diff --git a/composer.json b/composer.json
index 4c74c704..fccbc1bd 100644
--- a/composer.json
+++ b/composer.json
@@ -18,6 +18,7 @@
     },
     "require-dev": {
         "phpunit/phpunit": "^4.8.10||^5.0",
-        "react/socket": "^0.7"
+        "react/socket": "^0.7",
+        "clue/block-react": "^1.1"
     }
 }
diff --git a/src/RequestHeaderParser.php b/src/RequestHeaderParser.php
index db115248..792a0604 100644
--- a/src/RequestHeaderParser.php
+++ b/src/RequestHeaderParser.php
@@ -77,7 +77,8 @@ private function parseRequest($data)
         // detecting HTTPS is left up to the socket layer (TLS detection)
         if ($request->getUri()->getScheme() === 'https') {
             $request = $request->withUri(
-                $request->getUri()->withScheme('http')->withPort(443)
+                $request->getUri()->withScheme('http')->withPort(443),
+                true
             );
         }
 
diff --git a/src/Server.php b/src/Server.php
index 87ae5054..4cb6d6ea 100644
--- a/src/Server.php
+++ b/src/Server.php
@@ -254,6 +254,21 @@ public function handleRequest(ConnectionInterface $conn, RequestInterface $reque
             '[]'
         );
 
+        // Update request URI to "https" scheme if the connection is encrypted
+        if ($this->isConnectionEncrypted($conn)) {
+            // The request URI may omit default ports here, so try to parse port
+            // from Host header field (if possible)
+            $port = $request->getUri()->getPort();
+            if ($port === null) {
+                $port = parse_url('tcp://' . $request->getHeaderLine('Host'), PHP_URL_PORT);
+            }
+
+            $request = $request->withUri(
+                $request->getUri()->withScheme('https')->withPort($port),
+                true
+            );
+        }
+
         $callback = $this->callback;
         $promise = new Promise(function ($resolve, $reject) use ($callback, $request) {
             $resolve($callback($request));
@@ -384,4 +399,27 @@ private function handleResponseBody(ResponseInterface $response, ConnectionInter
         $connection->write(Psr7Implementation\str($response));
         $stream->pipe($connection);
     }
+
+    /**
+     * @param ConnectionInterface $conn
+     * @return bool
+     * @codeCoverageIgnore
+     */
+    private function isConnectionEncrypted(ConnectionInterface $conn)
+    {
+        // Legacy PHP < 7 does not offer any direct access to check crypto parameters
+        // We work around by accessing the context options and assume that only
+        // secure connections *SHOULD* set the "ssl" context options by default.
+        if (PHP_VERSION_ID < 70000) {
+            $context = isset($conn->stream) ? stream_context_get_options($conn->stream) : array();
+
+            return (isset($context['ssl']) && $context['ssl']);
+        }
+
+        // Modern PHP 7+ offers more reliable access to check crypto parameters
+        // by checking stream crypto meta data that is only then made available.
+        $meta = isset($conn->stream) ? stream_get_meta_data($conn->stream) : array();
+
+        return (isset($meta['crypto']) && $meta['crypto']);
+    }
 }
diff --git a/tests/FunctionalServerTest.php b/tests/FunctionalServerTest.php
new file mode 100644
index 00000000..4c7ed6ff
--- /dev/null
+++ b/tests/FunctionalServerTest.php
@@ -0,0 +1,204 @@
+<?php
+
+namespace React\Tests\Http;
+
+use React\Socket\Server as Socket;
+use React\EventLoop\Factory;
+use React\Http\Server;
+use Psr\Http\Message\RequestInterface;
+use React\Socket\Connector;
+use React\Socket\ConnectionInterface;
+use React\Stream\BufferedSink;
+use Clue\React\Block;
+use React\Http\Response;
+use React\Socket\SecureServer;
+
+class FunctionServerTest extends TestCase
+{
+    public function testPlainHttpOnRandomPort()
+    {
+        $loop = Factory::create();
+        $socket = new Socket(0, $loop);
+        $connector = new Connector($loop);
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri());
+        });
+
+        $result = $connector->connect($socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: " . $conn->getRemoteAddress() . "\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('http://' . $socket->getAddress() . '/', $response);
+
+        $socket->close();
+    }
+
+    public function testSecureHttpsOnRandomPort()
+    {
+        if (!function_exists('stream_socket_enable_crypto')) {
+            $this->markTestSkipped('Not supported on your platform (outdated HHVM?)');
+        }
+
+        $loop = Factory::create();
