diff --git a/posthog/feature_flags.py b/posthog/feature_flags.py
index dda34053..845f1d04 100644
--- a/posthog/feature_flags.py
+++ b/posthog/feature_flags.py
@@ -840,12 +840,22 @@ def relative_date_parse_for_feature_flag_matching(
         return None
 
 
+def _semver_numeric_identifier(part: str) -> int:
+    # Semver 2.0.0 §2: numeric identifiers MUST NOT include leading zeros.
+    if not part or not part.isdigit():
+        raise ValueError(f"Invalid semver numeric identifier: '{part}'")
+    if len(part) > 1 and part[0] == "0":
+        raise ValueError(f"Semver numeric identifier has leading zero: '{part}'")
+    return int(part)
+
+
 def parse_semver(value: str) -> tuple:
     """Parse a semver string into a comparable (major, minor, patch) integer tuple.
 
     Matches the behavior of the sortableSemver HogQL function:
     - Handles v-prefix, whitespace, pre-release suffixes
     - Defaults missing components to 0 (e.g., 1.2 -> 1.2.0)
+    - Rejects numeric identifiers with leading zeros per semver 2.0.0 §2
     Raises ValueError if parsing fails.
     """
     text = str(value).strip().lstrip("vV")
@@ -856,9 +866,9 @@ def parse_semver(value: str) -> tuple:
     if not parts or not parts[0]:
         raise ValueError("Invalid semver format")
 
-    major = int(parts[0])
-    minor = int(parts[1]) if len(parts) > 1 and parts[1] else 0
-    patch = int(parts[2]) if len(parts) > 2 and parts[2] else 0
+    major = _semver_numeric_identifier(parts[0])
+    minor = _semver_numeric_identifier(parts[1]) if len(parts) > 1 and parts[1] else 0
+    patch = _semver_numeric_identifier(parts[2]) if len(parts) > 2 and parts[2] else 0
 
     return (major, minor, patch)
 
@@ -902,11 +912,16 @@ def _wildcard_bounds(value: str) -> tuple:
         raise ValueError("Invalid wildcard pattern")
 
     if len(parts) == 1:
-        major = int(parts[0])
+        major = _semver_numeric_identifier(parts[0])
         return (major, 0, 0), (major + 1, 0, 0)
     elif len(parts) == 2:
-        major, minor = int(parts[0]), int(parts[1])
+        major, minor = (
+            _semver_numeric_identifier(parts[0]),
+            _semver_numeric_identifier(parts[1]),
+        )
         return (major, minor, 0), (major, minor + 1, 0)
     else:
-        major, minor, patch = int(parts[0]), int(parts[1]), int(parts[2])
+        major = _semver_numeric_identifier(parts[0])
+        minor = _semver_numeric_identifier(parts[1])
+        patch = _semver_numeric_identifier(parts[2])
         return (major, minor, patch), (major, minor, patch + 1)
diff --git a/posthog/test/test_feature_flags.py b/posthog/test/test_feature_flags.py
index 2170ce16..ffc3efd0 100644
--- a/posthog/test/test_feature_flags.py
+++ b/posthog/test/test_feature_flags.py
@@ -4495,7 +4495,7 @@ def test_match_properties_semver_with_prerelease(self):
         self.assertFalse(match_property(prop_pre, {"version": "1.2.2"}))
 
     def test_match_properties_semver_edge_cases(self):
-        """Test semver parsing handles v-prefix, whitespace, leading zeros, and other common formats."""
+        """Test semver parsing handles v-prefix, whitespace, and other common formats."""
         prop = self.property(key="version", value="1.2.3", operator="semver_eq")
 
         # v-prefix: "v1.2.3" -> extracts "1.2.3"
@@ -4507,9 +4507,6 @@ def test_match_properties_semver_edge_cases(self):
         # Trailing space: "1.2.3 " -> extracts "1.2.3"
         self.assertTrue(match_property(prop, {"version": "1.2.3 "}))
 
-        # Leading zeros: "01.02.03" -> int("01")=1, int("02")=2, int("03")=3
-        self.assertTrue(match_property(prop, {"version": "01.02.03"}))
-
         # Flag value with v-prefix
         prop_v = self.property(key="version", value="v1.2.3", operator="semver_eq")
         self.assertTrue(match_property(prop_v, {"version": "1.2.3"}))
@@ -4570,6 +4567,50 @@ def test_match_properties_semver_invalid_values(self):
         with self.assertRaises(InconclusiveMatchError):
             match_property(prop_bad, {"version": "1.2.3"})
 
+    # Semver 2.0.0 §2: numeric identifiers MUST NOT include leading zeros.
+    @parameterized.expand(
+        [
+            ("major", "01.2.3"),
+            ("minor", "1.02.3"),
+            ("patch", "1.2.03"),
+            ("all_components", "01.02.03"),
+            ("two_digit_minor", "1.07.3"),
+            ("triple_zero_major", "001.2.3"),
+        ]
+    )
+    def test_match_properties_semver_rejects_leading_zero_override_value(
+        self, _name, bad_value
+    ):
+        prop = self.property(key="version", value="1.2.3", operator="semver_eq")
+        with self.assertRaises(InconclusiveMatchError):
+            match_property(prop, {"version": bad_value})
+
+    @parameterized.expand(
+        [
+            ("zero_major", "0.1.0"),
+            ("zero_patch", "1.0.0"),
+            ("all_zero", "0.0.0"),
+        ]
+    )
+    def test_match_properties_semver_literal_zero_components_match(self, _name, value):
+        prop = self.property(key="version", value=value, operator="semver_eq")
+        self.assertTrue(match_property(prop, {"version": value}))
+
+    @parameterized.expand(
+        [
+            ("semver_gt", "01.2.3"),
+            ("semver_caret", "1.07.0"),
+            ("semver_tilde", "1.07.0"),
+            ("semver_wildcard", "01.*"),
+        ]
+    )
+    def test_match_properties_semver_rejects_leading_zero_flag_value(
+        self, operator, flag_value
+    ):
+        prop = self.property(key="version", value=flag_value, operator=operator)
+        with self.assertRaises(InconclusiveMatchError):
+            match_property(prop, {"version": "1.2.0"})
+
     def test_unknown_operator(self):
         property_a = self.property(key="key", value="2022-05-01", operator="is_unknown")
         with self.assertRaises(InconclusiveMatchError) as exception_context: