diff --git a/src/components/Chat/ChatInput.test.tsx b/src/components/Chat/ChatInput.test.tsx
index 8b6751b2..cfb810ac 100644
--- a/src/components/Chat/ChatInput.test.tsx
+++ b/src/components/Chat/ChatInput.test.tsx
@@ -21,6 +21,7 @@ const { mockClipboard } = vi.hoisted(() => ({
   mockClipboard: {
     removeClipboardImage: vi.fn(),
     saveClipboardImage: vi.fn(),
+    TEMP_IMAGES_DIRECTORY: '',
   },
 }));
 
@@ -360,8 +361,9 @@ describe('ChatInput', () => {
     mockTextInput.mockReset();
     mockClipboard.removeClipboardImage.mockReset();
     mockClipboard.saveClipboardImage.mockReset();
+    mockClipboard.TEMP_IMAGES_DIRECTORY = join(testDirectory, 'clipboard');
     mockClipboard.saveClipboardImage.mockReturnValue(
-      join(testDirectory, 'image-1.png'),
+      join(testDirectory, 'clipboard', 'image-1.png'),
     );
   });
 
@@ -660,6 +662,47 @@ describe('ChatInput', () => {
     });
   });
 
+  it('stages a dropped image adjacent to existing input text', async () => {
+    const { lastFrame } = renderInput();
+    const initialInputProps = mockTextInput.mock.calls.at(-1)?.[0] as
+      { onChange?: (value: string) => void } | undefined;
+    initialInputProps?.onChange?.('describe this');
+    await time.tick();
+
+    const updatedInputProps = mockTextInput.mock.calls.at(-1)?.[0] as
+      { onChange?: (value: string) => void } | undefined;
+    updatedInputProps?.onChange?.(
+      `describe this${join(testDirectory, 'screen.png')}`,
+    );
+    await time.tick();
+
+    expect(lastFrame()).toContain('[screen.png]');
+    expect(lastFrame()).toContain('describe this');
+    expect(lastFrame()).not.toContain(join(testDirectory, 'screen.png'));
+  });
+
+  it('preserves text and cursor position around a dropped image', async () => {
+    const { lastFrame } = renderInput();
+    const initialInputProps = mockTextInput.mock.calls.at(-1)?.[0] as
+      { onChange?: (value: string) => void } | undefined;
+    initialInputProps?.onChange?.('beforeafter');
+    await time.tick();
+
+    const updatedInputProps = mockTextInput.mock.calls.at(-1)?.[0] as
+      { onChange?: (value: string) => void } | undefined;
+    updatedInputProps?.onChange?.(
+      `before${join(testDirectory, 'screen.png')}after`,
+    );
+    await time.tick();
+
+    expect(lastFrame()).toContain('[screen.png]');
+    expect(lastFrame()).toContain('beforeafter');
+    expect(mockTextInput.mock.calls.at(-1)?.[0]).toMatchObject({
+      cursorPosition: 'before'.length,
+      value: 'beforeafter',
+    });
+  });
+
   it('stages a clipboard image on Ctrl+V', async () => {
     const { lastFrame, stdin } = renderInput();
 
@@ -667,7 +710,7 @@ describe('ChatInput', () => {
     await time.tick();
 
     expect(clipboard.saveClipboardImage).toHaveBeenCalledWith('image-1');
-    expect(lastFrame()).toContain('[image-1.png]');
+    expect(lastFrame()).toContain('[Image 1]');
   });
 
   it('shows an error when staging a clipboard image via Ctrl+V while a turn is active', async () => {
@@ -700,7 +743,7 @@ describe('ChatInput', () => {
     stdin.write('\x16');
     await time.tick();
 
-    expect(lastFrame()).toContain('[image-1.png]');
+    expect(lastFrame()).toContain('[Image 1]');
     expect(lastFrame()).not.toContain(
       'Ask anything... (/ commands, @ files, ! shell, Ctrl+V images)',
     );
@@ -740,14 +783,14 @@ describe('ChatInput', () => {
 
     stdin.write('\x16');
     await time.tick();
-    expect(lastFrame()).toContain('[image-1.png]');
+    expect(lastFrame()).toContain('[Image 1]');
 
     stdin.write(KEY.BACKSPACE);
     await time.tick();
 
-    expect(lastFrame()).not.toContain('[image-1.png]');
+    expect(lastFrame()).not.toContain('[Image 1]');
     expect(clipboard.removeClipboardImage).toHaveBeenCalledWith(
-      join(testDirectory, 'image-1.png'),
+      join(testDirectory, 'clipboard', 'image-1.png'),
     );
   });
 
@@ -773,7 +816,7 @@ describe('ChatInput', () => {
     await time.tick();
 
     expect(clipboard.removeClipboardImage).toHaveBeenCalledWith(
-      join(testDirectory, 'image-1.png'),
+      join(testDirectory, 'clipboard', 'image-1.png'),
     );
   });
 
@@ -1392,7 +1435,7 @@ describe('ChatInput', () => {
     stdin.write(KEY.CTRL_R);
     await time.tick();
 
-    expect(lastFrame()).toContain('[image-1.png]');
+    expect(lastFrame()).toContain('[Image 1]');
     expect(lastFrame()).not.toContain('bck-i-search');
   });
 
diff --git a/src/components/Chat/ChatInput.tsx b/src/components/Chat/ChatInput.tsx
index e4ca7940..020aea6f 100644
--- a/src/components/Chat/ChatInput.tsx
+++ b/src/components/Chat/ChatInput.tsx
@@ -9,7 +9,7 @@ import { clipboard } from '@/utils';
 import {
   type Attachment,
   extractImageAttachments,
-  getAttachmentLabel,
+  getAttachmentLabels,
 } from './attachments';
 import {
   CommandMenu,
@@ -43,11 +43,42 @@ function hasFileSuggestionQuery(input: string): boolean {
   return /(^|.)@\S+/.test(input);
 }
 
+function getInsertedText(previousInput: string, nextInput: string) {
+  let prefixLength = 0;
+  const maximumPrefixLength = Math.min(previousInput.length, nextInput.length);
+
+  while (
+    prefixLength < maximumPrefixLength &&
+    previousInput[prefixLength] === nextInput[prefixLength]
+  ) {
+    prefixLength += 1;
+  }
+
+  let suffixLength = 0;
+  const maximumSuffixLength = previousInput.length - prefixLength;
+
+  while (
+    suffixLength < maximumSuffixLength &&
+    previousInput[previousInput.length - suffixLength - 1] ===
+      nextInput[nextInput.length - suffixLength - 1]
+  ) {
+    suffixLength += 1;
+  }
+
+  return {
+    insertedText: nextInput.slice(
+      prefixLength,
+      nextInput.length - suffixLength,
+    ),
+    prefix: nextInput.slice(0, prefixLength),
+    suffix: suffixLength ? nextInput.slice(-suffixLength) : '',
+  };
+}
+
 function toAttachment(path: string, index: number, isTemp = false): Attachment {
   return {
     id: `${path}-${String(index)}`,
     isTemp,
-    label: getAttachmentLabel(path),
     path,
   };
 }
@@ -218,8 +249,12 @@ export function ChatInput({
       const didPaste = nextInput.length - input.length > 1;
 
       if (didPaste) {
+        const { insertedText, prefix, suffix } = getInsertedText(
+          input,
+          nextInput,
+        );
         const { attachments: nextAttachments, remainingInput } =
-          extractImageAttachments(nextInput);
+          extractImageAttachments(insertedText);
 
         if (nextAttachments.length) {
           if (isActive) {
@@ -228,8 +263,9 @@ export function ChatInput({
           }
 
           stageAttachments(nextAttachments);
-          setInput(remainingInput);
-          setCursorPosition(remainingInput.length);
+          const inputWithoutAttachments = `${prefix}${remainingInput}${suffix}`;
+          setInput(inputWithoutAttachments);
+          setCursorPosition(prefix.length + remainingInput.length);
           setHistoryIndex(null);
           resetHistorySearch();
           return;
@@ -467,8 +503,10 @@ export function ChatInput({
     }
   });
 
-  const attachmentPrefix = attachments
-    .map(({ label }) => `[${label}]`)
+  const attachmentPrefix = getAttachmentLabels(
+    attachments.map(({ path }) => path),
+  )
+    .map((label) => `[${label}]`)
     .join(' ');
 
   const wrapIndent =
diff --git a/src/components/Chat/attachments.test.ts b/src/components/Chat/attachments.test.ts
index e92e7c4e..660dea88 100644
--- a/src/components/Chat/attachments.test.ts
+++ b/src/components/Chat/attachments.test.ts
@@ -2,9 +2,12 @@ import { mkdirSync, mkdtempSync, rmSync, writeFileSync } from 'node:fs';
 import { tmpdir } from 'node:os';
 import { basename, join } from 'node:path';
 
+import { clipboard } from '@/utils';
+
 import {
   extractImageAttachments,
   getAttachmentLabel,
+  getAttachmentLabels,
   isReadableImagePath,
   resolveAttachmentPath,
 } from './attachments';
@@ -30,6 +33,17 @@ describe('attachments', () => {
     expect(getAttachmentLabel('/tmp/path/mockup.png')).toBe('mockup.png');
   });
 
