diff --git a/test/e2e/condition_matcher_test.go b/test/e2e/condition_matcher_test.go
index 8f2865554..ba9940b2e 100644
--- a/test/e2e/condition_matcher_test.go
+++ b/test/e2e/condition_matcher_test.go
@@ -53,7 +53,9 @@ func (m *ConditionMatcher) Matches(conditions []opv1.OperatorCondition) bool {
 		}
 
 		if m.MatchesType(&cond) && !m.MatchesStatus(&cond) {
-			return false
+			if !m.Any {
+				return false
+			}
 		}
 	}
 
diff --git a/test/e2e/condition_matcher_unit_test.go b/test/e2e/condition_matcher_unit_test.go
index d88ea3b72..6d511ddf9 100644
--- a/test/e2e/condition_matcher_unit_test.go
+++ b/test/e2e/condition_matcher_unit_test.go
@@ -101,6 +101,20 @@ func TestVerifyOperatorStatusCondition(t *testing.T) {
 			expectError:   true,
 			errorContains: "context deadline exceeded",
 		},
+		{
+			name: "Any mode succeeds when matching condition appears after non-matching one",
+			expectedConditions: map[string]opv1.ConditionStatus{
+				"Degraded": opv1.ConditionTrue,
+			},
+			initialObjects: []runtime.Object{
+				newCertManagerObjectWithConditions(
+					opv1.OperatorCondition{Type: controllerPrefix + "-static-resources-Degraded", Status: opv1.ConditionFalse},
+					opv1.OperatorCondition{Type: controllerPrefix + "Degraded", Status: opv1.ConditionTrue},
+				),
+			},
+			matchAny:    true,
+			expectError: false,
+		},
 		{
 			name: "A missing condition for Progressing",
 			expectedConditions: map[string]opv1.ConditionStatus{