diff --git a/internal/controller/helmrelease_controller.go b/internal/controller/helmrelease_controller.go
index 653295783..557918915 100644
--- a/internal/controller/helmrelease_controller.go
+++ b/internal/controller/helmrelease_controller.go
@@ -247,6 +247,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 
 		log.Info("all dependencies are ready")
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, v2.DependencyNotReadyReason) {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Get the HelmChart object for the release.
 	hc, err := r.getHelmChart(ctx, obj)
@@ -266,6 +270,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		conditions.MarkFalse(obj, meta.ReadyCondition, v2.ArtifactFailedReason, msg)
 		return ctrl.Result{}, err
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, aclv1.AccessDeniedReason, v2.ArtifactFailedReason) {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Check if the HelmChart is ready.
 	if ready, reason := isHelmChartReady(hc); !ready {
@@ -276,6 +284,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		// the watcher should trigger a reconciliation.
 		return jitter.JitteredRequeueInterval(ctrl.Result{RequeueAfter: obj.GetRequeueAfter()}), errWaitForChart
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, "HelmChartNotReady") {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Compose values based from the spec and references.
 	values, err := chartutil.ChartValuesFromReferences(ctx, r.Client, obj.Namespace, obj.GetValues(), obj.Spec.ValuesFrom...)
@@ -283,6 +295,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		conditions.MarkFalse(obj, meta.ReadyCondition, "ValuesError", err.Error())
 		return ctrl.Result{}, err
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, "ValuesError") {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Load chart from artifact.
 	loadedChart, err := loader.SecureLoadChartFromURL(loader.NewRetryableHTTPClient(ctx, r.artifactFetchRetries), hc.GetArtifact().URL, hc.GetArtifact().Digest)
@@ -297,6 +313,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		conditions.MarkFalse(obj, meta.ReadyCondition, v2.ArtifactFailedReason, fmt.Sprintf("Could not load chart: %s", err.Error()))
 		return ctrl.Result{}, err
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, v2.ArtifactFailedReason) {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Build the REST client getter.
 	getter, err := r.buildRESTClientGetter(ctx, obj)
@@ -304,6 +324,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		conditions.MarkFalse(obj, meta.ReadyCondition, "RESTClientError", err.Error())
 		return ctrl.Result{}, err
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, "RESETClientError") {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Attempt to adopt "legacy" v2beta1 release state on a best-effort basis.
 	// If this fails, the controller will fall back to performing an upgrade
@@ -354,6 +378,10 @@ func (r *HelmReleaseReconciler) reconcileRelease(ctx context.Context, patchHelpe
 		conditions.MarkFalse(obj, meta.ReadyCondition, "FactoryError", err.Error())
 		return ctrl.Result{}, err
 	}
+	// Remove any stale corresponding Ready=False condition with Unknown.
+	if hasConditionReason(obj, meta.ReadyCondition, "FactoryError") {
+		conditions.MarkUnknown(obj, meta.ReadyCondition, meta.ProgressingReason, "reconciliation in progress")
+	}
 
 	// Off we go!
 	if err = intreconcile.NewAtomicRelease(patchHelper, cfg, r.EventRecorder, r.FieldManager).Reconcile(ctx, &intreconcile.Request{
@@ -720,3 +748,14 @@ func isHelmChartReady(obj *sourcev1.HelmChart) (bool, string) {
 		return true, ""
 	}
 }
+
+// hasConditionReason returns if the given Getter's condition type t has any of
+// the given reasons.
+func hasConditionReason(from conditions.Getter, t string, reasons ...string) bool {
+	for _, reason := range reasons {
+		if conditions.GetReason(from, t) == reason {
+			return true
+		}
+	}
+	return false
+}
diff --git a/internal/controller/helmrelease_controller_test.go b/internal/controller/helmrelease_controller_test.go
index 08bd933c1..534df4a3e 100644
--- a/internal/controller/helmrelease_controller_test.go
+++ b/internal/controller/helmrelease_controller_test.go
@@ -2286,3 +2286,39 @@ func Test_isHelmChartReady(t *testing.T) {
 		})
 	}
 }
+
+func Test_hasConditionReason(t *testing.T) {
+	tests := []struct {
+		name           string
+		existingReason string
+		checkReasons   []string
+		want           bool
+	}{
+		{
+			name:           "no check reason",
+			existingReason: v2.DependencyNotReadyReason,
+			want:           false,
+		},
+		{
+			name:           "no known reason",
+			existingReason: v2.DependencyNotReadyReason,
+			checkReasons:   []string{v2.ArtifactFailedReason, acl.AccessDeniedReason},
+			want:           false,
+		},
+		{
+			name:           "known and unknown reasons",
+			existingReason: v2.ArtifactFailedReason,
+			checkReasons:   []string{acl.AccessDeniedReason, v2.ArtifactFailedReason},
+			want:           true,
+		},
+	}
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			obj := &v2.HelmRelease{}
+			conditions.MarkFalse(obj, meta.ReadyCondition, tt.existingReason, "foo")
+			if got := hasConditionReason(obj, meta.ReadyCondition, tt.checkReasons...); got != tt.want {
+				t.Errorf("hasConditionReason() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}