diff --git a/examples/README.md b/examples/README.md
index 84bf0f4452..90455dc4f4 100644
--- a/examples/README.md
+++ b/examples/README.md
@@ -6,6 +6,7 @@ Looking for `proxy.py` plugin examples?  Check [proxy/plugin](https://github.com
 
 Table of Contents
 =================
+* [Generic Work Acceptor and Executor](#generic-work-acceptor-and-executor)
 * [WebSocket Client](#websocket-client)
 * [TCP Echo Server](#tcp-echo-server)
 * [TCP Echo Client](#tcp-echo-client)
@@ -14,6 +15,17 @@ Table of Contents
 * [PubSub Eventing](#pubsub-eventing)
 * [Https Connect Tunnel](#https-connect-tunnel)
 
+## Generic Work Acceptor and Executor
+
+1. Makes use of `proxy.core.AcceptorPool` and `proxy.core.Work`
+2. Demonstrates how to perform generic work using `proxy.py` core.
+
+Start `web_scraper.py` as:
+
+```console
+❯ PYTHONPATH=. python examples/web_scraper.py
+```
+
 ## WebSocket Client
 
 1. Makes use of `proxy.http.websocket.WebsocketClient` which is built on-top of `asyncio`
@@ -22,7 +34,7 @@ Table of Contents
 
 Start `websocket_client.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/websocket_client.py
 Received b'hello' after 306 millisec
 Received b'hello' after 308 millisec
@@ -44,7 +56,7 @@ Received b'hello' after 309 millisec
 
 Start `tcp_echo_server.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/tcp_echo_server.py
 Connection accepted from ('::1', 53285, 0, 0)
 Connection closed by client ('::1', 53285, 0, 0)
@@ -57,7 +69,7 @@ Connection closed by client ('::1', 53285, 0, 0)
 
 Start `tcp_echo_client.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/tcp_echo_client.py
 b'hello'
 b'hello'
@@ -81,7 +93,7 @@ KeyboardInterrupt
 
 Start `ssl_echo_server.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/ssl_echo_server.py
 ```
 
@@ -92,7 +104,7 @@ Start `ssl_echo_server.py` as:
 
 Start `ssl_echo_client.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/ssl_echo_client.py
 ```
 
@@ -107,7 +119,7 @@ Start `ssl_echo_client.py` as:
 
 Start `pubsub_eventing.py` as:
 
-```bash
+```console
 ❯ PYTHONPATH=. python examples/pubsub_eventing.py
 DEBUG:proxy.core.event.subscriber:Subscribed relay sub id 5eb22010764f4d44900f41e2fb408ca6 from core events
 publisher starting
diff --git a/examples/web_scraper.py b/examples/web_scraper.py
new file mode 100644
index 0000000000..6d99da387b
--- /dev/null
+++ b/examples/web_scraper.py
@@ -0,0 +1,70 @@
+# -*- coding: utf-8 -*-
+"""
+    proxy.py
+    ~~~~~~~~
+    ⚡⚡⚡ Fast, Lightweight, Pluggable, TLS interception capable proxy server focused on
+    Network monitoring, controls & Application development, testing, debugging.
+
+    :copyright: (c) 2013-present by Abhinav Singh and contributors.
+    :license: BSD, see LICENSE for more details.
+"""
+import time
+import socket
+
+from typing import Dict
+
+from proxy.proxy import Proxy
+from proxy.core.acceptor import Work, AcceptorPool
+from proxy.common.types import Readables, Writables
+
+
+class WebScraper(Work):
+    """Demonstrates how to orchestrate a generic work acceptors and executors
+    workflow using proxy.py core.
+
+    By default, `WebScraper` expects to receive work from a file on disk.
+    Each line in the file must be a URL to scrape.  Received URL is scrapped
+    by the implementation in this class.
+
+    After scrapping, results are published to the eventing core.  One or several
+    result subscriber can then handle the result as necessary.  Currently, result
+    subscribers consume the scrapped response and write discovered URL in the
+    file on the disk.  This creates a feedback loop.  Allowing WebScraper to
+    continue endlessly.
+
+    NOTE: No loop detection is performed currently.
+
+    NOTE: File descriptor need not point to a file on disk.
+    Example, file descriptor can be a database connection.
+    For simplicity, imagine a Redis server connection handling
+    only PUBSUB protocol.
+    """
+
+    def get_events(self) -> Dict[socket.socket, int]:
+        """Return sockets and events (read or write) that we are interested in."""
+        return {}
+
+    def handle_events(
+            self,
+            readables: Readables,
+            writables: Writables,
+    ) -> bool:
+        """Handle readable and writable sockets.
+
+        Return True to shutdown work."""
+        return False
+
+
+if __name__ == '__main__':
+    with AcceptorPool(
+        flags=Proxy.initialize(
+            port=12345,
+            num_workers=1,
+            threadless=True,
+            keyfile='https-key.pem',
+            certfile='https-signed-cert.pem',
+        ),
+        work_klass=WebScraper,
+    ) as pool:
+        while True:
+            time.sleep(1)
diff --git a/proxy/core/acceptor/acceptor.py b/proxy/core/acceptor/acceptor.py
index 985b9860cc..00b66577a4 100644
--- a/proxy/core/acceptor/acceptor.py
+++ b/proxy/core/acceptor/acceptor.py
@@ -74,17 +74,17 @@ def __init__(
     ) -> None:
         super().__init__()
         self.flags = flags
+        # Eventing core queue
+        self.event_queue = event_queue
+        # Index assigned by `AcceptorPool`
+        self.idd = idd
         # Lock shared by all acceptor processes
         # to avoid concurrent accept over server socket
         self.lock = lock
-        # Index assigned by `AcceptorPool`
-        self.idd = idd
         # Queue over which server socket fd is received on start-up
         self.work_queue: connection.Connection = work_queue
         # Worker class
         self.work_klass = work_klass
-        # Eventing core queue
-        self.event_queue = event_queue
         # Selector & threadless states
         self.running = multiprocessing.Event()
         self.selector: Optional[selectors.DefaultSelector] = None
diff --git a/proxy/core/acceptor/pool.py b/proxy/core/acceptor/pool.py
index 6b50035833..8c83a9f984 100644
--- a/proxy/core/acceptor/pool.py
+++ b/proxy/core/acceptor/pool.py
@@ -25,11 +25,13 @@
 from ..event import EventQueue
 
 from ...common.flag import flags
-from ...common.constants import DEFAULT_BACKLOG, DEFAULT_IPV6_HOSTNAME, DEFAULT_NUM_WORKERS, DEFAULT_PORT
+from ...common.constants import DEFAULT_BACKLOG, DEFAULT_IPV6_HOSTNAME
+from ...common.constants import DEFAULT_NUM_WORKERS, DEFAULT_PORT
 
 logger = logging.getLogger(__name__)
 
-# Lock shared by worker processes
+# Lock shared by acceptors for
+# sequential acceptance of work.
 LOCK = multiprocessing.Lock()
 
 
@@ -61,20 +63,18 @@
 
 
 class AcceptorPool:
-    """AcceptorPool pre-spawns worker processes to utilize all cores available on the system.
-    A server socket is initialized and dispatched over a pipe to these workers.
-    Each worker process then concurrently accepts new client connection over
-    the initialized server socket.
+    """AcceptorPool is a helper class which pre-spawns `Acceptor` processes
+    to utilize all available CPU cores for accepting new work.
+
+    A file descriptor to consume work from is shared with `Acceptor` processes
+    over a pipe.  Each `Acceptor` process then concurrently accepts new work over
+    the shared file descriptor.
 
     Example usage:
 
-        pool = AcceptorPool(flags=..., work_klass=...)
-        try:
-            pool.setup()
+        with AcceptorPool(flags=..., work_klass=...) as pool:
             while True:
                 time.sleep(1)
-        finally:
-            pool.shutdown()
 
     `work_klass` must implement `work.Work` class.
     """
@@ -84,11 +84,16 @@ def __init__(
         work_klass: Type[Work], event_queue: Optional[EventQueue] = None,
     ) -> None:
         self.flags = flags
+        # Eventing core queue
+        self.event_queue: Optional[EventQueue] = event_queue
+        # File descriptor to use for accepting new work
         self.socket: Optional[socket.socket] = None
+        # Acceptor process instances
         self.acceptors: List[Acceptor] = []
+        # Work queue used to share file descriptor with acceptor processes
         self.work_queues: List[connection.Connection] = []
+        # Work class implementation
         self.work_klass = work_klass
-        self.event_queue: Optional[EventQueue] = event_queue
 
     def __enter__(self) -> 'AcceptorPool':
         self.setup()
@@ -102,19 +107,43 @@ def __exit__(
     ) -> None:
         self.shutdown()
 
-    def listen(self) -> None:
+    def setup(self) -> None:
+        """Listen on port and setup acceptors."""
+        self._listen()
+        # Override flags.port to match the actual port
+        # we are listening upon.  This is necessary to preserve
+        # the server port when `--port=0` is used.
+        assert self.socket
+        self.flags.port = self.socket.getsockname()[1]
+        self._start_acceptors()
+        # Send file descriptor to all acceptor processes.
+        assert self.socket is not None
+        for index in range(self.flags.num_workers):
+            send_handle(
+                self.work_queues[index],
+                self.socket.fileno(),
+                self.acceptors[index].pid,
+            )
+            self.work_queues[index].close()
+        self.socket.close()
+
+    def shutdown(self) -> None:
+        logger.info('Shutting down %d workers' % self.flags.num_workers)
+        for acceptor in self.acceptors:
+            acceptor.running.set()
+        for acceptor in self.acceptors:
+            acceptor.join()
+        logger.debug('Acceptors shutdown')
+
+    def _listen(self) -> None:
         self.socket = socket.socket(self.flags.family, socket.SOCK_STREAM)
         self.socket.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
         self.socket.bind((str(self.flags.hostname), self.flags.port))
         self.socket.listen(self.flags.backlog)
         self.socket.setblocking(False)
-        # Override flags.port to match the actual port
-        # we are listening upon.  This is necessary to preserve
-        # the server port when `--port=0` is used.
-        self.flags.port = self.socket.getsockname()[1]
 
-    def start_workers(self) -> None:
-        """Start worker processes."""
+    def _start_acceptors(self) -> None:
+        """Start acceptor processes."""
         for acceptor_id in range(self.flags.num_workers):
             work_queue = multiprocessing.Pipe()
             acceptor = Acceptor(
@@ -134,26 +163,3 @@ def start_workers(self) -> None:
