diff --git a/src/lib/indexedDB/filesystem.ts b/src/lib/indexedDB/filesystem.ts
index 293c16d..1c2c060 100644
--- a/src/lib/indexedDB/filesystem.ts
+++ b/src/lib/indexedDB/filesystem.ts
@@ -55,6 +55,10 @@ export const deleteDirectoryInfo = async (id: number) => {
   await filesystem.directory.delete(id);
 };
 
+export const getAllFileInfos = async () => {
+  return await filesystem.file.toArray();
+};
+
 export const getFileInfos = async (parentId: DirectoryId) => {
   return await filesystem.file.where({ parentId }).toArray();
 };
diff --git a/src/lib/server/db/file.ts b/src/lib/server/db/file.ts
index db450c7..c3169fc 100644
--- a/src/lib/server/db/file.ts
+++ b/src/lib/server/db/file.ts
@@ -341,6 +341,11 @@ export const getAllFilesByCategory = async (
   return files.map(({ file_id, depth }) => ({ id: file_id, isRecursive: depth > 0 }));
 };
 
+export const getAllFileIds = async (userId: number) => {
+  const files = await db.selectFrom("file").select("id").where("user_id", "=", userId).execute();
+  return files.map(({ id }) => id);
+};
+
 export const getAllFileIdsByContentHmac = async (
   userId: number,
   hskVersion: number,
diff --git a/src/lib/server/schemas/file.ts b/src/lib/server/schemas/file.ts
index 07fd943..8b9cfe9 100644
--- a/src/lib/server/schemas/file.ts
+++ b/src/lib/server/schemas/file.ts
@@ -42,6 +42,11 @@ export const fileThumbnailUploadRequest = z.object({
 });
 export type FileThumbnailUploadRequest = z.input<typeof fileThumbnailUploadRequest>;
 
+export const fileListResponse = z.object({
+  files: z.number().int().positive().array(),
+});
+export type FileListResponse = z.output<typeof fileListResponse>;
+
 export const duplicateFileScanRequest = z.object({
   hskVersion: z.number().int().positive(),
   contentHmac: z.string().base64().nonempty(),
diff --git a/src/lib/server/services/file.ts b/src/lib/server/services/file.ts
index 0e20676..ab98dbf 100644
--- a/src/lib/server/services/file.ts
+++ b/src/lib/server/services/file.ts
@@ -9,6 +9,7 @@ import { v4 as uuidv4 } from "uuid";
 import { IntegrityError } from "$lib/server/db/error";
 import {
   registerFile,
+  getAllFileIds,
   getAllFileIdsByContentHmac,
   getFile,
   setFileEncName,
@@ -148,6 +149,11 @@ export const uploadFileThumbnail = async (
   }
 };
 
+export const getFileList = async (userId: number) => {
+  const fileIds = await getAllFileIds(userId);
+  return { files: fileIds };
+};
+
 export const scanDuplicateFiles = async (
   userId: number,
   hskVersion: number,
diff --git a/src/lib/services/file.ts b/src/lib/services/file.ts
index 9ee6e1d..64d9fd4 100644
--- a/src/lib/services/file.ts
+++ b/src/lib/services/file.ts
@@ -1,14 +1,17 @@
 import { callGetApi } from "$lib/hooks";
+import { getAllFileInfos } from "$lib/indexedDB/filesystem";
 import { decryptData } from "$lib/modules/crypto";
 import {
   getFileCache,
   storeFileCache,
+  deleteFileCache,
   getFileThumbnailCache,
   storeFileThumbnailCache,
+  deleteFileThumbnailCache,
   downloadFile,
 } from "$lib/modules/file";
 import { getThumbnailUrl } from "$lib/modules/thumbnail";
-import type { FileThumbnailInfoResponse } from "$lib/server/schemas";
+import type { FileThumbnailInfoResponse, FileListResponse } from "$lib/server/schemas";
 
