diff --git a/pyproject.toml b/pyproject.toml
index 7613fba4fc..6efefc5666 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -79,7 +79,6 @@ module = [
     "onelogin.*",
     "openapi_core.*",
     "openapi_schema_validator.*",
-    "PIL.*",
     "premailer.*",
     "psycopg2.*",
     "pyinotify.*",
diff --git a/requirements/dev.txt b/requirements/dev.txt
index 8934cf87ec..910786296c 100644
--- a/requirements/dev.txt
+++ b/requirements/dev.txt
@@ -1688,6 +1688,10 @@ types-orjson==0.1.1 \
     --hash=sha256:7454bfbaed27900a844bb9d8e211b69f1c335f0b9e3541d4950a793db41c104d \
     --hash=sha256:92f85986261ea1a5cb215e4b35e4016631d35163a372f023918750f340ea737f
     # via -r requirements/mypy.in
+types-pillow==8.3.2 \
+    --hash=sha256:35fa2085164e550ef89d10c75963c5c9d673e8fd529343560b945eb6ac26891d \
+    --hash=sha256:7926e2d0a774184af16115207a4938b3d1089b3cfac658e837af6a6d2ed8cc2d
+    # via -r requirements/mypy.in
 types-polib==0.1.3 \
     --hash=sha256:54fb4d5a9edc2b2f7e3cd7ebbf8631dbcecdeb69e9e31597e81c2b5b3bd3613b \
     --hash=sha256:bd79bc1780e5d7fb6fd0dce59bb8d118ca81f8b2f14d5d05e21d2716e2e1937b
diff --git a/requirements/mypy.in b/requirements/mypy.in
index 98ad465199..194325ac25 100644
--- a/requirements/mypy.in
+++ b/requirements/mypy.in
@@ -18,6 +18,7 @@ types-Markdown
 types-oauthlib
 types-orjson
 types-polib
+types-Pillow
 types-Pygments
 types-python-dateutil
 types-pytz
diff --git a/requirements/mypy.txt b/requirements/mypy.txt
index 92b70b7b68..2b1bfb33fb 100644
--- a/requirements/mypy.txt
+++ b/requirements/mypy.txt
@@ -129,6 +129,10 @@ types-orjson==0.1.1 \
     --hash=sha256:7454bfbaed27900a844bb9d8e211b69f1c335f0b9e3541d4950a793db41c104d \
     --hash=sha256:92f85986261ea1a5cb215e4b35e4016631d35163a372f023918750f340ea737f
     # via -r requirements/mypy.in
+types-pillow==8.3.2 \
+    --hash=sha256:35fa2085164e550ef89d10c75963c5c9d673e8fd529343560b945eb6ac26891d \
+    --hash=sha256:7926e2d0a774184af16115207a4938b3d1089b3cfac658e837af6a6d2ed8cc2d
+    # via -r requirements/mypy.in
 types-polib==0.1.3 \
     --hash=sha256:54fb4d5a9edc2b2f7e3cd7ebbf8631dbcecdeb69e9e31597e81c2b5b3bd3613b \
     --hash=sha256:bd79bc1780e5d7fb6fd0dce59bb8d118ca81f8b2f14d5d05e21d2716e2e1937b
diff --git a/version.py b/version.py
index 5fee987203..f184106284 100644
--- a/version.py
+++ b/version.py
@@ -48,4 +48,4 @@ API_FEATURE_LEVEL = 92
 #   historical commits sharing the same major version, in which case a
 #   minor version bump suffices.
 
-PROVISION_VERSION = "153.10"
+PROVISION_VERSION = "153.11"
diff --git a/zerver/lib/upload.py b/zerver/lib/upload.py
index 7f58f7ed90..4c40e1133e 100644
--- a/zerver/lib/upload.py
+++ b/zerver/lib/upload.py
@@ -148,7 +148,9 @@ def resize_gif(im: GifImageFile, size: int = DEFAULT_EMOJI_SIZE) -> bytes:
         new_frame = ImageOps.pad(new_frame, (size, size), Image.ANTIALIAS)
         frames.append(new_frame)
         duration_info.append(im.info["duration"])
-        disposals.append(im.disposal_method)
+        disposals.append(
+            im.disposal_method  # type: ignore[attr-defined]  # private member missing from stubs
+        )
     out = io.BytesIO()
     frames[0].save(
         out,
@@ -168,6 +170,7 @@ def resize_emoji(image_data: bytes, size: int = DEFAULT_EMOJI_SIZE) -> bytes:
         im = Image.open(io.BytesIO(image_data))
         image_format = im.format
         if image_format == "GIF":
+            assert isinstance(im, GifImageFile)
             # There are a number of bugs in Pillow.GifImagePlugin which cause
             # results in resized gifs being broken. To work around this we
             # only resize under certain conditions to minimize the chance of