diff --git a/backend/src/collections/image-db/image-file-db.service.ts b/backend/src/collections/image-db/image-file-db.service.ts
index a2680ff..f11e8c1 100644
--- a/backend/src/collections/image-db/image-file-db.service.ts
+++ b/backend/src/collections/image-db/image-file-db.service.ts
@@ -2,7 +2,7 @@ import { Injectable } from '@nestjs/common';
 import { InjectRepository } from '@nestjs/typeorm';
 import { ImageEntryVariant } from 'picsur-shared/dist/dto/image-entry-variant.enum';
 import { AsyncFailable, Fail, FT, HasFailed } from 'picsur-shared/dist/types';
-import { In, IsNull, LessThan, Repository } from 'typeorm';
+import { In, IsNull, LessThan, Not, Repository } from 'typeorm';
 import { v4 as uuidv4 } from 'uuid';
 import { EImageDerivativeBackend } from '../../database/entities/images/image-derivative.entity';
 import { EImageFileBackend } from '../../database/entities/images/image-file.entity';
@@ -236,7 +236,7 @@ export class ImageFileDBService {
     try {
       let remaining = Infinity;
       let processed = 0;
-      
+
       while (remaining > 0) {
         const orphaned = await repo.findAndCount({
           where: {
@@ -265,4 +265,38 @@ export class ImageFileDBService {
       return Fail(FT.Database, e);
     }
   }
+
+  public async migrateFilesToFilekey(): AsyncFailable<number> {
+    return this.migrateRepoToFilekey(this.imageFileRepo);
+  }
+
+  public async migrateDerivativesToFilekey(): AsyncFailable<number> {
+    return this.migrateRepoToFilekey(this.imageDerivativeRepo);
+  }
+
+  private async migrateRepoToFilekey(
+    repo: Repository<EImageFileBackend | EImageDerivativeBackend>,
+  ): AsyncFailable<number> {
+    let processed = 0;
+
+    try {
+      while (true) {
+        const current = await repo.findOne({
+          where: {
+            data: Not(IsNull()),
+          },
+        });
+        if (!current) break;
+
+        const result = await this.getFileData(current);
+        if (HasFailed(result)) return result;
+
+        processed++;
+      }
+    } catch (e) {
+      return Fail(FT.Database, e);
+    }
+
+    return processed;
+  }
 }
diff --git a/backend/src/managers/image/image-manager.module.ts b/backend/src/managers/image/image-manager.module.ts
index 38e026a..589ba7c 100644
--- a/backend/src/managers/image/image-manager.module.ts
+++ b/backend/src/managers/image/image-manager.module.ts
@@ -39,7 +39,7 @@ export class ImageManagerModule implements OnModuleInit {
     await this.cleanupDerivatives();
     await this.cleanupExpired();
     await this.cleanupOrphanedFiles();
-    // TODO: Auto migrate all images to S3
+    await this.migrateFilesToFilekey();
   }
 
   private async cleanupDerivatives() {
@@ -98,4 +98,24 @@ export class ImageManagerModule implements OnModuleInit {
         `Cleaned up ${cleanedUpDerivatives} orphaned derivatives and ${cleanedUpFiles} orphaned files`,
       );
   }
+
+  private async migrateFilesToFilekey() {
+    const filesMigrated = await this.imageFileDB.migrateFilesToFilekey();
+    if (HasFailed(filesMigrated)) {
+      filesMigrated.print(this.logger);
+      return;
+    }
+
+    const derivativesMigrated =
+      await this.imageFileDB.migrateDerivativesToFilekey();
+    if (HasFailed(derivativesMigrated)) {
+      derivativesMigrated.print(this.logger);
+      return;
+    }
+
+    if (filesMigrated > 0 || derivativesMigrated > 0)
+      this.logger.log(
+        `Migrated ${filesMigrated} files and ${derivativesMigrated} derivatives to filekey`,
+      );
+  }
 }