diff --git a/pkg/monitortests/clusterversionoperator/legacycvomonitortests/operators.go b/pkg/monitortests/clusterversionoperator/legacycvomonitortests/operators.go
index e5b86f7e9c66..4fb0051ec51f 100644
--- a/pkg/monitortests/clusterversionoperator/legacycvomonitortests/operators.go
+++ b/pkg/monitortests/clusterversionoperator/legacycvomonitortests/operators.go
@@ -68,6 +68,17 @@ func testUpgradeOperatorStateTransitions(events monitorapi.Intervals, clientConf
 			return "", nil
 		}
 
+		// Determine if condition is within a the upgrade window.
+		inUpgradeWindow := operatorstateanalyzer.InUpgradeWindow(events, condition.LastTransitionTime.Time)
+
+		if condition.Status == configv1.ConditionFalse {
+			if condition.Type == configv1.OperatorAvailable {
+				if !inUpgradeWindow {
+					// Operators should never go Available=False outside of the upgrade window.
+					return "", nil
+				}
+			}
+		}
 		switch operator {
 		case "authentication":
 			if condition.Type == configv1.OperatorAvailable && condition.Status == configv1.ConditionFalse && (condition.Reason == "APIServices_Error" || condition.Reason == "APIServerDeployment_NoDeployment" || condition.Reason == "APIServerDeployment_NoPod" || condition.Reason == "APIServerDeployment_PreconditionNotFulfilled" || condition.Reason == "APIServices_PreconditionNotReady" || condition.Reason == "OAuthServerDeployment_NoDeployment" || condition.Reason == "OAuthServerRouteEndpointAccessibleController_EndpointUnavailable" || condition.Reason == "OAuthServerServiceEndpointAccessibleController_EndpointUnavailable" || condition.Reason == "WellKnown_NotReady") {