diff --git a/.changeset/brave-pianos-listen.md b/.changeset/brave-pianos-listen.md
new file mode 100644
index 0000000000..5e44958427
--- /dev/null
+++ b/.changeset/brave-pianos-listen.md
@@ -0,0 +1,5 @@
+---
+"@modelcontextprotocol/server-filesystem": patch
+---
+
+Name a broken symlink in the error message instead of reporting its parent directory as missing.
diff --git a/src/filesystem/__tests__/broken-symlink.test.ts b/src/filesystem/__tests__/broken-symlink.test.ts
new file mode 100644
index 0000000000..2084aaf988
--- /dev/null
+++ b/src/filesystem/__tests__/broken-symlink.test.ts
@@ -0,0 +1,57 @@
+import fs from "fs/promises";
+import os from "os";
+import path from "path";
+import { afterEach, beforeEach, describe, expect, it } from "vitest";
+import { validatePath } from "../lib.js";
+
+describe("a symlink with no target", () => {
+  let testDirectory: string;
+  let allowedDirs: string[];
+
+  beforeEach(async () => {
+    testDirectory = await fs.mkdtemp(
+      path.join(os.tmpdir(), "mcp-broken-symlink-"),
+    );
+    allowedDirs = [testDirectory];
+  });
+
+  afterEach(async () => {
+    await fs.rm(testDirectory, { recursive: true, force: true });
+  });
+
+  it("is named as such, not as a missing parent directory", async () => {
+    const link = path.join(testDirectory, "link.txt");
+    await fs.symlink(path.join(testDirectory, "gone.txt"), link);
+
+    await expect(validatePath(link, allowedDirs)).rejects.toThrow(
+      /Broken symlink/,
+    );
+    // the parent is right there, so the old message pointed at the wrong thing
+    await expect(fs.stat(testDirectory)).resolves.toBeDefined();
+  });
+
+  // Windows needs a privilege to create a symlink at all, and a self-referencing
+  // one is not reachable there the same way.
+  it.skipIf(process.platform === "win32")(
+    "leaves a realpath failure other than ENOENT alone",
+    async () => {
+      const loop = path.join(testDirectory, "loop");
+      await fs.symlink(loop, loop);
+
+      // A cycle fails realpath with ELOOP, not ENOENT, so validatePath throws
+      // before the equivalent-path walk runs at all. The guard is against a
+      // broader catch there that would rename every realpath failure.
+      await expect(validatePath(loop, allowedDirs)).rejects.toThrow(/^ELOOP/);
+    },
+  );
+
+  it("does not change what a genuinely missing path reports", async () => {
+    const missing = path.join(testDirectory, "nope", "file.txt");
+
+    // resolveUnicodeEquivalentPath returns the tail so create_directory can
+    // mkdir -p it; that is unrelated to the broken-symlink case.
+    await expect(validatePath(missing, allowedDirs)).resolves.toBe(
+      path.join(await fs.realpath(testDirectory), "nope", "file.txt"),
+    );
+  });
+});
diff --git a/src/filesystem/__tests__/server-paths.test.ts b/src/filesystem/__tests__/server-paths.test.ts
index d6a8995317..70970f518c 100644
--- a/src/filesystem/__tests__/server-paths.test.ts
+++ b/src/filesystem/__tests__/server-paths.test.ts
@@ -199,14 +199,14 @@ describe("symlinks", () => {
     expect(await fs.readdir(outside)).toEqual(["secret.txt"]);
   });
 
-  it("refuses to write through a dangling symlink, reporting a missing parent", async () => {
+  it("refuses to write through a dangling symlink, naming the symlink", async () => {
     const link = path.join(dir, "dangling");
     await fs.symlink(path.join(outside, "not-yet"), link);
     const result = await call(client, "write_file", {
       path: link,
       content: "x",
     });
-    expect(textOf(result)).toBe(`Parent directory does not exist: ${dir}`);
+    expect(textOf(result)).toBe(`Broken symlink: ${link}`);
     await expect(fs.stat(path.join(outside, "not-yet"))).rejects.toThrow();
   });
 
diff --git a/src/filesystem/lib.ts b/src/filesystem/lib.ts
index abb6b09cd4..3140206eae 100644
--- a/src/filesystem/lib.ts
+++ b/src/filesystem/lib.ts
@@ -175,9 +175,19 @@ async function resolveUnicodeEquivalentPath(
       return path.join(currentPath, ...relativeParts.slice(index));
     }
 
-    currentPath = await fs.realpath(
-      path.join(currentPath, equivalentMatches[0]),
-    );
+    const matchedPath = path.join(currentPath, equivalentMatches[0]);
+    try {
+      currentPath = await fs.realpath(matchedPath);
+    } catch (error) {
+      if ((error as NodeJS.ErrnoException).code === "ENOENT") {
+        // The entry is in the directory listing but realpath cannot follow it,
+        // so it is a symlink with nothing at the other end. Name that. Left as
+        // a bare ENOENT it reaches validatePath's catch, which reports a
+        // missing parent directory for a directory that is plainly there.
+        throw new Error(`Broken symlink: ${matchedPath}`, { cause: error });
+      }
+      throw error;
+    }
     if (
       !isPathWithinAllowedDirectories(
         normalizePath(currentPath),