diff --git a/backend/src/db/models/File.ts b/backend/src/db/models/File.ts
index 08e5e221f..1788052c4 100644
--- a/backend/src/db/models/File.ts
+++ b/backend/src/db/models/File.ts
@@ -1,6 +1,7 @@
 export default {
   url: { primary: true, type: 'string', uri: { allowRelative: true } },
   name: { type: 'string' },
+  extension: { type: 'string', allow: [null, ''] },
   type: { type: 'string' },
   duration: { type: 'number', allow: [null] },
   createdAt: { type: 'string', isoDate: true, default: () => new Date().toISOString() },
diff --git a/backend/src/graphql/resolvers/attachments/attachments.ts b/backend/src/graphql/resolvers/attachments/attachments.ts
index b9187d17d..6909d5814 100644
--- a/backend/src/graphql/resolvers/attachments/attachments.ts
+++ b/backend/src/graphql/resolvers/attachments/attachments.ts
@@ -28,6 +28,7 @@ export interface AddAttachmentOpts {
 export interface FileInput {
   upload?: Promise<FileUpload>
   name: string
+  extension?: string | null
   type: string
   duration?: number | null
 }
@@ -35,6 +36,7 @@ export interface FileInput {
 export interface File {
   url: string
   name: string
+  extension?: string | null
   type: string
   duration?: number | null
 }
@@ -145,8 +147,15 @@ export const attachments = (config: S3Config) => {
       uniqueFilename,
     })
 
-    const { name, type, duration } = fileInput
-    const file = { url, name, type, ...(duration != null && { duration }), ...fileAttributes }
+    const { name, extension, type, duration } = fileInput
+    const file = {
+      url,
+      name,
+      ...(extension && { extension }),
+      type,
+      ...(duration != null && { duration }),
+      ...fileAttributes,
+    }
     // const mimeType = uploadFile.mimetype.split('/')[0]
     // const nodeType = `Mime${mimeType.replace(/^./, mimeType[0].toUpperCase())}`
     // CREATE (file:${['File', nodeType].filter(Boolean).join(':')})
diff --git a/backend/src/graphql/resolvers/messages.ts b/backend/src/graphql/resolvers/messages.ts
index c92161786..336a6ef93 100644
--- a/backend/src/graphql/resolvers/messages.ts
+++ b/backend/src/graphql/resolvers/messages.ts
@@ -281,6 +281,7 @@ export default {
     }),
   },
   File: {
+    extension: (parent: { extension?: string | null }) => parent.extension ?? null,
     duration: (parent: { duration?: number | null }) => parent.duration ?? null,
   },
 }
diff --git a/backend/src/graphql/types/type/File.gql b/backend/src/graphql/types/type/File.gql
index e48837096..4c7296ca7 100644
--- a/backend/src/graphql/types/type/File.gql
+++ b/backend/src/graphql/types/type/File.gql
@@ -1,6 +1,7 @@
 type File {
   url: ID!
   name: String
+  extension: String
   type: String
   duration: Float
   # size: Int
@@ -12,6 +13,7 @@ type File {
 input FileInput {
   upload: Upload
   name: String
+  extension: String
   type: String
   duration: Float
 }
diff --git a/webapp/components/Chat/Chat.spec.js b/webapp/components/Chat/Chat.spec.js
index 075fc71f5..377bbae5e 100644
--- a/webapp/components/Chat/Chat.spec.js
+++ b/webapp/components/Chat/Chat.spec.js
@@ -712,7 +712,7 @@ describe('Chat.vue', () => {
         expect.objectContaining({
           variables: expect.objectContaining({
             files: expect.arrayContaining([
-              expect.objectContaining({ name: 'test', type: 'text/plain' }),
+              expect.objectContaining({ name: 'test', extension: 'txt', type: 'text/plain' }),
             ]),
           }),
         }),
diff --git a/webapp/components/Chat/Chat.vue b/webapp/components/Chat/Chat.vue
index e6ddf3e89..5c0dc277b 100644
--- a/webapp/components/Chat/Chat.vue
+++ b/webapp/components/Chat/Chat.vue
@@ -314,24 +314,12 @@ export default {
       commitUnreadRoomCount: 'chat/UPDATE_ROOM_COUNT',
     }),
 
-    lastMessageFiles(files) {
-      if (!files?.length) return undefined
-      return files.map((f) => {
-        if (f.extension) return f
-        const dotIndex = f.name?.lastIndexOf('.')
