diff --git a/game/commander/tasks/primitive/oca.py b/game/commander/tasks/primitive/oca.py
index 0fdcc547..6877150d 100644
--- a/game/commander/tasks/primitive/oca.py
+++ b/game/commander/tasks/primitive/oca.py
@@ -25,7 +25,7 @@ class PlanOcaStrike(PackagePlanningTask[ControlPoint]):
     def propose_flights(self) -> None:
         size = self.get_flight_size()
         if self.target.cptype == self.target.cptype.AIRBASE:
-            self.propose_flight(FlightType.OCA_RUNWAY, size)
+            self.propose_flight(FlightType.OCA_RUNWAY, size)  # type:ignore[unreachable]
         if self.aircraft_cold_start:
             self.propose_flight(FlightType.OCA_AIRCRAFT, 2)
         self.propose_common_escorts()
diff --git a/game/missiongenerator/aircraft/waypoints/antishipingress.py b/game/missiongenerator/aircraft/waypoints/antishipingress.py
index c9c390a9..c73d9308 100644
--- a/game/missiongenerator/aircraft/waypoints/antishipingress.py
+++ b/game/missiongenerator/aircraft/waypoints/antishipingress.py
@@ -35,5 +35,7 @@ class AntiShipIngressBuilder(PydcsWaypointBuilder):
                 )
                 continue
 
-            task = AttackGroup(miz_group.id, group_attack=True, weapon_type=WeaponType.Auto)
+            task = AttackGroup(
+                miz_group.id, group_attack=True, weapon_type=WeaponType.Auto
+            )
             waypoint.tasks.append(task)
diff --git a/game/missiongenerator/kneeboard.py b/game/missiongenerator/kneeboard.py
index 40459085..87bb816a 100644
--- a/game/missiongenerator/kneeboard.py
+++ b/game/missiongenerator/kneeboard.py
@@ -73,16 +73,16 @@ class KneeboardPageWriter:
         # probably do), we'll need to split some of this information off into a
         # second page.
         self.title_font = ImageFont.truetype(
-            "courbd.ttf", 32, layout_engine=ImageFont.LAYOUT_BASIC
+            "courbd.ttf", 32, layout_engine=ImageFont.Layout.BASIC
         )
         self.heading_font = ImageFont.truetype(
-            "courbd.ttf", 24, layout_engine=ImageFont.LAYOUT_BASIC
+            "courbd.ttf", 24, layout_engine=ImageFont.Layout.BASIC
         )
         self.content_font = ImageFont.truetype(
-            "courbd.ttf", 16, layout_engine=ImageFont.LAYOUT_BASIC
+            "courbd.ttf", 16, layout_engine=ImageFont.Layout.BASIC
         )
         self.table_font = ImageFont.truetype(
-            "courbd.ttf", 20, layout_engine=ImageFont.LAYOUT_BASIC
+            "courbd.ttf", 20, layout_engine=ImageFont.Layout.BASIC
         )
         self.draw = ImageDraw.Draw(self.image)
         self.page_margin = page_margin
@@ -116,7 +116,7 @@ class KneeboardPageWriter:
             )
 
         self.draw.text(self.position, text, font=font, fill=fill)
-        width, height = self.draw.textsize(text, font=font)
+        width, height = self.draw.textsize(text, font=font)  # type:ignore[attr-defined]
         self.y += height + self.line_spacing
         self.text_buffer.append(text)
 
@@ -170,14 +170,14 @@ class KneeboardPageWriter:
     def wrap_line_with_font(
         inputstr: str, max_width: int, font: ImageFont.FreeTypeFont
     ) -> str:
-        if font.getsize(inputstr)[0] <= max_width:
+        if font.getsize(inputstr)[0] <= max_width:  # type:ignore[attr-defined]
             return inputstr
         tokens = inputstr.split(" ")
         output = ""
         segments = []
         for token in tokens:
             combo = output + " " + token
-            if font.getsize(combo)[0] > max_width:
+            if font.getsize(combo)[0] > max_width:  # type:ignore[attr-defined]
                 segments.append(output + "\n")
                 output = token
             else:
@@ -339,7 +339,7 @@ class BriefingPage(KneeboardPage):
         self.flight_plan_font = ImageFont.truetype(
             "courbd.ttf",
             16,
-            layout_engine=ImageFont.LAYOUT_BASIC,
+            layout_engine=ImageFont.Layout.BASIC,
         )
 
     def write(self, path: Path) -> None:
diff --git a/requirements.txt b/requirements.txt
index 0a486df7..2dac60f3 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -26,8 +26,8 @@ nodeenv==1.8.0
 packaging==23.1
 pathspec==0.11.1
 pefile==2023.2.7
-Pillow==10.0.0
-platformdirs==3.8.1
+Pillow==9.5.0
+platformdirs==3.9.0
 pluggy==1.2.0
 pre-commit==3.3.3
 pydantic==2.0.3
@@ -49,7 +49,7 @@ Shapely==2.0.1
 shiboken2==5.15.2.1
 six==1.16.0
 sniffio==1.3.0
-starlette==0.30.0
+starlette==0.27.0
 tabulate==0.9.0
 text-unidecode==1.3
 toml==0.10.2