diff --git a/dictation_function/src/test/common/context.ts b/dictation_function/src/test/common/context.ts
new file mode 100644
index 0000000..7d2f017
--- /dev/null
+++ b/dictation_function/src/test/common/context.ts
@@ -0,0 +1,16 @@
+import { InvocationContext } from "@azure/functions";
+
+export class TestInvocationContext extends InvocationContext {
+  contents: string[] = [];
+  getLogs(): string[] {
+    return this.contents;
+  }
+  log(...args: any[]): void {
+    super.log(args);
+    this.contents.push(args.toString());
+  }
+  error(...args: any[]): void {
+    super.error(args);
+    this.contents.push(args.toString());
+  }
+}
diff --git a/dictation_function/src/test/deleteAudioFiles.spec.ts b/dictation_function/src/test/deleteAudioFiles.spec.ts
index f165e4b..a6f2ad7 100644
--- a/dictation_function/src/test/deleteAudioFiles.spec.ts
+++ b/dictation_function/src/test/deleteAudioFiles.spec.ts
@@ -15,7 +15,7 @@ import {
   makeTestAccount,
   makeTestTask,
 } from "./common/utility";
-import { TASK_STATUS } from "../constants";
+import { MANUAL_RECOVERY_REQUIRED, TASK_STATUS } from "../constants";
 import { TestLogger } from "./common/logger";
 import { AudioFile } from "../entity/audio_file.entity";
 import { QueryDeepPartialEntity } from "typeorm/query-builder/QueryPartialEntity";
@@ -30,6 +30,7 @@ import {
   LicenseArchive,
 } from "../entity/license.entity";
 import { AudioOptionItem } from "../entity/audio_option_item.entity";
+import { TestInvocationContext } from "./common/context";
 
 describe("getProcessTargets | 削除対象を特定するQueryが正常に動作するか確認する", () => {
   let source: DataSource | null = null;
@@ -1493,4 +1494,136 @@ describe("deleteAudioFilesProcessing", () => {
       expect(optionItems.length).toEqual(4);
     }
   });
+
+  it("Blobの削除でエラーが発生した場合、アラーム発報用のログが出力される", async () => {
+    if (!source) fail();
+
+    // 2024/02/29 00:00:00を"今"とする
+    const now = new Date("2024-02-29T00:00:00Z");
+
+    const { account: account01, admin: admin01 } = await makeTestAccount(
+      source,
+      {
+        file_retention_days: 2,
+        auto_file_delete: true,
+      }
+    );
+
+    // 2日と1秒前(削除対象)のタスクを作成
+    const { file: file1 } = await makeTestTask(
+      source,
+      account01.id,
+      admin01.id,
+      "case03",
+      {
+        status: TASK_STATUS.FINISHED,
+        job_number: "job03",
+        finished_at: new Date("2024-02-26T23:59:59Z"),
+      }
+    );
+
+    const args: { accountId: number; fileName: string; country: string }[] = [];
+    const blobstorage = new AudioBlobStorageService();
+    Object.defineProperty(blobstorage, blobstorage.deleteFile.name, {
+      value: async (
+        context: InvocationContext,
+        accountId: number,
+        country: string,
+        fileName: string
+      ): Promise<void> => {
+        throw new Error(
+          `delete blob failed. succeeded: ${false}, errorCode: ${"ERROR_CODE"}, date: ${"DATE"}`
+        );
+      },
+      writable: true,
+    });
+
+    {
+      // DB全体のレコードを確認
+      const tasks = await getTasks(source);
+      expect(tasks.length).toEqual(1);
+      const files = await getAudioFiles(source);
+      expect(files.length).toEqual(1);
+      const optionItems = await getAudioOptionItems(source);
+      expect(optionItems.length).toEqual(2);
+    }
+
+    const context = new TestInvocationContext();
+    await deleteAudioFilesProcessing(context, source, blobstorage, now);
+
+    const log = context
+      .getLogs()
+      .find((log) => log.includes(MANUAL_RECOVERY_REQUIRED));
+    expect(log).toBeDefined();
+    expect(log).toEqual(
+      `[MANUAL_RECOVERY_REQUIRED] file delete failed. target={"id":"1","audio_file_id":"1","account_id":"1","country":"US","file_name":"testcase03.wav"}`
+    );
+  });
+
+  it("DBの削除でエラーが発生した場合、アラーム発報用のログが出力される", async () => {
+    if (!source) fail();
+
+    // 2024/02/29 00:00:00を"今"とする
+    const now = new Date("2024-02-29T00:00:00Z");
+
+    const { account: account01, admin: admin01 } = await makeTestAccount(
+      source,
+      {
+        file_retention_days: 2,
+        auto_file_delete: true,
+      }
+    );
+
+    // 2日と1秒前(削除対象)のタスクを作成
+    await makeTestTask(source, account01.id, admin01.id, "case03", {
+      status: TASK_STATUS.FINISHED,
+      job_number: "job03",
+      finished_at: new Date("2024-02-26T23:59:59Z"),
+    });
+
+    const args: { accountId: number; fileName: string; country: string }[] = [];
+    const blobstorage = new AudioBlobStorageService();
+    Object.defineProperty(blobstorage, blobstorage.deleteFile.name, {
+      value: async (
+        context: InvocationContext,
+        accountId: number,
+        country: string,
+        fileName: string
+      ): Promise<void> => {
+        args.push({ accountId, country, fileName });
+      },
+      writable: true,
+    });
+
+    {
+      // DB全体のレコードを確認
+      const tasks = await getTasks(source);
+      expect(tasks.length).toEqual(1);
+      const files = await getAudioFiles(source);
+      expect(files.length).toEqual(1);
+      const optionItems = await getAudioOptionItems(source);
+      expect(optionItems.length).toEqual(2);
+    }
+
+    Object.defineProperty(source, "transaction", {
+      value: async () => {
+        throw new Error("transaction error");
+      },
+      writable: true,
+    });
+
+    const context = new TestInvocationContext();
+
+    await expect(
+      deleteAudioFilesProcessing(context, source, blobstorage, now)
+    ).rejects.toThrow();
+
+    const log = context
+      .getLogs()
+      .find((log) => log.includes(MANUAL_RECOVERY_REQUIRED));
+    expect(log).toBeDefined();
+    expect(log).toEqual(
+      `[MANUAL_RECOVERY_REQUIRED] Failed to execute auto file deletion function. error=Error: transaction error`
+    );
+  });
 });