diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2523dcf36..f7211e99b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,7 @@
   Includes example addon which applies custom definitions for selected gRPC traffic (@mame82)
 * Fix a crash caused when editing string option (#4852, @rbdixon)
 * Base container image bumped to Debian 11 Bullseye (@Kriechi)
+* Upstream replays don't do CONNECT on plaintext HTTP requests (#4876, @HoffmannP)
 
 ## 28 September 2021: mitmproxy 7.0.4
 
diff --git a/mitmproxy/addons/clientplayback.py b/mitmproxy/addons/clientplayback.py
index b75034933..8dea6f794 100644
--- a/mitmproxy/addons/clientplayback.py
+++ b/mitmproxy/addons/clientplayback.py
@@ -78,7 +78,10 @@ class ReplayHandler(server.ConnectionHandler):
 
         super().__init__(context)
 
-        self.layer = layers.HttpLayer(context, HTTPMode.transparent)
+        if options.mode.startswith("upstream:"):
+            self.layer = layers.HttpLayer(context, HTTPMode.upstream)
+        else:
+            self.layer = layers.HttpLayer(context, HTTPMode.transparent)
         self.layer.connections[client] = MockServer(flow, context.fork())
         self.flow = flow
         self.done = asyncio.Event()
diff --git a/test/mitmproxy/addons/test_clientplayback.py b/test/mitmproxy/addons/test_clientplayback.py
index ad68c1d26..4de48ffe5 100644
--- a/test/mitmproxy/addons/test_clientplayback.py
+++ b/test/mitmproxy/addons/test_clientplayback.py
@@ -31,13 +31,13 @@ async def test_playback(mode, concurrency):
             writer.close()
             handler_ok.set()
             return
+        req = await reader.readline()
         if mode == "upstream":
-            conn_req = await reader.readuntil(b"\r\n\r\n")
-            assert conn_req == b'CONNECT address:22 HTTP/1.1\r\n\r\n'
-            writer.write(b"HTTP/1.1 200 Connection Established\r\n\r\n")
+            assert req == b'GET http://address:22/path HTTP/1.1\r\n'
+        else:
+            assert req == b'GET /path HTTP/1.1\r\n'
         req = await reader.readuntil(b"data")
         assert req == (
-            b'GET /path HTTP/1.1\r\n'
             b'header: qvalue\r\n'
             b'content-length: 4\r\n'
             b'\r\n'
@@ -59,6 +59,8 @@ async def test_playback(mode, concurrency):
             flow.request.content = b"data"
             if mode == "upstream":
                 tctx.options.mode = f"upstream:http://{addr[0]}:{addr[1]}"
+                flow.request.authority = f"{addr[0]}:{addr[1]}"
+                flow.request.host, flow.request.port = 'address', 22
             else:
                 flow.request.host, flow.request.port = addr
             cp.start_replay([flow])
@@ -70,6 +72,37 @@ async def test_playback(mode, concurrency):
                 assert flow.response.status_code == 204
 
 
+@pytest.mark.asyncio
+async def test_playback_https_upstream():
+    handler_ok = asyncio.Event()
+
+    async def handler(reader: asyncio.StreamReader, writer: asyncio.StreamWriter):
+        conn_req = await reader.readuntil(b"\r\n\r\n")
+        assert conn_req == b'CONNECT address:22 HTTP/1.1\r\n\r\n'
+        writer.write(b"HTTP/1.1 502 Bad Gateway\r\n\r\n")
+        await writer.drain()
+        assert not await reader.read()
+        handler_ok.set()
+
+    cp = ClientPlayback()
+    ps = Proxyserver()
+    with taddons.context(cp, ps) as tctx:
+        tctx.configure(cp)
+        async with tcp_server(handler) as addr:
+            cp.running()
+            flow = tflow.tflow()
+            flow.request.scheme = b"https"
+            flow.request.content = b"data"
+            tctx.options.mode = f"upstream:http://{addr[0]}:{addr[1]}"
+            cp.start_replay([flow])
+            assert cp.count() == 1
+            await asyncio.wait_for(cp.queue.join(), 5)
+            await asyncio.wait_for(handler_ok.wait(), 5)
+            cp.done()
+            assert flow.response is None
+            assert str(flow.error) == f'Upstream proxy {addr[0]}:{addr[1]} refused HTTP CONNECT request: 502 Bad Gateway'
+
+
 @pytest.mark.asyncio
 async def test_playback_crash(monkeypatch):
     async def raise_err():