diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/NunjucksWorkflowRunner.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/NunjucksWorkflowRunner.ts
index 190c880280..d746cf859f 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/NunjucksWorkflowRunner.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/NunjucksWorkflowRunner.ts
@@ -26,7 +26,7 @@ import fs from 'fs-extra';
 import path from 'path';
 import nunjucks from 'nunjucks';
 import { JsonArray, JsonObject, JsonValue } from '@backstage/types';
-import { InputError, NotAllowedError } from '@backstage/errors';
+import { InputError, NotAllowedError, stringifyError } from '@backstage/errors';
 import { PassThrough } from 'stream';
 import { generateExampleOutput, isTruthy } from './helper';
 import { validate as validateJsonSchema } from 'jsonschema';
@@ -353,9 +353,22 @@ export class NunjucksWorkflowRunner implements WorkflowRunner {
             key: string,
             fn: () => Promise<U>,
           ) {
-            const value = await fn();
-            task.updateCheckpoint?.(key, value);
-            return value;
+            try {
+              const value = await fn();
+              task.updateCheckpoint?.({
+                key,
+                status: 'success',
+                value,
+              });
+              return value;
+            } catch (err) {
+              task.updateCheckpoint?.({
+                key,
+                status: 'failed',
+                reason: stringifyError(err),
+              });
+              throw err;
+            }
           },
           createTemporaryDirectory: async () => {
             const tmpDir = await fs.mkdtemp(
diff --git a/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts b/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
index 8762253436..01722edba9 100644
--- a/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
+++ b/plugins/scaffolder-backend/src/scaffolder/tasks/StorageTaskBroker.ts
@@ -16,7 +16,11 @@
 
 import { Config } from '@backstage/config';
 import { TaskSpec } from '@backstage/plugin-scaffolder-common';
-import { TaskSecrets, TaskState } from '@backstage/plugin-scaffolder-node';
+import {
+  TaskSecrets,
+  TaskState,
+  UpdateCheckpointOptions,
+} from '@backstage/plugin-scaffolder-node';
 import { JsonObject, Observable } from '@backstage/types';
 import { Logger } from 'winston';
 import ObservableImpl from 'zen-observable';
@@ -91,8 +95,12 @@ export class TaskManager implements TaskContext {
     });
   }
 
-  async updateCheckpoint?(key: string, value: JsonObject): Promise<void> {
-    this.task.state = { [key]: value };
+  async updateCheckpoint?(options: UpdateCheckpointOptions): Promise<void> {
+    if (this.task.state) {
+      this.task.state[options.key] = { ...options };
+    } else {
+      this.task.state = { [options.key]: options };
+    }
     await this.storage.saveCheckpoint?.({
       taskId: this.task.taskId,
       state: this.task.state,
diff --git a/plugins/scaffolder-backend/src/util/defineCheckpoint.ts b/plugins/scaffolder-backend/src/util/defineCheckpoint.ts
index 6656005684..c349bdc7f3 100644
--- a/plugins/scaffolder-backend/src/util/defineCheckpoint.ts
+++ b/plugins/scaffolder-backend/src/util/defineCheckpoint.ts
@@ -16,15 +16,11 @@
 
 import { JsonObject } from '@backstage/types';
 
-export type DefineCheckpointProps<U> = {
+export const defineCheckpoint = async <U extends JsonObject>(props: {
   checkpoint?: (key: string, fn: () => Promise<U>) => Promise<U>;
   key: string;
   fn: () => Promise<U>;
-};
-
-export const defineCheckpoint = async <U extends JsonObject>(
-  props: DefineCheckpointProps<U>,
-): Promise<U> => {
+}): Promise<U> => {
   const { checkpoint, fn, key } = props;
   return checkpoint
     ? checkpoint?.(key, async () => {
diff --git a/plugins/scaffolder-node/src/tasks/index.ts b/plugins/scaffolder-node/src/tasks/index.ts
index 99638e48af..4e66f1c0e3 100644
--- a/plugins/scaffolder-node/src/tasks/index.ts
+++ b/plugins/scaffolder-node/src/tasks/index.ts
@@ -26,4 +26,5 @@ export type {
   TaskEventType,
   TaskState,
   TaskStatus,
+  UpdateCheckpointOptions,
 } from './types';
diff --git a/plugins/scaffolder-node/src/tasks/types.ts b/plugins/scaffolder-node/src/tasks/types.ts
index 7136211671..f57353c917 100644
--- a/plugins/scaffolder-node/src/tasks/types.ts
+++ b/plugins/scaffolder-node/src/tasks/types.ts
@@ -31,7 +31,14 @@ export type TaskSecrets = Record<string, string> & {
  *
  * @public
  */
-export type TaskState = Record<string, JsonObject>;
+export type TaskState = {
+  [key: string]:
+    | { status: 'failed'; reason: string }
+    | {
+        status: 'success';
+        value: JsonObject;
+      };
+};
 
 /**
  * The status of each step of the Task
@@ -108,6 +115,24 @@ export type TaskBrokerDispatchOptions = {
   createdBy?: string;
 };
 
+/**
+ * The options passed to {@link TaskBroker.updateCheckpoint}
+ * Parameters to store the result of the executed checkpoint
+ *
+ * @public
+ */
+export type UpdateCheckpointOptions =
+  | {
+      key: string;
+      status: 'success';
+      value: JsonObject;
+    }
+  | {
+      key: string;
+      status: 'failed';
+      reason: string;
+    };
+
 /**
  * Task
  *
@@ -126,7 +151,7 @@ export interface TaskContext {
 
   emitLog(message: string, logMetadata?: JsonObject): Promise<void>;
 
-  updateCheckpoint?(key: string, value: JsonObject): Promise<void>;
+  updateCheckpoint?(options: UpdateCheckpointOptions): Promise<void>;
 
   getWorkspaceName(): Promise<string>;
 }