diff --git a/CHANGELOG.md b/CHANGELOG.md
index d3af5bf77..1e789ee4a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,7 @@
   Processing will only resume once the event hook has finished. (@Prinzhorn)
 * Allow addon hooks to be async (@nneonneo, #4207)
 * Reintroduce `Flow.live`, which signals if a flow belongs to a currently active connection. (@mhils, #4207)
+* Speculative fix for some rare HTTP/2 connection stalls (#5158, @EndUser509)
 
 ## 28 September 2021: mitmproxy 7.0.4
 
diff --git a/mitmproxy/proxy/server.py b/mitmproxy/proxy/server.py
index 16595b86b..11e3b92de 100644
--- a/mitmproxy/proxy/server.py
+++ b/mitmproxy/proxy/server.py
@@ -88,6 +88,9 @@ class ConnectionHandler(metaclass=abc.ABCMeta):
         self.layer = layer.NextLayer(context, ask_on_start=True)
         self.timeout_watchdog = TimeoutWatchdog(self.on_timeout)
 
+        # workaround for https://bugs.python.org/issue40124 / https://bugs.python.org/issue29930
+        self._drain_lock = asyncio.Lock()
+
     async def handle_client(self) -> None:
         watch = asyncio_utils.create_task(
             self.timeout_watchdog.watch(),
@@ -253,13 +256,14 @@ class ConnectionHandler(metaclass=abc.ABCMeta):
         Drain all writers to create some backpressure. We won't continue reading until there's space available in our
         write buffers, so if we cannot write fast enough our own read buffers run full and the TCP recv stream is throttled.
         """
-        for transport in self.transports.values():
-            if transport.writer is not None:
-                try:
-                    await transport.writer.drain()
-                except OSError as e:
-                    if transport.handler is not None:
-                        asyncio_utils.cancel_task(transport.handler, f"Error sending data: {e}")
+        async with self._drain_lock:
+            for transport in self.transports.values():
+                if transport.writer is not None:
+                    try:
+                        await transport.writer.drain()
+                    except OSError as e:
+                        if transport.handler is not None:
+                            asyncio_utils.cancel_task(transport.handler, f"Error sending data: {e}")
 
     async def on_timeout(self) -> None:
         self.log(f"Closing connection due to inactivity: {self.client}")