diff --git a/apps/advisor/pkg/app/app.go b/apps/advisor/pkg/app/app.go
index ba84a14f7f7..fae11df0c6c 100644
--- a/apps/advisor/pkg/app/app.go
+++ b/apps/advisor/pkg/app/app.go
@@ -78,7 +78,7 @@ func New(cfg app.Config) (app.App, error) {
 									}
 								}()
 							}
-							if req.Action == resource.AdmissionActionUpdate {
+							if req.Action == resource.AdmissionActionUpdate && retryAnnotationChanged(req.OldObject, req.Object) {
 								go func() {
 									logger := log.WithContext(ctx).With("check", check.ID())
 									logger.Debug("Updating check", "namespace", req.Object.GetNamespace(), "name", req.Object.GetName())
diff --git a/apps/advisor/pkg/app/utils.go b/apps/advisor/pkg/app/utils.go
index 80f71cc679e..4ab55391bb1 100644
--- a/apps/advisor/pkg/app/utils.go
+++ b/apps/advisor/pkg/app/utils.go
@@ -7,6 +7,7 @@ import (
 	"slices"
 	"strings"
 	"sync"
+	"time"
 
 	"github.com/grafana/grafana-app-sdk/logging"
 	"github.com/grafana/grafana-app-sdk/resource"
@@ -15,6 +16,8 @@ import (
 	"github.com/grafana/grafana/pkg/services/contexthandler"
 )
 
+var retryAnnotationPollingInterval = 1 * time.Second
+
 func getCheck(obj resource.Object, checkMap map[string]checks.Check) (checks.Check, error) {
 	labels := obj.GetLabels()
 	objTypeLabel, ok := labels[checks.TypeLabel]
@@ -100,13 +103,17 @@ func processCheckRetry(ctx context.Context, log logging.Logger, client resource.
 	status := checks.GetStatusAnnotation(obj)
 	if status == "" || status == checks.StatusAnnotationError {
 		// Check not processed yet or errored
+		log.Debug("Check not processed yet or errored, skipping retry", "check", obj.GetName(), "status", status)
 		return nil
 	}
 	// Get the item to retry from the annotation
 	itemToRetry := checks.GetRetryAnnotation(obj)
 	if itemToRetry == "" {
 		// No item to retry, nothing to do
+		log.Debug("No item to retry, skipping retry", "check", obj.GetName())
 		return nil
+	} else {
+		log.Debug("Item to retry found", "check", obj.GetName(), "item", itemToRetry)
 	}
 	c, ok := obj.(*advisorv0alpha1.Check)
 	if !ok {
@@ -165,14 +172,23 @@ func processCheckRetry(ctx context.Context, log logging.Logger, client resource.
 		// Failure not in the list of items to retry, keep it
 		return false
 	})
+	// Wait for the retry annotation to be persisted before patching the object
+	err = waitForRetryAnnotation(ctx, log, client, obj, itemToRetry)
+	if err != nil {
+		return err
+	}
+	// Set the status
 	err = checks.SetStatus(ctx, client, obj, c.Status)
+	log.Debug("Status set", "check", obj.GetName(), "status.count", c.Status.Report.Count)
 	if err != nil {
 		return err
 	}
 	// Delete the retry annotation to mark the check as processed
 	annotations := checks.DeleteAnnotations(ctx, obj, []string{checks.RetryAnnotation})
+	err = checks.SetAnnotations(ctx, client, obj, annotations)
+	log.Debug("Annotations set", "check", obj.GetName(), "annotations", annotations)
 
-	return checks.SetAnnotations(ctx, client, obj, annotations)
+	return err
 }
 
 func runStepsInParallel(ctx context.Context, log logging.Logger, spec *advisorv0alpha1.CheckSpec, steps []checks.Step, items []any) ([]advisorv0alpha1.CheckReportFailure, error) {
@@ -234,3 +250,47 @@ func filterSteps(checkType resource.Object, steps []checks.Step) ([]checks.Step,
 	}
 	return steps, nil
 }
+
+// retryAnnotationChanged compares the retry annotation between old and new objects
+func retryAnnotationChanged(oldObj, newObj resource.Object) bool {
+	if oldObj == nil || newObj == nil {
+		return true // If either is nil, consider it changed
+	}
+
+	// Compare annotations
+	oldAnnotations := oldObj.GetAnnotations()
+	newAnnotations := newObj.GetAnnotations()
+	return newAnnotations[checks.RetryAnnotation] != "" &&
+		oldAnnotations[checks.RetryAnnotation] != newAnnotations[checks.RetryAnnotation]
+}
+
+// waitForRetryAnnotation waits for the retry annotation to match the item to retry
+func waitForRetryAnnotation(ctx context.Context, log logging.Logger, client resource.Client, obj resource.Object, itemToRetry string) error {
+	currentObj, err := client.Get(ctx, resource.Identifier{
+		Namespace: obj.GetNamespace(),
+		Name:      obj.GetName(),
+	})
+	if err != nil {
+		return err
+	}
+	retries := 0
+	currentRetryAnnotation := checks.GetRetryAnnotation(currentObj)
+	for currentRetryAnnotation != itemToRetry {
+		log.Debug("Waiting for retry annotation to be persisted", "check", obj.GetName(), "item", itemToRetry, "currentRetryAnnotation", currentRetryAnnotation)
+		time.Sleep(retryAnnotationPollingInterval)
+		retries++
+		if retries > 5 {
+			return fmt.Errorf("timeout waiting for retry annotation to be persisted")
+		}
+		currentObj, err = client.Get(ctx, resource.Identifier{
+			Namespace: obj.GetNamespace(),
+			Name:      obj.GetName(),
+		})
+		if err != nil {
+			return err
+		}
+		currentRetryAnnotation = checks.GetRetryAnnotation(currentObj)
+	}
+	log.Debug("Retry annotation persisted", "check", obj.GetName(), "item", itemToRetry)
+	return nil
+}
diff --git a/apps/advisor/pkg/app/utils_test.go b/apps/advisor/pkg/app/utils_test.go
index 663d7cfdcf6..ea905feee2a 100644
--- a/apps/advisor/pkg/app/utils_test.go
+++ b/apps/advisor/pkg/app/utils_test.go
@@ -6,6 +6,7 @@ import (
 	"fmt"
 	"net/http"
 	"testing"
+	"time"
 
