diff --git a/src/utils/files.ts b/src/utils/files.ts
index 74b371d26..8b91eba56 100644
--- a/src/utils/files.ts
+++ b/src/utils/files.ts
@@ -15,7 +15,16 @@ export async function getTempFilePath(filename: string) {
   return filepath;
 }
 
-export async function resolveCanonicalPath(filePath: string): Promise<string> {
+// Upper bound on the number of nested symlinks resolved for a not-yet-existing
+// target. Mirrors the kernel's SYMLOOP_MAX and prevents an unbounded loop when
+// dangling symlinks form a cycle (fs.realpath() would report such a cycle as
+// ELOOP, but it never reaches those links because their targets do not exist).
+const MAX_SYMLINK_DEPTH = 40;
+
+export async function resolveCanonicalPath(
+  filePath: string,
+  symlinkDepth = 0,
+): Promise<string> {
   const absolutePath = path.resolve(filePath);
   try {
     // Get the true canonical path, resolving all symlinks.
@@ -31,6 +40,34 @@ export async function resolveCanonicalPath(filePath: string): Promise<string> {
       let current = absolutePath;
       const missingSegments: string[] = [];
       while (true) {
+        // A dangling symlink (one whose target does not exist yet) is reported
+        // as ENOENT by fs.realpath(), so the walk below would otherwise treat
+        // the link's own name as an ordinary missing segment and re-append it
+        // verbatim. That yields an in-tree path even though a follow-the-link
+        // write lands wherever the link points. Resolve such a link explicitly
+        // so the returned canonical path reflects the real write destination
+        // and MCP roots validation cannot be bypassed by a symlink placed
+        // inside a configured root.
+        let linkStat;
+        try {
+          linkStat = await fs.lstat(current);
+        } catch {
+          linkStat = undefined;
+        }
+        if (linkStat?.isSymbolicLink()) {
+          if (symlinkDepth >= MAX_SYMLINK_DEPTH) {
+            throw err;
+          }
+          const linkTarget = path.resolve(
+            path.dirname(current),
+            await fs.readlink(current),
+          );
+          return await resolveCanonicalPath(
+            path.join(linkTarget, ...missingSegments),
+            symlinkDepth + 1,
+          );
+        }
+
         const parent = path.dirname(current);
         if (parent === current) {
           // Reached root directory but still couldn't resolve anything.
diff --git a/tests/utils/files.test.ts b/tests/utils/files.test.ts
index 2cfc5e401..fade73a03 100644
--- a/tests/utils/files.test.ts
+++ b/tests/utils/files.test.ts
@@ -92,4 +92,58 @@ describe('resolveCanonicalPath', () => {
       await fs.rm(tmpDir, {recursive: true, force: true});
     }
   });
+
+  it('should resolve a dangling symlink to its target rather than its own path', async () => {
+    const tmpDir = await fs.mkdtemp(
+      path.join(os.tmpdir(), 'resolve-canonical-test-'),
+    );
+    try {
+      const insideDir = path.join(tmpDir, 'inside');
+      const outsideDir = path.join(tmpDir, 'outside');
+      await fs.mkdir(insideDir);
+      await fs.mkdir(outsideDir);
+
+      // A symlink that lives inside `insideDir` but points at a not-yet-created
+      // file under `outsideDir`. fs.realpath() reports ENOENT for such a link,
+      // so it must be resolved explicitly to its target.
+      const danglingLink = path.join(insideDir, 'report.txt');
+      const linkTarget = path.join(outsideDir, 'pwned.txt');
+      await fs.symlink(linkTarget, danglingLink);
+
+      const resolved = await resolveCanonicalPath(danglingLink);
+      assert.strictEqual(
+        resolved,
+        path.join(await fs.realpath(outsideDir), 'pwned.txt'),
+      );
+    } finally {
+      await fs.rm(tmpDir, {recursive: true, force: true});
+    }
+  });
+
+  it('should resolve a not-yet-existing file through a dangling directory symlink', async () => {
+    const tmpDir = await fs.mkdtemp(
+      path.join(os.tmpdir(), 'resolve-canonical-test-'),
+    );
+    try {
+      const insideDir = path.join(tmpDir, 'inside');
+      await fs.mkdir(insideDir);
+
+      // `escape` is a directory symlink inside `insideDir` whose target does
+      // not exist yet. Both the target directory and the final file are
+      // missing, so the walk must still resolve the intermediate symlink.
+      const escapeLink = path.join(insideDir, 'escape');
+      const escapeTarget = path.join(tmpDir, 'outside-dir');
+      await fs.symlink(escapeTarget, escapeLink, 'dir');
+
+      const filePath = path.join(escapeLink, 'out.txt');
+
+      const resolved = await resolveCanonicalPath(filePath);
+      assert.strictEqual(
+        resolved,
+        path.join(await fs.realpath(tmpDir), 'outside-dir', 'out.txt'),
+      );
+    } finally {
+      await fs.rm(tmpDir, {recursive: true, force: true});
+    }
+  });
 });