diff --git a/bot/adapters/discord/client.py b/bot/adapters/discord/client.py
index fa5612f..46bc911 100644
--- a/bot/adapters/discord/client.py
+++ b/bot/adapters/discord/client.py
@@ -383,12 +383,16 @@ async def _send_post(
             if e.status != 413:  # Payload too large
                 raise e
             if post.buffer is not None:
-                logger.info('File too large, resizing...')
+                logger.info('File too large, resizing...', size=len(post.buffer))
                 post.buffer.seek(0)
                 post.buffer = await utils.resize(buffer=post.buffer, extension=extension)
                 return await self._send_post(post=post, send_func=send_func, author=author)
 
             raise exceptions.BotError('Failed to send message') from e
+        except utils.SSL_ERRORS as e:
+            # Retry on SSL errors
+            logger.error("SSL Error, retrying", error=str(e))
+            return await self._send_post(post=post, send_func=send_func, author=author)
 
     async def _send_comments(
         self,
diff --git a/bot/common/utils.py b/bot/common/utils.py
index 09a3bf5..4d17469 100644
--- a/bot/common/utils.py
+++ b/bot/common/utils.py
@@ -9,12 +9,20 @@
 import typing
 from contextlib import contextmanager
 
+import aiohttp
 import magic
 from PIL import Image as pil_image
 from django import db as django_db
+from requests import exceptions as requests_exceptions
 
 emoji = ['😼', '😺', '😸', '😹', '😻', '🙀', '😿', '😾', '😩', '🙈', '🙉', '🙊', '😳']
 
+SSL_ERRORS = (
+    requests_exceptions.SSLError,
+    aiohttp.ClientSSLError,
+    aiohttp.ClientConnectorSSLError,
+)
+
 
 def find_first_url(string: str) -> typing.Optional[str]:
     urls = re.findall(r'(https?://[^\s]+)', string)