+  it('numbers clipboard images while preserving file attachment labels', () => {
+    expect(
+      getAttachmentLabels([
+        join(testDirectory, 'diagram.png'),
+        join(clipboard.TEMP_IMAGES_DIRECTORY, 'first-uuid.png'),
+        join(testDirectory, 'nested', 'mockup.jpg'),
+        join(clipboard.TEMP_IMAGES_DIRECTORY, 'second-uuid.png'),
+      ]),
+    ).toEqual(['diagram.png', 'Image 1', 'mockup.jpg', 'Image 2']);
+  });
+
   it('detects readable image paths', () => {
     expect(isReadableImagePath('./diagram.png')).toBe(true);
     expect(isReadableImagePath('./missing.png')).toBe(false);
diff --git a/src/components/Chat/attachments.ts b/src/components/Chat/attachments.ts
index 371efd50..cb520f4d 100644
--- a/src/components/Chat/attachments.ts
+++ b/src/components/Chat/attachments.ts
@@ -1,10 +1,11 @@
 import { existsSync, statSync } from 'node:fs';
-import { basename, extname, isAbsolute, resolve } from 'node:path';
+import { basename, extname, isAbsolute, relative, resolve } from 'node:path';
+
+import { clipboard } from '@/utils';
 
 export interface Attachment {
   id: string;
   isTemp: boolean;
-  label: string;
   path: string;
 }
 
@@ -48,6 +49,28 @@ export function getAttachmentLabel(path: string): string {
   return basename(path);
 }
 
+function isClipboardImagePath(path: string): boolean {
+  const relativePath = relative(clipboard.TEMP_IMAGES_DIRECTORY, path);
+  return (
+    relativePath !== '' &&
+    !relativePath.startsWith('..') &&
+    !isAbsolute(relativePath)
+  );
+}
+
+export function getAttachmentLabels(paths: string[]): string[] {
+  let clipboardImageIndex = 0;
+
+  return paths.map((path) => {
+    if (!isClipboardImagePath(path)) {
+      return getAttachmentLabel(path);
+    }
+
+    clipboardImageIndex += 1;
+    return `Image ${String(clipboardImageIndex)}`;
+  });
+}
+
 export function isReadableImagePath(path: string): boolean {
   const normalizedPath = normalizeCandidatePath(path);
   const extension = extname(normalizedPath).toLowerCase();
diff --git a/src/components/Messages/Message.tsx b/src/components/Messages/Message.tsx
index 06d7c9ac..96ca7871 100644
--- a/src/components/Messages/Message.tsx
+++ b/src/components/Messages/Message.tsx
@@ -7,6 +7,7 @@ import { ROLE, UI } from '@/constants';
 import { useTheme } from '@/contexts';
 import type { Message as OllamaMessage } from '@/utils/ollama';
 
+import { getAttachmentLabels } from '../Chat/attachments';
 import {
   getAssistantContentWidth,
   getCodeBlockHeight,
@@ -112,11 +113,9 @@ export function Message({
 
   if (isUser) {
     const attachments = message.images ?? [];
-    // v8 ignore start
-    const attachmentPrefix = attachments
-      .map((path) => `[${path.split(/[\\/]/).at(-1) ?? path}]`)
+    const attachmentPrefix = getAttachmentLabels(attachments)
+      .map((label) => `[${label}]`)
       .join(' ');
-    // v8 ignore stop
 
     return (
       <Box flexDirection="column" marginBottom={marginBottom}>
diff --git a/src/components/Messages/Messages.test.tsx b/src/components/Messages/Messages.test.tsx
index a79e63b5..020d337a 100644
--- a/src/components/Messages/Messages.test.tsx
+++ b/src/components/Messages/Messages.test.tsx
@@ -2,6 +2,7 @@ import { useStdout } from 'ink';
 
 import { ROLE, UI } from '@/constants';
 import type { Role } from '@/types';
+import { clipboard } from '@/utils';
 import type { Message } from '@/utils/ollama';
 import { renderWithTheme } from '@/utils/testing';
 
@@ -104,6 +105,30 @@ describe('Messages', () => {
     expect(lastFrame()).toContain('hello');
   });
 
+  it('numbers clipboard images while preserving file attachment labels', () => {
+    const { lastFrame } = renderWithTheme(
+      <Messages
+        messages={[
+          {
+            role: ROLE.USER,
+            content: 'compare these',
+            images: [
+              `${clipboard.TEMP_IMAGES_DIRECTORY}/first-uuid.png`,
+              '/tmp/design.png',
+              `${clipboard.TEMP_IMAGES_DIRECTORY}/second-uuid.png`,
+            ],
+          },
+        ]}
+        isLoading={false}
+        sessionId=""
+      />,
+    );
+
+    expect(lastFrame()).toContain(
+      '[Image 1] [design.png] [Image 2] compare these',
+    );
+  });
+
   it('renders user attachment without content and no extra space', () => {
     const messageWithImageOnly: Message = {
       role: ROLE.USER,