diff --git a/.gitmodules b/.gitmodules
index 5e04c6d..6450f1e 100644
--- a/.gitmodules
+++ b/.gitmodules
@@ -1,4 +1,4 @@
 [submodule "tests/Engine/EngineTests/EngineTestData"]
 	path = tests/Engine/EngineTests/EngineTestData
 	url = git@github.com:Flagsmith/engine-test-data.git
-	tag = v3.5.0
+	tag = v3.7.0
diff --git a/src/Engine/Engine.php b/src/Engine/Engine.php
index 9056701..f092b78 100644
--- a/src/Engine/Engine.php
+++ b/src/Engine/Engine.php
@@ -219,21 +219,42 @@ private static function _contextMatchesRule(
             }
         }
 
-        if ($rule->type === SegmentRuleType::ANY && !$any) {
+        if ($rule->type === SegmentRuleType::ANY && !$any && !empty($rule->conditions)) {
             return false;
         }
 
+        $anySubRule = false;
         foreach ($rule->rules as $subRule) {
-            $ruleMatches = self::_contextMatchesRule(
+            $subRuleMatches = self::_contextMatchesRule(
                 $context,
                 $subRule,
                 $segmentKey,
             );
-            if (!$ruleMatches) {
-                return false;
+
+            switch ($rule->type) {
+                case SegmentRuleType::ALL:
+                    if (!$subRuleMatches) {
+                        return false;
+                    }
+                    break;
+                case SegmentRuleType::NONE:
+                    if ($subRuleMatches) {
+                        return false;
+                    }
+                    break;
+                case SegmentRuleType::ANY:
+                    if ($subRuleMatches) {
+                        $anySubRule = true;
+                        break 2;
+                    }
+                    break;
             }
         }
 
+        if ($rule->type === SegmentRuleType::ANY && !$anySubRule && !empty($rule->rules)) {
+            return false;
+        }
+
         return true;
     }
 
diff --git a/tests/Engine/EngineTests/EngineTestData b/tests/Engine/EngineTests/EngineTestData
index 7840a13..4b29dc7 160000
--- a/tests/Engine/EngineTests/EngineTestData
+++ b/tests/Engine/EngineTests/EngineTestData
@@ -1 +1 @@
-Subproject commit 7840a1349b601df3b6b4a089f40864f659801afb
+Subproject commit 4b29dc772a764364af2dd504ecefbdf74cf5473f