diff --git a/dictation_server/src/features/tasks/tasks.service.spec.ts b/dictation_server/src/features/tasks/tasks.service.spec.ts
index 3eaef7d..c74de6b 100644
--- a/dictation_server/src/features/tasks/tasks.service.spec.ts
+++ b/dictation_server/src/features/tasks/tasks.service.spec.ts
@@ -1421,12 +1421,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがTypistで、タスクのチェックアウト権限が個人指定である時、タスクをチェックアウトできる', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: typistUserId } = await makeTestUser(source, {
@@ -1486,12 +1481,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがTypistで、タスクのチェックアウト権限がグループ指定である時、タスクをチェックアウトできる', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: typistUserId } = await makeTestUser(source, {
@@ -1551,12 +1541,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがTypistで、タスクのステータスがPendingである時、タスクをチェックアウトできる', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: typistUserId } = await makeTestUser(source, {
@@ -1610,12 +1595,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがTypistで、対象のタスクのStatus[Uploaded,Inprogress,Pending]以外の時、タスクをチェックアウトできない', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     await makeTestUser(source, {
@@ -1642,26 +1622,27 @@ describe('checkout', () => {
     );
 
     const service = module.get<TasksService>(TasksService);
-    await expect(
-      service.checkout(
+    try {
+      await service.checkout(
         makeContext('trackingId'),
         1,
         ['typist'],
         'typist-user-external-id',
-      ),
-    ).rejects.toEqual(
-      new HttpException(makeErrorResponse('E010601'), HttpStatus.BAD_REQUEST),
-    );
+      );
+      fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.BAD_REQUEST);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010601'));
+      } else {
+        fail();
+      }
+    }
   });
 
   it('ユーザーのRoleがTypistで、チェックアウト権限が存在しない時、タスクをチェックアウトできない', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     await makeTestUser(source, {
@@ -1688,26 +1669,153 @@ describe('checkout', () => {
     );
 
     const service = module.get<TasksService>(TasksService);
-    await expect(
-      service.checkout(
+    try {
+      await service.checkout(
         makeContext('trackingId'),
         1,
         ['typist'],
         'typist-user-external-id',
-      ),
-    ).rejects.toEqual(
-      new HttpException(makeErrorResponse('E010602'), HttpStatus.BAD_REQUEST),
+      );
+      fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.BAD_REQUEST);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010602'));
+      } else {
+        fail();
+      }
+    }
+  });
+
+  it('ユーザーのRoleがTypistで、既にチェックアウト中のタスク（InProgress）がある時、タスクをチェックアウトできない', async () => {
+    if (!source) fail();
+    const module = await makeTestingModule(source);
+    if (!module) fail();
+    const { id: accountId } = await makeTestSimpleAccount(source);
+    const { id: typistUserId } = await makeTestUser(source, {
+      account_id: accountId,
+      external_id: 'typist-user-external-id',
+      role: 'typist',
+    });
+    const { id: authorUserId } = await makeTestUser(source, {
+      account_id: accountId,
+      external_id: 'author-user-external-id',
+      role: 'author',
+      author_id: 'MY_AUTHOR_ID',
+    });
+
+    await createTask(
+      source,
+      accountId,
+      authorUserId,
+      'MY_AUTHOR_ID',
+      '',
+      '01',
+      '00000001',
+      TASK_STATUS.IN_PROGRESS,
+      typistUserId,
     );
+    const { taskId, audioFileId } = await createTask(
+      source,
+      accountId,
+      authorUserId,
+      'MY_AUTHOR_ID',
+      '',
+      '01',
+      '00000002',
+      TASK_STATUS.UPLOADED,
+    );
+
+    await createCheckoutPermissions(source, taskId, typistUserId);
+
+    const service = module.get<TasksService>(TasksService);
+
+    try {
+      await service.checkout(
+        makeContext('trackingId'),
+        audioFileId,
+        ['typist'],
+        'typist-user-external-id',
+      );
+      fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.BAD_REQUEST);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010601'));
+      } else {
+        fail();
+      }
+    }
+  });
+
+  it('ユーザーのRoleがTypistで、別ユーザーによってチェックアウト中のタスク（InProgress）がある時、タスクをチェックアウトできる', async () => {
+    if (!source) fail();
+    const module = await makeTestingModule(source);
+    if (!module) fail();
+    const { id: accountId } = await makeTestSimpleAccount(source);
+    const { id: typistUserId1 } = await makeTestUser(source, {
+      account_id: accountId,
+      external_id: 'typist-user-external-id1',
+      role: 'typist',
+    });
+    const { id: typistUserId2 } = await makeTestUser(source, {
+      account_id: accountId,
+      external_id: 'typist-user-external-id2',
+      role: 'typist',
+    });
+    const { id: authorUserId } = await makeTestUser(source, {
+      account_id: accountId,
+      external_id: 'author-user-external-id',
+      role: 'author',
+      author_id: 'MY_AUTHOR_ID',
+    });
+
+    await createTask(
+      source,
+      accountId,
+      authorUserId,
+      'MY_AUTHOR_ID',
+      '',
+      '01',
+      '00000001',
+      TASK_STATUS.IN_PROGRESS,
+      typistUserId1,
+    );
+    const { taskId } = await createTask(
+      source,
+      accountId,
+      authorUserId,
+      'MY_AUTHOR_ID',
+      '',
+      '01',
+      '00000002',
+      TASK_STATUS.UPLOADED,
+    );
+
+    await createCheckoutPermissions(source, taskId, typistUserId2);
+
+    const service = module.get<TasksService>(TasksService);
+
+    await service.checkout(
+      makeContext('trackingId'),
+      2,
+      ['typist'],
+      'typist-user-external-id2',
+    );
+
+    const resultTask = await getTask(source, taskId);
+    const permisions = await getCheckoutPermissions(source, taskId);
+
+    expect(resultTask?.status).toEqual(TASK_STATUS.IN_PROGRESS);
+    expect(resultTask?.typist_user_id).toEqual(typistUserId2);
+    expect(permisions.length).toBe(1);
+    expect(permisions[0].task_id).toBe(taskId);
+    expect(permisions[0].user_id).toBe(typistUserId2);
   });
 
