diff --git a/.env-transcribe-sample b/.env-transcribe-sample
index eb715fed33..f2cb7b28c2 100644
--- a/.env-transcribe-sample
+++ b/.env-transcribe-sample
@@ -18,6 +18,8 @@ HTR_CLI_IMAGES_FOLDER=
 QUEUE_DRIVER=pg
 # QUEUE_DRIVER=sqlite
 
+FILE_STORAGE_MAINTENANCE_INTERVAL=3600000
+FILE_STORAGE_TTL=604800000 # one week
 
 # =============================================================================
 # Queue driver
diff --git a/packages/transcribe/src/api/app.ts b/packages/transcribe/src/api/app.ts
index 04e1fb13c4..dd792b1231 100644
--- a/packages/transcribe/src/api/app.ts
+++ b/packages/transcribe/src/api/app.ts
@@ -29,13 +29,14 @@ const init = async (logger: LoggerWrapper) => {
 	const queue = await createQueue(envVariables, true);
 
 	const fileStorage = new FileStorage();
+	fileStorage.initMaintenance(envVariables.FILE_STORAGE_TTL, envVariables.FILE_STORAGE_MAINTENANCE_INTERVAL);
 
 	app.context.queue = queue;
 	app.context.storage = fileStorage;
 
 	const htrCli = new HtrCli(envVariables.HTR_CLI_DOCKER_IMAGE, envVariables.HTR_CLI_IMAGES_FOLDER);
 
-	const jobProcessor = new JobProcessor(queue, htrCli);
+	const jobProcessor = new JobProcessor(queue, htrCli, fileStorage);
 
 	logger.info('Starting worker');
 	await jobProcessor.init();
diff --git a/packages/transcribe/src/api/handler/createJob.test.ts b/packages/transcribe/src/api/handler/createJob.test.ts
index a37969ba9f..6a008f6d68 100644
--- a/packages/transcribe/src/api/handler/createJob.test.ts
+++ b/packages/transcribe/src/api/handler/createJob.test.ts
@@ -45,6 +45,7 @@ describe('createJob', () => {
 				filePath: 'file-id',
 			},
 			id: result.jobId,
+			retryCount: 0,
 		});
 	});
 
diff --git a/packages/transcribe/src/env.ts b/packages/transcribe/src/env.ts
index 5d147b64b0..fe43b79607 100644
--- a/packages/transcribe/src/env.ts
+++ b/packages/transcribe/src/env.ts
@@ -1,10 +1,11 @@
+import { Day, Hour, Minute, Second } from '@joplin/utils/time';
 
 export const defaultEnvValues: EnvVariables = {
 	SERVER_PORT: 4567,
 	API_KEY: '',
-	QUEUE_TTL: 900000,
+	QUEUE_TTL: 15 * Minute,
 	QUEUE_RETRY_COUNT: 2,
-	QUEUE_MAINTENANCE_INTERVAL: 60000,
+	QUEUE_MAINTENANCE_INTERVAL: 60 * Second,
 	HTR_CLI_DOCKER_IMAGE: 'joplin/htr-cli:0.0.2',
 	HTR_CLI_IMAGES_FOLDER: '',
 	QUEUE_DRIVER: 'pg', // 'sqlite'
@@ -12,6 +13,8 @@ export const defaultEnvValues: EnvVariables = {
 	QUEUE_DATABASE_NAME: '',
 	QUEUE_DATABASE_USER: '',
 	QUEUE_DATABASE_PORT: 5432,
+	FILE_STORAGE_MAINTENANCE_INTERVAL: 1 * Hour,
+	FILE_STORAGE_TTL: 7 * Day,
 	QUEUE_DATABASE_HOST: 'localhost',
 };
 
