diff --git a/History.md b/History.md
index 1fd7337..7836590 100644
--- a/History.md
+++ b/History.md
@@ -4,6 +4,7 @@ unreleased
   * Fix content negotiation when no `Accept` header
   * Properly support all HTTP methods
   * Support vanilla node.js http servers
+  * Treat `ENAMETOOLONG` as code 414
 
 1.0.3 / 2014-05-20
 ==================
diff --git a/index.js b/index.js
index 3fa44cf..42f4d50 100644
--- a/index.js
+++ b/index.js
@@ -109,9 +109,16 @@ exports = module.exports = function serveIndex(root, options){
 
     // check if we have a directory
     fs.stat(path, function(err, stat){
-      if (err) return 'ENOENT' == err.code
-        ? next()
-        : next(err);
+      if (err && err.code === 'ENOENT') {
+        return next();
+      }
+
+      if (err) {
+        err.status = err.code === 'ENAMETOOLONG'
+          ? 414
+          : 500;
+        return next(err);
+      }
 
       if (!stat.isDirectory()) return next();
 
diff --git a/test/test.js b/test/test.js
index 74bffc6..1321652 100644
--- a/test/test.js
+++ b/test/test.js
@@ -75,6 +75,15 @@ describe('serveIndex(root)', function () {
     .expect(404, 'Not Found', done)
   })
 
+  it('should treat an ENAMETOOLONG as a 414', function (done) {
+    var path = Array(11000).join('foobar')
+    var server = createServer()
+
+    request(server)
+    .get('/' + path)
+    .expect(414, done)
+  })
+
   it('should skip non-directories', function (done) {
     var server = createServer()
 
@@ -373,7 +382,7 @@ function createServer(dir, opts) {
   return http.createServer(function (req, res) {
     _serveIndex(req, res, function (err) {
       res.statusCode = err ? (err.status || 500) : 404
-      res.end(err ? err.mesage : 'Not Found')
+      res.end(err ? err.message : 'Not Found')
     })
   })
 }