diff --git a/lib/fs.js b/lib/fs.js
index d48a3f6..94f0435 100755
--- a/lib/fs.js
+++ b/lib/fs.js
@@ -12,10 +12,10 @@ const internals = {
     methods: {
         promised: ['open', 'close', 'fstat', 'readdir'],
         raw: ['createReadStream']
-    }
+    },
+    notFound: new Set(['ENOENT', 'ENOTDIR'])
 };
 
-
 exports.File = class {
 
     constructor(path) {
@@ -34,7 +34,7 @@ exports.File = class {
         catch (err) {
             const data = { path: this.path };
 
-            if (this.path.indexOf('\u0000') !== -1 || err.code === 'ENOENT') {
+            if (this.path.indexOf('\u0000') !== -1 || internals.notFound.has(err.code)) {
                 throw Boom.notFound(null, data);
             }
 
diff --git a/test/directory.js b/test/directory.js
index fd6d3e1..1963fc1 100755
--- a/test/directory.js
+++ b/test/directory.js
@@ -73,6 +73,16 @@ describe('directory', () => {
             expect(res.request.response._error.data.path).to.equal(Path.join(__dirname, 'xyz'));
         });
 
+        it('returns a 404 when requesting an unknown file when part of the path matches a filename', async () => {
+
+            const server = await provisionServer();
+            server.route({ method: 'GET', path: '/directory/{path*}', handler: { directory: { path: './' } } });
+
+            const res = await server.inject('/directory/directory.js/xyz');
+            expect(res.statusCode).to.equal(404);
+            expect(res.request.response._error.data.path).to.equal(Path.join(__dirname, 'directory.js', 'xyz'));
+        });
+
         it('returns a file when requesting a file from the directory', async () => {
 
             const server = await provisionServer();