             self.acceptors.append(acceptor)
             self.work_queues.append(work_queue[0])
         logger.info('Started %d workers' % self.flags.num_workers)
-
-    def shutdown(self) -> None:
-        logger.info('Shutting down %d workers' % self.flags.num_workers)
-        for acceptor in self.acceptors:
-            acceptor.running.set()
-        for acceptor in self.acceptors:
-            acceptor.join()
-        logger.debug('Acceptors shutdown')
-
-    def setup(self) -> None:
-        """Listen on port, setup workers and pass server socket to workers."""
-        self.listen()
-        self.start_workers()
-        # Send server socket to all acceptor processes.
-        assert self.socket is not None
-        for index in range(self.flags.num_workers):
-            send_handle(
-                self.work_queues[index],
-                self.socket.fileno(),
-                self.acceptors[index].pid,
-            )
-            self.work_queues[index].close()
-        self.socket.close()
diff --git a/proxy/core/base/tcp_server.py b/proxy/core/base/tcp_server.py
index 9931ae34e7..b0b44500d8 100644
--- a/proxy/core/base/tcp_server.py
+++ b/proxy/core/base/tcp_server.py
@@ -15,8 +15,8 @@
 from abc import abstractmethod
 from typing import Dict, Any, Optional
 
-from proxy.core.acceptor import Work
-from proxy.common.types import Readables, Writables
+from ...core.acceptor import Work
+from ...common.types import Readables, Writables
 
 logger = logging.getLogger(__name__)
 
diff --git a/proxy/core/base/tcp_tunnel.py b/proxy/core/base/tcp_tunnel.py
index 6763a96fce..94e058c1c5 100644
--- a/proxy/core/base/tcp_tunnel.py
+++ b/proxy/core/base/tcp_tunnel.py
@@ -8,9 +8,10 @@
     :copyright: (c) 2013-present by Abhinav Singh and contributors.
     :license: BSD, see LICENSE for more details.
 """
-from abc import abstractmethod
 import socket
 import selectors
+
+from abc import abstractmethod
 from typing import Any, Optional, Dict
 
 from ...http.parser import HttpParser, httpParserTypes
diff --git a/proxy/core/connection/__init__.py b/proxy/core/connection/__init__.py
index ee44bc14a6..9da32f6cda 100644
--- a/proxy/core/connection/__init__.py
+++ b/proxy/core/connection/__init__.py
@@ -11,6 +11,7 @@
 from .connection import TcpConnection, TcpConnectionUninitializedException, tcpConnectionTypes
 from .client import TcpClientConnection
 from .server import TcpServerConnection
+from .pool import ConnectionPool
 
 __all__ = [
     'TcpConnection',
@@ -18,4 +19,5 @@
     'TcpServerConnection',
     'TcpClientConnection',
     'tcpConnectionTypes',
+    'ConnectionPool',
 ]
diff --git a/proxy/core/connection/client.py b/proxy/core/connection/client.py
index bbc72f207e..a0c6a00b09 100644
--- a/proxy/core/connection/client.py
+++ b/proxy/core/connection/client.py
@@ -22,7 +22,7 @@ def __init__(
         self,
         conn: Union[ssl.SSLSocket, socket.socket],
         addr: Tuple[str, int],
-    ):
+    ) -> None:
         super().__init__(tcpConnectionTypes.CLIENT)
         self._conn: Optional[Union[ssl.SSLSocket, socket.socket]] = conn
         self.addr: Tuple[str, int] = addr
diff --git a/proxy/core/connection/connection.py b/proxy/core/connection/connection.py
index daf464337d..2827185b56 100644
--- a/proxy/core/connection/connection.py
+++ b/proxy/core/connection/connection.py
@@ -39,12 +39,14 @@ class TcpConnection(ABC):
     when reading and writing into the socket.
 
     Implement the connection property abstract method to return
-    a socket connection object."""
+    a socket connection object.
+    """
 
-    def __init__(self, tag: int):
+    def __init__(self, tag: int) -> None:
+        self.tag: str = 'server' if tag == tcpConnectionTypes.SERVER else 'client'
         self.buffer: List[memoryview] = []
         self.closed: bool = False
-        self.tag: str = 'server' if tag == tcpConnectionTypes.SERVER else 'client'
+        self._reusable: bool = False
 
     @property
     @abstractmethod
@@ -95,3 +97,14 @@ def flush(self) -> int:
         del mv
         logger.debug('flushed %d bytes to %s' % (sent, self.tag))
         return sent
+
