First, sign in to Hotmail through Outlook.com; the result will show whether the problem is with your Microsoft account/service or only Classic Outlook on this PC.
1. Test the mailbox online
- Close Classic Outlook.
- Open a web browser and go to Outlook.com.
- Select Sign in and use the same Hotmail address and password.
Hotmail now operates through Outlook.com, and its password is the same as the Microsoft account password.^1^
- If the mailbox opens online: Your account is working. Continue with the Classic Outlook repair below.
- If Outlook.com also keeps loading or says “Try again”: Check Microsoft’s service status. If the status is not green, wait until service is restored.^1^
- If the service is healthy but you cannot sign in online: Run Microsoft’s account sign-in helper. It covers password, blocked-account, and account-recovery problems.^2^
2. If web access works, repair the Outlook profile
In Classic Outlook:
- Select File.
- Select Account Settings → Account Settings.
- Open the Email tab.
- Select the Hotmail account and choose Repair.
- Complete the wizard, close Outlook, and open it again.
Microsoft documents profile repair for desktop Outlook connection failures.^3^
The Repair option is unavailable for Outlook 2016 accounts connected to Exchange. If the option is absent, use the troubleshooter below instead.
3. If Outlook still says “Try again”
On Windows 10 or later:
- Open the Windows Get Help app.
- In its search box, enter Outlook password problem.
- Run the Classic Outlook authentication check troubleshooter and apply its recommendations.
If it identifies no authentication problem, run the Classic Outlook connectivity troubleshooter. These tools must run on the same PC as Classic Outlook and do not apply to new Outlook.^4^
If none of these paths works, note whether Outlook.com opened successfully and copy the exact message shown by Get Help. That information distinguishes a local Outlook configuration issue from an account-side failure.
References
- How to sign in to Hotmail | Microsoft Support
- I can't sign in to my Microsoft account | Microsoft Support
- Fix your Outlook email connection by repairing your profile
- Classic Outlook troubleshooters | Microsoft Support