diff --git a/packages/data-schemas/src/methods/chatProject.spec.ts b/packages/data-schemas/src/methods/chatProject.spec.ts
index 53f283a5a0..f21a075665 100644
--- a/packages/data-schemas/src/methods/chatProject.spec.ts
+++ b/packages/data-schemas/src/methods/chatProject.spec.ts
@@ -2,7 +2,7 @@ import mongoose from 'mongoose';
 import { v4 as uuidv4 } from 'uuid';
 import { RetentionMode } from 'librechat-data-provider';
 import { MongoMemoryServer } from 'mongodb-memory-server';
-import type { IChatProject, IConversation, IMessage, ISharedLink } from '~/types';
+import type { IChatProject, IConversation, IMessage, IMongoFile, ISharedLink } from '~/types';
 import { createChatProjectMethods, type ChatProjectMethods } from './chatProject';
 import { createModels } from '~/models';
 
@@ -23,6 +23,7 @@ let ChatProject: mongoose.Model<IChatProject>;
 let Conversation: mongoose.Model<IConversation>;
 let Message: mongoose.Model<IMessage>;
 let SharedLink: mongoose.Model<ISharedLink>;
+let File: mongoose.Model<IMongoFile>;
 let methods: ChatProjectMethods;
 let modelsToCleanup: string[] = [];
 
@@ -38,6 +39,7 @@ beforeAll(async () => {
   Conversation = mongoose.models.Conversation as mongoose.Model<IConversation>;
   Message = mongoose.models.Message as mongoose.Model<IMessage>;
   SharedLink = mongoose.models.SharedLink as mongoose.Model<ISharedLink>;
+  File = mongoose.models.File as mongoose.Model<IMongoFile>;
   methods = createChatProjectMethods(mongoose);
 
   await mongoose.connect(mongoUri);
@@ -59,6 +61,7 @@ afterEach(async () => {
   await Conversation.deleteMany({});
   await Message.deleteMany({});
   await SharedLink.deleteMany({});
+  await File.deleteMany({});
 });
 
 async function createConversation(user: string, conversationId: string, title: string) {
@@ -304,7 +307,7 @@ describe('ChatProject methods', () => {
     expect(deleteResult.deletedCount).toBe(0);
   });
 
-  it('forces ephemeral retention on a permanent chat, its messages, and shares when assigning', async () => {
+  it('forces ephemeral retention on a permanent chat, its messages, shares, and files when assigning', async () => {
     const project = await methods.createChatProject(user, { name: 'Ephemeral' });
     await createConversation(user, 'convo-1', 'Permanent');
     await Message.create([
@@ -312,6 +315,13 @@ describe('ChatProject methods', () => {
       { messageId: uuidv4(), conversationId: 'convo-1', user, text: 'second' },
     ]);
     await SharedLink.create({ conversationId: 'convo-1', user, shareId: uuidv4() });
+    const fileId = uuidv4();
+    await File.collection.insertOne({
+      file_id: fileId,
+      conversationId: 'convo-1',
+      user: new mongoose.Types.ObjectId(),
+      expiredAt: null,
+    });
 
     const result = await methods.assignConversationToProject(
       user,
@@ -340,6 +350,9 @@ describe('ChatProject methods', () => {
 
     const share = await SharedLink.findOne({ user, conversationId: 'convo-1' }).lean<ISharedLink>();
     expect(share?.expiredAt).toBeInstanceOf(Date);
+
+    const file = await File.findOne({ file_id: fileId }).lean<IMongoFile>();
+    expect(file?.expiredAt).toBeInstanceOf(Date);
   });
 
   it('forces ephemeral retention when removing a chat from its project', async () => {
@@ -380,6 +393,13 @@ describe('ChatProject methods', () => {
     await methods.assignConversationToProject(user, 'convo-1', projectId);
     await methods.assignConversationToProject(user, 'convo-2', projectId);
     await Message.create({ messageId: uuidv4(), conversationId: 'convo-1', user, text: 'hi' });
+    const fileId = uuidv4();
+    await File.collection.insertOne({
+      file_id: fileId,
+      conversationId: 'convo-1',
+      user: new mongoose.Types.ObjectId(),
+      expiredAt: null,
+    });
 
     await methods.deleteChatProject(user, projectId, ephemeralConfig);
 
