diff --git a/apps/mobile/src/host/client.ts b/apps/mobile/src/host/client.ts
index 97689f8235..3e4652d1b4 100644
--- a/apps/mobile/src/host/client.ts
+++ b/apps/mobile/src/host/client.ts
@@ -174,6 +174,7 @@ class Unreachable extends Error {}
 
 const UPLOAD_TOO_LARGE = 'The file is larger than the Host accepts.';
 const uploadTimeoutMs = 120_000;
+const OCTET_STREAM = 'application/octet-stream';
 
 export class MethodRefused extends Error {
   constructor(
@@ -432,8 +433,8 @@ export function createHostClient(options: HostClientOptions): HostClient {
         `${route}${DEVICE_PREFIX}/api/botharness/attachment/upload?${new URLSearchParams({ name })}`,
         {
           method: 'POST',
-          body: data,
-          headers: { ...authorization, 'content-type': 'application/octet-stream' },
+          body: data.type === OCTET_STREAM ? data : new Blob([data], { type: OCTET_STREAM }),
+          headers: { ...authorization, 'content-type': OCTET_STREAM },
           signal,
         },
       );
diff --git a/apps/mobile/src/host/pick-files.ts b/apps/mobile/src/host/pick-files.ts
index 6474378bf3..e67fc1bf86 100644
--- a/apps/mobile/src/host/pick-files.ts
+++ b/apps/mobile/src/host/pick-files.ts
@@ -1,4 +1,5 @@
 import * as DocumentPicker from 'expo-document-picker';
+import { File, Paths } from 'expo-file-system';
 import * as ImagePicker from 'expo-image-picker';
 
 import type { OutgoingFile } from './conversation';
@@ -19,6 +20,20 @@ function readUri(uri: string): () => Promise<Blob> {
   return async () => (await fetch(uri)).blob();
 }
 
+function readDataUri(uri: string, name: string): () => Promise<Blob> {
+  return async () => {
+    const file = new File(Paths.cache, `${Date.now()}-${name}`);
+    await file.write(uri.slice(uri.indexOf(',') + 1), { encoding: 'base64' });
+    try {
+      return await (await fetch(file.uri)).blob();
+    } finally {
+      try {
+        file.delete();
+      } catch {}
+    }
+  };
+}
+
 function extension(mime: string | undefined): string {
   const subtype = mime?.split('/')[1]?.replace(/[^a-z0-9]/gu, '');
   return subtype === undefined || subtype === '' ? '' : `.${subtype === 'jpeg' ? 'jpg' : subtype}`;
@@ -50,12 +65,13 @@ function fromDocument(asset: DocumentPicker.DocumentPickerAsset): PickedFile {
 export function fromClipboardImage(data: string): PickedFile {
   picked += 1;
   const mime = /^data:([^;,]+)/u.exec(data)?.[1];
+  const name = `pasted-${picked}${extension(mime)}`;
   return {
     id: `pick-${picked}`,
     kind: 'image',
     uri: data,
-    name: `pasted-${picked}${extension(mime)}`,
-    read: readUri(data),
+    name,
+    read: readDataUri(data, name),
   };
 }
 
diff --git a/apps/mobile/test/clipboard-image.test.tsx b/apps/mobile/test/clipboard-image.test.tsx
index 5cdd408f6f..d99f6858f1 100644
--- a/apps/mobile/test/clipboard-image.test.tsx
+++ b/apps/mobile/test/clipboard-image.test.tsx
@@ -21,6 +21,27 @@ vi.mock('react-native', () => ({
 }));
 vi.mock('expo-image-picker', () => ({}));
 vi.mock('expo-document-picker', () => ({}));
+const written: Array<{ uri: string; content: string; encoding?: string; deleted: boolean }> = [];
+vi.mock('expo-file-system', () => ({
+  Paths: { cache: 'file:///cache' },
+  File: class {
+    readonly entry: (typeof written)[number];
+    constructor(directory: string, name: string) {
+      this.entry = { uri: `${directory}/${name}`, content: '', deleted: false };
+      written.push(this.entry);
+    }
+    get uri() {
+      return this.entry.uri;
+    }
+    async write(content: string, options?: { encoding?: string }) {
+      this.entry.content = content;
+      if (options?.encoding !== undefined) this.entry.encoding = options.encoding;
+    }
+    delete() {
+      this.entry.deleted = true;
+    }
+  },
+}));
 vi.mock('expo-clipboard', () => ({
   ContentType: { IMAGE: 'image', PLAIN_TEXT: 'plain-text' },
   isPasteButtonAvailable: true,
@@ -138,4 +159,22 @@ describe('clipboard image offer', () => {
     expect(file).toMatchObject({ kind: 'image', uri: 'data:image/jpeg;base64,AAAA' });
     expect(file.name).toMatch(/^pasted-\d+\.jpg$/u);
   });
+
+  it('reads a pasted image from a cache file because Android fetch cannot open data: URIs', async () => {
+    const fetched: string[] = [];
+    const image = new Blob(['jpeg'], { type: 'image/jpeg' });
+    vi.stubGlobal('fetch', async (uri: string) => {
+      fetched.push(uri);
+      return { blob: async () => image };
+    });
+    try {
+      const file = fromClipboardImage('data:image/jpeg;base64,AAAA');
+      expect(await file.read()).toBe(image);
+      expect(written.at(-1)).toMatchObject({ content: 'AAAA', encoding: 'base64', deleted: true });
+      expect(fetched).toEqual([written.at(-1)!.uri]);
+      expect(fetched[0]).toMatch(/^file:\/\/\/cache\/\d+-pasted-\d+\.jpg$/u);
+    } finally {
+      vi.unstubAllGlobals();
+    }
+  });
 });
diff --git a/apps/mobile/test/conversation.test.ts b/apps/mobile/test/conversation.test.ts
index 9e1acb7a0e..093836c94e 100644
--- a/apps/mobile/test/conversation.test.ts
+++ b/apps/mobile/test/conversation.test.ts
@@ -525,6 +525,22 @@ describe('DM conversation', () => {
     ]);
   });
 
