diff --git a/monty/__main__.py b/monty/__main__.py
index 10b514e2..d816e899 100644
--- a/monty/__main__.py
+++ b/monty/__main__.py
@@ -94,11 +94,6 @@ async def main() -> None:
         sync_commands_debug=True,
         sync_on_cog_actions=True,
     )
-
-    kwargs = {}
-    if constants.Client.proxy is not None:
-        kwargs["proxy"] = constants.Client.proxy
-
     bot = Monty(
         redis_session=redis_session,
         command_prefix=constants.Client.default_command_prefix,
@@ -106,7 +101,7 @@ async def main() -> None:
         allowed_mentions=disnake.AllowedMentions(everyone=False),
         intents=_intents,
         command_sync_flags=command_sync_flags,
-        **kwargs,
+        proxy=constants.Client.proxy,
     )
 
     try:
diff --git a/monty/bot.py b/monty/bot.py
index 82045f0f..84e1d101 100644
--- a/monty/bot.py
+++ b/monty/bot.py
@@ -18,6 +18,7 @@
 import redis
 import redis.asyncio
 import sqlalchemy as sa
+import yarl
 from disnake.ext import commands
 from multidict import CIMultiDict, CIMultiDictProxy
 from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker, create_async_engine
@@ -64,6 +65,12 @@ def __init__(self, redis_session: redis.asyncio.Redis, proxy: str = None, **kwar
         if TEST_GUILDS:
             kwargs["test_guilds"] = TEST_GUILDS
             log.warn("registering as test_guilds")
+
+        if proxy:
+            kwargs["proxy"] = proxy  # pass proxy to disnake client
+            if "connector" not in kwargs:
+                kwargs["connector"] = self.create_connector(proxy=proxy)
+
         super().__init__(**kwargs)
 
         self.redis_session = redis_session
@@ -180,20 +187,40 @@ async def _request(
             sys.version_info, constants.Client.version, constants.Source.github
         )
 
+        # this is also used by gql
+        self.http_request_class = self._create_http_request_class(proxy=proxy)
+
         self.http_session = aiohttp.ClientSession(
-            connector=aiohttp.TCPConnector(
-                resolver=aiohttp.AsyncResolver(),
-                family=socket.AF_INET,
-                verify_ssl=not bool(proxy and proxy.startswith("http://")),
-            ),
+            connector=self.create_connector(proxy=proxy),
+            request_class=self.http_request_class,
             trace_configs=trace_configs,
             headers=multidict.CIMultiDict({"User-agent": user_agent}),
         )
-        if proxy:
-            partial_request = functools.partial(_request, self.http_session, proxy=proxy)
-        else:
-            partial_request = functools.partial(_request, self.http_session)
-        self.http_session._request = partial_request
+        self.http_session._request = functools.partial(_request, self.http_session)
+
+    def create_connector(self, proxy: str = None) -> aiohttp.BaseConnector:
+        """Create a TCPConnector, changing the ssl setting based on the proxy value."""
+        return aiohttp.TCPConnector(
+            resolver=aiohttp.AsyncResolver(),
+            family=socket.AF_INET,
+            ssl=not (proxy and proxy.startswith("http://")),
+        )
+
+    def _create_http_request_class(self, proxy: str = None) -> type[aiohttp.ClientRequest]:
+        """Create a ClientRequest type, which inserts the proxy into every request's args (if set)."""
+        if not proxy:
+            return aiohttp.ClientRequest  # default
+
+        proxy_url = yarl.URL(proxy)
+        verify_ssl = not proxy.startswith("http://")
+
+        class ProxyClientRequest(aiohttp.ClientRequest):
+            def __init__(self, *args: Any, **kwargs: Any):
+                kwargs["proxy"] = proxy_url
+                kwargs["ssl"] = verify_ssl
+                super().__init__(*args, **kwargs)
+
+        return ProxyClientRequest
 
     async def get_self_invite_perms(self) -> disnake.Permissions:
         """Sets the internal invite_permissions and fetches them."""
diff --git a/monty/exts/info/github_info.py b/monty/exts/info/github_info.py
index c86b590b..5c37ed89 100644
--- a/monty/exts/info/github_info.py
+++ b/monty/exts/info/github_info.py
@@ -208,7 +208,14 @@ def __init__(self, bot: Monty) -> None:
         self.bot = bot
 
         transport = AIOHTTPTransport(
-            url="https://api.github.com/graphql", timeout=20, headers=GITHUB_REQUEST_HEADERS, ssl=True
+            url="https://api.github.com/graphql",
+            timeout=20,
+            headers=GITHUB_REQUEST_HEADERS,
+            ssl=True,
+            client_session_args={
+                # used for applying proxy settings
+                "request_class": bot.http_request_class,
+            },
         )
 
         self.gql = gql.Client(transport=transport, fetch_schema_from_transport=True)