diff --git a/.gitmodules b/.gitmodules
index 8a03ce7..1f21fdc 100644
--- a/.gitmodules
+++ b/.gitmodules
@@ -1,4 +1,4 @@
 [submodule "tests/engine_tests/engine-test-data"]
 	path = tests/engine_tests/engine-test-data
 	url = https://github.com/flagsmith/engine-test-data.git
-	tag = v3.3.0
+	branch = copilot/add-in-operator-edge-cases
diff --git a/flag_engine/segments/evaluator.py b/flag_engine/segments/evaluator.py
index abf3013..8589b62 100644
--- a/flag_engine/segments/evaluator.py
+++ b/flag_engine/segments/evaluator.py
@@ -271,6 +271,9 @@ def context_matches_condition(
     )
 
     if condition["operator"] == constants.IN:
+        # Guard against comparing null and boolean values to numeric strings
+        if any(context_value is value for value in (None, True, False)):
+            return False
         if isinstance(segment_value := condition["value"], list):
             in_values = segment_value
         else:
@@ -284,12 +287,7 @@ def context_matches_condition(
             except ValueError:
                 in_values = segment_value.split(",")
         in_values = [str(value) for value in in_values]
-        # Guard against comparing boolean values to numeric strings.
-        if isinstance(context_value, int) and not (
-            context_value is True or context_value is False
-        ):
-            context_value = str(context_value)
-        return context_value in in_values
+        return str(context_value) in in_values
 
     condition = typing.cast(StrValueSegmentCondition, condition)
 
diff --git a/tests/engine_tests/engine-test-data b/tests/engine_tests/engine-test-data
index 024f7bf..c8ed747 160000
--- a/tests/engine_tests/engine-test-data
+++ b/tests/engine_tests/engine-test-data
@@ -1 +1 @@
-Subproject commit 024f7bf6d2aa2090fae69874c87cf39e3d8b711e
+Subproject commit c8ed747afcc19300d78564cf0233926311db72d1