diff --git a/extensions/sql-migration/src/constants/strings.ts b/extensions/sql-migration/src/constants/strings.ts
index bb3b971329..95cc07f7c3 100644
--- a/extensions/sql-migration/src/constants/strings.ts
+++ b/extensions/sql-migration/src/constants/strings.ts
@@ -796,6 +796,8 @@ export function VALIDATE_IR_VALIDATION_STATUS(state: string | undefined, errors?
 	}
 }
 
+export const VALIDATE_IR_ERROR_GATEWAY_TIMEOUT = localize('sql.migration.validate.error.gatewaytimeout', "A time-out was encountered while validating a resource connection. Learn more: https://aka.ms/dms-migrations-troubleshooting.");
+
 export function VALIDATE_IR_VALIDATION_STATUS_ERROR_COUNT(state: string | undefined, errorCount: number): string {
 	const status = state ?? '';
 	return errorCount > 1
diff --git a/extensions/sql-migration/src/dialog/validationResults/validateIrDialog.ts b/extensions/sql-migration/src/dialog/validationResults/validateIrDialog.ts
index 2e41152e39..126400f71d 100644
--- a/extensions/sql-migration/src/dialog/validationResults/validateIrDialog.ts
+++ b/extensions/sql-migration/src/dialog/validationResults/validateIrDialog.ts
@@ -11,9 +11,18 @@ import { MigrationStateModel, MigrationTargetType, NetworkShare, ValidateIrState
 import { EOL } from 'os';
 import { IconPathHelper } from '../../constants/iconPathHelper';
 import { getEncryptConnectionValue, getSourceConnectionProfile, getTrustServerCertificateValue } from '../../api/sqlUtils';
+import { logError, TelemetryViews } from '../../telemetry';
 
 const DialogName = 'ValidateIrDialog';
 
+enum HttpStatusCodes {
+	GatewayTimeout = "504\r\n",
+}
+
+enum HttpStatusExceptionCodes {
+	ConnectionTimeoutError = "ConnectionTimeoutError",
+}
+
 enum ValidationResultIndex {
 	message = 0,
 	icon = 1,
@@ -405,10 +414,12 @@ export class ValidateIrDialog {
 					return true;
 				}
 			} catch (error) {
+				const err = this._formatError(error);
+				logError(TelemetryViews.ValidIrDialog, err.message, error);
 				await this._updateValidateIrResults(
 					testNumber,
 					ValidateIrState.Failed,
-					[constants.VALIDATE_IR_VALIDATION_RESULT_API_ERROR(sourceDatabase, error)]);
+					[constants.VALIDATE_IR_VALIDATION_RESULT_API_ERROR(sourceDatabase, err)]);
 			}
 			return false;
 		};
@@ -447,6 +458,16 @@ export class ValidateIrDialog {
 		}
 	}
 
+	private _formatError(error: Error): Error {
+		if (error?.message?.startsWith(HttpStatusCodes.GatewayTimeout)) {
+			return {
+				name: HttpStatusExceptionCodes.ConnectionTimeoutError,
+				message: constants.VALIDATE_IR_ERROR_GATEWAY_TIMEOUT,
+			};
+		}
+		return error;
+	}
+
 	private async _validateSqlDbMigration(): Promise<void> {
 		const currentConnection = await getSourceConnectionProfile();
 		const sourceServerName = currentConnection?.serverName!;
@@ -464,8 +485,8 @@ export class ValidateIrDialog {
 			testSourceConnectivity: boolean,
 			testTargetConnectivity: boolean): Promise<boolean> => {
 
-			await this._updateValidateIrResults(testNumber, ValidateIrState.Running);
 			try {
+				await this._updateValidateIrResults(testNumber, ValidateIrState.Running);
 				const response = await validateIrSqlDatabaseMigrationSettings(
 					this._model,
 					sourceServerName,
@@ -488,10 +509,12 @@ export class ValidateIrDialog {
 					return true;
 				}
 			} catch (error) {
+				const err = this._formatError(error);
+				logError(TelemetryViews.ValidIrDialog, err.message, error);
 				await this._updateValidateIrResults(
 					testNumber,
 					ValidateIrState.Failed,
-					[constants.VALIDATE_IR_VALIDATION_RESULT_API_ERROR(sourceDatabase, error)]);
+					[constants.VALIDATE_IR_VALIDATION_RESULT_API_ERROR(sourceDatabase, err)]);
 			}
 			return false;
 		};
diff --git a/extensions/sql-migration/src/telemetry.ts b/extensions/sql-migration/src/telemetry.ts
index 41829136f5..7b8e60e686 100644
--- a/extensions/sql-migration/src/telemetry.ts
+++ b/extensions/sql-migration/src/telemetry.ts
@@ -43,6 +43,7 @@ export enum TelemetryViews {
 	LoginMigrationSelectorPage = 'LoginMigrationSelectorPage',
 	LoginMigrationStatusPage = 'LoginMigrationStatusPage',
 	TdeConfigurationDialog = 'TdeConfigurationDialog',
+	ValidIrDialog = 'validIrDialog',
 }
 
 export enum TelemetryAction {