@@ -397,5 +417,8 @@ describe('ChatProject methods', () => {
     const message = await Message.findOne({ user, conversationId: 'convo-1' }).lean<IMessage>();
     expect(message?.isTemporary).toBe(true);
     expect(message?.expiredAt).toBeInstanceOf(Date);
+
+    const file = await File.findOne({ file_id: fileId }).lean<IMongoFile>();
+    expect(file?.expiredAt).toBeInstanceOf(Date);
   });
 });
diff --git a/packages/data-schemas/src/methods/chatProject.ts b/packages/data-schemas/src/methods/chatProject.ts
index 45772512d7..d2a98036c7 100644
--- a/packages/data-schemas/src/methods/chatProject.ts
+++ b/packages/data-schemas/src/methods/chatProject.ts
@@ -6,6 +6,7 @@ import type {
   IChatProjectDocument,
   IConversation,
   IMessage,
+  IMongoFile,
   ISharedLink,
 } from '~/types';
 import {
@@ -287,10 +288,12 @@ export function createChatProjectMethods(mongoose: typeof import('mongoose')): C
     const Conversation = mongoose.models.Conversation as Model<IConversation>;
     const Message = mongoose.models.Message as Model<IMessage>;
     const SharedLink = mongoose.models.SharedLink as Model<ISharedLink>;
+    const File = mongoose.models.File as Model<IMongoFile>;
     return cascadeForcedRetentionByProject(
       Conversation,
       Message,
       SharedLink,
+      File,
       user,
       chatProjectId,
       resolveForcedRetentionDate(interfaceConfig),
@@ -308,10 +311,12 @@ export function createChatProjectMethods(mongoose: typeof import('mongoose')): C
     const Conversation = mongoose.models.Conversation as Model<IConversation>;
     const Message = mongoose.models.Message as Model<IMessage>;
     const SharedLink = mongoose.models.SharedLink as Model<ISharedLink>;
+    const File = mongoose.models.File as Model<IMongoFile>;
     return cascadeForcedConversationRetention(
       Conversation,
       Message,
       SharedLink,
+      File,
       user,
       conversationId,
       resolveForcedRetentionDate(interfaceConfig),
diff --git a/packages/data-schemas/src/methods/message.ts b/packages/data-schemas/src/methods/message.ts
index c666b818cc..f2ec44b0df 100644
--- a/packages/data-schemas/src/methods/message.ts
+++ b/packages/data-schemas/src/methods/message.ts
@@ -1,6 +1,6 @@
 import { RetentionMode, isForcedTemporaryRetention } from 'librechat-data-provider';
 import type { DeleteResult, FilterQuery, Model } from 'mongoose';
-import type { AppConfig, IConversation, IMessage, ISharedLink } from '~/types';
+import type { AppConfig, IConversation, IMessage, IMongoFile, ISharedLink } from '~/types';
 import {
   capForcedRetentionExpiry,
   capForcedRetentionToParent,
@@ -213,10 +213,12 @@ export function createMessageMethods(mongoose: typeof import('mongoose')): Messa
       if (isForcedRetention && cascadeExpiredAt instanceof Date) {
         const Conversation = mongoose.models.Conversation as Model<IConversation>;
         const SharedLink = mongoose.models.SharedLink as Model<ISharedLink>;
+        const File = mongoose.models.File as Model<IMongoFile>;
         await cascadeForcedConversationRetention(
           Conversation,
           Message,
           SharedLink,
+          File,
           userId,
           conversationId,
           cascadeExpiredAt,
@@ -409,6 +411,7 @@ export function createMessageMethods(mongoose: typeof import('mongoose')): Messa
     const Message = mongoose.models.Message as Model<IMessage>;
     const Conversation = mongoose.models.Conversation as Model<IConversation>;
     const SharedLink = mongoose.models.SharedLink as Model<ISharedLink>;
+    const File = mongoose.models.File as Model<IMongoFile>;
 
     if (metadata?.capExpiryToConversation === true) {
       forcedExpiredAt = await capForcedRetentionToParent(
@@ -435,6 +438,7 @@ export function createMessageMethods(mongoose: typeof import('mongoose')): Messa
       Conversation,
       Message,
       SharedLink,
+      File,
       userId,
       conversationId,
       forcedExpiredAt,
@@ -475,11 +479,13 @@ export function createMessageMethods(mongoose: typeof import('mongoose')): Messa
     const Message = mongoose.models.Message as Model<IMessage>;
     const Conversation = mongoose.models.Conversation as Model<IConversation>;
     const SharedLink = mongoose.models.SharedLink as Model<ISharedLink>;
+    const File = mongoose.models.File as Model<IMongoFile>;
 