 export const requestFileDownload = async (
   fileId: number,
@@ -41,3 +44,18 @@ export const requestFileThumbnailDownload = async (fileId: number, dataKey: Cryp
   storeFileThumbnailCache(fileId, thumbnailBuffer); // Intended
   return getThumbnailUrl(thumbnailBuffer);
 };
+
+export const requestDeletedFilesCleanup = async () => {
+  const res = await callGetApi("/api/file/list");
+  if (!res.ok) return;
+
+  const { files: liveFiles }: FileListResponse = await res.json();
+  const liveFilesSet = new Set(liveFiles);
+  const maybeCachedFiles = await getAllFileInfos();
+
+  await Promise.all(
+    maybeCachedFiles
+      .filter(({ id }) => !liveFilesSet.has(id))
+      .flatMap(({ id }) => [deleteFileCache(id), deleteFileThumbnailCache(id)]),
+  );
+};
diff --git a/src/routes/(fullscreen)/auth/login/+page.svelte b/src/routes/(fullscreen)/auth/login/+page.svelte
index 0adfe98..813b130 100644
--- a/src/routes/(fullscreen)/auth/login/+page.svelte
+++ b/src/routes/(fullscreen)/auth/login/+page.svelte
@@ -9,6 +9,7 @@
     requestLogin,
     requestClientRegistrationAndSessionUpgrade,
     requestMasterKeyDownload,
+    requestDeletedFilesCleanup,
   } from "./service";
 
   let { data } = $props();
@@ -41,6 +42,7 @@
         $masterKeyStore ||
         (await requestMasterKeyDownload($clientKeyStore!.decryptKey, $clientKeyStore!.verifyKey))
       ) {
+        await requestDeletedFilesCleanup();
         await goto(data.redirectPath);
       } else {
         await redirect("/client/pending");
diff --git a/src/routes/(fullscreen)/auth/login/service.ts b/src/routes/(fullscreen)/auth/login/service.ts
index ada0f5f..88613f1 100644
--- a/src/routes/(fullscreen)/auth/login/service.ts
+++ b/src/routes/(fullscreen)/auth/login/service.ts
@@ -2,6 +2,7 @@ import { callPostApi } from "$lib/hooks";
 import type { LoginRequest } from "$lib/server/schemas";
 
 export { requestLogout } from "$lib/services/auth";
+export { requestDeletedFilesCleanup } from "$lib/services/file";
 export {
   requestClientRegistrationAndSessionUpgrade,
   requestMasterKeyDownload,
diff --git a/src/routes/(fullscreen)/key/generate/+page.svelte b/src/routes/(fullscreen)/key/generate/+page.svelte
index 141c085..090651f 100644
--- a/src/routes/(fullscreen)/key/generate/+page.svelte
+++ b/src/routes/(fullscreen)/key/generate/+page.svelte
@@ -15,6 +15,7 @@
     importClientKeys,
     requestClientRegistrationAndSessionUpgrade,
     requestInitialMasterKeyAndHmacSecretRegistration,
+    requestDeletedFilesCleanup,
   } from "./service";
 
   import IconKey from "~icons/material-symbols/key";
@@ -104,6 +105,7 @@
       return;
     }
 
+    await requestDeletedFilesCleanup();
     await goto("/client/pending?redirect=" + encodeURIComponent(data.redirectPath));
   };
 
diff --git a/src/routes/(fullscreen)/key/generate/service.ts b/src/routes/(fullscreen)/key/generate/service.ts
index 2faef15..1ba4a4c 100644
--- a/src/routes/(fullscreen)/key/generate/service.ts
+++ b/src/routes/(fullscreen)/key/generate/service.ts
@@ -15,6 +15,7 @@ import { deserializeClientKeys } from "$lib/modules/key";
 import { clientKeyStore } from "$lib/stores";
 
 export { requestLogout } from "$lib/services/auth";
+export { requestDeletedFilesCleanup } from "$lib/services/file";
 export {
   requestClientRegistrationAndSessionUpgrade,
   requestInitialMasterKeyAndHmacSecretRegistration,
diff --git a/src/routes/api/file/list/+server.ts b/src/routes/api/file/list/+server.ts
new file mode 100644
index 0000000..c1b6888
--- /dev/null
+++ b/src/routes/api/file/list/+server.ts
@@ -0,0 +1,11 @@
+import { json } from "@sveltejs/kit";
+import { authorize } from "$lib/server/modules/auth";
+import { fileListResponse, type FileListResponse } from "$lib/server/schemas";
+import { getFileList } from "$lib/server/services/file";
+import type { RequestHandler } from "./$types";
+
+export const GET: RequestHandler = async ({ locals }) => {
+  const { userId } = await authorize(locals, "activeClient");
+  const { files } = await getFileList(userId);
+  return json(fileListResponse.parse({ files } satisfies FileListResponse));
+};