@@ -28,6 +31,8 @@ export interface EnvVariables {
 	QUEUE_DATABASE_NAME: string;
 	QUEUE_DATABASE_USER: string;
 	QUEUE_DATABASE_PORT: number;
+	FILE_STORAGE_MAINTENANCE_INTERVAL: number;
+	FILE_STORAGE_TTL: number;
 	QUEUE_DATABASE_HOST: string;
 }
 
diff --git a/packages/transcribe/src/services/FileStorage.test.ts b/packages/transcribe/src/services/FileStorage.test.ts
index 4802ec0e5e..25a9353230 100644
--- a/packages/transcribe/src/services/FileStorage.test.ts
+++ b/packages/transcribe/src/services/FileStorage.test.ts
@@ -1,9 +1,16 @@
-import { copyFile, exists, remove } from 'fs-extra';
+import { readdir, copyFile, exists, remove } from 'fs-extra';
 import { join } from 'path';
 import FileStorage from './FileStorage';
+import initiateLogger from './initiateLogger';
+import Logger from '@joplin/utils/Logger';
 
 describe('FileStorage', () => {
 
+	beforeAll(() => {
+		initiateLogger();
+		Logger.globalLogger.enabled = false;
+	});
+
 	it('should move file to storage folder', async () => {
 		await copyFile('./images/htr_sample.png', './test_file.png');
 
@@ -30,5 +37,26 @@ describe('FileStorage', () => {
 		await remove(join('images', name));
 	});
 
+	it('should remove files that are older than the given date', async () => {
+		const mockedFilenames = [
+			`${new Date('2025-03-01 17:44').getTime()}_should_delete`,
+			`${new Date('2025-03-02 17:44').getTime()}_should_delete`,
+			`${new Date('2025-03-04 17:44').getTime()}_not_deleted`,
+		];
+		const mockedFiles = mockedFilenames.map(name => join('images', name));
+		for (const file of mockedFiles) {
+			await copyFile('./images/htr_sample.png', file);
+		}
+
+		const fs = new FileStorage();
+		await fs.removeOldFiles(new Date('2025-03-03 12:00'));
+		const files = await readdir('images');
+		expect(files.length).toBe(2);
+		expect(files.includes(mockedFilenames[2])).toBe(true);
+
+		for (const file of mockedFiles) {
+			await remove(file);
+		}
+	});
 });
 
diff --git a/packages/transcribe/src/services/FileStorage.ts b/packages/transcribe/src/services/FileStorage.ts
index 7452851aa3..806ea3a194 100644
--- a/packages/transcribe/src/services/FileStorage.ts
+++ b/packages/transcribe/src/services/FileStorage.ts
@@ -1,13 +1,58 @@
 import { join } from 'path';
-import { move } from 'fs-extra';
+import { move, readdir, remove } from 'fs-extra';
 import { randomBytes } from 'crypto';
 import { ContentStorage } from '../types';
+import Logger from '@joplin/utils/Logger';
+
+const logger = Logger.create('FileStorage');
 