     await cascadeForcedRetentionByTag(
       Conversation,
       Message,
       SharedLink,
+      File,
       userId,
       tag,
       forcedExpiredAt,
diff --git a/packages/data-schemas/src/utils/retention.ts b/packages/data-schemas/src/utils/retention.ts
index 946d6244f6..76d2562a5c 100644
--- a/packages/data-schemas/src/utils/retention.ts
+++ b/packages/data-schemas/src/utils/retention.ts
@@ -219,14 +219,15 @@ export const capForcedRetentionToParent = async (
 
 /**
  * Converts or re-caps a parent conversation to the forced deadline and, when that first
- * brings the conversation into the forced window, backfills its lagging messages. Shared
- * by every forced-retention message-write path so a single conversation/message rule is
- * enforced regardless of which save touched the chat.
+ * brings the conversation into the forced window, backfills its lagging messages, shares, and
+ * files. Shared by every forced-retention message-write path so a single conversation/message
+ * rule is enforced regardless of which save touched the chat.
  */
 export const cascadeForcedConversationRetention = async (
   Conversation: Model<IConversation>,
   Message: Model<IMessage>,
   SharedLink: Model<ISharedLink>,
+  File: Model<IMongoFile>,
   userId: string,
   conversationId: string,
   forcedExpiredAt: Date,
@@ -243,6 +244,7 @@ export const cascadeForcedConversationRetention = async (
   if (convoResult.modifiedCount > 0) {
     await forceConversationMessagesTemporary(Message, userId, conversationId, expiredAt);
     await capConversationSharedLinks(SharedLink, userId, conversationId, expiredAt);
+    await capConversationFiles(File, conversationId, expiredAt);
   }
 };
 
@@ -252,13 +254,14 @@ export const cascadeForcedConversationRetention = async (
  * (`Conversation.updateMany`) without setting `isTemporary`/`expiredAt` would otherwise leave a
  * permanent chat visible and non-expiring after an install switched to ephemeral. Chats are
  * bucketed by their capped deadline so each bucket converts the chats, backfills their messages,
- * and caps their shares in one pass; the gap filter keeps it a no-op for chats that already
- * conform and never extends a chat that already expires sooner.
+ * and caps their shares and files in one pass; the gap filter keeps it a no-op for chats that
+ * already conform and never extends a chat that already expires sooner.
  */
 const cascadeForcedRetentionForConversationSet = async (
   Conversation: Model<IConversation>,
   Message: Model<IMessage>,
   SharedLink: Model<ISharedLink>,
+  File: Model<IMongoFile>,
   userId: string,
   conversationMatch: FilterQuery<IConversation>,
   forcedExpiredAt: Date,
@@ -319,6 +322,13 @@ const cascadeForcedRetentionForConversationSet = async (
       },
       { $set: { expiredAt } },
     );
+    await File.updateMany(
+      {
+        conversationId: { $in: conversationIds },
+        $or: [{ expiredAt: null }, { expiredAt: { $gt: expiredAt } }],
+      },
+      { $set: { expiredAt } },
+    );
   }
 };
 
@@ -332,6 +342,7 @@ export const cascadeForcedRetentionByTag = (
   Conversation: Model<IConversation>,
   Message: Model<IMessage>,
   SharedLink: Model<ISharedLink>,
+  File: Model<IMongoFile>,
   userId: string,
   tag: string,
   forcedExpiredAt: Date,
@@ -340,6 +351,7 @@ export const cascadeForcedRetentionByTag = (
     Conversation,
     Message,
     SharedLink,
+    File,
     userId,
     { tags: tag } as FilterQuery<IConversation>,
     forcedExpiredAt,
@@ -355,6 +367,7 @@ export const cascadeForcedRetentionByProject = (
   Conversation: Model<IConversation>,
   Message: Model<IMessage>,
   SharedLink: Model<ISharedLink>,
+  File: Model<IMongoFile>,
   userId: string,
   chatProjectId: string,
   forcedExpiredAt: Date,
@@ -363,6 +376,7 @@ export const cascadeForcedRetentionByProject = (
     Conversation,
     Message,
     SharedLink,
+    File,
     userId,
     { chatProjectId } as FilterQuery<IConversation>,
     forcedExpiredAt,