diff --git a/.changeset/memory-skill-files-path-normalisation.md b/.changeset/memory-skill-files-path-normalisation.md
new file mode 100644
index 0000000000..0c4a6a07d3
--- /dev/null
+++ b/.changeset/memory-skill-files-path-normalisation.md
@@ -0,0 +1,5 @@
+---
+'@modelcontextprotocol/server': patch
+---
+
+`memorySkillFiles.list()` and `memorySkillFiles.read()` normalise the path they are given the same way the record index normalises its keys, so `list('sub/')`, `list('./sub')` and `read('./SKILL.md')` resolve instead of reporting a missing directory or file, and a `..` segment is rejected before it can reach the record.
diff --git a/packages/server/src/ext/skills/files.ts b/packages/server/src/ext/skills/files.ts
index 8b93955ddf..009500bc76 100644
--- a/packages/server/src/ext/skills/files.ts
+++ b/packages/server/src/ext/skills/files.ts
@@ -39,6 +39,16 @@ function indexRecord(keys: readonly string[]): MemoryIndex {
     return { dirs, files };
 }
 
+// `''` is the record root; every other path is normalised the same way the
+// index normalises record keys, so `sub/` and `./SKILL.md` resolve.
+function normaliseDir(dir: string): string {
+    return dir === '' ? '' : splitRelativePath(dir, 'directory').join('/');
+}
+
+function normalisePath(path: string): string {
+    return splitRelativePath(path, 'file path').join('/');
+}
+
 /**
  * An in-memory adapter. The record is re-read whenever a walk starts — `list('')` — so `reload()` sees later changes.
  * Other calls use the index from that read (built on first use if no walk has started), so their cost does not grow
@@ -52,14 +62,17 @@ export function memorySkillFiles(files: Record<string, string | Uint8Array>): Sk
     };
     return {
         async list(dir) {
-            const children = (dir === '' ? reindex() : (index ?? reindex())).dirs.get(dir);
+            const normalised = normaliseDir(dir);
+            const children = (normalised === '' ? reindex() : (index ?? reindex())).dirs.get(normalised);
             if (children !== undefined) return Array.from(children.values(), entry => ({ ...entry }));
-            if (dir === '') return [];
+            if (normalised === '') return [];
             throw new Error(`no such directory: ${dir}`);
         },
         async read(path) {
+            // Validation comes first: a `..` segment must never reach the record.
+            const normalised = normalisePath(path);
             // Keys written as `./a/b` or `a//b` are found through the index.
-            const key = Object.hasOwn(files, path) ? path : (index ?? reindex()).files.get(path);
+            const key = Object.hasOwn(files, normalised) ? normalised : (index ?? reindex()).files.get(normalised);
             const content = key === undefined ? undefined : files[key];
             if (content === undefined) throw new Error(`no such file: ${path}`);
             return typeof content === 'string' ? encodeUtf8(content) : content;
diff --git a/packages/server/test/ext/skills/files.test.ts b/packages/server/test/ext/skills/files.test.ts
new file mode 100644
index 0000000000..80d5cc03ff
--- /dev/null
+++ b/packages/server/test/ext/skills/files.test.ts
@@ -0,0 +1,56 @@
+import { describe, expect, it } from 'vitest';
+
+import { memorySkillFiles } from '../../../src/ext/skills/index';
+
+const RECORD = {
+    'SKILL.md': '# skill',
+    'sub/other.txt': 'other'
+};
+
+describe('memorySkillFiles', () => {
+    it('lists a directory given with a trailing slash or a leading dot segment', async () => {
+        const files = memorySkillFiles(RECORD);
+
+        await expect(files.list('sub/')).resolves.toEqual([{ name: 'other.txt', kind: 'file' }]);
+        await expect(files.list('./sub')).resolves.toEqual([{ name: 'other.txt', kind: 'file' }]);
+    });
+
+    it('lists the root for an empty directory', async () => {
+        const files = memorySkillFiles(RECORD);
+
+        await expect(files.list('')).resolves.toEqual(
+            expect.arrayContaining([
+                { name: 'SKILL.md', kind: 'file' },
+                { name: 'sub', kind: 'directory' }
+            ])
+        );
+    });
+
+    it('reads a file given in a non-canonical form', async () => {
+        const files = memorySkillFiles(RECORD);
+
+        await expect(files.read('./SKILL.md')).resolves.toEqual(expect.any(Uint8Array));
+        await expect(files.read('sub//other.txt')).resolves.toEqual(expect.any(Uint8Array));
+    });
+
+    it('finds a record key that is itself non-canonical', async () => {
+        const files = memorySkillFiles({ './SKILL.md': '# skill' });
+
+        await expect(files.read('SKILL.md')).resolves.toEqual(expect.any(Uint8Array));
+    });
+
+    it('rejects a path that could leave the record', async () => {
+        const files = memorySkillFiles(RECORD);
+
+        await expect(files.list('..')).rejects.toThrow(TypeError);
+        await expect(files.read('../SKILL.md')).rejects.toThrow(TypeError);
+        await expect(files.read('')).rejects.toThrow(TypeError);
+    });
+
+    it('still reports a missing path', async () => {
+        const files = memorySkillFiles(RECORD);
+
+        await expect(files.list('missing')).rejects.toThrow('no such directory: missing');
+        await expect(files.read('missing.txt')).rejects.toThrow('no such file: missing.txt');
+    });
+});