diff --git a/server/shared/image-attachments.ts b/server/shared/image-attachments.ts
index 94cc85a6..752be34e 100644
--- a/server/shared/image-attachments.ts
+++ b/server/shared/image-attachments.ts
@@ -1,4 +1,4 @@
-import { promises as fs } from 'node:fs';
+import { promises as fs, realpathSync } from 'node:fs';
 import os from 'node:os';
 import path from 'node:path';
 
@@ -99,6 +99,18 @@ function isPathInsideDirectory(candidate: string, directory: string): boolean {
   return path.resolve(candidate).startsWith(resolvedRoot);
 }
 
+function getDirectoryPathVariants(directory: string): string[] {
+  const resolvedDirectory = path.resolve(directory);
+  try {
+    const canonicalDirectory = path.resolve(realpathSync(directory));
+    return canonicalDirectory === resolvedDirectory
+      ? [resolvedDirectory]
+      : [resolvedDirectory, canonicalDirectory];
+  } catch {
+    return [resolvedDirectory];
+  }
+}
+
 /**
  * Second layer of the image trust boundary (the first is the chat.send filter
  * in the websocket gateway): provider builders only reference files that live
@@ -107,9 +119,10 @@ function isPathInsideDirectory(candidate: string, directory: string): boolean {
  * refused, so a caller-supplied descriptor can never leak arbitrary files.
  */
 export function isAllowedImageSourcePath(resolvedPath: string, cwd?: string): boolean {
-  return (
-    isPathInsideDirectory(resolvedPath, getGlobalImageAssetsDir()) ||
-    isPathInsideDirectory(resolvedPath, cwd || process.cwd())
+  return [getGlobalImageAssetsDir(), cwd || process.cwd()].some((directory) =>
+    getDirectoryPathVariants(directory).some((directoryVariant) =>
+      isPathInsideDirectory(resolvedPath, directoryVariant)
+    )
   );
 }
 
@@ -276,7 +289,13 @@ export async function buildClaudeUserContent(
     }
 
     try {
-      const bytes = await fs.readFile(resolvedPath);
+      const canonicalPath = await fs.realpath(resolvedPath);
+      if (!isAllowedImageSourcePath(canonicalPath, cwd)) {
+        console.warn(`[Images] Refusing to read symlinked image outside allowed roots: ${descriptor.path}`);
+        continue;
+      }
+
+      const bytes = await fs.readFile(canonicalPath);
       blocks.push({
         type: 'image',
         source: {
diff --git a/server/shared/tests/image-attachments.test.ts b/server/shared/tests/image-attachments.test.ts
index c4f4abbd..0ddba881 100644
--- a/server/shared/tests/image-attachments.test.ts
+++ b/server/shared/tests/image-attachments.test.ts
@@ -1,5 +1,5 @@
 import assert from 'node:assert/strict';
-import { mkdtemp, rm, writeFile } from 'node:fs/promises';
+import { mkdtemp, rm, symlink, writeFile } from 'node:fs/promises';
 import os from 'node:os';
 import path from 'node:path';
 import test from 'node:test';
@@ -21,6 +21,32 @@ const PNG_BYTES = Buffer.from(
   'base64',
 );
 
+const SYMLINK_UNSUPPORTED_CODES = new Set(['EACCES', 'EINVAL', 'ENOSYS', 'ENOTSUP', 'EPERM']);
+
+function isErrnoException(error: unknown): error is NodeJS.ErrnoException {
+  return error instanceof Error && 'code' in error;
+}
+
+async function createSymlinkIfSupported(
+  target: string,
+  linkPath: string,
+  type: 'dir' | 'file' | 'junction',
+): Promise<boolean> {
+  try {
+    await symlink(target, linkPath, type);
+    return true;
+  } catch (error) {
+    if (
+      isErrnoException(error) &&
+      typeof error.code === 'string' &&
+      SYMLINK_UNSUPPORTED_CODES.has(error.code)
+    ) {
+      return false;
+    }
+    throw error;
+  }
+}
+
 test('normalizeImageDescriptors accepts objects and bare paths, drops junk', () => {
   const descriptors = normalizeImageDescriptors([
     { path: '.cloudcli/assets/a.png', name: 'a.png', mimeType: 'image/png' },
@@ -176,6 +202,61 @@ test('buildClaudeUserContent skips unsupported types and unreadable files', asyn
   }
 });
 
+test('buildClaudeUserContent refuses symlinked images outside allowed roots', async (t) => {
+  const tempDir = await mkdtemp(path.join(os.tmpdir(), 'image-attachments-'));
+  const outsideDir = await mkdtemp(path.join(os.tmpdir(), 'image-attachments-outside-'));
+  try {
+    const outsideFile = path.join(outsideDir, 'secret.png');
+    await writeFile(outsideFile, PNG_BYTES);
+
+    const linkPath = path.join(tempDir, 'linked-secret.png');
+    if (!(await createSymlinkIfSupported(outsideFile, linkPath, 'file'))) {
+      t.skip('Symlink creation is not supported in this environment');
+      return;
+    }
+
+    const content = await buildClaudeUserContent(
+      'prompt',
+      [{ path: 'linked-secret.png', mimeType: 'image/png' }],
+      tempDir,
+    );
+
+    assert.deepEqual(content, [{ type: 'text', text: 'prompt' }]);
+  } finally {
+    await rm(tempDir, { recursive: true, force: true });
+    await rm(outsideDir, { recursive: true, force: true });
+  }
+});
+
+test('buildClaudeUserContent accepts images under a symlinked cwd', async (t) => {
+  const realProjectDir = await mkdtemp(path.join(os.tmpdir(), 'image-attachments-project-'));
+  const linkParentDir = await mkdtemp(path.join(os.tmpdir(), 'image-attachments-link-'));
+  try {
+    await writeFile(path.join(realProjectDir, 'shot.png'), PNG_BYTES);
+
+    const linkCwd = path.join(linkParentDir, 'project-link');
+    const linkType = process.platform === 'win32' ? 'junction' : 'dir';
+    if (!(await createSymlinkIfSupported(realProjectDir, linkCwd, linkType))) {
+      t.skip('Symlink creation is not supported in this environment');
+      return;
+    }
+
+    const content = await buildClaudeUserContent(
+      'prompt',
+      [{ path: 'shot.png', mimeType: 'image/png' }],
+      linkCwd,
+    );
+
+    assert.equal(content.length, 2);
+    assert.equal(content[1].type, 'image');
+    const imageBlock = content[1] as Extract<(typeof content)[number], { type: 'image' }>;
+    assert.equal(imageBlock.source.data, PNG_BYTES.toString('base64'));
+  } finally {
+    await rm(linkParentDir, { recursive: true, force: true });
+    await rm(realProjectDir, { recursive: true, force: true });
+  }
+});
+
 test('buildCodexInputItems emits text plus absolute local_image paths', () => {
   const cwd = path.join(os.tmpdir(), 'codex-project');
   const items = buildCodexInputItems('Describe this image:', [{ path: '.cloudcli/assets/pic.jpg' }], cwd);