diff --git a/trains_agent/backend_api/session/session.py b/trains_agent/backend_api/session/session.py
index f747fa7..3a169cb 100644
--- a/trains_agent/backend_api/session/session.py
+++ b/trains_agent/backend_api/session/session.py
@@ -40,6 +40,7 @@ class Session(TokenManager):
     _session_requests = 0
     _session_initial_timeout = (3.0, 10.)
     _session_timeout = (10.0, 30.)
+    _session_initial_connect_retry = 4
     _write_session_data_size = 15000
     _write_session_timeout = (30.0, 30.)
 
@@ -96,7 +97,7 @@ class Session(TokenManager):
         else:
             self.config = load()
             if initialize_logging:
-                self.config.initialize_logging()
+                self.config.initialize_logging(debug=kwargs.get('debug', False))
 
         token_expiration_threshold_sec = self.config.get(
             "auth.token_expiration_threshold_sec", 60
@@ -145,7 +146,7 @@ class Session(TokenManager):
 
         # limit the reconnect retries, so we get an error if we are starting the session
         http_no_retries_config = dict(**http_retries_config)
-        http_no_retries_config['connect'] = 3
+        http_no_retries_config['connect'] = self._session_initial_connect_retry
         self.__http_session = get_http_session_with_retry(**http_no_retries_config)
         # try to connect with the server
         self.refresh_token()
diff --git a/trains_agent/backend_config/config.py b/trains_agent/backend_config/config.py
index 40cfb69..8a63f5c 100644
--- a/trains_agent/backend_config/config.py
+++ b/trains_agent/backend_config/config.py
@@ -190,7 +190,7 @@ class Config(object):
     def reload(self):
         self.replace(self._reload())
 
-    def initialize_logging(self):
+    def initialize_logging(self, debug=False):
         logging_config = self._config.get("logging", None)
         if not logging_config:
             return False
@@ -217,6 +217,8 @@ class Config(object):
         )
         for logger in loggers:
             handlers = logger.get("handlers", None)
+            if debug:
+                logger['level'] = 'DEBUG'
             if not handlers:
                 continue
             logger["handlers"] = [h for h in handlers if h not in deleted]
diff --git a/trains_agent/session.py b/trains_agent/session.py
index f1122a8..4ec08c3 100644
--- a/trains_agent/session.py
+++ b/trains_agent/session.py
@@ -73,9 +73,11 @@ class Session(_Session):
             os.environ[LOCAL_CONFIG_FILE_OVERRIDE_VAR] = config_file
             if not Path(config_file).is_file():
                 raise ValueError("Could not open configuration file: {}".format(config_file))
+
         cpu_only = kwargs.get('cpu_only')
         if cpu_only:
             os.environ['CUDA_VISIBLE_DEVICES'] = os.environ['NVIDIA_VISIBLE_DEVICES'] = 'none'
+
         if kwargs.get('gpus') and not os.environ.get('KUBERNETES_SERVICE_HOST') \
                 and not os.environ.get('KUBERNETES_PORT'):
             # CUDA_VISIBLE_DEVICES does not support 'all'
@@ -84,6 +86,7 @@ class Session(_Session):
                 os.environ['NVIDIA_VISIBLE_DEVICES'] = kwargs.get('gpus')
             else:
                 os.environ['CUDA_VISIBLE_DEVICES'] = os.environ['NVIDIA_VISIBLE_DEVICES'] = kwargs.get('gpus')
+
         if kwargs.get('only_load_config'):
             from trains_agent.backend_api.config import load
             self.config = load()