoint".
+// src/tasks/types.d.ts:103:5 - (ae-undocumented) Missing documentation for "serializeWorkspace".
+// src/tasks/types.d.ts:106:5 - (ae-undocumented) Missing documentation for "cleanWorkspace".
+// src/tasks/types.d.ts:107:5 - (ae-undocumented) Missing documentation for "rehydrateWorkspace".
+// src/tasks/types.d.ts:111:5 - (ae-undocumented) Missing documentation for "getWorkspaceName".
+// src/tasks/types.d.ts:112:5 - (ae-undocumented) Missing documentation for "getInitiatorCredentials".
+// src/tasks/types.d.ts:120:5 - (ae-undocumented) Missing documentation for "cancel".
+// src/tasks/types.d.ts:121:5 - (ae-undocumented) Missing documentation for "retry".
+// src/tasks/types.d.ts:122:5 - (ae-undocumented) Missing documentation for "claim".
+// src/tasks/types.d.ts:123:5 - (ae-undocumented) Missing documentation for "recoverTasks".
+// src/tasks/types.d.ts:124:5 - (ae-undocumented) Missing documentation for "dispatch".
+// src/tasks/types.d.ts:125:5 - (ae-undocumented) Missing documentation for "vacuumTasks".
+// src/tasks/types.d.ts:128:5 - (ae-undocumented) Missing documentation for "event$".
+// src/tasks/types.d.ts:134:5 - (ae-undocumented) Missing documentation for "get".
+// src/tasks/types.d.ts:135:5 - (ae-undocumented) Missing documentation for "list".
+// src/tasks/types.d.ts:155:5 - (ae-undocumented) Missing documentation for "list".
 // src/types.d.ts:3:1 - (ae-undocumented) Missing documentation for "TemplateFilter".
 // src/types.d.ts:5:1 - (ae-undocumented) Missing documentation for "TemplateGlobal".
 ```
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/report.api.md b/plugins/scaffolder-react/report.api.md
index cf5f08dae8..d7cf450bf5 100644
--- a/plugins/scaffolder-react/report.api.md
+++ b/plugins/scaffolder-react/report.api.md
@@ -235,6 +235,7 @@ export interface ScaffolderApi {
   listTasks?(options: { filterByOwnership: 'owned' | 'all' }): Promise<{
     tasks: ScaffolderTask[];
   }>;
+  retry?(taskId: string): Promise<void>;
   scaffold(
     options: ScaffolderScaffoldOptions,
   ): Promise<ScaffolderScaffoldResponse>;
@@ -454,6 +455,8 @@ export interface ScaffolderStreamLogsOptions {
   // (undocumented)
   after?: number;
   // (undocumented)
+  isTaskRecoverable?: boolean;
+  // (undocumented)
   taskId: string;
 }
 
@@ -562,25 +565,26 @@ export const useTemplateSecrets: () => ScaffolderUseTemplateSecrets;
 // src/api/types.d.ts:105:5 - (ae-undocumented) Missing documentation for "taskId".
 // src/api/types.d.ts:113:5 - (ae-undocumented) Missing documentation for "allowedHosts".
 // src/api/types.d.ts:121:5 - (ae-undocumented) Missing documentation for "integrations".
-// src/api/types.d.ts:133:5 - (ae-undocumented) Missing documentation for "taskId".
-// src/api/types.d.ts:134:5 - (ae-undocumented) Missing documentation for "after".
-// src/api/types.d.ts:137:1 - (ae-undocumented) Missing documentation for "ScaffolderDryRunOptions".
-// src/api/types.d.ts:138:5 - (ae-undocumented) Missing documentation for "template".
-// src/api/types.d.ts:139:5 - (ae-undocumented) Missing documentation for "values".
-// src/api/types.d.ts:140:5 - (ae-undocumented) Missing documentation for "secrets".
-// src/api/types.d.ts:141:5 - (ae-undocumented) Missing documentation for "directoryContents".
-// src/api/types.d.ts:147:1 - (ae-undocumented) Missing documentation for "ScaffolderDryRunResponse".
-// src/api/types.d.ts:148:5 - (ae-undocumented) Missing documentation for "directoryContents".
-// src/api/types.d.ts:153:5 - (ae-undocumented) Missing documentation for "log".
-// src/api/types.d.ts:154:5 - (ae-undocumented) Missing documentation for "steps".
-// src/api/types.d.ts:155:5 - (ae-undocumented) Missing documentation for "output".
-// src/api/types.d.ts:163:5 - (ae-undocumented) Missing documentation for "getTemplateParameterSchema".
-// src/api/types.d.ts:171:5 - (ae-undocumented) Missing documentation for "getTask".
-// src/api/types.d.ts:178:5 - (ae-undocumented) Missing documentation for "listTasks".
-// src/api/types.d.ts:183:5 - (ae-undocumented) Missing documentation for "getIntegrationsList".
-// src/api/types.d.ts:188:5 - (ae-undocumented) Missing documentation for "streamLogs".
-// src/api/types.d.ts:189:5 - (ae-undocumented) Missing documentation for "dryRun".
-// src/api/types.d.ts:190:5 - (ae-undocumented) Missing documentation for "autocomplete".
+// src/api/types.d.ts:133:5 - (ae-undocumented) Missing documentation for "isTaskRecoverable".
+// src/api/types.d.ts:134:5 - (ae-undocumented) Missing documentation for "taskId".
+// src/api/types.d.ts:135:5 - (ae-undocumented) Missing documentation for "after".
+// src/api/types.d.ts:138:1 - (ae-undocumented) Missing documentation for "ScaffolderDryRunOptions".
+// src/api/types.d.ts:139:5 - (ae-undocumented) Missing documentation for "template".
+// src/api/types.d.ts:140:5 - (ae-undocumented) Missing documentation for "values".
+// src/api/types.d.ts:141:5 - (ae-undocumented) Missing documentation for "secrets".
+// src/api/types.d.ts:142:5 - (ae-undocumented) Missing documentation for "directoryContents".
+// src/api/types.d.ts:148:1 - (ae-undocumented) Missing documentation for "ScaffolderDryRunResponse".
+// src/api/types.d.ts:149:5 - (ae-undocumented) Missing documentation for "directoryContents".
+// src/api/types.d.ts:154:5 - (ae-undocumented) Missing documentation for "log".
+// src/api/types.d.ts:155:5 - (ae-undocumented) Missing documentation for "steps".
+// src/api/types.d.ts:156:5 - (ae-undocumented) Missing documentation for "output".
+// src/api/types.d.ts:164:5 - (ae-undocumented) Missing documentation for "getTemplateParameterSchema".
+// src/api/types.d.ts:172:5 - (ae-undocumented) Missing documentation for "getTask".
+// src/api/types.d.ts:185:5 - (ae-undocumented) Missing documentation for "listTasks".
+// src/api/types.d.ts:190:5 - (ae-undocumented) Missing documentation for "getIntegrationsList".
+// src/api/types.d.ts:195:5 - (ae-undocumented) Missing documentation for "streamLogs".
+// src/api/types.d.ts:196:5 - (ae-undocumented) Missing documentation for "dryRun".
+// src/api/types.d.ts:197:5 - (ae-undocumented) Missing documentation for "autocomplete".
 // src/components/types.d.ts:7:1 - (ae-undocumented) Missing documentation for "TemplateGroupFilter".
 // src/extensions/types.d.ts:13:5 - (ae-undocumented) Missing documentation for "uiSchema".
 // src/extensions/types.d.ts:30:5 - (ae-undocumented) Missing documentation for ""ui:options"".
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/report-alpha.api.md b/plugins/scaffolder/report-alpha.api.md
index 051bfee955..4319362ef9 100644
--- a/plugins/scaffolder/report-alpha.api.md
+++ b/plugins/scaffolder/report-alpha.api.md
@@ -259,6 +259,7 @@ export const scaffolderTranslationRef: TranslationRef<
     readonly 'ongoingTask.title': 'Run of';
     readonly 'ongoingTask.contextMenu.cancel': 'Cancel';
     readonly 'ongoingTask.contextMenu.startOver': 'Start Over';
+    readonly 'ongoingTask.contextMenu.retry': 'Retry';
     readonly 'ongoingTask.contextMenu.hideLogs': 'Hide Logs';
     readonly 'ongoingTask.contextMenu.showLogs': 'Show Logs';
     readonly 'ongoingTask.contextMenu.hideButtonBar': 'Hide Button Bar';
@@ -267,6 +268,7 @@ export const scaffolderTranslationRef: TranslationRef<
     readonly 'ongoingTask.pageTitle.hasTemplateName': 'Run of {{templateName}}';
     readonly 'ongoingTask.pageTitle.noTemplateName': 'Scaffolder Run';
     readonly 'ongoingTask.cancelButtonTitle': 'Cancel';
+    readonly 'ongoingTask.retryButtonTitle': 'Retry';
     readonly 'ongoingTask.startOverButtonTitle': 'Start Over';
     readonly 'ongoingTask.hideLogsButtonTitle': 'Hide Logs';
     readonly 'ongoingTask.showLogsButtonTitle': 'Show Logs';
diff --git a/plugins/scaffolder/report.api.md b/plugins/scaffolder/report.api.md
index 1adaa8f167..b93a59a82c 100644
--- a/plugins/scaffolder/report.api.md
+++ b/plugins/scaffolder/report.api.md
@@ -556,6 +556,8 @@ export class ScaffolderClient implements ScaffolderApi_2 {
     tasks: ScaffolderTask_2[];
   }>;
   // (undocumented)
+  retry?(taskId: string): Promise<void>;
+  // (undocumented)
   scaffold(
     options: ScaffolderScaffoldOptions_2,
   ): Promise<ScaffolderScaffoldResponse_2>;
@@ -676,7 +678,8 @@ export const useTemplateSecrets: () => ScaffolderUseTemplateSecrets_2;
 // src/api.d.ts:33:5 - (ae-undocumented) Missing documentation for "dryRun".
 // src/api.d.ts:36:5 - (ae-undocumented) Missing documentation for "listActions".
 // src/api.d.ts:37:5 - (ae-undocumented) Missing documentation for "cancelTask".
-// src/api.d.ts:38:5 - (ae-undocumented) Missing documentation for "autocomplete".
+// src/api.d.ts:38:5 - (ae-undocumented) Missing documentation for "retry".
+// src/api.d.ts:39:5 - (ae-undocumented) Missing documentation for "autocomplete".
 // src/components/OngoingTask/OngoingTask.d.ts:6:22 - (ae-undocumented) Missing documentation for "OngoingTask".
 // src/components/fields/EntityPicker/schema.d.ts:15:22 - (ae-undocumented) Missing documentation for "EntityPickerFieldSchema".
 // src/components/fields/EntityTagsPicker/schema.d.ts:4:22 - (ae-undocumented) Missing documentation for "EntityTagsPickerFieldSchema".