 export default class FileStorage implements ContentStorage {
 
+	private isMaintenanceRunning = false;
+
 	public async store(filepath: string) {
-		const randomName = randomBytes(16).toString('hex');
+		const time = new Date().getTime();
+		const random = randomBytes(16).toString('hex');
+		const randomName = `${time}_${random}`;
 		await move(filepath, join('images', randomName));
 		return randomName;
 	}
+
+	public async remove(filename: string) {
+		logger.info(`Deleting: ${filename}`);
+		await remove(join('images', filename));
+	}
+
+	public initMaintenance(retentionDuration: number, maintenanceInterval: number) {
+		logger.info('Maintenance started.');
+		setInterval(async () => {
+			if (this.isMaintenanceRunning) return;
+
+			this.isMaintenanceRunning = true;
+			const olderThan = new Date(new Date().getTime() - retentionDuration);
+			logger.info(`Deleting files older than: ${olderThan}`);
+			await this.removeOldFiles(olderThan);
+			this.isMaintenanceRunning = false;
+		}, maintenanceInterval);
+	}
+
+	public async removeOldFiles(olderThan: Date) {
+		const files = await readdir('images');
+		const filesToBeDeleted = files
+			.map(f => {
+				const datetimePart = parseInt(f.split('_')[0], 10);
+				return {
+					filepath: f,
+					timestamp: new Date(datetimePart),
+				};
+			})
+			.filter(f => {
+				return f.timestamp.getTime() < olderThan.getTime();
+			});
+
+		logger.info(`Files found to be deleted: ${filesToBeDeleted.length}`);
+		for (const file of filesToBeDeleted) {
+			await this.remove(file.filepath);
+		}
+	}
 }
diff --git a/packages/transcribe/src/services/queue/PgBossQueue.ts b/packages/transcribe/src/services/queue/PgBossQueue.ts
index 98b1db17ef..b43c31aff1 100644
--- a/packages/transcribe/src/services/queue/PgBossQueue.ts
+++ b/packages/transcribe/src/services/queue/PgBossQueue.ts
@@ -1,6 +1,6 @@
 import Logger from '@joplin/utils/Logger';
 import PgBoss = require('pg-boss');
-import { BaseQueue, JobData, JobWithResult, QueueConfiguration } from '../../types';
+import { BaseQueue, JobData, JobWithData, JobWithResult, QueueConfiguration } from '../../types';
 import { ErrorBadRequest } from '../../errors';
 import { Day, Minute, Second } from '@joplin/utils/time';
 
@@ -58,7 +58,7 @@ export default class PgBossQueue implements BaseQueue {
 	}
 
 	public async fetch() {
-		const jobs = await this.boss.fetch<JobData>(this.queue, { batchSize: 1 });
+		const jobs = await this.boss.fetch<JobData>(this.queue, { batchSize: 1, includeMetadata: true });
 		if (jobs.length === 0) return null;
 		return jobs[0];
 	}
@@ -80,6 +80,10 @@ export default class PgBossQueue implements BaseQueue {
 		return result as JobWithResult;
 	}
 
+	public hasJobFailedTooManyTimes(job: JobWithData): boolean {
+		return job.retryCount >= this.options.retryCount;
+	}
+
 	public async stop() {
 		return this.boss.stop();
 	}
diff --git a/packages/transcribe/src/services/queue/SqliteQueue.ts b/packages/transcribe/src/services/queue/SqliteQueue.ts
index 04d887c99b..3c0ad33a49 100644
--- a/packages/transcribe/src/services/queue/SqliteQueue.ts
+++ b/packages/transcribe/src/services/queue/SqliteQueue.ts
@@ -1,4 +1,4 @@
-import { BaseQueue, JobData, JobStates, jobStateToEnum, QueueConfiguration, Result } from '../../types';
+import { BaseQueue, JobData, JobStates, jobStateToEnum, JobWithData, QueueConfiguration, Result } from '../../types';
 import KnexConstructor, { Knex } from 'knex';
 import Logger from '@joplin/utils/Logger';
 import { formatMsToUTC, goBackInTime, Minute, msleep, Second } from '@joplin/utils/time';
@@ -101,7 +101,11 @@ export default class SqliteQueue implements BaseQueue {
 			updated_on: this.sqlite.fn.now(),
 		}).table('job').where({ id: job.id });
 
-		return { id: job.id, data: JSON.parse(job.data) };
+		return {
+			id: job.id,
+			retryCount: job.retry_count,
+			data: JSON.parse(job.data),
+		};
 	}
 
 	public async fail(jobId: string, error: Error) {
@@ -196,6 +200,10 @@ export default class SqliteQueue implements BaseQueue {
 		}
 	}
 