+        $socket = new Socket(0, $loop);
+        $socket = new SecureServer($socket, $loop, array(
+            'local_cert' => __DIR__ . '/../examples/localhost.pem'
+        ));
+        $connector = new Connector($loop, array(
+            'tls' => array('verify_peer' => false)
+        ));
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri());
+        });
+
+        $result = $connector->connect('tls://' . $socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: " . $conn->getRemoteAddress() . "\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('https://' . $socket->getAddress() . '/', $response);
+
+        $socket->close();
+    }
+
+    public function testPlainHttpOnStandardPortReturnsUriWithNoPort()
+    {
+        $loop = Factory::create();
+        try {
+            $socket = new Socket(80, $loop);
+        } catch (\RuntimeException $e) {
+            $this->markTestSkipped('Listening on port 80 failed (root and unused?)');
+        }
+        $connector = new Connector($loop);
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri());
+        });
+
+        $result = $connector->connect($socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: 127.0.0.1\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('http://127.0.0.1/', $response);
+
+        $socket->close();
+    }
+
+    public function testSecureHttpsOnStandardPortReturnsUriWithNoPort()
+    {
+        if (!function_exists('stream_socket_enable_crypto')) {
+            $this->markTestSkipped('Not supported on your platform (outdated HHVM?)');
+        }
+
+        $loop = Factory::create();
+        try {
+            $socket = new Socket(443, $loop);
+        } catch (\RuntimeException $e) {
+            $this->markTestSkipped('Listening on port 443 failed (root and unused?)');
+        }
+        $socket = new SecureServer($socket, $loop, array(
+            'local_cert' => __DIR__ . '/../examples/localhost.pem'
+        ));
+        $connector = new Connector($loop, array(
+            'tls' => array('verify_peer' => false)
+        ));
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri());
+        });
+
+        $result = $connector->connect('tls://' . $socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: 127.0.0.1\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('https://127.0.0.1/', $response);
+
+        $socket->close();
+    }
+
+    public function testPlainHttpOnHttpsStandardPortReturnsUriWithPort()
+    {
+        $loop = Factory::create();
+        try {
+            $socket = new Socket(443, $loop);
+        } catch (\RuntimeException $e) {
+            $this->markTestSkipped('Listening on port 443 failed (root and unused?)');
+        }
+        $connector = new Connector($loop);
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri());
+        });
+
+        $result = $connector->connect($socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: " . $conn->getRemoteAddress() . "\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('http://127.0.0.1:443/', $response);
+
+        $socket->close();
+    }
+
+    public function testSecureHttpsOnHttpStandardPortReturnsUriWithPort()
+    {
+        if (!function_exists('stream_socket_enable_crypto')) {
+            $this->markTestSkipped('Not supported on your platform (outdated HHVM?)');
+        }
+
+        $loop = Factory::create();
+        try {
+            $socket = new Socket(80, $loop);
+        } catch (\RuntimeException $e) {
+            $this->markTestSkipped('Listening on port 80 failed (root and unused?)');
+        }
+        $socket = new SecureServer($socket, $loop, array(
+            'local_cert' => __DIR__ . '/../examples/localhost.pem'
+        ));
+        $connector = new Connector($loop, array(
+            'tls' => array('verify_peer' => false)
+        ));
+
+        $server = new Server($socket, function (RequestInterface $request) {
+            return new Response(200, array(), (string)$request->getUri() . 'x' . $request->getHeaderLine('Host'));
+        });
+
+        $result = $connector->connect('tls://' . $socket->getAddress())->then(function (ConnectionInterface $conn) {
+            $conn->write("GET / HTTP/1.0\r\nHost: " . $conn->getRemoteAddress() . "\r\n\r\n");
+
+            return BufferedSink::createPromise($conn);
+        });
+
+        $response = Block\await($result, $loop, 1.0);
+
+        $this->assertContains("HTTP/1.0 200 OK", $response);
+        $this->assertContains('https://127.0.0.1:80/', $response);
+
+        $socket->close();
+    }
+}