diff --git a/mitmproxy/proxy/server.py b/mitmproxy/proxy/server.py
index 50a2b76b8..5171fbee6 100644
--- a/mitmproxy/proxy/server.py
+++ b/mitmproxy/proxy/server.py
@@ -48,6 +48,8 @@ class ProxyServer(tcp.TCPServer):
             if config.options.mode == "transparent":
                 platform.init_transparent_mode()
         except Exception as e:
+            if self.socket:
+                self.socket.close()
             raise exceptions.ServerException(
                 'Error starting proxy server: ' + repr(e)
             ) from e
diff --git a/mitmproxy/tools/main.py b/mitmproxy/tools/main.py
index d8fac077a..568c51770 100644
--- a/mitmproxy/tools/main.py
+++ b/mitmproxy/tools/main.py
@@ -13,8 +13,7 @@ from mitmproxy.tools import cmdline  # noqa
 from mitmproxy import exceptions  # noqa
 from mitmproxy import options  # noqa
 from mitmproxy import optmanager  # noqa
-from mitmproxy.proxy import config  # noqa
-from mitmproxy.proxy import server  # noqa
+from mitmproxy import proxy
 from mitmproxy.utils import version_check  # noqa
 from mitmproxy.utils import debug  # noqa
 
@@ -49,15 +48,7 @@ def process_options(parser, opts, args):
             adict[n] = getattr(args, n)
     opts.merge(adict)
 
-    pconf = config.ProxyConfig(opts)
-    if opts.server:
-        try:
-            return server.ProxyServer(pconf)
-        except exceptions.ServerException as v:
-            print(str(v), file=sys.stderr)
-            sys.exit(1)
-    else:
-        return server.DummyServer(pconf)
+    return proxy.config.ProxyConfig(opts)
 
 
 def run(MasterKlass, args, extra=None):  # pragma: no cover
@@ -74,7 +65,16 @@ def run(MasterKlass, args, extra=None):  # pragma: no cover
     master = None
     try:
         unknown = optmanager.load_paths(opts, args.conf)
-        server = process_options(parser, opts, args)
+        pconf = process_options(parser, opts, args)
+        if pconf.options.server:
+            try:
+                server = proxy.server.ProxyServer(pconf)
+            except exceptions.ServerException as v:
+                print(str(v), file=sys.stderr)
+                sys.exit(1)
+        else:
+            server = proxy.server.DummyServer(pconf)
+
         master = MasterKlass(opts, server)
         master.addons.trigger("configure", opts.keys())
         master.addons.trigger("tick")
diff --git a/test/mitmproxy/test_proxy.py b/test/mitmproxy/test_proxy.py
index e1d0da006..299abab3c 100644
--- a/test/mitmproxy/test_proxy.py
+++ b/test/mitmproxy/test_proxy.py
@@ -32,8 +32,7 @@ class TestProcessProxyOptions:
         opts = options.Options()
         cmdline.common_options(parser, opts)
         args = parser.parse_args(args=args)
-        main.process_options(parser, opts, args)
-        pconf = config.ProxyConfig(opts)
+        pconf = main.process_options(parser, opts, args)
         return parser, pconf
 
     def assert_noerr(self, *args):