+	public hasJobFailedTooManyTimes(job: JobWithData): boolean {
+		return job.retryCount >= this.options.retryCount;
+	}
+
 	public async stop() {
 		if (this.maintenanceIntervalRef) {
 			clearInterval(this.maintenanceIntervalRef);
diff --git a/packages/transcribe/src/types.ts b/packages/transcribe/src/types.ts
index fbb3fa06ed..faad9ad8e3 100644
--- a/packages/transcribe/src/types.ts
+++ b/packages/transcribe/src/types.ts
@@ -47,10 +47,12 @@ export interface BaseQueue {
 	complete(jobId: string, data: Result): Promise<void>;
 	getJobById(id: string): Promise<JobWithResult>;
 	stop(): Promise<void>;
+	hasJobFailedTooManyTimes(job: JobWithData): boolean;
 }
 
 export interface ContentStorage {
 	store(filepath: string): Promise<string>;
+	remove(filepath: string): Promise<void>;
 }
 
 export type AppDefinedContext = {
@@ -62,6 +64,7 @@ export type AppContext = Context & AppDefinedContext;
 
 export type JobWithData = {
 	id: string;
+	retryCount: number;
 	data: JobData;
 };
 
diff --git a/packages/transcribe/src/workers/JobProcessor.test.ts b/packages/transcribe/src/workers/JobProcessor.test.ts
index d919eb4484..1bdbe76f77 100644
--- a/packages/transcribe/src/workers/JobProcessor.test.ts
+++ b/packages/transcribe/src/workers/JobProcessor.test.ts
@@ -5,6 +5,9 @@ import JobProcessor from './JobProcessor';
 import HtrCli from '../core/HtrCli';
 import { Minute, msleep, Second } from '@joplin/utils/time';
 import { BaseQueue, OutputSuccess } from '../types';
+import FileStorage from '../services/FileStorage';
+import { join } from 'path';
+import { copy, exists } from 'fs-extra';
 
 // since the model is not deterministic, it can, sometimes, output slightly difference responses
 const cleanUpResult = (result: string) => {
@@ -33,13 +36,14 @@ describe('JobProcessor', () => {
 
 	skipByDefault('should execute work on job in the queue', async () => {
 		jest.useRealTimers();
-		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', 'images'), 1000);
+		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', join(process.cwd(), 'images')), new FileStorage(), 1000);
 		await tw.init();
 
-		const jobId = await queue.send({ filePath: 'htr_sample.png' });
+		await copy(join('images', 'htr_sample.png'), join('images', 'htr_sample_copy.png'));
+		const jobId = await queue.send({ filePath: 'htr_sample_copy.png' });
 
-		for (let i = 0; i < 20; i++) {
-			await msleep(30 * Second);
+		for (let i = 0; i < 36; i++) {
+			await msleep(10 * Second);
 			const response = await queue.getJobById(jobId);
 
 			if (response.state === 'active') continue;
@@ -55,14 +59,15 @@ describe('JobProcessor', () => {
 
 	skipByDefault('should execute work on job in the queue even if one fails', async () => {
 		jest.useRealTimers();
-		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', 'images'), 1000);
+		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', join(process.cwd(), 'images')), new FileStorage(), 1000);
 		await tw.init();
+		await copy(join('images', 'htr_sample.png'), join('images', 'htr_sample_copy_2.png'));
 
 		const jobId1 = await queue.send({ filePath: 'non-existing-file' });
-		const jobId2 = await queue.send({ filePath: 'htr_sample.png' });
+		const jobId2 = await queue.send({ filePath: 'htr_sample_copy_2.png' });
 
