diff --git a/HandlePubKeyRevoke/__tests__/handler.test.ts b/HandlePubKeyRevoke/__tests__/handler.test.ts
index 9cf32b4..2c77568 100644
--- a/HandlePubKeyRevoke/__tests__/handler.test.ts
+++ b/HandlePubKeyRevoke/__tests__/handler.test.ts
@@ -96,8 +96,10 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "false" },
         properties: expect.objectContaining({
           detail: "PERMANENT",
+          assertionRef: "unknown",
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
           maxRetryCount: "5"
@@ -128,11 +130,13 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "true" },
         properties: expect.objectContaining({
           detail: "TRANSIENT",
           fatal: "false",
           isSuccess: "false",
           modelId: "",
+          assertionRef: aValidAssertionRef,
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
           maxRetryCount: "5"
@@ -145,6 +149,47 @@ describe("handleRevoke", () => {
     ]);
   });
 
+  it("GIVEN a valid revoke message WHEN findLastVersion fails the last retry THEN it should throw with a transient failure without sampling", async () => {
+    findLastVersionByModelIdMock.mockImplementationOnce(() =>
+      TE.left(toCosmosErrorResponse("Cannot reach cosmosDB"))
+    );
+    await expect(
+      handleRevoke(
+        {
+          ...contextMock,
+          executionContext: {
+            retryContext: { retryCount: 4, maxRetryCount: 5 }
+          }
+        },
+        mockAppinsights as any,
+        lollipopKeysModelMock,
+        masterAlgo,
+        aValidRevokeInput
+      )
+    ).rejects.toBeDefined();
+
+    expect(mockAppinsights.trackException).toHaveBeenCalled();
+    expect(mockAppinsights.trackException).toHaveBeenCalledWith(
+      expect.objectContaining({
+        tagOverrides: { samplingEnabled: "false" },
+        properties: expect.objectContaining({
+          detail: "TRANSIENT",
+          fatal: "false",
+          isSuccess: "false",
+          modelId: "",
+          assertionRef: aValidAssertionRef,
+          name: "lollipop.pubKeys.revoke.failure",
+          retryCount: "4",
+          maxRetryCount: "5"
+        })
+      })
+    );
+    expect(findLastVersionByModelIdMock).toHaveBeenCalledTimes(1);
+    expect(findLastVersionByModelIdMock).toHaveBeenCalledWith([
+      aValidRevokeInput.assertion_ref
+    ]);
+  });
+
   it("GIVEN a valid revoke message WHEN findLastVersion returns none THEN it should success without perform any upsert", async () => {
     findLastVersionByModelIdMock.mockImplementationOnce(() => TE.right(O.none));
     const result = await handleRevoke(
@@ -243,8 +288,10 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "false" },
         properties: expect.objectContaining({
           detail: "PERMANENT",
+          assertionRef: aValidAssertionRef,
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
           maxRetryCount: "5"
@@ -285,8 +332,10 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "false" },
         properties: expect.objectContaining({
           detail: "PERMANENT",
+          assertionRef: aValidAssertionRef,
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
           maxRetryCount: "5"
@@ -331,8 +380,10 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "true" },
         properties: expect.objectContaining({
           detail: "TRANSIENT",
+          assertionRef: aValidAssertionRef,
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
           maxRetryCount: "5"
@@ -371,10 +422,12 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "true" },
         properties: expect.objectContaining({
           detail: "TRANSIENT",
           name: "lollipop.pubKeys.revoke.failure",
           retryCount: "1",
+          assertionRef: aValidAssertionRef,
           maxRetryCount: "5",
           errorMessage: expect.stringContaining(
             "Cannot find a master lollipopPubKey"
@@ -414,8 +467,10 @@ describe("handleRevoke", () => {
     expect(mockAppinsights.trackException).toHaveBeenCalled();
     expect(mockAppinsights.trackException).toHaveBeenCalledWith(
       expect.objectContaining({
+        tagOverrides: { samplingEnabled: "true" },
         properties: expect.objectContaining({
           detail: "TRANSIENT",
+          assertionRef: aValidAssertionRef,
           errorMessage: expect.stringContaining(
             "Cannot decode a VALID master lollipopPubKey"
           ),
diff --git a/HandlePubKeyRevoke/handler.ts b/HandlePubKeyRevoke/handler.ts
index 748b210..4c105d1 100644
--- a/HandlePubKeyRevoke/handler.ts
+++ b/HandlePubKeyRevoke/handler.ts
@@ -100,6 +100,15 @@ const extractPubKeysToRevoke = (
     )
   );
 
+/**
+ *
+ * @param context The function context
+ * @returns `true` if retryCount >= maxRetryCount-1, `false` otherwise
+ */
+const isLastRetry = (context: Context): boolean =>
+  (context.executionContext.retryContext?.retryCount ?? 0) >=
+  (context.executionContext.retryContext?.maxRetryCount ?? 0) - 1;
+
 const revokePubKey = (lollipopKeysModel: LolliPOPKeysModel) => (
   notPendingLollipopPubKey: NotPendingLolliPopPubKeys
 ): TE.TaskEither<CosmosErrors, RetrievedLolliPopPubKeys> =>
@@ -164,6 +173,12 @@ export const handleRevoke = (
       trackException(telemetryClient, {
         exception: new Error(error),
         properties: {
+          assertionRef: pipe(
+            rawRevokeMessage,
+            RevokeAssertionRefInfo.decode,
+            E.map(message => message.assertion_ref),
+            E.getOrElse(() => "unknown")
+          ),
           detail: err.kind,
           errorMessage: error,
           fatal: PermanentFailure.is(err).toString(),
@@ -177,7 +192,10 @@ export const handleRevoke = (
             context.executionContext.retryContext?.retryCount ?? "undefined"
           )
         },
-        tagOverrides: { samplingEnabled: "false" }
+        tagOverrides: {
+          samplingEnabled:
+            !isTransient || isLastRetry(context) ? "false" : "true"
+        }
       });
       context.log.error(error);
       if (isTransient) {