+    def is_reusable(self) -> bool:
+        return self._reusable
+
+    def mark_inuse(self) -> None:
+        self._reusable = False
+
+    def reset(self) -> None:
+        assert not self.closed
+        self._reusable = True
+        self.buffer = []
diff --git a/proxy/core/connection/pool.py b/proxy/core/connection/pool.py
new file mode 100644
index 0000000000..5f5745c93a
--- /dev/null
+++ b/proxy/core/connection/pool.py
@@ -0,0 +1,110 @@
+# -*- coding: utf-8 -*-
+"""
+    proxy.py
+    ~~~~~~~~
+    ⚡⚡⚡ Fast, Lightweight, Pluggable, TLS interception capable proxy server focused on
+    Network monitoring, controls & Application development, testing, debugging.
+
+    :copyright: (c) 2013-present by Abhinav Singh and contributors.
+    :license: BSD, see LICENSE for more details.
+"""
+import logging
+
+from typing import Set, Dict, Tuple
+
+from ...common.flag import flags
+from .server import TcpServerConnection
+
+logger = logging.getLogger(__name__)
+
+
+flags.add_argument(
+    '--enable-conn-pool',
+    action='store_true',
+    default=False,
+    help='Default: False.  (WIP) Enable upstream connection pooling.',
+)
+
+
+class ConnectionPool:
+    """Manages connection pool to upstream servers.
+
+    `ConnectionPool` avoids need to reconnect with the upstream
+    servers repeatedly when a reusable connection is available
+    in the pool.
+
+    A separate pool is maintained for each upstream server.
+    So internally, it's a pool of pools.
+
+    TODO: Listen for read events from the connections
+    to remove them from the pool when peer closes the
+    connection.  This can also be achieved lazily by
+    the pool users.  Example, if acquired connection
+    is stale, reacquire.
+
+    TODO: Ideally, ConnectionPool must be shared across
+    all cores to make SSL session cache to also work
+    without additional out-of-bound synchronizations.
+
+    TODO: ConnectionPool currently WON'T work for
+    HTTPS connection. This is because of missing support for
+    session cache, session ticket, abbr TLS handshake
+    and other necessary features to make it work.
+
+    NOTE: However, for all HTTP only connections, ConnectionPool
+    can be used to save upon connection setup time and
+    speed-up performance of requests.
+    """
+
+    def __init__(self) -> None:
+        # Pools of connection per upstream server
+        self.pools: Dict[Tuple[str, int], Set[TcpServerConnection]] = {}
+
+    def acquire(self, host: str, port: 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]:
+                if old_conn.is_reusable():
+                    old_conn.mark_inuse()
+                    logger.debug(
+                        'Reusing connection#{2} for upstream {0}:{1}'.format(
+                            host, port, 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)
+        logger.debug(
+            'Created new connection#{2} for upstream {0}:{1}'.format(
+                host, port, id(new_conn),
+            ),
+        )
+        return True, new_conn
+
+    def release(self, conn: TcpServerConnection) -> None:
+        """Release the connection.
+
+        If the connection has not been closed,
+        then it will be retained in the pool for reusability.
+        """
+        if conn.closed:
+            logger.debug(
+                'Removing connection#{2} from pool from upstream {0}:{1}'.format(
+                    conn.addr[0], conn.addr[1], id(conn),
+                ),
+            )
+            self.pools[conn.addr].remove(conn)
+        else:
+            logger.debug(
+                'Retaining connection#{2} to upstream {0}:{1}'.format(
+                    conn.addr[0], conn.addr[1], id(conn),
+                ),
+            )
+            assert not conn.is_reusable()
+            # Reset for reusability
+            conn.reset()
diff --git a/proxy/core/connection/server.py b/proxy/core/connection/server.py
index fb92937ba8..30692fda71 100644
--- a/proxy/core/connection/server.py
+++ b/proxy/core/connection/server.py
@@ -21,7 +21,7 @@
 class TcpServerConnection(TcpConnection):
     """Establishes connection to upstream server."""
 