-        const ext = dotIndex > 0 ? f.name.substring(dotIndex + 1) : f.type?.split('/').pop()
-        const name = dotIndex > 0 ? f.name.substring(0, dotIndex) : f.name
-        return { ...f, name, extension: ext }
-      })
-    },
-
     lastMessageContent(content, files) {
       const text = (content || '').trim()
       if (text) return text.substring(0, 30)
       if (!files?.length) return ''
+      if (files[0].type?.startsWith('audio/') || files[0].audio) return ''
       const f = files[0]
-      const isAudio = f.type?.startsWith('audio/') || f.audio
-      if (isAudio) return ''
       const name = f.extension ? `${f.name}.${f.extension}` : f.name || ''
       return `\uD83D\uDCCE ${name}`
     },
@@ -657,7 +645,7 @@ export default {
       changedRoom.lastMessage = {
         ...msg,
         content: this.lastMessageContent(msg.content, msg.files),
-        files: this.lastMessageFiles(msg.files),
+        files: msg.files,
       }
       changedRoom.lastMessageAt = msg.date
       changedRoom.index = new Date().toISOString()
@@ -730,11 +718,11 @@ export default {
         ? files.map((file) => ({
             upload: new File(
               [file.blob],
-              // Captured audio already has the right extension in the name
               file.extension ? `${file.name}.${file.extension}` : file.name,
               { type: file.type },
             ),
             name: file.name,
+            extension: file.extension || undefined,
             type: file.type,
             ...(file.duration != null && { duration: file.duration }),
           }))
@@ -766,7 +754,7 @@ export default {
       if (roomIndex !== -1) {
         const changedRoom = { ...this.rooms[roomIndex] }
         changedRoom.lastMessage.content = this.lastMessageContent(content, files)
-        changedRoom.lastMessage.files = this.lastMessageFiles(files)
+        changedRoom.lastMessage.files = files
         changedRoom.index = new Date().toISOString()
         this.rooms = [changedRoom, ...this.rooms.filter((r) => r.id !== roomId)]
         this.$nextTick(() => {
@@ -852,7 +840,7 @@ export default {
           ? {
               ...room.lastMessage,
               content: this.lastMessageContent(room.lastMessage?.content, room.lastMessage?.files),
-              files: this.lastMessageFiles(room.lastMessage?.files),
+              files: room.lastMessage?.files,
             }
           : { content: '' },
         users: room.users.map((u) => {
diff --git a/webapp/graphql/Messages.js b/webapp/graphql/Messages.js
index 62a4be336..472ef3cfa 100644
--- a/webapp/graphql/Messages.js
+++ b/webapp/graphql/Messages.js
@@ -24,6 +24,7 @@ export const createMessageMutation = () => {
         files {
           url
           name
+          extension
           #size
           type
           duration
@@ -64,6 +65,7 @@ export const messageQuery = () => {
         files {
           url
           name
+          extension
           #size
           type
           #audio
@@ -99,6 +101,7 @@ export const chatMessageAdded = () => {
         files {
           url
           name
+          extension
           #size
           type
           #audio
diff --git a/webapp/graphql/Rooms.js b/webapp/graphql/Rooms.js
index 58f92295b..8f9b57402 100644
--- a/webapp/graphql/Rooms.js
+++ b/webapp/graphql/Rooms.js
@@ -69,6 +69,7 @@ export const roomQuery = () => gql`
         files {
           url
           name
+          extension
           type
           duration
         }