diff --git a/pkg/cvo/cvo.go b/pkg/cvo/cvo.go
index fda11e5a3..1c6bca50b 100644
--- a/pkg/cvo/cvo.go
+++ b/pkg/cvo/cvo.go
@@ -121,6 +121,11 @@ type Operator struct {
 	upgradeable           *upgradeable
 	upgradeableChecks     []upgradeableCheck
 
+	// minimumUpgradeableCheckInterval is the minimum duration before another
+	// synchronization of the upgradeable status can happen during failing
+	// precondition checks.
+	minimumUpgradeableCheckInterval time.Duration
+
 	// verifier, if provided, will be used to check an update before it is executed.
 	// Any error will prevent an update payload from being accessed.
 	verifier verify.Interface
@@ -179,10 +184,11 @@ func New(
 			Image: releaseImage,
 		},
 
-		statusInterval:             15 * time.Second,
-		minimumUpdateCheckInterval: minimumInterval,
-		payloadDir:                 overridePayloadDir,
-		defaultUpstreamServer:      "https://api.openshift.com/api/upgrades_info/v1/graph",
+		statusInterval:                  15 * time.Second,
+		minimumUpdateCheckInterval:      minimumInterval,
+		minimumUpgradeableCheckInterval: 15 * time.Second,
+		payloadDir:                      overridePayloadDir,
+		defaultUpstreamServer:           "https://api.openshift.com/api/upgrades_info/v1/graph",
 
 		client:        client,
 		kubeClient:    kubeClient,
@@ -627,7 +633,7 @@ func (optr *Operator) upgradeableSync(ctx context.Context, key string) error {
 		return nil
 	}
 
-	return optr.syncUpgradeable()
+	return optr.syncUpgradeable(config)
 }
 
 // isOlderThanLastUpdate returns true if the cluster version is older than
diff --git a/pkg/cvo/upgradeable.go b/pkg/cvo/upgradeable.go
index 465a875a2..d42b7f318 100644
--- a/pkg/cvo/upgradeable.go
+++ b/pkg/cvo/upgradeable.go
@@ -33,12 +33,13 @@ const (
 
 var adminAckGateRegexp = regexp.MustCompile(adminAckGateFmt)
 
-// syncUpgradeable. The status is only checked if it has been more than
-// the minimumUpdateCheckInterval since the last check.
-func (optr *Operator) syncUpgradeable() error {
-	// updates are only checked at most once per minimumUpdateCheckInterval or if the generation changes
+// syncUpgradeable synchronizes the upgradeable status only if it has been more than
+// the minimumUpdateCheckInterval since the last synchronization or the precondition
+// checks on the payload are failing for less than minimumUpdateCheckInterval, and it has
+// been more than the minimumUpgradeableCheckInterval since the last synchronization.
+func (optr *Operator) syncUpgradeable(config *configv1.ClusterVersion) error {
 	u := optr.getUpgradeable()
-	if u != nil && u.RecentlyChanged(optr.minimumUpdateCheckInterval) {
+	if u != nil && u.RecentlyChanged(optr.minimumUpdateCheckInterval) && !shouldSyncUpgradeableDueToPreconditionChecks(optr, config, u) {
 		klog.V(2).Infof("Upgradeable conditions were recently checked, will try later.")
 		return nil
 	}
@@ -92,8 +93,14 @@ type upgradeable struct {
 	Conditions []configv1.ClusterOperatorStatusCondition
 }
 
+// hasPassedDurationSinceTime checks if a certain amount of time specified by duration
+// has passed since time. Returns true if the duration has passed, returns false otherwise.
+func hasPassedDurationSinceTime(t time.Time, duration time.Duration) bool {
+	return time.Now().After(t.Add(duration))
+}
+
 func (u *upgradeable) RecentlyChanged(interval time.Duration) bool {
-	return u.At.After(time.Now().Add(-interval))
+	return !hasPassedDurationSinceTime(u.At, interval)
 }
 
 func (u *upgradeable) NeedsUpdate(original *configv1.ClusterVersion) *configv1.ClusterVersion {
@@ -442,3 +449,22 @@ func (optr *Operator) adminGatesEventHandler() cache.ResourceEventHandler {
 		DeleteFunc: optr.deleteFunc,
 	}
 }
+
+// shouldSyncUpgradeableDueToPreconditionChecks checks if the upgradeable status should
+// be synchronized due to the precondition checks. It checks whether the precondition
+// checks on the payload are failing for less than minimumUpdateCheckInterval, and it has
+// been more than the minimumUpgradeableCheckInterval since the last synchronization.
+// This means, upon precondition failure, we will synchronize the upgradeable status
+// more frequently at beginning of an upgrade.
+//
+// shouldSyncUpgradeableDueToPreconditionChecks expects the parameters not to be nil.
+//
+// Function returns true if the synchronization should happen, returns false otherwise.
+func shouldSyncUpgradeableDueToPreconditionChecks(optr *Operator, config *configv1.ClusterVersion, u *upgradeable) bool {
+	cond := resourcemerge.FindOperatorStatusCondition(config.Status.Conditions, DesiredReleaseAccepted)
+	if cond != nil && cond.Reason == "PreconditionChecks" && cond.Status == configv1.ConditionFalse &&
+		hasPassedDurationSinceTime(u.At, optr.minimumUpgradeableCheckInterval) && !hasPassedDurationSinceTime(cond.LastTransitionTime.Time, optr.minimumUpdateCheckInterval) {
+		return true
+	}
+	return false
+}