diff --git a/.changeset/filesystem-dangling-symlink-message.md b/.changeset/filesystem-dangling-symlink-message.md
new file mode 100644
index 0000000000..4a2439496e
--- /dev/null
+++ b/.changeset/filesystem-dangling-symlink-message.md
@@ -0,0 +1,5 @@
+---
+"@modelcontextprotocol/server-filesystem": patch
+---
+
+Report a dangling symlink as a broken symlink. A request through a symlink whose target does not exist is still refused, but the error now names the symlink instead of saying its parent directory, which exists, does not.
diff --git a/src/filesystem/__tests__/lib.test.ts b/src/filesystem/__tests__/lib.test.ts
index 15ee98abf1..b1e720ec86 100644
--- a/src/filesystem/__tests__/lib.test.ts
+++ b/src/filesystem/__tests__/lib.test.ts
@@ -402,6 +402,24 @@ describe("Lib Functions", () => {
         ).rejects.toThrow("EACCES lstat");
       });
 
+      // #5191: only an ENOENT from an existing entry's realpath means a
+      // broken symlink; any other failure is reported as it is.
+      it("reports a realpath failure other than ENOENT on an existing component as is", async () => {
+        const base =
+          process.platform === "win32" ? "C:\\Users\\test" : "/home/user";
+        const enoentError = new Error("ENOENT") as NodeJS.ErrnoException;
+        enoentError.code = "ENOENT";
+        mockFs.realpath
+          .mockRejectedValueOnce(enoentError)
+          .mockResolvedValueOnce(base)
+          .mockRejectedValueOnce(new Error("EACCES realpath"));
+        mockReaddirNames.mockResolvedValueOnce(["link"]);
+
+        await expect(
+          validatePath(path.join(base, "link", "a"), allowedDirs),
+        ).rejects.toThrow("EACCES realpath");
+      });
+
       it("rejects when no ancestor directory exists at all", async () => {
         const newFilePath =
           process.platform === "win32"
diff --git a/src/filesystem/__tests__/server-paths.test.ts b/src/filesystem/__tests__/server-paths.test.ts
index 803cfb41a6..d24ee98076 100644
--- a/src/filesystem/__tests__/server-paths.test.ts
+++ b/src/filesystem/__tests__/server-paths.test.ts
@@ -314,7 +314,7 @@ describe("symlinks", () => {
         ).toBe("x");
       });
 
-      it("refuses to write under a respelled dangling symlink, reporting a missing parent", async () => {
+      it("refuses to write under a respelled dangling symlink, naming it as broken (#5191)", async () => {
         await fs.symlink(
           path.join(outside, "not-yet"),
           path.join(dir, "dangling"),
@@ -324,24 +324,51 @@ describe("symlinks", () => {
           content: "x",
         });
         expect(textOf(result)).toBe(
-          `Parent directory does not exist: ${path.join(dir, "DANGLING")}`,
+          `Broken symlink: ${path.join(dir, "DANGLING")} points to a target that does not exist`,
         );
         await expect(fs.stat(path.join(outside, "not-yet"))).rejects.toThrow();
       });
     },
   );
 
-  it("refuses to write through a dangling symlink, reporting a missing parent", async () => {
+  // #5191: the refusal is right, and the message names the symlink rather
+  // than reporting its parent, which exists, as missing.
+  it("refuses to write through a dangling symlink, naming it as broken (#5191)", 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} points to a target that does not exist`,
+    );
     await expect(fs.stat(path.join(outside, "not-yet"))).rejects.toThrow();
   });
 
+  it("refuses to read a dangling symlink, naming it as broken (#5191)", async () => {
+    const link = path.join(dir, "dangling");
+    await fs.symlink(path.join(dir, "gone.txt"), link);
+    const result = await read(link);
+    expect(result.isError).toBe(true);
+    expect(textOf(result)).toBe(
+      `Broken symlink: ${link} points to a target that does not exist`,
+    );
+  });
+
+  it("names a dangling symlink in the middle of a path as broken (#5191)", async () => {
+    const link = path.join(dir, "dangling-dir");
+    await fs.symlink(path.join(dir, "gone"), link);
+    const result = await call(client, "write_file", {
+      path: path.join(link, "f.txt"),
+      content: "x",
+    });
+    expect(textOf(result)).toBe(
+      `Broken symlink: ${link} points to a target that does not exist`,
+    );
+    await expect(fs.stat(path.join(dir, "gone"))).rejects.toThrow();
+  });
+
   it("reports a realpath failure other than ENOENT as is", async () => {
     await fs.writeFile(path.join(dir, "file.txt"), "");
     const result = await read(path.join(dir, "file.txt", "child"));
diff --git a/src/filesystem/lib.ts b/src/filesystem/lib.ts
index 775145e708..87f4aeca57 100644
--- a/src/filesystem/lib.ts
+++ b/src/filesystem/lib.ts
@@ -429,7 +429,21 @@ async function resolveUnicodeEquivalentPath(
       return path.join(currentPath, ...relativeParts.slice(index));
     }
 
-    currentPath = await realpathWithTimeout(candidate);
+    try {
+      currentPath = await realpathWithTimeout(candidate);
+    } catch (error) {
+      // The entry exists (lstat found it just above) but realpath cannot
+      // follow it, so it is a symlink whose target is missing. Name it: a bare
+      // ENOENT reaches validatePath's catch, which would report its parent,
+      // a directory that plainly exists, as missing (#5191).
+      if ((error as NodeJS.ErrnoException).code === "ENOENT") {
+        throw new Error(
+          `Broken symlink: ${candidate} points to a target that does not exist`,
+          { cause: error },
+        );
+      }
+      throw error;
+    }
     if (
       !isPathWithinAllowedDirectories(
         normalizePathFormat(currentPath),