diff --git a/changelog/1585.bugfix.rst b/changelog/1585.bugfix.rst
new file mode 100644
index 0000000000..e38df25f3b
--- /dev/null
+++ b/changelog/1585.bugfix.rst
@@ -0,0 +1 @@
+Fix a deadlock where cancelling a request while it was waiting out a global rate limit would leave every subsequent request waiting forever.
diff --git a/disnake/http.py b/disnake/http.py
index b9bca14ae6..d682dbc06a 100644
--- a/disnake/http.py
+++ b/disnake/http.py
@@ -409,14 +409,19 @@ async def request(
                                 )
                                 self._global_over.clear()
 
-                            await asyncio.sleep(retry_after)
-                            _log.debug("Done sleeping for the rate limit. Retrying...")
-
-                            # release the global lock now that the
-                            # global rate limit has passed
-                            if is_global:
-                                self._global_over.set()
-                                _log.debug("Global rate limit is now over.")
+                            try:
+                                await asyncio.sleep(retry_after)
+                                _log.debug("Done sleeping for the rate limit. Retrying...")
+                            finally:
+                                # release the global lock now that the
+                                # global rate limit has passed.
+                                # this has to happen in a finally, otherwise a
+                                # request cancelled while sleeping would leave
+                                # the event cleared forever, and every later
+                                # request would block on it indefinitely
+                                if is_global:
+                                    self._global_over.set()
+                                    _log.debug("Global rate limit is now over.")
 
                             continue
 
diff --git a/tests/test_http.py b/tests/test_http.py
index 6a9512a287..ba05f41eba 100644
--- a/tests/test_http.py
+++ b/tests/test_http.py
@@ -1,9 +1,13 @@
 # SPDX-License-Identifier: MIT
 
+import asyncio
+from typing import ClassVar
+
 import pytest
+from typing_extensions import Self
 
 import disnake
-from disnake.http import HTTPClient
+from disnake.http import HTTPClient, Route
 
 
 @pytest.mark.parametrize(
@@ -46,3 +50,50 @@
 )
 def test_format_gateway_url(url: str, params: disnake.GatewayParams, expected: str) -> None:
     assert HTTPClient._format_gateway_url(url, params=params) == expected
+
+
+class _GlobalRateLimitResponse:
+    """A ``429`` carrying ``global: true``, as sent by Discord."""
+
+    status = 429
+    headers: ClassVar[dict[str, str]] = {
+        "content-type": "application/json",
+        "Via": "1.1 google",
+    }
+
+    async def text(self, encoding: str = "utf-8") -> str:
+        return '{"global": true, "retry_after": 60.0}'
+
+    async def __aenter__(self) -> Self:
+        return self
+
+    async def __aexit__(self, *exc_info: object) -> bool:
+        return False
+
+
+class _GlobalRateLimitSession:
+    def request(self, method: str, url: str, **kwargs: object) -> _GlobalRateLimitResponse:
+        return _GlobalRateLimitResponse()
+
+
+@pytest.mark.asyncio
+async def test_global_rate_limit_released_on_cancellation() -> None:
+    # a request cancelled while sleeping off a global rate limit must still
+    # re-set `_global_over`, otherwise every later request blocks on it forever
+    http = HTTPClient(loop=asyncio.get_running_loop())
+    http._HTTPClient__session = _GlobalRateLimitSession()  # pyright: ignore[reportAttributeAccessIssue]
+
+    task = asyncio.create_task(http.request(Route("GET", "/users/@me")))
+
+    # let the request reach the sleep, with the global event now cleared
+    for _ in range(10):
+        await asyncio.sleep(0)
+        if not http._global_over.is_set():
+            break
+    assert not http._global_over.is_set()
+
+    task.cancel()
+    with pytest.raises(asyncio.CancelledError):
+        await task
+
+    assert http._global_over.is_set()