diff --git a/toot/http.py b/toot/http.py
index 4e62bda..14acdd0 100644
--- a/toot/http.py
+++ b/toot/http.py
@@ -3,7 +3,7 @@ from requests.exceptions import RequestException
 
 from toot import __version__
 from toot.exceptions import NotFoundError, ApiError
-from toot.logging import log_request, log_response
+from toot.logging import log_request, log_request_exception, log_response
 
 
 def send_request(request, allow_redirects=True):
@@ -19,6 +19,7 @@ def send_request(request, allow_redirects=True):
             settings = session.merge_environment_settings(prepared.url, {}, None, None, None)
             response = session.send(prepared, allow_redirects=allow_redirects, **settings)
     except RequestException as ex:
+        log_request_exception(request, ex)
         raise ApiError(f"Request failed: {str(ex)}")
 
     log_response(response)
diff --git a/toot/logging.py b/toot/logging.py
index 7c321ad..a19ad2e 100644
--- a/toot/logging.py
+++ b/toot/logging.py
@@ -2,7 +2,7 @@ import json
 import sys
 
 from logging import getLogger
-from requests import Request, Response
+from requests import Request, RequestException, Response
 from urllib.parse import urlencode
 
 logger = getLogger("toot")
@@ -56,6 +56,10 @@ def log_response(response: Response):
         logger.debug(f" <-- {content}")
 
 
+def log_request_exception(request: Request, ex: RequestException):
+    logger.debug(f" <-- {request.method} {_url(request)} Exception: {ex}")
+
+
 def _url(request):
     url = request.url
     if request.params: