feat: support multi-file drag and drop of images

packages/cli/src/ui/components/shared/text-buffer.test.ts

@@ -637,6 +637,46 @@ describe('useTextBuffer', () => {
       act(() => result.current.insert(shortText, { paste: true }));
       expect(getBufferState(result).text).toBe(shortText);
     });
+
+    it('should prepend @ to multiple valid file paths on insert', () => {
+      // Use Set to model reality: individual paths exist, combined string doesn't
+      const validPaths = new Set(['/path/to/file1.txt', '/path/to/file2.txt']);
+      const { result } = renderHook(() =>
+        useTextBuffer({ viewport, isValidPath: (p) => validPaths.has(p) }),
+      );
+      const filePaths = '/path/to/file1.txt /path/to/file2.txt';
+      act(() => result.current.insert(filePaths, { paste: true }));
+      expect(getBufferState(result).text).toBe(
+        '@/path/to/file1.txt @/path/to/file2.txt ',
+      );
+    });
+
+    it('should handle multiple paths with escaped spaces', () => {
+      // Use Set to model reality: individual paths exist, combined string doesn't
+      const validPaths = new Set(['/path/to/my file.txt', '/other/path.txt']);
+      const { result } = renderHook(() =>
+        useTextBuffer({ viewport, isValidPath: (p) => validPaths.has(p) }),
+      );
+      const filePaths = '/path/to/my\\ file.txt /other/path.txt';
+      act(() => result.current.insert(filePaths, { paste: true }));
+      expect(getBufferState(result).text).toBe(
+        '@/path/to/my\\ file.txt @/other/path.txt ',
+      );
+    });
+
+    it('should only prepend @ to valid paths in multi-path paste', () => {
+      const { result } = renderHook(() =>
+        useTextBuffer({
+          viewport,
+          isValidPath: (p) => p.endsWith('.txt'),
+        }),
+      );
+      const filePaths = '/valid/file.txt /invalid/file.jpg';
+      act(() => result.current.insert(filePaths, { paste: true }));
+      expect(getBufferState(result).text).toBe(
+        '@/valid/file.txt /invalid/file.jpg ',
+      );
+    });
   });
 
   describe('Shell Mode Behavior', () => {

packages/cli/src/ui/components/shared/text-buffer.ts

@@ -9,14 +9,15 @@ import fs from 'node:fs';
 import os from 'node:os';
 import pathMod from 'node:path';
 import { useState, useCallback, useEffect, useMemo, useReducer } from 'react';
-import { unescapePath, coreEvents, CoreEvent } from '@google/gemini-cli-core';
+import { coreEvents, CoreEvent } from '@google/gemini-cli-core';
 import {
   toCodePoints,
   cpLen,
   cpSlice,
   stripUnsafeCharacters,
   getCachedStringWidth,
 } from '../../utils/textUtils.js';
+import { parsePastedPaths } from '../../utils/clipboardUtils.js';
 import type { Key } from '../../contexts/KeypressContext.js';
 import type { VimAction } from './vim-buffer-actions.js';
 import { handleVimAction } from './vim-buffer-actions.js';
@@ -1675,8 +1676,10 @@ export function useTextBuffer({
         }
 
         potentialPath = potentialPath.trim();
-        if (isValidPath(unescapePath(potentialPath))) {
-          ch = `@${potentialPath} `;
+
+        const processed = parsePastedPaths(potentialPath, isValidPath);
+        if (processed) {
+          ch = processed;
         }
       }
 

packages/cli/src/ui/utils/clipboardUtils.test.ts

@@ -9,6 +9,8 @@ import {
   clipboardHasImage,
   saveClipboardImage,
   cleanupOldClipboardImages,
+  splitEscapedPaths,
+  parsePastedPaths,
 } from './clipboardUtils.js';
 
