diff --git a/packages/core/src/utils/memoryImportProcessor.test.ts b/packages/core/src/utils/memoryImportProcessor.test.ts
index 3c9a74b604..78d584f0b2 100644
--- a/packages/core/src/utils/memoryImportProcessor.test.ts
+++ b/packages/core/src/utils/memoryImportProcessor.test.ts
@@ -6,6 +6,8 @@
 
 import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
 import * as fs from 'node:fs/promises';
+import * as fsSync from 'node:fs';
+import * as os from 'node:os';
 import * as path from 'node:path';
 import { marked } from 'marked';
 import { processImports, validateImportPath } from './memoryImportProcessor.js';
@@ -867,5 +869,46 @@ describe('memoryImportProcessor', () => {
       );
       expect(validateImportPath(dotPath, basePath, [allowedPath])).toBe(true);
     });
+
+    it('should reject paths that escape allowed directories via symbolic links', () => {
+      const tmpDir = fsSync.realpathSync(os.tmpdir());
+      const testRoot = fsSync.mkdtempSync(path.join(tmpDir, 'gemini-test-'));
+      const allowedDir = path.join(testRoot, 'allowed');
+      const outsideDir = path.join(testRoot, 'outside');
+      const symlinkDir = path.join(allowedDir, 'sym_outside');
+
+      try {
+        // Create real directories and files on disk
+        fsSync.mkdirSync(allowedDir, { recursive: true });
+        fsSync.mkdirSync(outsideDir, { recursive: true });
+        fsSync.writeFileSync(path.join(outsideDir, 'sensitive.md'), 'secret');
+
+        // Create a symbolic link pointing outside the allowed directory
+        try {
+          fsSync.symlinkSync(outsideDir, symlinkDir, 'dir');
+        } catch (err: unknown) {
+          if (
+            process.platform === 'win32' &&
+            err &&
+            typeof err === 'object' &&
+            'code' in err &&
+            err.code === 'EPERM'
+          ) {
+            // Skip the test if the user lacks symlink creation privileges on Windows
+            return;
+          }
+          throw err;
+        }
+
+        const importPath = 'sym_outside/sensitive.md';
+
+        expect(validateImportPath(importPath, allowedDir, [allowedDir])).toBe(
+          false,
+        );
+      } finally {
+        // Cleanup
+        fsSync.rmSync(testRoot, { recursive: true, force: true });
+      }
+    });
   });
 });
diff --git a/packages/core/src/utils/memoryImportProcessor.ts b/packages/core/src/utils/memoryImportProcessor.ts
index dc4b0b8537..cd4b9aa111 100644
--- a/packages/core/src/utils/memoryImportProcessor.ts
+++ b/packages/core/src/utils/memoryImportProcessor.ts
@@ -6,7 +6,7 @@
 
 import * as fs from 'node:fs/promises';
 import * as path from 'node:path';
-import { isSubpath } from './paths.js';
+import { isSubpath, resolveToRealPath } from './paths.js';
 import { debugLogger } from './debugLogger.js';
 
 // Simple console logger for import processing
@@ -397,9 +397,28 @@ export function validateImportPath(
     return false;
   }
 
-  const resolvedPath = path.resolve(basePath, importPath);
+  let resolvedPath: string;
+  try {
+    // Canonicalize the path on the actual physical disk to resolve symlinks
+    resolvedPath = resolveToRealPath(path.resolve(basePath, importPath));
+  } catch {
+    // If path resolution fails (e.g., infinite recursion or invalid path), fail-closed and reject it
+    return false;
+  }
 
-  return allowedDirectories.some((allowedDir) =>
-    isSubpath(allowedDir, resolvedPath),
+  const realAllowedDirs = allowedDirectories
+    .map((dir) => {
+      const trimmed = dir.trim();
+      if (!trimmed) return null;
+      try {
+        return resolveToRealPath(trimmed);
+      } catch {
+        return null;
+      }
+    })
+    .filter((dir): dir is string => dir !== null);
+
+  return realAllowedDirs.some((realAllowedDir) =>
+    isSubpath(realAllowedDir, resolvedPath),
   );
 }