diff --git a/proxy/core/connection/pool.py b/proxy/core/connection/pool.py
index 5f92066b9d..a9b0585a01 100644
--- a/proxy/core/connection/pool.py
+++ b/proxy/core/connection/pool.py
@@ -13,8 +13,9 @@
        reusability
 """
 import logging
+import selectors
 
-from typing import Set, Dict, Tuple
+from typing import TYPE_CHECKING, Set, Dict, Tuple
 
 from ...common.flag import flags
 from ...common.types import Readables, Writables
@@ -66,11 +67,21 @@ class UpstreamConnectionPool(Work[TcpServerConnection]):
 
     def __init__(self) -> None:
         # Pools of connection per upstream server
+        self.connections: Dict[int, TcpServerConnection] = {}
         self.pools: Dict[Tuple[str, int], Set[TcpServerConnection]] = {}
 
-    def acquire(self, host: str, port: int) -> Tuple[bool, TcpServerConnection]:
+    def add(self, addr: Tuple[str, int]) -> TcpServerConnection:
+        # Create new connection
+        new_conn = TcpServerConnection(addr[0], addr[1])
+        new_conn.connect()
+        if addr not in self.pools:
+            self.pools[addr] = set()
+        self.pools[addr].add(new_conn)
+        self.connections[new_conn.connection.fileno()] = new_conn
+        return new_conn
+
+    def acquire(self, addr: Tuple[str, int]) -> Tuple[bool, TcpServerConnection]:
         """Returns a connection for use with the server."""
-        addr = (host, port)
         # Return a reusable connection if available
         if addr in self.pools:
             for old_conn in self.pools[addr]:
@@ -78,18 +89,14 @@ def acquire(self, host: str, port: int) -> Tuple[bool, TcpServerConnection]:
                     old_conn.mark_inuse()
                     logger.debug(
                         'Reusing connection#{2} for upstream {0}:{1}'.format(
-                            host, port, id(old_conn),
+                            addr[0], addr[1], id(old_conn),
                         ),
                     )
                     return False, old_conn
-        # Create new connection
-        new_conn = TcpServerConnection(*addr)
-        if addr not in self.pools:
-            self.pools[addr] = set()
-        self.pools[addr].add(new_conn)
+        new_conn = self.add(addr)
         logger.debug(
             'Created new connection#{2} for upstream {0}:{1}'.format(
-                host, port, id(new_conn),
+                addr[0], addr[1], id(new_conn),
             ),
         )
         return True, new_conn
@@ -118,7 +125,17 @@ def release(self, conn: TcpServerConnection) -> None:
             conn.reset()
 
     async def get_events(self) -> Dict[int, int]:
-        return await super().get_events()
-
-    async def handle_events(self, readables: Readables, writables: Writables) -> bool:
-        return await super().handle_events(readables, writables)
+        events = {}
+        for connections in self.pools.values():
+            for conn in connections:
+                events[conn.connection.fileno()] = selectors.EVENT_READ
+        return events
+
+    async def handle_events(self, readables: Readables, _writables: Writables) -> bool:
+        for r in readables:
+            if TYPE_CHECKING:
+                assert isinstance(r, int)
+            conn = self.connections[r]
+            self.pools[conn.addr].remove(conn)
+            del self.connections[r]
+        return False
diff --git a/proxy/core/connection/server.py b/proxy/core/connection/server.py
index 7aae5371cc..2c2af73f99 100644
--- a/proxy/core/connection/server.py
+++ b/proxy/core/connection/server.py
@@ -25,7 +25,7 @@ class TcpServerConnection(TcpConnection):
     def __init__(self, host: str, port: int) -> None:
         super().__init__(tcpConnectionTypes.SERVER)
         self._conn: Optional[Union[ssl.SSLSocket, socket.socket]] = None
-        self.addr: Tuple[str, int] = (host, int(port))
+        self.addr: Tuple[str, int] = (host, port)
         self.closed = True
 
