diff --git a/server/src/services/asset-media.service.spec.ts b/server/src/services/asset-media.service.spec.ts
index 2e6a5b36ba..5a9a85f179 100644
--- a/server/src/services/asset-media.service.spec.ts
+++ b/server/src/services/asset-media.service.spec.ts
@@ -269,6 +269,10 @@ describe(AssetMediaService.name, () => {
         'random-uuid.jpg',
       );
     });
+
+    it('should accept filenames with just an extension', () => {
+      expect(sut.getUploadFilename(uploadFile.filename(UploadFieldName.ASSET_DATA, '.jpg'))).toEqual('random-uuid.jpg');
+    });
   });
 
   describe('getUploadFolder', () => {
diff --git a/server/src/services/asset-media.service.ts b/server/src/services/asset-media.service.ts
index 1da5146d91..077bff3db2 100644
--- a/server/src/services/asset-media.service.ts
+++ b/server/src/services/asset-media.service.ts
@@ -1,5 +1,4 @@
 import { BadRequestException, Injectable, InternalServerErrorException, NotFoundException } from '@nestjs/common';
-import { extname } from 'node:path';
 import sanitize from 'sanitize-filename';
 import { StorageCore } from 'src/cores/storage.core';
 import { AuthSharedLink } from 'src/database';
@@ -92,8 +91,7 @@ export class AssetMediaService extends BaseService {
   getUploadFilename({ auth, fieldName, file, body }: UploadRequest): string {
     requireUploadAccess(auth);
 
-    const extension = extname(body.filename || file.originalName);
-
+    const extension = getFilenameExtension(body.filename || file.originalName);
     const lookup = {
       [UploadFieldName.ASSET_DATA]: extension,
       [UploadFieldName.SIDECAR_DATA]: '.xmp',
diff --git a/server/src/services/storage-template.service.ts b/server/src/services/storage-template.service.ts
index ae857870af..e4f2dcacf7 100644
--- a/server/src/services/storage-template.service.ts
+++ b/server/src/services/storage-template.service.ts
@@ -20,7 +20,7 @@ import { ArgOf } from 'src/repositories/event.repository';
 import { BaseService } from 'src/services/base.service';
 import { JobOf, StorageAsset } from 'src/types';
 import { getAssetFile } from 'src/utils/asset.util';
-import { getLivePhotoMotionFilename } from 'src/utils/file';
+import { getFilenameExtension, getLivePhotoMotionFilename } from 'src/utils/file';
 
 const storageTokens = {
   secondOptions: ['s', 'ss', 'SSS'],
@@ -267,10 +267,10 @@ export class StorageTemplateService extends BaseService {
     const { storageLabel, filename } = metadata;
 
     try {
-      const filenameWithoutExtension = path.basename(filename, path.extname(filename));
+      const filenameWithoutExtension = path.basename(filename, getFilenameExtension(filename));
 
       const source = asset.originalPath;
-      let extension = path.extname(source).split('.').pop() as string;
+      let extension = getFilenameExtension(source).split('.').pop() as string;
       const sanitized = sanitize(path.basename(filenameWithoutExtension, `.${extension}`));
       extension = extension?.toLowerCase();
       const rootPath = StorageCore.getLibraryFolder({ id: asset.ownerId, storageLabel });
diff --git a/server/src/utils/file.ts b/server/src/utils/file.ts
index c77f7bb7a7..24d555f2fe 100644
--- a/server/src/utils/file.ts
+++ b/server/src/utils/file.ts
@@ -9,15 +9,19 @@ import { ImmichReadStream } from 'src/repositories/storage.repository';
 import { isConnectionAborted } from 'src/utils/misc';
 
 export function getFileNameWithoutExtension(path: string): string {
-  return basename(path, extname(path));
+  return basename(path, getFilenameExtension(path));
 }
 
-export function getFilenameExtension(path: string): string {
-  return extname(path);
+export function getFilenameExtension(path: string) {
+  const extension = extname(path);
+  if (!extension && path.startsWith('.') && !path.includes('.', 1)) {
+    return path;
+  }
+  return extension;
 }
 
 export function getLivePhotoMotionFilename(stillName: string, motionName: string) {
-  return getFileNameWithoutExtension(stillName) + extname(motionName);
+  return getFileNameWithoutExtension(stillName) + getFilenameExtension(motionName);
 }
 
 export class ImmichFileResponse {
diff --git a/server/src/utils/mime-types.ts b/server/src/utils/mime-types.ts
index 43e7f0565a..327cf5d73c 100644
--- a/server/src/utils/mime-types.ts
+++ b/server/src/utils/mime-types.ts
@@ -1,5 +1,5 @@
-import { extname } from 'node:path';
 import { AssetType } from 'src/enum';
+import { getFilenameExtension } from 'src/utils/file';
 
 const raw = {
   '.3fr': ['image/3fr', 'image/x-hasselblad-3fr'],
@@ -132,10 +132,12 @@ const sidecar: Record<string, string[]> = {
 
 const types = { ...image, ...video, ...sidecar };
 
-const isType = (filename: string, record: Record<string, string[]>) =>
-  Object.hasOwn(record, extname(filename).toLowerCase());
+const isType = (filename: string, r: Record<string, string[]>) =>
+  Object.hasOwn(r, getFilenameExtension(filename).toLowerCase());
+
+const lookup = (filename: string) =>
+  types[getFilenameExtension(filename).toLowerCase()]?.[0] ?? 'application/octet-stream';
 
-const lookup = (filename: string) => types[extname(filename).toLowerCase()]?.[0] ?? 'application/octet-stream';
 const toExtension = (mimeType: string) => {
   return (
     extensionOverrides[mimeType] || Object.entries(types).find(([, mimeTypes]) => mimeTypes.includes(mimeType))?.[0]
@@ -158,7 +160,8 @@ export const mimeTypes = {
   isProfile: (filename: string) => isType(filename, profile),
   isSidecar: (filename: string) => isType(filename, sidecar),
   isVideo: (filename: string) => isType(filename, video),
-  canBeTransparent: (filename: string) => transparentCapableExtensions.has(extname(filename).toLowerCase()),
+  canBeTransparent: (filename: string) =>
+    transparentCapableExtensions.has(getFilenameExtension(filename).toLowerCase()),
   isRaw: (filename: string) => isType(filename, raw),
   lookup,
   /** return an extension (including a leading `.`) for a mime-type */