diff --git a/internal/bridge/crunchybridgecluster/crunchybridgecluster_controller.go b/internal/bridge/crunchybridgecluster/crunchybridgecluster_controller.go
index cb071f4858..bfd358fecc 100644
--- a/internal/bridge/crunchybridgecluster/crunchybridgecluster_controller.go
+++ b/internal/bridge/crunchybridgecluster/crunchybridgecluster_controller.go
@@ -265,12 +265,15 @@ func (r *CrunchyBridgeClusterReconciler) Reconcile(ctx context.Context, req ctrl
 		return ctrl.Result{}, nil
 	}
 
-	// Remove cluster invalid status if found
-	if invalid != nil &&
-		invalid.Status == metav1.ConditionFalse &&
-		invalid.Reason == "ClusterInvalid" {
-		meta.RemoveStatusCondition(&crunchybridgecluster.Status.Conditions,
-			v1beta1.ConditionCreating)
+	// check for an upgrade error and return until observedGeneration has
+	// been incremented by updating the CR with valid value(s).
+	invalidUpgrade := meta.FindStatusCondition(crunchybridgecluster.Status.Conditions,
+		v1beta1.ConditionUpgrading)
+	if invalidUpgrade != nil &&
+		invalidUpgrade.Status == metav1.ConditionFalse &&
+		invalidUpgrade.Reason == "UpgradeError" &&
+		invalidUpgrade.ObservedGeneration == crunchybridgecluster.GetGeneration() {
+		return ctrl.Result{}, nil
 	}
 
 	// We should only be missing the ID if no create has been issued
@@ -350,6 +353,14 @@ func (r *CrunchyBridgeClusterReconciler) Reconcile(ctx context.Context, req ctrl
 			return ctrl.Result{}, nil
 		}
 		crunchybridgecluster.Status.ID = cluster.ID
+
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionUnknown,
+			Reason:             "UpgradeConditionUnknown",
+			Message:            "The condition of the upgrade(s) is unknown.",
+		})
 		return ctrl.Result{RequeueAfter: 3 * time.Minute}, nil
 	}
 
@@ -381,7 +392,25 @@ func (r *CrunchyBridgeClusterReconciler) Reconcile(ctx context.Context, req ctrl
 		return ctrl.Result{}, err
 	}
 	clusterUpgradeDetails.AddDataToClusterStatus(crunchybridgecluster)
-	// TODO: Update the ConditionUpdating status here
+	if len(clusterUpgradeDetails.Operations) != 0 {
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionTrue,
+			Reason:             clusterUpgradeDetails.Operations[0].Flavor,
+			Message: fmt.Sprintf(
+				"Performing an upgrade of type %v with a state of %v.",
+				clusterUpgradeDetails.Operations[0].Flavor, clusterUpgradeDetails.Operations[0].State),
+		})
+	} else {
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionFalse,
+			Reason:             "NoUpgradesInProgress",
+			Message:            "No upgrades being performed",
+		})
+	}
 
 	// Reconcile roles and their secrets
 	err = r.reconcilePostgresRoles(ctx, key, crunchybridgecluster)
@@ -479,11 +508,30 @@ func (r *CrunchyBridgeClusterReconciler) handleUpgrade(ctx context.Context,
 		// TODO(crunchybridgecluster): consider what errors we might get
 		// and what different results/requeue times we want to return.
 		// Currently: don't requeue and wait for user to change spec.
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionFalse,
+			Reason:             "UpgradeError",
+			Message: fmt.Sprintf(
+				"Error performing an upgrade: %s", err),
+		})
 		log.Error(err, "Error while attempting cluster upgrade")
 		return ctrl.Result{}, nil
 	}
 	clusterUpgrade.AddDataToClusterStatus(crunchybridgecluster)
 
+	if len(clusterUpgrade.Operations) != 0 {
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionTrue,
+			Reason:             clusterUpgrade.Operations[0].Flavor,
+			Message: fmt.Sprintf(
+				"Performing an upgrade of type %v with a state of %v.",
+				clusterUpgrade.Operations[0].Flavor, clusterUpgrade.Operations[0].State),
+		})
+	}
 	return ctrl.Result{RequeueAfter: 3 * time.Minute}, nil
 }
 
@@ -507,11 +555,29 @@ func (r *CrunchyBridgeClusterReconciler) handleUpgradeHA(ctx context.Context,
 		// TODO(crunchybridgecluster): consider what errors we might get
 		// and what different results/requeue times we want to return.
 		// Currently: don't requeue and wait for user to change spec.
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionFalse,
+			Reason:             "UpgradeError",
+			Message: fmt.Sprintf(
+				"Error performing an HA upgrade: %s", err),
+		})
 		log.Error(err, "Error while attempting cluster HA change")
 		return ctrl.Result{}, nil
 	}
 	clusterUpgrade.AddDataToClusterStatus(crunchybridgecluster)
-
+	if len(clusterUpgrade.Operations) != 0 {
+		meta.SetStatusCondition(&crunchybridgecluster.Status.Conditions, metav1.Condition{
+			ObservedGeneration: crunchybridgecluster.GetGeneration(),
+			Type:               v1beta1.ConditionUpgrading,
+			Status:             metav1.ConditionTrue,
+			Reason:             clusterUpgrade.Operations[0].Flavor,
+			Message: fmt.Sprintf(
+				"Perfoming an upgrade of type %v with a state of %v.",
+				clusterUpgrade.Operations[0].Flavor, clusterUpgrade.Operations[0].State),
+		})
+	}
 	return ctrl.Result{RequeueAfter: 3 * time.Minute}, nil
 }
 
diff --git a/pkg/apis/postgres-operator.crunchydata.com/v1beta1/crunchy_bridgecluster_types.go b/pkg/apis/postgres-operator.crunchydata.com/v1beta1/crunchy_bridgecluster_types.go
index b710dcf58e..c72d648847 100644
--- a/pkg/apis/postgres-operator.crunchydata.com/v1beta1/crunchy_bridgecluster_types.go
+++ b/pkg/apis/postgres-operator.crunchydata.com/v1beta1/crunchy_bridgecluster_types.go
@@ -182,12 +182,12 @@ type UpgradeOperation struct {
 // TODO(crunchybridgecluster) Think through conditions
 // CrunchyBridgeClusterStatus condition types.
 const (
-	ConditionUnknown  = ""
-	ConditionPending  = "Pending"
-	ConditionCreating = "Creating"
-	ConditionUpdating = "Updating"
-	ConditionReady    = "Ready"
-	ConditionDeleting = "Deleting"
+	ConditionUnknown   = ""
+	ConditionPending   = "Pending"
+	ConditionCreating  = "Creating"
+	ConditionUpgrading = "Upgrading"
+	ConditionReady     = "Ready"
+	ConditionDeleting  = "Deleting"
 )
 
 // +kubebuilder:object:root=true