     @property
diff --git a/proxy/http/proxy/server.py b/proxy/http/proxy/server.py
index 228d8ecc34..fdb74d7176 100644
--- a/proxy/http/proxy/server.py
+++ b/proxy/http/proxy/server.py
@@ -586,29 +586,6 @@ def handle_pipeline_response(self, raw: memoryview) -> None:
     def connect_upstream(self) -> None:
         host, port = self.request.host, self.request.port
         if host and port:
-            if self.flags.enable_conn_pool:
-                assert self.upstream_conn_pool
-                with self.lock:
-                    created, self.upstream = self.upstream_conn_pool.acquire(
-                        text_(host), port,
-                    )
-            else:
-                created, self.upstream = True, TcpServerConnection(
-                    text_(host), port,
-                )
-            if not created:
-                # NOTE: Acquired connection might be in an unusable state.
-                #
-                # This can only be confirmed by reading from connection.
-                # For stale connections, we will receive None, indicating
-                # to drop the connection.
-                #
-                # If that happen, we must acquire a fresh connection.
-                logger.info(
-                    'Reusing connection to upstream %s:%d' %
-                    (text_(host), port),
-                )
-                return
             try:
                 logger.debug(
                     'Connecting to upstream %s:%d' %
@@ -622,14 +599,37 @@ def connect_upstream(self) -> None:
                     )
                     if upstream_ip or source_addr:
                         break
-                # Connect with overridden upstream IP and source address
-                # if any of the plugin returned a non-null value.
-                self.upstream.connect(
-                    addr=None if not upstream_ip else (
-                        upstream_ip, port,
-                    ), source_address=source_addr,
-                )
-                self.upstream.connection.setblocking(False)
+                if self.flags.enable_conn_pool:
+                    assert self.upstream_conn_pool
+                    with self.lock:
+                        created, self.upstream = self.upstream_conn_pool.acquire(
+                            (text_(host), port),
+                        )
+                else:
+                    created, self.upstream = True, TcpServerConnection(
+                        text_(host), port,
+                    )
+                    # Connect with overridden upstream IP and source address
+                    # if any of the plugin returned a non-null value.
+                    self.upstream.connect(
+                        addr=None if not upstream_ip else (
+                            upstream_ip, port,
+                        ), source_address=source_addr,
+                    )
+                    self.upstream.connection.setblocking(False)
+                if not created:
+                    # NOTE: Acquired connection might be in an unusable state.
+                    #
+                    # This can only be confirmed by reading from connection.
+                    # For stale connections, we will receive None, indicating
+                    # to drop the connection.
+                    #
+                    # If that happen, we must acquire a fresh connection.
+                    logger.info(
+                        'Reusing connection to upstream %s:%d' %
+                        (text_(host), port),
+                    )
+                    return
                 logger.debug(
                     'Connected to upstream %s:%s' %
                     (text_(host), port),
@@ -640,7 +640,7 @@ def connect_upstream(self) -> None:
                         text_(host), port, str(e),
                     ),
                 )
-                if self.flags.enable_conn_pool:
+                if self.flags.enable_conn_pool and self.upstream:
                     assert self.upstream_conn_pool
                     with self.lock:
                         self.upstream_conn_pool.release(self.upstream)
diff --git a/tests/core/test_conn_pool.py b/tests/core/test_conn_pool.py
index db3de3d7c0..e00436cd2f 100644
--- a/tests/core/test_conn_pool.py
+++ b/tests/core/test_conn_pool.py
@@ -8,9 +8,12 @@
     :copyright: (c) 2013-present by Abhinav Singh and contributors.
     :license: BSD, see LICENSE for more details.
 """
+import pytest
 import unittest
+import selectors
 
 from unittest import mock
+from pytest_mock import MockerFixture
 
 from proxy.core.connection import UpstreamConnectionPool
 
@@ -28,7 +31,7 @@ def test_acquire_and_release_and_reacquire(self, mock_tcp_server_connection: moc
         ]
         mock_conn.closed = False
         # Acquire
-        created, conn = pool.acquire(*addr)
+        created, conn = pool.acquire(addr)
         self.assertTrue(created)
         mock_tcp_server_connection.assert_called_once_with(*addr)
         self.assertEqual(conn, mock_conn)
@@ -39,7 +42,7 @@ def test_acquire_and_release_and_reacquire(self, mock_tcp_server_connection: moc
         self.assertEqual(len(pool.pools[addr]), 1)
         self.assertTrue(conn in pool.pools[addr])
         # Reacquire
-        created, conn = pool.acquire(*addr)
+        created, conn = pool.acquire(addr)
         self.assertFalse(created)
         mock_conn.reset.assert_called_once()
         self.assertEqual(conn, mock_conn)
@@ -57,7 +60,7 @@ def test_closed_connections_are_removed_on_release(
         mock_conn.closed = True
         mock_conn.addr = addr
         # Acquire
-        created, conn = pool.acquire(*addr)
+        created, conn = pool.acquire(addr)
         self.assertTrue(created)
         mock_tcp_server_connection.assert_called_once_with(*addr)
         self.assertEqual(conn, mock_conn)
@@ -67,7 +70,45 @@ def test_closed_connections_are_removed_on_release(
         pool.release(conn)
         self.assertEqual(len(pool.pools[addr]), 0)
         # Acquire
-        created, conn = pool.acquire(*addr)
+        created, conn = pool.acquire(addr)
         self.assertTrue(created)
         self.assertEqual(mock_tcp_server_connection.call_count, 2)
         mock_conn.is_reusable.assert_not_called()
+
+
+class TestConnectionPoolAsync:
+
+    @pytest.mark.asyncio    # type: ignore[misc]
+    async def test_get_events(self, mocker: MockerFixture) -> None:
+        mock_tcp_server_connection = mocker.patch(
+            'proxy.core.connection.pool.TcpServerConnection',
+        )
+        pool = UpstreamConnectionPool()
+        addr = ('localhost', 1234)
+        mock_conn = mock_tcp_server_connection.return_value
+        pool.add(addr)
+        mock_tcp_server_connection.assert_called_once_with(*addr)
+        mock_conn.connect.assert_called_once()
+        events = await pool.get_events()
+        print(events)
+        assert events == {
+            mock_conn.connection.fileno.return_value: selectors.EVENT_READ,
+        }
+        assert pool.pools[addr].pop() == mock_conn
+        assert len(pool.pools[addr]) == 0
+        assert pool.connections[mock_conn.connection.fileno.return_value] == mock_conn
+
+    @pytest.mark.asyncio    # type: ignore[misc]
+    async def test_handle_events(self, mocker: MockerFixture) -> None:
+        mock_tcp_server_connection = mocker.patch(
+            'proxy.core.connection.pool.TcpServerConnection',
+        )
+        pool = UpstreamConnectionPool()
+        mock_conn = mock_tcp_server_connection.return_value
+        addr = mock_conn.addr
+        pool.add(addr)
+        assert len(pool.pools[addr]) == 1
+        assert len(pool.connections) == 1
+        await pool.handle_events([mock_conn.connection.fileno.return_value], [])
+        assert len(pool.pools[addr]) == 0
+        assert len(pool.connections) == 0