 	"github.com/grafana/grafana-app-sdk/logging"
 	"github.com/grafana/grafana-app-sdk/resource"
@@ -249,7 +250,9 @@ func TestProcessCheckRetry_SkipMissingItem(t *testing.T) {
 		t.Fatal(err)
 	}
 	meta.SetCreatedBy("user:1")
-	client := &mockClient{}
+	client := &mockClient{
+		res: obj,
+	}
 	typesClient := &mockTypesClient{}
 	ctx := context.TODO()
 
@@ -281,7 +284,9 @@ func TestProcessCheckRetry_Success(t *testing.T) {
 		t.Fatal(err)
 	}
 	meta.SetCreatedBy("user:1")
-	client := &mockClient{}
+	client := &mockClient{
+		res: obj,
+	}
 	typesClient := &mockTypesClient{}
 	ctx := context.TODO()
 
@@ -296,6 +301,51 @@ func TestProcessCheckRetry_Success(t *testing.T) {
 	assert.Empty(t, obj.Status.Report.Failures)
 }
 
+func TestProcessCheckRetry_Success_Polling(t *testing.T) {
+	retryAnnotationPollingInterval = 1 * time.Millisecond
+	obj := &advisorv0alpha1.Check{}
+	obj.SetAnnotations(map[string]string{
+		checks.RetryAnnotation:  "item",
+		checks.StatusAnnotation: checks.StatusAnnotationProcessed,
+	})
+	obj.Status.Report.Failures = []advisorv0alpha1.CheckReportFailure{
+		{
+			ItemID: "item",
+			StepID: "step",
+		},
+	}
+	meta, err := utils.MetaAccessor(obj)
+	if err != nil {
+		t.Fatal(err)
+	}
+	meta.SetCreatedBy("user:1")
+	retryCount := 0
+	client := &mockClient{
+		get: func(ctx context.Context, id resource.Identifier) (resource.Object, error) {
+			if retryCount > 0 {
+				// obj contains the retry annotation
+				return obj, nil
+			}
+			retryCount++
+			oldObject := &advisorv0alpha1.Check{}
+			oldObject.SetAnnotations(map[string]string{
+				checks.RetryAnnotation: "",
+			})
+			return oldObject, nil
+		},
+	}
+	typesClient := &mockTypesClient{}
+	ctx := context.TODO()
+
+	check := &mockCheck{
+		items: []any{"item"},
+	}
+
+	err = processCheckRetry(ctx, logging.DefaultLogger, client, typesClient, obj, check)
+	assert.NoError(t, err)
+	assert.Equal(t, 1, retryCount)
+}
+
 func TestRunStepsInParallel_ConcurrentHeaderAccess(t *testing.T) {
 	// Create an HTTP request with headers to simulate the real scenario
 	req, err := http.NewRequest("GET", "/test", nil)
@@ -360,6 +410,8 @@ func TestRunStepsInParallel_ConcurrentHeaderAccess(t *testing.T) {
 type mockClient struct {
 	resource.Client
 	values []any
+	res    resource.Object
+	get    func(ctx context.Context, id resource.Identifier) (resource.Object, error)
 }
 
 func (m *mockClient) PatchInto(ctx context.Context, id resource.Identifier, req resource.PatchRequest, opts resource.PatchOptions, obj resource.Object) error {
@@ -368,6 +420,13 @@ func (m *mockClient) PatchInto(ctx context.Context, id resource.Identifier, req
 	return nil
 }
 
+func (m *mockClient) Get(ctx context.Context, id resource.Identifier) (resource.Object, error) {
+	if m.get != nil {
+		return m.get(ctx, id)
+	}
+	return m.res, nil
+}
+
 type mockTypesClient struct {
 	resource.Client
 	res resource.Object