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..f189a6a03c 100644
--- a/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx
+++ b/plugins/scaffolder/src/components/OngoingTask/ContextMenu.tsx
@@ -23,7 +23,8 @@ import Popover from '@material-ui/core/Popover';
 import { makeStyles, Theme, useTheme } from '@material-ui/core/styles';
 import { useAsync } from '@react-hookz/web';
 import Cancel from '@material-ui/icons/Cancel';
-import Retry from '@material-ui/icons/Repeat';
+import Repeat from '@material-ui/icons/Repeat';
+import Replay from '@material-ui/icons/Replay';
 import Toc from '@material-ui/icons/Toc';
 import ControlPointIcon from '@material-ui/icons/ControlPoint';
 import MoreVert from '@material-ui/icons/MoreVert';
@@ -41,8 +42,11 @@ import { scaffolderTranslationRef } from '../../translation';
 
 type ContextMenuProps = {
   cancelEnabled?: boolean;
+  canRetry: boolean;
+  isRetryableTask: boolean;
   logsVisible?: boolean;
   buttonBarVisible?: boolean;
+  onRetry?: () => void;
   onStartOver?: () => void;
   onToggleLogs?: (state: boolean) => void;
   onToggleButtonBar?: (state: boolean) => void;
@@ -58,8 +62,11 @@ const useStyles = makeStyles<Theme, { fontColor: string }>(() => ({
 export const ContextMenu = (props: ContextMenuProps) => {
   const {
     cancelEnabled,
+    canRetry,
+    isRetryableTask,
     logsVisible,
     buttonBarVisible,
+    onRetry,
     onStartOver,
     onToggleLogs,
     onToggleButtonBar,
@@ -147,10 +154,22 @@ export const ContextMenu = (props: ContextMenuProps) => {
             data-testid="start-over-task"
           >
             <ListItemIcon>
-              <Retry fontSize="small" />
+              <Repeat fontSize="small" />
             </ListItemIcon>
             <ListItemText primary={t('ongoingTask.contextMenu.startOver')} />
           </MenuItem>
+          {isRetryableTask && (
+            <MenuItem
+              onClick={onRetry}
+              disabled={cancelEnabled || !canRetry}
+              data-testid="retry-task"
+            >
+              <ListItemIcon>
+                <Replay fontSize="small" />
+              </ListItemIcon>
+              <ListItemText primary={t('ongoingTask.contextMenu.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..ffcc377995 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 +206,12 @@ export const OngoingTask = (props: {
       >
         <ContextMenu
           cancelEnabled={cancelEnabled}
+          canRetry={canRetry}
+          isRetryableTask={isRetryableTask}
           logsVisible={logsVisible}
           buttonBarVisible={buttonBarVisible}
           onStartOver={startOver}
+          onRetry={triggerRetry}
           onToggleLogs={setLogVisibleState}
           onToggleButtonBar={setButtonBarVisibleState}
           taskId={taskId}
@@ -229,7 +248,7 @@ export const OngoingTask = (props: {
                     className={classes.cancelButton}
                     disabled={
                       !cancelEnabled ||
-                      cancelStatus !== 'not-executed' ||
+                      (cancelStatus !== 'not-executed' && !isRetryableTask) ||
                       !canCancelTask
                     }
                     onClick={triggerCancel}
@@ -237,6 +256,16 @@ export const OngoingTask = (props: {
                   >
                     {t('ongoingTask.cancelButtonTitle')}
                   </Button>
+                  {isRetryableTask && (
+                    <Button
+                      className={classes.retryButton}
+                      disabled={cancelEnabled || !canRetry}
+                      onClick={triggerRetry}
+                      data-testid="retry-button"
+                    >
+                      {t('ongoingTask.retryButtonTitle')}
+                    </Button>
+                  )}
                   <Button
                     className={classes.logsVisibilityButton}
                     color="primary"
diff --git a/plugins/scaffolder/src/translation.ts b/plugins/scaffolder/src/translation.ts
index 99b9a69afa..ba39c80b7c 100644
--- a/plugins/scaffolder/src/translation.ts
+++ b/plugins/scaffolder/src/translation.ts
@@ -172,6 +172,7 @@ export const scaffolderTranslationRef = createTranslationRef({
       },
       subtitle: 'Task {{taskId}}',
       cancelButtonTitle: 'Cancel',
+      retryButtonTitle: 'Retry',
       startOverButtonTitle: 'Start Over',
       hideLogsButtonTitle: 'Hide Logs',
       showLogsButtonTitle: 'Show Logs',
@@ -179,6 +180,7 @@ export const scaffolderTranslationRef = createTranslationRef({
         hideLogs: 'Hide Logs',
         showLogs: 'Show Logs',
         hideButtonBar: 'Hide Button Bar',
+        retry: 'Retry',
         showButtonBar: 'Show Button Bar',
         startOver: 'Start Over',
         cancel: 'Cancel',