-    def __init__(self, host: str, port: int):
+    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))
@@ -38,7 +38,7 @@ def connect(self, addr: Optional[Tuple[str, int]] = None, source_address: Option
             self._conn = new_socket_connection(
                 addr or self.addr, source_address=source_address,
             )
-        self.closed = False
+            self.closed = False
 
     def wrap(self, hostname: str, ca_file: Optional[str]) -> None:
         ctx = ssl.create_default_context(
diff --git a/proxy/http/proxy/server.py b/proxy/http/proxy/server.py
index 43d1b67377..6226b37568 100644
--- a/proxy/http/proxy/server.py
+++ b/proxy/http/proxy/server.py
@@ -36,7 +36,8 @@
 from ...common.pki import gen_public_key, gen_csr, sign_csr
 
 from ...core.event import eventNames
-from ...core.connection import TcpServerConnection, TcpConnectionUninitializedException
+from ...core.connection import TcpServerConnection, ConnectionPool
+from ...core.connection import TcpConnectionUninitializedException
 from ...common.flag import flags
 
 logger = logging.getLogger(__name__)
@@ -112,9 +113,13 @@ class HttpProxyPlugin(HttpProtocolHandlerPlugin):
         ),
     )
 
-    # Used to synchronization during certificate generation.
+    # Used to synchronization during certificate generation and
+    # connection pool operations.
     lock = threading.Lock()
 
+    # Shared connection pool
+    pool = ConnectionPool()
+
     def __init__(
             self,
             *args: Any, **kwargs: Any,
@@ -175,6 +180,15 @@ def get_descriptors(
 
         return r, w
 
+    def _close_and_release(self) -> bool:
+        if self.flags.enable_conn_pool:
+            assert self.upstream and not self.upstream.closed
+            self.upstream.closed = True
+            with self.lock:
+                self.pool.release(self.upstream)
+            self.upstream = None
+        return True
+
     def write_to_descriptors(self, w: Writables) -> bool:
         if (self.upstream and self.upstream.connection not in w) or not self.upstream:
             # Currently, we just call write/read block of each plugins.  It is
@@ -200,12 +214,12 @@ def write_to_descriptors(self, w: Writables) -> bool:
                 logger.error(
                     'BrokenPipeError when flushing buffer for server',
                 )
-                return True
+                return self._close_and_release()
             except OSError as e:
                 logger.exception(
                     'OSError when flushing buffer to server', exc_info=e,
                 )
-                return True
+                return self._close_and_release()
         return False
 
     def read_from_descriptors(self, r: Readables) -> bool:
@@ -229,6 +243,7 @@ def read_from_descriptors(self, r: Readables) -> bool:
             try:
                 raw = self.upstream.recv(self.flags.server_recvbuf_size)
             except TimeoutError as e:
+                self._close_and_release()
                 if e.errno == errno.ETIMEDOUT:
                     logger.warning(
                         '%s:%d timed out on recv' %
@@ -245,19 +260,22 @@ def read_from_descriptors(self, r: Readables) -> bool:
                         '%s:%d unreachable on recv' %
                         self.upstream.addr,
                     )
-                    return True
                 if e.errno == errno.ECONNRESET:
-                    logger.warning('Connection reset by upstream: %r' % e)
+                    logger.warning(
+                        'Connection reset by upstream: {0}:{1}'.format(
+                            *self.upstream.addr,
+                        ),
+                    )
                 else:
                     logger.exception(
                         'Exception while receiving from %s connection %r with reason %r' %
                         (self.upstream.tag, self.upstream.connection, e),
                     )
-                return True
+                return self._close_and_release()
 
             if raw is None:
                 logger.debug('Server closed connection, tearing down...')
-                return True
+                return self._close_and_release()
 
             for plugin in self.plugins.values():
                 raw = plugin.handle_upstream_chunk(raw)
@@ -324,10 +342,16 @@ def on_client_connection_close(self) -> None:
         for plugin in self.plugins.values():
             plugin.on_upstream_connection_close()
 
-        # If server was never initialized, return
+        # If server was never initialized or was _close_and_release
         if self.upstream is None:
             return
 