   it('ユーザーのRoleがAuthorで、アップロードした音声ファイルに紐づいたタスクをチェックアウトできる(Uploaded)', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: authorUserId } = await makeTestUser(source, {
@@ -1740,12 +1848,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがAuthorで、アップロードした音声ファイルに紐づいたタスクをチェックアウトできる(Finished)', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: authorUserId } = await makeTestUser(source, {
@@ -1766,6 +1869,7 @@ describe('checkout', () => {
     );
 
     const service = module.get<TasksService>(TasksService);
+
     expect(
       await service.checkout(
         makeContext('trackingId'),
@@ -1778,12 +1882,7 @@ describe('checkout', () => {
 
   it('ユーザーのRoleがAuthorで、アップロードした音声ファイルに紐づいたタスクが存在しない場合、タスクをチェックアウトできない', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     await makeTestUser(source, {
@@ -1794,26 +1893,27 @@ describe('checkout', () => {
     });
 
     const service = module.get<TasksService>(TasksService);
-    await expect(
-      service.checkout(
+    try {
+      await service.checkout(
         makeContext('trackingId'),
         1,
         ['author'],
         'author-user-external-id',
       ),
-    ).rejects.toEqual(
-      new HttpException(makeErrorResponse('E010601'), HttpStatus.BAD_REQUEST),
-    );
+        fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.NOT_FOUND);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010601'));
+      } else {
+        fail();
+      }
+    }
   });
 
   it('ユーザーのRoleがAuthorで、音声ファイルに紐づいたタスクでユーザーと一致するAuthorIDでない場合、タスクをチェックアウトできない', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     const { id: authorUserId } = await makeTestUser(source, {
@@ -1834,26 +1934,27 @@ describe('checkout', () => {
     );
 
     const service = module.get<TasksService>(TasksService);
-    await expect(
-      service.checkout(
+    try {
+      await service.checkout(
         makeContext('trackingId'),
         1,
         ['author'],
         'author-user-external-id',
-      ),
-    ).rejects.toEqual(
-      new HttpException(makeErrorResponse('E010602'), HttpStatus.BAD_REQUEST),
-    );
+      );
+      fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.BAD_REQUEST);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010602'));
+      } else {
+        fail();
+      }
+    }
   });
 
   it('ユーザーのRoleに[Typist,author]が設定されていない時、タスクをチェックアウトできない', async () => {
     if (!source) fail();
-    const notificationhubServiceMockValue =
-      makeDefaultNotificationhubServiceMockValue();
-    const module = await makeTaskTestingModuleWithNotificaiton(
-      source,
-      notificationhubServiceMockValue,
-    );
+    const module = await makeTestingModule(source);
     if (!module) fail();
     const { id: accountId } = await makeTestSimpleAccount(source);
     await makeTestUser(source, {
@@ -1864,16 +1965,22 @@ describe('checkout', () => {
     });
 
