diff --git a/src/epplibwrapper/client.py b/src/epplibwrapper/client.py
index 80ed278ff..cfb41f4ea 100644
--- a/src/epplibwrapper/client.py
+++ b/src/epplibwrapper/client.py
@@ -106,6 +106,7 @@ class EPPLibWrapper:
                 # Flag that the pool is frozen,
                 # then restart the pool.
                 self.pool_status.pool_hanging = True
+                logger.error("Pool timed out")
                 self.start_connection_pool()
         except (ValueError, ParsingError) as err:
             message = f"{cmd_type} failed to execute due to some syntax error."
@@ -174,6 +175,7 @@ class EPPLibWrapper:
 
     def _create_pool(self, client, login, options):
         """Creates and returns new pool instance"""
+        logger.info("New pool was created")
         return EPPConnectionPool(client, login, options)
 
     def start_connection_pool(self, restart_pool_if_exists=True):
@@ -187,7 +189,7 @@ class EPPLibWrapper:
         # Since we reuse the same creds for each pool, we can test on
         # one socket, and if successful, then we know we can connect.
         if not self._test_registry_connection_success():
-            logger.warning("Cannot contact the Registry")
+            logger.warning("start_connection_pool() -> Cannot contact the Registry")
             self.pool_status.connection_success = False
         else:
             self.pool_status.connection_success = True
@@ -197,6 +199,7 @@ class EPPLibWrapper:
             if self._pool is not None and restart_pool_if_exists:
                 logger.info("Connection pool restarting...")
                 self.kill_pool()
+                logger.info("Old pool killed")
 
             self._pool = self._create_pool(self._client, self._login, self.pool_options)
 
@@ -221,6 +224,7 @@ class EPPLibWrapper:
         credentials are valid, and/or if the Registrar
         can be contacted
         """
+        # This is closed in test_connection_success
         socket = Socket(self._client, self._login)
         can_login = False
 
diff --git a/src/epplibwrapper/socket.py b/src/epplibwrapper/socket.py
index f79e60917..79c44aa9a 100644
--- a/src/epplibwrapper/socket.py
+++ b/src/epplibwrapper/socket.py
@@ -31,6 +31,7 @@ class Socket:
 
     def connect(self):
         """Use epplib to connect."""
+        logger.info("Opening socket on connection pool")
         self.client.connect()
         response = self.client.send(self.login)
         if self.is_login_error(response.code):
@@ -40,11 +41,13 @@ class Socket:
 
     def disconnect(self):
         """Close the connection."""
+        logger.info("Closing socket on connection pool")
         try:
             self.client.send(commands.Logout())
             self.client.close()
-        except Exception:
+        except Exception as err:
             logger.warning("Connection to registry was not cleanly closed.")
+            logger.error(err)
 
     def send(self, command):
         """Sends a command to the registry.
@@ -77,19 +80,17 @@ class Socket:
             try:
                 self.client.connect()
                 response = self.client.send(self.login)
-            except LoginError as err:
-                if err.should_retry() and counter < 10:
+            except (LoginError, OSError) as err:
+                logger.error(err)
+                should_retry = True
+                if isinstance(err, LoginError):
+                    should_retry = err.should_retry()
+                if should_retry and counter < 3:
                     counter += 1
                     sleep((counter * 50) / 1000)  # sleep 50 ms to 150 ms
                 else:  # don't try again
                     return False
-            # Occurs when an invalid creds are passed in - such as on localhost
-            except OSError as err:
-                logger.error(err)
-                return False
             else:
-                self.disconnect()
-
                 # If we encounter a login error, fail
                 if self.is_login_error(response.code):
                     logger.warning("A login error was found in test_connection_success")
@@ -97,3 +98,5 @@ class Socket:
 
                 # Otherwise, just return true
                 return True
+            finally:
+                self.disconnect()
diff --git a/src/epplibwrapper/utility/pool.py b/src/epplibwrapper/utility/pool.py
index 442f6257a..93edb2782 100644
--- a/src/epplibwrapper/utility/pool.py
+++ b/src/epplibwrapper/utility/pool.py
@@ -98,6 +98,7 @@ class EPPConnectionPool(ConnectionPool):
         """Kills all active connections in the pool."""
         try:
             if len(self.conn) > 0 or len(self.greenlets) > 0:
+                logger.info("Attempting to kill connections")
                 gevent.killall(self.greenlets)
 
                 self.greenlets.clear()
@@ -107,6 +108,7 @@ class EPPConnectionPool(ConnectionPool):
 
                 # Clear the semaphore
                 self.lock = BoundedSemaphore(self.size)
+                logger.info("Finished killing connections")
             else:
                 logger.info("No connections to kill.")
         except Exception as err: