diff --git a/libmproxy/flow.py b/libmproxy/flow.py
index 1a052f51d..59312cebf 100644
--- a/libmproxy/flow.py
+++ b/libmproxy/flow.py
@@ -240,9 +240,13 @@ class ServerPlaybackState:
         _, _, path, _, query, _ = urlparse.urlparse(r.url)
         queriesArray = urlparse.parse_qsl(query, keep_blank_values=True)
 
+        # scheme should match the client connection to be able to replay
+        # although r.scheme may have been changed to http to connect to upstream server
+        scheme = "https" if flow.client_conn and flow.client_conn.ssl_established else "http"
+
         key = [
             str(r.port),
-            str(r.scheme),
+            str(scheme),
             str(r.method),
             str(path),
         ]
diff --git a/libmproxy/protocol/http.py b/libmproxy/protocol/http.py
index da15066bf..2bb1f5287 100644
--- a/libmproxy/protocol/http.py
+++ b/libmproxy/protocol/http.py
@@ -1297,7 +1297,6 @@ class HTTPHandler(ProtocolHandler):
                 self.c.set_server_address((request.host, request.port))
                 # Update server_conn attribute on the flow
                 flow.server_conn = self.c.server_conn
-                self.c.establish_server_connection()
                 self.c.client_conn.send(
                     ('HTTP/%s.%s 200 ' % (request.httpversion[0], request.httpversion[1])) +
                     'Connection established\r\n' +
@@ -1498,7 +1497,10 @@ class HTTPHandler(ProtocolHandler):
                     "Received CONNECT request to SSL port. "
                     "Upgrading to SSL...", "debug"
                 )
-                self.c.establish_ssl(server=True, client=True)
+                server_ssl = not self.c.config.no_upstream_cert
+                if server_ssl:
+                    self.c.establish_server_connection()
+                self.c.establish_ssl(server=server_ssl, client=True)
                 self.c.log("Upgrade to SSL completed.", "debug")
 
             if self.c.config.check_tcp(address):
diff --git a/libmproxy/protocol/primitives.py b/libmproxy/protocol/primitives.py
index 2f8ea3e05..a9193c5f4 100644
--- a/libmproxy/protocol/primitives.py
+++ b/libmproxy/protocol/primitives.py
@@ -236,7 +236,7 @@ class LiveConnection(object):
         ssl_mismatch = (
             ssl is not None and
             (
-                ssl != self.c.server_conn.ssl_established
+                (self.c.server_conn.connection and ssl != self.c.server_conn.ssl_established)
                 or
                 (sni is not None and sni != self.c.server_conn.sni)
             )
diff --git a/test/test_server.py b/test/test_server.py
index 2805e936c..9df4ef824 100644
--- a/test/test_server.py
+++ b/test/test_server.py
@@ -800,6 +800,17 @@ class TestFakeResponse(tservers.HTTPProxTest):
         assert "header_response" in f.headers.keys()
 
 
+class TestServerConnect(tservers.HTTPProxTest):
+    masterclass = MasterFakeResponse
+    no_upstream_cert = True
+    ssl = True
+    def test_unnecessary_serverconnect(self):
+        """A replayed/fake response with no_upstream_cert should not connect to an upstream server"""
+        assert self.pathod("200").status_code == 200
+        for msg in self.proxy.tmaster.log:
+            assert "serverconnect" not in msg
+
+
 class MasterKillRequest(tservers.TestMaster):
     def handle_request(self, f):
         f.reply(KILL)