 describe('clipboardUtils', () => {
@@ -73,4 +75,166 @@ describe('clipboardUtils', () => {
       await expect(cleanupOldClipboardImages('.')).resolves.not.toThrow();
     });
   });
+
+  describe('splitEscapedPaths', () => {
+    it('should return single path when no spaces', () => {
+      expect(splitEscapedPaths('/path/to/image.png')).toEqual([
+        '/path/to/image.png',
+      ]);
+    });
+
+    it('should split simple space-separated paths', () => {
+      expect(splitEscapedPaths('/img1.png /img2.png')).toEqual([
+        '/img1.png',
+        '/img2.png',
+      ]);
+    });
+
+    it('should split three paths', () => {
+      expect(splitEscapedPaths('/a.png /b.jpg /c.heic')).toEqual([
+        '/a.png',
+        '/b.jpg',
+        '/c.heic',
+      ]);
+    });
+
+    it('should preserve escaped spaces within filenames', () => {
+      expect(splitEscapedPaths('/my\\ image.png')).toEqual(['/my\\ image.png']);
+    });
+
+    it('should handle multiple paths with escaped spaces', () => {
+      expect(splitEscapedPaths('/my\\ img1.png /my\\ img2.png')).toEqual([
+        '/my\\ img1.png',
+        '/my\\ img2.png',
+      ]);
+    });
+
+    it('should handle path with multiple escaped spaces', () => {
+      expect(splitEscapedPaths('/path/to/my\\ cool\\ image.png')).toEqual([
+        '/path/to/my\\ cool\\ image.png',
+      ]);
+    });
+
+    it('should handle multiple consecutive spaces between paths', () => {
+      expect(splitEscapedPaths('/img1.png   /img2.png')).toEqual([
+        '/img1.png',
+        '/img2.png',
+      ]);
+    });
+
+    it('should handle trailing and leading whitespace', () => {
+      expect(splitEscapedPaths('  /img1.png /img2.png  ')).toEqual([
+        '/img1.png',
+        '/img2.png',
+      ]);
+    });
+
+    it('should return empty array for empty string', () => {
+      expect(splitEscapedPaths('')).toEqual([]);
+    });
+
+    it('should return empty array for whitespace only', () => {
+      expect(splitEscapedPaths('   ')).toEqual([]);
+    });
+  });
+
+  describe('parsePastedPaths', () => {
+    it('should return null for empty string', () => {
+      const result = parsePastedPaths('', () => true);
+      expect(result).toBe(null);
+    });
+
+    it('should add @ prefix to single valid path', () => {
+      const result = parsePastedPaths('/path/to/file.txt', () => true);
+      expect(result).toBe('@/path/to/file.txt ');
+    });
+
+    it('should return null for single invalid path', () => {
+      const result = parsePastedPaths('/path/to/file.txt', () => false);
+      expect(result).toBe(null);
+    });
+
+    it('should add @ prefix to all valid paths', () => {
+      // Use Set to model reality: individual paths exist, combined string doesn't
+      const validPaths = new Set(['/path/to/file1.txt', '/path/to/file2.txt']);
+      const result = parsePastedPaths(
+        '/path/to/file1.txt /path/to/file2.txt',
+        (p) => validPaths.has(p),
+      );
+      expect(result).toBe('@/path/to/file1.txt @/path/to/file2.txt ');
+    });
+
+    it('should only add @ prefix to valid paths', () => {
+      const result = parsePastedPaths(
+        '/valid/file.txt /invalid/file.jpg',
+        (p) => p.endsWith('.txt'),
+      );
+      expect(result).toBe('@/valid/file.txt /invalid/file.jpg ');
+    });
+
+    it('should return null if no paths are valid', () => {
+      const result = parsePastedPaths(
+        '/path/to/file1.txt /path/to/file2.txt',
+        () => false,
+      );
+      expect(result).toBe(null);
+    });
+
+    it('should handle paths with escaped spaces', () => {
+      // Use Set to model reality: individual paths exist, combined string doesn't
+      const validPaths = new Set(['/path/to/my file.txt', '/other/path.txt']);
+      const result = parsePastedPaths(
+        '/path/to/my\\ file.txt /other/path.txt',
+        (p) => validPaths.has(p),
+      );
+      expect(result).toBe('@/path/to/my\\ file.txt @/other/path.txt ');
+    });
+
+    it('should unescape paths before validation', () => {
+      // Use Set to model reality: individual paths exist, combined string doesn't
+      const validPaths = new Set(['/my file.txt', '/other.txt']);
+      const validatedPaths: string[] = [];
+      parsePastedPaths('/my\\ file.txt /other.txt', (p) => {
+        validatedPaths.push(p);
+        return validPaths.has(p);
+      });
+      // First checks entire string, then individual unescaped segments
+      expect(validatedPaths).toEqual([
+        '/my\\ file.txt /other.txt',
+        '/my file.txt',
+        '/other.txt',
+      ]);
+    });
+
+    it('should handle single path with unescaped spaces from copy-paste', () => {
+      const result = parsePastedPaths('/path/to/my file.txt', () => true);
+      expect(result).toBe('@/path/to/my\\ file.txt ');
+    });
+
+    it('should handle Windows path', () => {
+      const result = parsePastedPaths('C:\\Users\\file.txt', () => true);
+      expect(result).toBe('@C:\\Users\\file.txt ');
+    });
+
+    it('should handle Windows path with unescaped spaces', () => {
+      const result = parsePastedPaths('C:\\My Documents\\file.txt', () => true);
+      expect(result).toBe('@C:\\My\\ Documents\\file.txt ');
+    });
+
+    it('should handle multiple Windows paths', () => {
+      const validPaths = new Set(['C:\\file1.txt', 'D:\\file2.txt']);
+      const result = parsePastedPaths('C:\\file1.txt D:\\file2.txt', (p) =>
+        validPaths.has(p),
+      );
+      expect(result).toBe('@C:\\file1.txt @D:\\file2.txt ');
+    });
+
+    it('should handle Windows UNC path', () => {
+      const result = parsePastedPaths(
+        '\\\\server\\share\\file.txt',
+        () => true,
+      );
+      expect(result).toBe('@\\\\server\\share\\file.txt ');
+    });
+  });
 });