-		for (let i = 0; i < 20; i++) {
-			await msleep(30 * Second);
+		for (let i = 0; i < 36; i++) {
+			await msleep(10 * Second);
 			const response1 = await queue.getJobById(jobId1);
 			if (response1.state === 'active') continue;
 			expect(response1.state).toEqual('failed');
@@ -76,4 +81,56 @@ describe('JobProcessor', () => {
 			return;
 		}
 	}, 6 * Minute);
+
+	skipIfCI('should remove file sent to queue if job is completed', async () => {
+		jest.useRealTimers();
+		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', join(process.cwd(), 'images')), new FileStorage(), 1000);
+		await tw.init();
+		const imagePath = join('images', 'htr_sample_copy_3.png');
+		await copy(join('images', 'htr_sample.png'), imagePath);
+
+		const jobId = await queue.send({ filePath: 'htr_sample_copy_3.png' });
+
+		for (let i = 0; i < 36; i++) {
+			await msleep(10 * Second);
+			const response = await queue.getJobById(jobId);
+
+			if (response.state === 'active') continue;
+
+			expect(response.id).toEqual(jobId);
+			expect(response.state).toEqual('completed');
+
+			const isFilePresent = await exists(imagePath);
+			expect(isFilePresent).toBe(false);
+			return;
+		}
+
+	}, 6 * Minute);
+
+	skipIfCI('should remove file sent to queue if job fails too many times', async () => {
+		jest.useRealTimers();
+		const fileStorage = new FileStorage();
+		const mockedFileStorageRemove = jest.fn();
+		fileStorage.remove = mockedFileStorageRemove;
+		const tw = new JobProcessor(queue, new HtrCli('joplin/htr-cli:0.0.2', join(process.cwd(), 'images')), fileStorage, 1000);
+		await tw.init();
+
+		// file doesn't exist to force a fail, but the call to remove the file should still exist
+		const jobId = await queue.send({ filePath: 'non_existing_file.png' });
+
+		for (let i = 0; i < 36; i++) {
+			await msleep(10 * Second);
+			const response = await queue.getJobById(jobId);
+
+			if (response.state === 'active') continue;
+
+			expect(response.id).toEqual(jobId);
+			expect(response.state).toEqual('failed');
+
+			expect(mockedFileStorageRemove).toHaveBeenCalledWith('non_existing_file.png');
+			return;
+		}
+
+	}, 6 * Minute);
+
 });
diff --git a/packages/transcribe/src/workers/JobProcessor.ts b/packages/transcribe/src/workers/JobProcessor.ts
index 5b19e291a2..f3bd6200b8 100644
--- a/packages/transcribe/src/workers/JobProcessor.ts
+++ b/packages/transcribe/src/workers/JobProcessor.ts
@@ -1,5 +1,5 @@
 import Logger from '@joplin/utils/Logger';
-import { BaseQueue, JobWithData, WorkHandler } from '../types';
+import { BaseQueue, ContentStorage, JobWithData, WorkHandler } from '../types';
 
 const logger = Logger.create('JobProcessor');
 
@@ -10,10 +10,12 @@ export default class JobProcessor {
 	private checkInteval = 5000;
 	private currentJob: JobWithData | null = null;
 	private workHandler: WorkHandler;
+	private contentStorage: ContentStorage;
 
-	public constructor(queue: BaseQueue, workHandler: WorkHandler, checkInterval?: number) {
+	public constructor(queue: BaseQueue, workHandler: WorkHandler, contentStorage: ContentStorage, checkInterval?: number) {
 		this.queue = queue;
 		this.workHandler = workHandler;
+		this.contentStorage = contentStorage;
 		this.checkInteval = checkInterval ?? 5000;
 		logger.info('Created JobProcessor');
 	}
@@ -48,6 +50,7 @@ export default class JobProcessor {
 		logger.info(`Processing job ${this.currentJob.id}`);
 		const transcription = await this.workHandler.run(this.currentJob.data.filePath);
 		await this.queue.complete(this.currentJob.id, { result: transcription });
+		await this.contentStorage.remove(this.currentJob.data.filePath);
 	}
 
 	public async runOnce() {
@@ -58,6 +61,9 @@ export default class JobProcessor {
 			const e = error as Error;
 			if (this.currentJob) {
 				await this.queue.fail(this.currentJob.id, e);
+				if (this.queue.hasJobFailedTooManyTimes(this.currentJob)) {
+					await this.contentStorage.remove(this.currentJob.data.filePath);
+				}
 			}
 		} finally {
 			this.currentJob = null;