diff --git a/changelog/fragments/helm_operator_uninstall_error_handling_change.yaml b/changelog/fragments/helm_operator_uninstall_error_handling_change.yaml
new file mode 100644
index 0000000000..9d98462ad5
--- /dev/null
+++ b/changelog/fragments/helm_operator_uninstall_error_handling_change.yaml
@@ -0,0 +1,14 @@
+entries:
+  - description: >
+      For Helm-based operators delete resource, if the Helm uninstall completed with error, then keep trying to uninstall until there is no error on the Helm uninstall.
+
+    kind: "change"
+
+    breaking: true
+
+    migration:
+      header: For Helm-based operators delete resource, the finalizer will not be removed until the Helm uninstall is completed without error.
+      body: >
+        In the prior releases, Helm-based operators delete resource will remove it's finalizer even if the Helm uninstallation completed with error.
+        With this change, Helm-based operators will keep attempting to perform Helm uninstall until it completes without error.
+        Only then, will the finalizer be removed.
diff --git a/internal/helm/release/manager.go b/internal/helm/release/manager.go
index 2d494f42c2..daff407a12 100644
--- a/internal/helm/release/manager.go
+++ b/internal/helm/release/manager.go
@@ -361,7 +361,34 @@ func (m manager) UninstallRelease(ctx context.Context, opts ...UninstallOption)
 			return nil, fmt.Errorf("failed to apply uninstall option: %w", err)
 		}
 	}
+
+	// Get history of this release
+	h, err := m.storageBackend.History(m.releaseName)
+	if err != nil {
+		return nil, fmt.Errorf("failed to get release history: %w", err)
+	}
+	releaseutil.SortByRevision(h)
+	lastRelease := h[len(h)-1]
+
+	// Helm uninstall on a "uninstalled" status doesn't actually perform any resource deletes.
+	// See: https://github.com/helm/helm/blob/v3.4.2/pkg/action/uninstall.go#L83-L91
+	// Set the release to "uninstalling" status and trigger the uninstall again.
+	if lastRelease.Info != nil && lastRelease.Info.Status == rpb.StatusUninstalled {
+		lastRelease.Info.Status = rpb.StatusUninstalling
+		if err := m.storageBackend.Update(lastRelease); err != nil {
+			return nil, err
+		}
+	}
+
+	// Always keep the release record in case the uninstall errors.
+	uninstall.KeepHistory = true
+
 	uninstallResponse, err := uninstall.Run(m.releaseName)
+	if err == nil {
+		// Uninstall was successful so purge the release by running the uninstall again.
+		uninstall.KeepHistory = false
+		uninstallResponse, err = uninstall.Run(m.releaseName)
+	}
 	if uninstallResponse == nil {
 		return nil, err
 	}