diff --git a/extensions/azurecore/src/account-provider/auths/azureAuth.ts b/extensions/azurecore/src/account-provider/auths/azureAuth.ts
index 4464c05658..eab7ec53f7 100644
--- a/extensions/azurecore/src/account-provider/auths/azureAuth.ts
+++ b/extensions/azurecore/src/account-provider/auths/azureAuth.ts
@@ -145,14 +145,21 @@ export abstract class AzureAuth implements vscode.Disposable {
 					Logger.error(ex.originalMessageAndException);
 				}
 			} else {
+				const message = ex.errorMessage || ex.message;
+				if (message) {
+					loginComplete?.reject(new AzureAuthError(message, message, undefined));
+					return {
+						canceled: false,
+						errorCode: ex.errorCode,
+						errorMessage: message
+					};
+				}
 				Logger.error(ex);
 
 			}
 			return {
 				canceled: false
 			};
-		} finally {
-			loginComplete?.reject(new AzureAuthError(localize('azureAuth.unidentifiedError', "Unidentified error with azure authentication"), 'Unidentified error with azure auth', undefined));
 		}
 	}
 
diff --git a/src/sql/azdata.proposed.d.ts b/src/sql/azdata.proposed.d.ts
index 6b33307645..041459f793 100644
--- a/src/sql/azdata.proposed.d.ts
+++ b/src/sql/azdata.proposed.d.ts
@@ -432,6 +432,18 @@ declare module 'azdata' {
 		azurePortalEndpoint?: string;
 	}
 
+	export interface PromptFailedResult {
+		/**
+		 * Error code used for non-user cancelled sign in errors
+		 */
+		errorCode?: string;
+
+		/**
+		 * Error message used for non-user cancelled sign in errors
+		 */
+		errorMessage?: string;
+	}
+
 	export namespace diagnostics {
 		/**
 		 * Represents a diagnostics provider of accounts.
diff --git a/src/sql/workbench/services/accountManagement/browser/accountManagementService.ts b/src/sql/workbench/services/accountManagement/browser/accountManagementService.ts
index 70ec8c7c0b..ce9a024352 100644
--- a/src/sql/workbench/services/accountManagement/browser/accountManagementService.ts
+++ b/src/sql/workbench/services/accountManagement/browser/accountManagementService.ts
@@ -143,15 +143,18 @@ export class AccountManagementService implements IAccountManagementService {
 		return this.doWithProvider(providerId, async (provider) => {
 			const notificationHandler = this._notificationService.notify(loginNotification);
 			try {
-				let account = await provider.provider.prompt();
-				if (this.isCanceledResult(account)) {
-					return;
+				let accountResult = await provider.provider.prompt();
+				if (!this.isAccountResult(accountResult)) {
+					if (accountResult.canceled === true) {
+						return;
+					} else {
+						throw new Error(localize('addAccountFailedMessage', `${0} \nError Message: ${1}`, accountResult.errorCode, accountResult.errorMessage));
+					}
 				}
-
-				let result = await this._accountStore.addOrUpdate(account);
+				let result = await this._accountStore.addOrUpdate(accountResult);
 				if (!result) {
 					this._logService.error('adding account failed');
-					throw Error('Adding account failed, check Azure Accounts log for more info.')
+					throw new Error(localize('addAccountFailedGeneric', 'Adding account failed, check Azure Accounts log for more info.'));
 				}
 				if (result.accountAdded) {
 					// Add the account to the list
@@ -190,8 +193,8 @@ export class AccountManagementService implements IAccountManagementService {
 		});
 	}
 
-	private isCanceledResult(result: azdata.Account | azdata.PromptFailedResult): result is azdata.PromptFailedResult {
-		return (<azdata.PromptFailedResult>result).canceled;
+	private isAccountResult(result: azdata.Account | azdata.PromptFailedResult): result is azdata.Account {
+		return typeof (<azdata.Account>result).displayInfo === 'object';
 	}
 
 	/**
@@ -200,23 +203,25 @@ export class AccountManagementService implements IAccountManagementService {
 	 * @return Promise to return an account
 	 */
 	public refreshAccount(account: azdata.Account): Promise<azdata.Account> {
-		let self = this;
-
 		return this.doWithProvider(account.key.providerId, async (provider) => {
 			let refreshedAccount = await provider.provider.refresh(account);
-			if (self.isCanceledResult(refreshedAccount)) {
-				// Pattern here is to throw if this fails. Handled upstream.
-				throw new Error(localize('refreshFailed', "Refresh account was canceled by the user"));
+			if (!this.isAccountResult(refreshedAccount)) {
+				if (refreshedAccount.canceled) {
+					// Pattern here is to throw if this fails. Handled upstream.
+					throw new Error(localize('refreshCanceled', "Refresh account was canceled by the user"));
+				} else {
+					throw new Error(localize('refreshFailed', `${0} \nError Message: ${1}`, refreshedAccount.errorCode, refreshedAccount.errorMessage));
+				}
 			} else {
 				account = refreshedAccount;
 			}
 
-			let result = await self._accountStore.addOrUpdate(account);
+			let result = await this._accountStore.addOrUpdate(account);
 			if (result.accountAdded) {
 				// Double check that there isn't a matching account
 				let indexToRemove = this.findAccountIndex(provider.accounts, result.changedAccount);
 				if (indexToRemove >= 0) {
-					self._accountStore.remove(provider.accounts[indexToRemove].key);
+					this._accountStore.remove(provider.accounts[indexToRemove].key);
 					provider.accounts.splice(indexToRemove, 1);
 				}
 				// Add the account to the list
@@ -232,7 +237,7 @@ export class AccountManagementService implements IAccountManagementService {
 				}
 			}
 
-			self.fireAccountListUpdate(provider, result.accountAdded);
+			this.fireAccountListUpdate(provider, result.accountAdded);
 			return result.changedAccount!;
 		});
 	}