+        if self.flags.enable_conn_pool:
+            # Release the connection for reusability
+            with self.lock:
+                self.pool.release(self.upstream)
+            return
+
         try:
             try:
                 self.upstream.connection.shutdown(socket.SHUT_WR)
@@ -516,10 +540,31 @@ 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:
-            self.upstream = TcpServerConnection(text_(host), port)
+            if self.flags.enable_conn_pool:
+                with self.lock:
+                    created, self.upstream = self.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:%s' %
+                    'Connecting to upstream %s:%d' %
                     (text_(host), port),
                 )
                 # Invoke plugin.resolve_dns
@@ -543,11 +588,17 @@ def connect_upstream(self) -> None:
                     (text_(host), port),
                 )
             except Exception as e:  # TimeoutError, socket.gaierror
-                logger.exception(
-                    'Unable to connect with upstream server', exc_info=e,
+                logger.warning(
+                    'Unable to connect with upstream %s:%d due to %s' % (
+                        text_(host), port, str(e),
+                    ),
                 )
-                self.upstream.closed = True
-                raise ProxyConnectionFailed(text_(host), port, repr(e)) from e
+                if self.flags.enable_conn_pool:
+                    with self.lock:
+                        self.pool.release(self.upstream)
+                raise ProxyConnectionFailed(
+                    text_(host), port, repr(e),
+                ) from e
         else:
             logger.exception('Both host and port must exist')
             raise HttpProtocolException()
diff --git a/tests/core/test_conn_pool.py b/tests/core/test_conn_pool.py
new file mode 100644
index 0000000000..3eaad052f3
--- /dev/null
+++ b/tests/core/test_conn_pool.py
@@ -0,0 +1,73 @@
+# -*- coding: utf-8 -*-
+"""
+    proxy.py
+    ~~~~~~~~
+    ⚡⚡⚡ Fast, Lightweight, Pluggable, TLS interception capable proxy server focused on
+    Network monitoring, controls & Application development, testing, debugging.
+
+    :copyright: (c) 2013-present by Abhinav Singh and contributors.
+    :license: BSD, see LICENSE for more details.
+"""
+import unittest
+
+from unittest import mock
+
+from proxy.core.connection import ConnectionPool
+
+
+class TestConnectionPool(unittest.TestCase):
+
+    @mock.patch('proxy.core.connection.pool.TcpServerConnection')
+    def test_acquire_and_release_and_reacquire(self, mock_tcp_server_connection: mock.Mock) -> None:
+        pool = ConnectionPool()
+        addr = ('localhost', 1234)
+        # Mock
+        mock_conn = mock_tcp_server_connection.return_value
+        mock_conn.is_reusable.side_effect = [
+            False, True, True,
+        ]
+        mock_conn.closed = False
+        # Acquire
+        created, conn = pool.acquire(*addr)
+        self.assertTrue(created)
+        mock_tcp_server_connection.assert_called_once_with(*addr)
+        self.assertEqual(conn, mock_conn)
+        self.assertEqual(len(pool.pools[addr]), 1)
+        self.assertTrue(conn in pool.pools[addr])
+        # Release (connection must be retained because not closed)
+        pool.release(conn)
+        self.assertEqual(len(pool.pools[addr]), 1)
+        self.assertTrue(conn in pool.pools[addr])
+        # Reacquire
+        created, conn = pool.acquire(*addr)
+        self.assertFalse(created)
+        mock_conn.reset.assert_called_once()
+        self.assertEqual(conn, mock_conn)
+        self.assertEqual(len(pool.pools[addr]), 1)
+        self.assertTrue(conn in pool.pools[addr])
+
+    @mock.patch('proxy.core.connection.pool.TcpServerConnection')
+    def test_closed_connections_are_removed_on_release(
+            self, mock_tcp_server_connection: mock.Mock,
+    ) -> None:
+        pool = ConnectionPool()
+        addr = ('localhost', 1234)
+        # Mock
+        mock_conn = mock_tcp_server_connection.return_value
+        mock_conn.closed = True
+        mock_conn.addr = addr
+        # Acquire
+        created, conn = pool.acquire(*addr)
+        self.assertTrue(created)
+        mock_tcp_server_connection.assert_called_once_with(*addr)
+        self.assertEqual(conn, mock_conn)
+        self.assertEqual(len(pool.pools[addr]), 1)
+        self.assertTrue(conn in pool.pools[addr])
+        # Release
+        pool.release(conn)
+        self.assertEqual(len(pool.pools[addr]), 0)
+        # Acquire
+        created, conn = pool.acquire(*addr)
+        self.assertTrue(created)
+        self.assertEqual(mock_tcp_server_connection.call_count, 2)
+        mock_conn.is_reusable.assert_not_called()