diff --git a/mitmproxy/addons/upstream_auth.py b/mitmproxy/addons/upstream_auth.py
index 96c2767f7..c3053bed1 100644
--- a/mitmproxy/addons/upstream_auth.py
+++ b/mitmproxy/addons/upstream_auth.py
@@ -51,7 +51,7 @@ class UpstreamAuth:
 
     def requestheaders(self, f: http.HTTPFlow):
         if self.auth:
-            if f.mode == "upstream" and not f.server_conn.via:
+            if ctx.options.mode.startswith("upstream") and f.request.scheme == "http":
                 f.request.headers["Proxy-Authorization"] = self.auth
             elif ctx.options.mode.startswith("reverse"):
                 f.request.headers["Authorization"] = self.auth
diff --git a/mitmproxy/test/tflow.py b/mitmproxy/test/tflow.py
index 615e92434..fc477be9d 100644
--- a/mitmproxy/test/tflow.py
+++ b/mitmproxy/test/tflow.py
@@ -10,7 +10,7 @@ from mitmproxy.test.tutils import treq, tresp
 from wsproto.frame_protocol import Opcode
 
 
-def ttcpflow(client_conn=True, server_conn=True, messages=True, err=None):
+def ttcpflow(client_conn=True, server_conn=True, messages=True, err=None) -> tcp.TCPFlow:
     if client_conn is True:
         client_conn = tclient_conn()
     if server_conn is True:
@@ -91,7 +91,7 @@ def twebsocketflow(messages=True, err=None, close_code=None, close_reason='') ->
     return flow
 
 
-def tflow(client_conn=True, server_conn=True, req=True, resp=None, err=None):
+def tflow(client_conn=True, server_conn=True, req=True, resp=None, err=None) -> http.HTTPFlow:
     """
     @type client_conn: bool | None | mitmproxy.proxy.connection.ClientConnection
     @type server_conn: bool | None | mitmproxy.proxy.connection.ServerConnection
@@ -126,7 +126,7 @@ class DummyFlow(flow.Flow):
         super().__init__("dummy", client_conn, server_conn, live)
 
 
-def tdummyflow(client_conn=True, server_conn=True, err=None):
+def tdummyflow(client_conn=True, server_conn=True, err=None) -> DummyFlow:
     if client_conn is True:
         client_conn = tclient_conn()
     if server_conn is True:
diff --git a/test/mitmproxy/addons/test_upstream_auth.py b/test/mitmproxy/addons/test_upstream_auth.py
index 8c8627275..67ec55927 100644
--- a/test/mitmproxy/addons/test_upstream_auth.py
+++ b/test/mitmproxy/addons/test_upstream_auth.py
@@ -33,20 +33,18 @@ def test_simple():
         tctx.configure(up, upstream_auth="foo:bar")
 
         f = tflow.tflow()
-        f.mode = "upstream"
-        up.requestheaders(f)
+        up.http_connect_upstream(f)
         assert "proxy-authorization" in f.request.headers
 
         f = tflow.tflow()
         up.requestheaders(f)
         assert "proxy-authorization" not in f.request.headers
+        assert "authorization" not in f.request.headers
+
+        tctx.configure(up, mode="upstream:127.0.0.1")
+        up.requestheaders(f)
+        assert "proxy-authorization" in f.request.headers
 
         tctx.configure(up, mode="reverse:127.0.0.1")
-        f = tflow.tflow()
-        f.mode = "transparent"
         up.requestheaders(f)
         assert "authorization" in f.request.headers
-
-        f = tflow.tflow()
-        up.http_connect_upstream(f)
-        assert "proxy-authorization" in f.request.headers