+  it('uploads a typed photo as octet-stream so the Host accepts it', async () => {
+    const host = new FakeHost();
+    host.channel(DM);
+    const target = open(host);
+    await until(target, (s) => s.status === 'live');
+    const photo = async () => new Blob(['png'], { type: 'image/png' });
+    const id = target.send('', [{ name: 'IMG_0001.PNG', kind: 'image', read: photo }]);
+    const sent = (s: ConversationSnapshot) => s.messages.find((message) => message.id === id);
+    await until(target, (s) => sent(s)?.delivery !== 'pending');
+    expect(sent(target.getSnapshot())?.delivery).toBe('committed');
+    expect(host.uploads).toEqual([
+      { name: 'IMG_0001.PNG', type: 'application/octet-stream', text: 'png' },
+    ]);
+    expect(host.calls.filter((call) => call.method === 'channelSend')).toHaveLength(1);
+  });
+
   it('shows picked files at once and keeps their local copies after the Host commits them', async () => {
     const host = new FakeHost();
     host.channel(DM);
diff --git a/apps/mobile/test/fake-host.ts b/apps/mobile/test/fake-host.ts
index 86c4e87cb0..9119be5515 100644
--- a/apps/mobile/test/fake-host.ts
+++ b/apps/mobile/test/fake-host.ts
@@ -144,8 +144,11 @@ export class FakeHost {
       if (parsed.pathname === '/botharness-device/api/botharness/attachment/upload') {
         if (this.failing.has('upload')) throw new TypeError('Network request failed');
         const name = parsed.searchParams.get('name') ?? '';
-        const text = await (init.body as Blob).text();
-        this.uploads.push({ name, type: init.headers?.['content-type'] ?? '', text });
+        const body = init.body as Blob;
+        const text = await body.text();
+        this.uploads.push({ name, type: body.type, text });
+        if (body.type !== 'application/octet-stream')
+          return response(502, '{"code":"host-session-unavailable"}');
         return response(
           200,
           JSON.stringify({
diff --git a/apps/mobile/test/incoming-share.test.ts b/apps/mobile/test/incoming-share.test.ts
index 6bc46f0e08..6f08f9b2a3 100644
--- a/apps/mobile/test/incoming-share.test.ts
+++ b/apps/mobile/test/incoming-share.test.ts
@@ -14,6 +14,7 @@ const drafts = vi.hoisted(() => {
 });
 
 vi.mock('expo-document-picker', () => ({}));
+vi.mock('expo-file-system', () => ({}));
 vi.mock('expo-image-picker', () => ({}));
 vi.mock('../src/host/native-source-drafts', () => ({ sourceDrafts: drafts.sourceDrafts }));
 
diff --git a/changes/2444-mobile-attachment-upload.md b/changes/2444-mobile-attachment-upload.md
new file mode 100644
index 0000000000..1dfe41b9df
--- /dev/null
+++ b/changes/2444-mobile-attachment-upload.md
@@ -0,0 +1,11 @@
+---
+section: Fixed
+---
+
+## en
+
+- The phone app sends photos, files and pasted images again. They stayed on "Not sent · Tap to retry" because the upload went out with the image's own type, which the Host does not accept, and on Android a pasted image could not be read at all ([#2444](https://github.com/BotHarness/DeepSeekBot/pull/2444)).
+
+## zh
+
+- 手机端又能发送照片、文件和粘贴的图片了。之前上传时带的是图片自身的类型，Host 不接受，所以一直显示「未发送 · 轻点重试」；Android 上粘贴的图片还会读取失败（[#2444](https://github.com/BotHarness/DeepSeekBot/pull/2444)）。