packages/cli/src/ui/utils/clipboardUtils.ts

@@ -6,7 +6,12 @@
 
 import * as fs from 'node:fs/promises';
 import * as path from 'node:path';
-import { debugLogger, spawnAsync } from '@google/gemini-cli-core';
+import {
+  debugLogger,
+  spawnAsync,
+  unescapePath,
+  escapePath,
+} from '@google/gemini-cli-core';
 
 /**
  * Supported image file extensions based on Gemini API.
@@ -21,6 +26,9 @@ export const IMAGE_EXTENSIONS = [
   '.heif',
 ];
 
+/** Matches strings that start with a path prefix (/, ~, ., Windows drive letter, or UNC path) */
+const PATH_PREFIX_PATTERN = /^([/~.]|[a-zA-Z]:|\\\\)/;
+
 /**
  * Checks if the system clipboard contains an image (macOS only for now)
  * @returns true if clipboard contains an image
@@ -101,16 +109,18 @@ export async function saveClipboardImage(
           if (stats.size > 0) {
             return tempFilePath;
           }
-        } catch {
+        } catch (e) {
           // File doesn't exist, continue to next format
+          debugLogger.debug('Clipboard image file not found:', tempFilePath, e);
         }
       }
 
       // Clean up failed attempt
       try {
         await fs.unlink(tempFilePath);
-      } catch {
+      } catch (e) {
         // Ignore cleanup errors
+        debugLogger.debug('Failed to clean up temp file:', tempFilePath, e);
       }
     }
 
@@ -146,7 +156,91 @@ export async function cleanupOldClipboardImages(
         }
       }
     }
-  } catch {
+  } catch (e) {
     // Ignore errors in cleanup
+    debugLogger.debug('Failed to clean up old clipboard images:', e);
+  }
+}
+
+/**
+ * Splits text into individual path segments, respecting escaped spaces.
+ * Unescaped spaces act as separators between paths, while "\ " is preserved
+ * as part of a filename.
+ *
+ * Example: "/img1.png /path/my\ image.png" → ["/img1.png", "/path/my\ image.png"]
+ *
+ * @param text The text to split
+ * @returns Array of path segments (still escaped)
+ */
+export function splitEscapedPaths(text: string): string[] {
+  const paths: string[] = [];
+  let current = '';
+  let i = 0;
+
+  while (i < text.length) {
+    const char = text[i];
+
+    if (char === '\\' && i + 1 < text.length && text[i + 1] === ' ') {
+      // Escaped space - part of filename, preserve the escape sequence
+      current += '\\ ';
+      i += 2;
+    } else if (char === ' ') {
+      // Unescaped space - path separator
+      if (current.trim()) {
+        paths.push(current.trim());
+      }
+      current = '';
+      i++;
+    } else {
+      current += char;
+      i++;
+    }
+  }
+
+  // Don't forget the last segment
+  if (current.trim()) {
+    paths.push(current.trim());
+  }
+
+  return paths;
+}
+
+/**
+ * Processes pasted text containing file paths, adding @ prefix to valid paths.
+ * Handles both single and multiple space-separated paths.
+ *
+ * @param text The pasted text (potentially space-separated paths)
+ * @param isValidPath Function to validate if a path exists/is valid
+ * @returns Processed string with @ prefixes on valid paths, or null if no valid paths
+ */
+export function parsePastedPaths(
+  text: string,
+  isValidPath: (path: string) => boolean,
+): string | null {
+  // First, check if the entire text is a single valid path
+  if (PATH_PREFIX_PATTERN.test(text) && isValidPath(text)) {
+    return `@${escapePath(text)} `;
+  }
+
+  // Otherwise, try splitting on unescaped spaces
+  const segments = splitEscapedPaths(text);
+  if (segments.length === 0) {
+    return null;
   }
+
+  let anyValidPath = false;
+  const processedPaths = segments.map((segment) => {
+    // Quick rejection: skip segments that can't be paths
+    if (!PATH_PREFIX_PATTERN.test(segment)) {
+      return segment;
+    }
+    const unescaped = unescapePath(segment);
+    if (isValidPath(unescaped)) {
+      anyValidPath = true;
+      return `@${segment}`;
+    }
+    return segment;
+  });
+
+  return anyValidPath ? processedPaths.join(' ') + ' ' : null;
 }