diff --git a/helper/monitor_open_files.sh b/helper/monitor_open_files.sh
index f353e0db..d4214e8b 100755
--- a/helper/monitor_open_files.sh
+++ b/helper/monitor_open_files.sh
@@ -20,15 +20,20 @@ if [[ -z "$PROXY_PY_PID" ]]; then
   exit 1
 fi
 
-OPEN_FILES_BY_MAIN=$(lsof -p "$PROXY_PY_PID" | wc -l)
-echo "[$PROXY_PY_PID] Main process: $OPEN_FILES_BY_MAIN"
+while true;
+do
+  OPEN_FILES_BY_MAIN=$(lsof -p "$PROXY_PY_PID" | wc -l)
+  echo "[$PROXY_PY_PID] Main process: $OPEN_FILES_BY_MAIN"
 
-pgrep -P "$PROXY_PY_PID" | while read -r acceptorPid; do
-  OPEN_FILES_BY_ACCEPTOR=$(lsof -p "$acceptorPid" | wc -l)
-  echo "[$acceptorPid] Acceptor process: $OPEN_FILES_BY_ACCEPTOR"
+  pgrep -P "$PROXY_PY_PID" | while read -r acceptorPid; do
+    OPEN_FILES_BY_ACCEPTOR=$(lsof -p "$acceptorPid" | wc -l)
+    echo "[$acceptorPid] Acceptor process: $OPEN_FILES_BY_ACCEPTOR"
 
-  pgrep -P "$acceptorPid" | while read -r childPid; do
-    OPEN_FILES_BY_CHILD_PROC=$(lsof -p "$childPid" | wc -l)
-    echo "  [$childPid] child process: $OPEN_FILES_BY_CHILD_PROC"
+    pgrep -P "$acceptorPid" | while read -r childPid; do
+      OPEN_FILES_BY_CHILD_PROC=$(lsof -p "$childPid" | wc -l)
+      echo "  [$childPid] child process: $OPEN_FILES_BY_CHILD_PROC"
+    done
   done
+
+  sleep 1
 done
diff --git a/proxy/core/connection/connection.py b/proxy/core/connection/connection.py
index d0bebe26..63cb62e3 100644
--- a/proxy/core/connection/connection.py
+++ b/proxy/core/connection/connection.py
@@ -87,7 +87,11 @@ class TcpConnection(ABC):
         # TODO: Assemble multiple packets if total
         # size remains below max send size.
         max_send_size = max_send_size or DEFAULT_MAX_SEND_SIZE
-        sent: int = self.send(mv[:max_send_size])
+        try:
+            sent: int = self.send(mv[:max_send_size])
+        except BlockingIOError:
+            logger.warning('BlockingIOError when trying send to {0}'.format(self.tag))
+            return 0
         if sent == len(mv):
             self.buffer.pop(0)
             self._num_buffer -= 1
diff --git a/proxy/http/handler.py b/proxy/http/handler.py
index b8d207d5..581e911a 100644
--- a/proxy/http/handler.py
+++ b/proxy/http/handler.py
@@ -49,6 +49,8 @@ class HttpProtocolHandler(BaseTcpServerHandler[HttpClientConnection]):
         if not self.flags.threadless:
             self.selector = selectors.DefaultSelector()
         self.plugin: Optional[HttpProtocolHandlerPlugin] = None
+        self.writes_teared: bool = False
+        self.reads_teared: bool = False
 
     ##
     # initialize, is_inactive, shutdown, get_events, handle_events
@@ -137,23 +139,26 @@ class HttpProtocolHandler(BaseTcpServerHandler[HttpClientConnection]):
     ) -> bool:
         """Returns True if proxy must tear down."""
         # Flush buffer for ready to write sockets
-        teardown = await self.handle_writables(writables)
-        if teardown:
+        self.writes_teared = await self.handle_writables(writables)
+        if self.writes_teared:
             return True
         # Invoke plugin.write_to_descriptors
         if self.plugin:
-            teardown = await self.plugin.write_to_descriptors(writables)
-            if teardown:
+            self.writes_teared = await self.plugin.write_to_descriptors(writables)
+            if self.writes_teared:
                 return True
-        # Read from ready to read sockets
-        teardown = await self.handle_readables(readables)
-        if teardown:
+        # Read from ready to read sockets if reads have not already teared down
+        if not self.reads_teared:
+            self.reads_teared = await self.handle_readables(readables)
+            if not self.reads_teared:
+                # Invoke plugin.read_from_descriptors
+                if self.plugin:
+                    self.reads_teared = await self.plugin.read_from_descriptors(
+                        readables,
+                    )
+        # Wait until client buffer has flushed when reads has teared down but we can still write
+        if self.reads_teared and not self.work.has_buffer():
             return True
-        # Invoke plugin.read_from_descriptors
-        if self.plugin:
-            teardown = await self.plugin.read_from_descriptors(readables)
-            if teardown:
-                return True
         return False
 
     def handle_data(self, data: memoryview) -> Optional[bool]:
diff --git a/proxy/http/proxy/server.py b/proxy/http/proxy/server.py
index f18f45fc..70d3369e 100644
--- a/proxy/http/proxy/server.py
+++ b/proxy/http/proxy/server.py
@@ -175,7 +175,11 @@ class HttpProxyPlugin(HttpProtocolHandlerPlugin):
         return r, w
 
     async def write_to_descriptors(self, w: Writables) -> bool:
-        if (self.upstream and self.upstream.connection.fileno() not in w) or not self.upstream:
+        if (
+            self.upstream
+            and not self.upstream.closed
+            and self.upstream.connection.fileno() not in w
+        ) or not self.upstream:
             # Currently, we just call write/read block of each plugins.  It is
             # plugins responsibility to ignore this callback, if passed descriptors
             # doesn't contain the descriptor they registered.
@@ -208,9 +212,9 @@ class HttpProxyPlugin(HttpProtocolHandlerPlugin):
 
     async def read_from_descriptors(self, r: Readables) -> bool:
         if (
-            self.upstream and not
-            self.upstream.closed and
-            self.upstream.connection.fileno() not in r
+            self.upstream
+            and not self.upstream.closed
+            and self.upstream.connection.fileno() not in r
         ) or not self.upstream:
             # Currently, we just call write/read block of each plugins.  It is
             # plugins responsibility to ignore this callback, if passed descriptors