     const service = module.get<TasksService>(TasksService);
-    await expect(
-      service.checkout(
+    try {
+      await service.checkout(
         makeContext('trackingId'),
         1,
         ['none'],
         'none-user-external-id',
-      ),
-    ).rejects.toEqual(
-      new HttpException(makeErrorResponse('E010602'), HttpStatus.BAD_REQUEST),
-    );
+      );
+      fail();
+    } catch (e) {
+      if (e instanceof HttpException) {
+        expect(e.getStatus()).toBe(HttpStatus.BAD_REQUEST);
+        expect(e.getResponse()).toEqual(makeErrorResponse('E010602'));
+      } else {
+        fail();
+      }
+    }
   });
 });
 
diff --git a/dictation_server/src/features/tasks/tasks.service.ts b/dictation_server/src/features/tasks/tasks.service.ts
index ccd1f9d..408f7ef 100644
--- a/dictation_server/src/features/tasks/tasks.service.ts
+++ b/dictation_server/src/features/tasks/tasks.service.ts
@@ -19,6 +19,7 @@ import { AdB2cUser } from '../../gateways/adb2c/types/types';
 import { CheckoutPermission } from '../../repositories/checkout_permissions/entity/checkout_permission.entity';
 import {
   AccountNotMatchError,
+  AlreadyHasInProgressTaskError,
   CheckoutPermissionNotFoundError,
   StatusNotMatchError,
   TaskAuthorIdNotMatchError,
@@ -295,6 +296,7 @@ export class TasksService {
             );
           case AccountNotMatchError:
           case StatusNotMatchError:
+          case AlreadyHasInProgressTaskError:
             throw new HttpException(
               makeErrorResponse('E010601'),
               HttpStatus.BAD_REQUEST,
diff --git a/dictation_server/src/repositories/tasks/errors/types.ts b/dictation_server/src/repositories/tasks/errors/types.ts
index 3d2b2d4..b82c3ed 100644
--- a/dictation_server/src/repositories/tasks/errors/types.ts
+++ b/dictation_server/src/repositories/tasks/errors/types.ts
@@ -14,3 +14,5 @@ export class StatusNotMatchError extends Error {}
 export class TypistUserNotMatchError extends Error {}
 // Account不一致エラー
 export class AccountNotMatchError extends Error {}
+// タスクチェックアウト済みエラー
+export class AlreadyHasInProgressTaskError extends Error {}
diff --git a/dictation_server/src/repositories/tasks/tasks.repository.service.ts b/dictation_server/src/repositories/tasks/tasks.repository.service.ts
index 0c8b4cc..784dcec 100644
--- a/dictation_server/src/repositories/tasks/tasks.repository.service.ts
+++ b/dictation_server/src/repositories/tasks/tasks.repository.service.ts
@@ -6,6 +6,7 @@ import {
   FindOptionsOrderValue,
   In,
   IsNull,
+  Not,
   Repository,
 } from 'typeorm';
 import { Task } from './entity/task.entity';
@@ -26,6 +27,7 @@ import { UserGroup } from '../user_groups/entity/user_group.entity';
 import { User } from '../users/entity/user.entity';
 import {
   AccountNotMatchError,
+  AlreadyHasInProgressTaskError,
   CheckoutPermissionNotFoundError,
   StatusNotMatchError,
   TaskAuthorIdNotMatchError,
@@ -163,6 +165,24 @@ export class TasksRepositoryService {
           `task not found. audio_file_id:${audio_file_id}`,
         );
       }
+
+      // 指定したタスク以外に実行ユーザー担当のInprogressのタスクが存在する場合はエラー
+      const tasks = await taskRepo.find({
+        where: {
+          audio_file_id: Not(audio_file_id),
+          status: TASK_STATUS.IN_PROGRESS,
+          typist_user_id: user_id,
+        },
+      });
+
+      if (tasks.length > 0) {
+        throw new AlreadyHasInProgressTaskError(
+          `checkout task already exists. task:${tasks.map(
+            (x) => x.audio_file_id,
+          )}`,
+        );
+      }
+
       // アカウントチェック
       if (task.account_id !== account_id) {
         throw new AccountNotMatchError(