diff --git a/index.js b/index.js
index 1655053d..9d484426 100644
--- a/index.js
+++ b/index.js
@@ -606,17 +606,27 @@ SendStream.prototype.sendFile = function sendFile (path) {
     var pathEndsWithSep = path[path.length - 1] === sep
     if (err && err.code === 'ENOENT' && !extname(path) && !pathEndsWithSep) {
       // not found, check extensions
-      return next(err)
+      return next(err, false)
     }
     if (err) return self.onStatError(err)
-    if (stat.isDirectory()) return self.redirect(path)
+    if (stat.isDirectory()) {
+      // if extensions are configured and path has no extension, try extensions first
+      if (self._extensions.length > 0 && !extname(path) && !pathEndsWithSep) {
+        return next(null, true)
+      }
+      return self.redirect(path)
+    }
     if (pathEndsWithSep) return self.error(404)
     self.emit('file', path, stat)
     self.send(path, stat)
   })
 
-  function next (err) {
+  function next (err, isDir) {
     if (self._extensions.length <= i) {
+      // if original path was a directory, redirect to it
+      if (isDir) {
+        return self.redirect(path)
+      }
       return err
         ? self.onStatError(err)
         : self.error(404)
@@ -626,8 +636,8 @@ SendStream.prototype.sendFile = function sendFile (path) {
 
     debug('stat "%s"', p)
     fs.stat(p, function (err, stat) {
-      if (err) return next(err)
-      if (stat.isDirectory()) return next()
+      if (err) return next(err, isDir)
+      if (stat.isDirectory()) return next(null, isDir)
       self.emit('file', p, stat)
       self.send(p, stat)
     })
diff --git a/test/fixtures/about.html b/test/fixtures/about.html
new file mode 100644
index 00000000..a5d3a7fc
--- /dev/null
+++ b/test/fixtures/about.html
@@ -0,0 +1 @@
+About Page
\ No newline at end of file
diff --git a/test/fixtures/about/team.html b/test/fixtures/about/team.html
new file mode 100644
index 00000000..00812726
--- /dev/null
+++ b/test/fixtures/about/team.html
@@ -0,0 +1 @@
+Team Page
\ No newline at end of file
diff --git a/test/send.js b/test/send.js
index b8242821..02ac1f3e 100644
--- a/test/send.js
+++ b/test/send.js
@@ -917,6 +917,36 @@ describe('send(file, options)', function () {
         .get('/thing.html')
         .expect(404, done)
     })
+
+    it('should serve file with extension when no directory exists', function (done) {
+      // /contact (no directory exists) → serves contact.html
+      request(createServer({ extensions: ['html'], root: fixtures }))
+        .get('/tobi')
+        .expect(200, '<p>tobi</p>', done)
+    })
+
+    it('should serve file with extension when directory also exists', function (done) {
+      // /about (directory exists) → serves about.html (not redirect to /about/)
+      request(createServer({ extensions: ['html'], root: fixtures }))
+        .get('/about')
+        .expect(200, 'About Page', done)
+    })
+
+    it('should redirect when directory exists and extensions not configured', function (done) {
+      // When extensions are not configured, should still redirect when directory exists
+      request(createServer({ root: fixtures }))
+        .get('/about')
+        .expect('Location', '/about/')
+        .expect(301, done)
+    })
+
+    it('should redirect to directory when file with extension does not exist', function (done) {
+      // /about with only about/ directory → redirects to /about/
+      request(createServer({ extensions: ['html'], root: fixtures }))
+        .get('/pets')
+        .expect('Location', '/pets/')
+        .expect(301, done)
+    })
   })
 
   describe('lastModified', function () {