diff --git a/src/index.ts b/src/index.ts
index fd6a994..332ff7d 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -22,6 +22,7 @@ export {
   SmartTransactionMinedTx,
   SmartTransactionCancellationReason,
   SmartTransactionStatuses,
+  OriginalTransactionStatus,
   ClientId,
   Feature,
   Kind,
diff --git a/src/types.ts b/src/types.ts
index 43081b5..95abbfe 100644
--- a/src/types.ts
+++ b/src/types.ts
@@ -76,6 +76,29 @@ export enum ClientId {
   Extension = 'extension',
 }
 
+export enum OriginalTransactionStatus {
+  PENDING = 'PENDING',
+  PENDING_CANCELLED = 'PENDING_CANCELLED',
+
+  VALIDATED = 'VALIDATED',
+  REVERTED = 'REVERTED',
+  NONCE_TOO_LOW = 'NONCE_TOO_LOW',
+  CANCELLED = 'CANCELLED',
+
+  FAILED = 'FAILED',
+  FAILED_WOULD_REVERT = 'FAILED_WOULD_REVERT',
+  FAILED_INSUFFICIENT_FUNDS = 'FAILED_INSUFFICIENT_FUNDS',
+  FAILED_UNKNOWN = 'FAILED_UNKNOWN',
+  FAILED_TIMEOUT = 'FAILED_TIMEOUT',
+  FAILED_GAS_TOO_LOW = 'FAILED_GAS_TOO_LOW',
+  FAILED_NONCE_TOO_HIGH = 'FAILED_NONCE_TOO_HIGH',
+
+  LEAKED_VALIDATED = 'LEAKED_VALIDATED',
+  LEAKED_REVERTED = 'LEAKED_REVERTED',
+  CANCELLED_LEAKED_VALIDATED = 'CANCELLED_LEAKED_VALIDATED',
+  CANCELLED_LEAKED_REVERTED = 'CANCELLED_LEAKED_REVERTED',
+}
+
 export const cancellationReasonToStatusMap = {
   [SmartTransactionCancellationReason.WOULD_REVERT]:
     SmartTransactionStatuses.CANCELLED,
@@ -93,6 +116,7 @@ export type SmartTransactionsStatus = {
   error?: string;
   cancellationFeeWei: number;
   cancellationReason?: SmartTransactionCancellationReason;
+  originalTransactionStatus?: OriginalTransactionStatus;
   deadlineRatio: number;
   minedHash: string;
   minedTx: SmartTransactionMinedTx;
diff --git a/src/utils.test.ts b/src/utils.test.ts
index 04db634..8ad50b2 100644
--- a/src/utils.test.ts
+++ b/src/utils.test.ts
@@ -13,6 +13,7 @@ import {
   APIType,
   SmartTransactionStatuses,
   SmartTransactionCancellationReason,
+  OriginalTransactionStatus,
   ClientId,
 } from './types';
 import * as utils from './utils';
@@ -578,6 +579,41 @@ describe('src/utils.js', () => {
       );
     });
 
+    it('includes originalTransactionStatus in error message when available', () => {
+      const updateTransactionMock = jest.fn();
+      const smartTransaction = {
+        ...createSmartTransaction(SmartTransactionStatuses.CANCELLED),
+        statusMetadata: {
+          cancellationFeeWei: 0,
+          deadlineRatio: 0,
+          minedHash: '',
+          minedTx: SmartTransactionMinedTx.NOT_MINED,
+          isSettled: false,
+          originalTransactionStatus:
+            OriginalTransactionStatus.FAILED_WOULD_REVERT,
+        },
+      };
+
+      utils.markRegularTransactionsAsFailed({
+        smartTransaction,
+        getRegularTransactions: () => [mockTransaction],
+        updateTransaction: updateTransactionMock,
+      });
+
+      expect(updateTransactionMock).toHaveBeenCalledWith(
+        {
+          ...mockTransaction,
+          status: TransactionStatus.failed,
+          error: {
+            name: 'SmartTransactionFailed',
+            message:
+              'Smart transaction failed with status: cancelled, originalTransactionStatus: FAILED_WOULD_REVERT',
+          },
+        },
+        'Smart transaction status: cancelled',
+      );
+    });
+
     it('throws error if original transaction cannot be found', () => {
       const updateTransactionMock = jest.fn();
       const getRegularTransactionsMock = jest.fn(() => []);
@@ -665,4 +701,57 @@ describe('src/utils.js', () => {
       );
     });
   });
+
+  describe('getSmartTransactionMetricsProperties', () => {
+    it('includes stx_original_transaction_status from statusMetadata', () => {
+      const smartTransaction = {
+        uuid: 'test-uuid',
+        status: SmartTransactionStatuses.SUCCESS,
+        time: Date.now(),
+        statusMetadata: {
+          cancellationFeeWei: 0,
+          deadlineRatio: 0.5,
+          minedHash: '0xabc',
+          minedTx: SmartTransactionMinedTx.SUCCESS,
+          isSettled: true,
+          duplicated: false,
+          timedOut: false,
+          proxied: false,
+          originalTransactionStatus: OriginalTransactionStatus.VALIDATED,
+        },
+      };
+
+      const result =
+        utils.getSmartTransactionMetricsProperties(smartTransaction);
+
+      expect(result).toStrictEqual(
+        expect.objectContaining({
+          stx_original_transaction_status: OriginalTransactionStatus.VALIDATED,
+          stx_duplicated: false,
+          stx_timed_out: false,
+          stx_proxied: false,
+        }),
+      );
+    });
+
+    it('returns undefined for stx_original_transaction_status when not in statusMetadata', () => {
+      const smartTransaction = {
+        uuid: 'test-uuid',
+        status: SmartTransactionStatuses.PENDING,
+        time: Date.now(),
+        statusMetadata: {
+          cancellationFeeWei: 0,
+          deadlineRatio: 0,
+          minedHash: '',
+          minedTx: SmartTransactionMinedTx.NOT_MINED,
+          isSettled: false,
+        },
+      };
+
+      const result =
+        utils.getSmartTransactionMetricsProperties(smartTransaction);
+
+      expect(result.stx_original_transaction_status).toBeUndefined();
+    });
+  });
 });
diff --git a/src/utils.ts b/src/utils.ts
index d1d1bb6..92b4aee 100644
--- a/src/utils.ts
+++ b/src/utils.ts
@@ -213,6 +213,8 @@ export const getSmartTransactionMetricsProperties = (
     stx_duplicated: smartTransactionStatusMetadata?.duplicated,
     stx_timed_out: smartTransactionStatusMetadata?.timedOut,
     stx_proxied: smartTransactionStatusMetadata?.proxied,
+    stx_original_transaction_status:
+      smartTransactionStatusMetadata?.originalTransactionStatus,
   };
 };
 
@@ -275,7 +277,8 @@ export const markRegularTransactionsAsFailed = ({
   getRegularTransactions: TransactionControllerGetTransactionsAction['handler'];
   updateTransaction: TransactionControllerUpdateTransactionAction['handler'];
 }) => {
-  const { transactionId, status, txHashes } = smartTransaction;
+  const { transactionId, status, statusMetadata, txHashes } = smartTransaction;
+  const originalTransactionStatus = statusMetadata?.originalTransactionStatus;
 
   const transactionsToFail = getRegularTransactions().filter(
     (tx) => (tx.hash && txHashes?.includes(tx.hash)) || tx.id === transactionId,
@@ -285,6 +288,10 @@ export const markRegularTransactionsAsFailed = ({
     throw new Error('Cannot find regular transaction to mark it as failed');
   }
 
+  const errorMessage = originalTransactionStatus
+    ? `Smart transaction failed with status: ${status}, originalTransactionStatus: ${originalTransactionStatus}`
+    : `Smart transaction failed with status: ${status}`;
+
   for (const tx of transactionsToFail) {
     if (tx.status === TransactionStatus.failed) {
       continue; // Already marked as failed.
@@ -294,7 +301,7 @@ export const markRegularTransactionsAsFailed = ({
       status: TransactionStatus.failed,
       error: {
         name: 'SmartTransactionFailed',
-        message: `Smart transaction failed with status: ${status}`,
+        message: errorMessage,
       },
     };