diff --git a/cheroot/workers/threadpool.py b/cheroot/workers/threadpool.py
index 3437d9bda9..2c2de790f0 100644
--- a/cheroot/workers/threadpool.py
+++ b/cheroot/workers/threadpool.py
@@ -6,6 +6,7 @@
 """
 
 import collections
+import logging
 import threading
 import time
 import socket
@@ -118,7 +119,52 @@ def run(self):
                 keep_conn_open = False
                 try:
                     keep_conn_open = conn.communicate()
+                except ConnectionError as connection_error:
+                    keep_conn_open = False  # Drop the connection cleanly
+                    self.server.error_log(
+                        'Got a connection error while handling a '
+                        f'connection from {conn.remote_addr !s}:'
+                        f'{conn.remote_port !s} ({connection_error !s})',
+                        level=logging.INFO,
+                    )
+                    continue
+                except (KeyboardInterrupt, SystemExit) as shutdown_request:
+                    # Shutdown request
+                    keep_conn_open = False  # Drop the connection cleanly
+                    self.server.error_log(
+                        'Got a server shutdown request while handling a '
+                        f'connection from {conn.remote_addr !s}:'
+                        f'{conn.remote_port !s} ({shutdown_request !s})',
+                        level=logging.DEBUG,
+                    )
+                    raise SystemExit(
+                        str(shutdown_request),
+                    ) from shutdown_request
+                except Exception as unhandled_error:
+                    # NOTE: Only a shutdown request should bubble up to the
+                    # NOTE: external cleanup code. Otherwise, this thread dies.
+                    # NOTE: If this were to happen, the threadpool would still
+                    # NOTE: list a dead thread without knowing its state. And
+                    # NOTE: the calling code would fail to schedule processing
+                    # NOTE: of new requests.
+                    self.server.error_log(
+                        'Unhandled error while processing an incoming '
+                        f'connection {unhandled_error !r}',
+                        level=logging.ERROR,
+                        traceback=True,
+                    )
+                    continue  # Prevent the thread from dying
                 finally:
+                    # NOTE: Any exceptions coming from within `finally` may
+                    # NOTE: kill the thread, causing the threadpool to only
+                    # NOTE: contain references to dead threads rendering the
+                    # NOTE: server defunct, effectively meaning a DoS.
+                    # NOTE: Ideally, things called here should process
+                    # NOTE: everything recoverable internally. Any unhandled
+                    # NOTE: errors will bubble up into the outer try/except
+                    # NOTE: block. They will be treated as fatal and turned
+                    # NOTE: into server shutdown requests and then reraised
+                    # NOTE: unconditionally.
                     if keep_conn_open:
                         self.server.put_conn(conn)
                     else:
@@ -130,8 +176,29 @@ def run(self):
                         self.work_time += time.time() - self.start_time
                         self.start_time = None
                     self.conn = None
-        except (KeyboardInterrupt, SystemExit) as ex:
-            self.server.interrupt = ex
+        except (KeyboardInterrupt, SystemExit) as interrupt_exc:
+            interrupt_cause = interrupt_exc.__cause__ or interrupt_exc
+            self.server.error_log(
+                f'Setting the server interrupt flag to {interrupt_cause !r}',
+                level=logging.DEBUG,
+            )
+            self.server.interrupt = interrupt_cause
+        except BaseException as underlying_exc:
+            # NOTE: This is the last resort logging with the last dying breath
+            # NOTE: of the worker. It is only reachable when exceptions happen
+            # NOTE: in the `finally` branch of the internal try/except block.
+            self.server.error_log(
+                'A fatal exception happened. Setting the server interrupt flag'
+                f'to {underlying_exc !r} and giving up.'
+                '\N{NEW LINE}\N{NEW LINE}'
+                'Please, report this on the Cheroot tracker at '
+                '<https://github.com/cherrypy/cheroot/issues/new/choose>, '
+                'providing a full reproducer with as much context and details as possible.',
+                level=logging.CRITICAL,
+                traceback=True,
+            )
+            self.server.interrupt = underlying_exc
+            raise
 
 
 class ThreadPool: