The Additional Details provides more details and often tells you how to resolve the issue. For iPhone users, reinstalling Outlook or updating to the latest iOS often resolves stuck sign-in loops instantly. Many users have both personal Microsoft accounts (e.g., Outlook.com) and work/school Office 365 accounts. If both are signed in simultaneously, the system can confuse the authentication path. Log out of all accounts and sign in with only one — preferably the one with your Office 365 subscription.

Stay Updated

A developer console is a feature of most browsers that can be used to inspect and modify the code and elements of a website. To access it, open your browser and go to the website you are trying to log in to, then right-click on the login page and select inspect or inspect element. This step-by-step guide walks you through proven fixes for Outlook with Microsoft 365, Exchange, IMAP/POP, and hybrid accounts so you can sign in once and stay signed in.

• Stale cached credentials are the #1 reason for looping prompts.
• In this guide, you learn how to isolate a sign-in failure in the sign-ins report, and use it to understand the root cause of the failure.
• Incorrect mail servers or ports will force Outlook to ask for credentials repeatedly.
• A developer console is a feature of most browsers that can be used to inspect and modify the code and elements of a website.

Fix 3 — Repair or Recreate the Outlook Profile

Incorrect system time can break your connection to Microsoft’s authentication servers. Always enable Set time automatically and select the correct region in your Windows settings. If your clock is even a few minutes off, login may fail. In addition, the sign-in logs can also help you troubleshoot sign-in failures for users in your organization. In this guide, you learn how to isolate a sign-in failure in the sign-ins report, and use it to understand the root cause of the failure. Our certified tech specialists listen, diagnose, and resolve your issues quickly, whether it’s a device, software, or security problem.

Customer Support

If your Office 365 login keeps failing, showing a blank screen, or getting stuck on "signing in," don’t worry — this is one of the most common Microsoft 365 issues users face in 2025. The problem usually occurs due to authentication token mismatches, cached credentials, or browser session conflicts. In this guide, we’ll walk you through every step to fix Office 365 login problems on both Windows and the web version. If none of the above steps work, you may need to use a more advanced troubleshooting tool to diagnose and fix the login issue.

Fix 5 — Delete Cached Tokens & Re-Authenticate

Fix issues with Windows, browsers, email, and other essential tools. Incorrect mail servers or ports will force Outlook to ask for credentials repeatedly. Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support. If your admin enabled Modern Authentication mailbox not updating on IMAP (MFA), try disabling it temporarily via Azure Active Directory → Properties. Alternatively, generate an app-specific password if using Outlook 2016 or older. Tell us the issue, no long waits, no tech jargon.

However, with some basic troubleshooting skills, you can quickly identify and resolve the most common causes of login problems. In this article, we will cover the most effective ways to troubleshoot a login issue, from checking the basics to using advanced tools. Sometimes, the problem may not be with your browser or system, but with diagnose Office activation conflicts your network or device.

This resets your authentication cache and forces a fresh token request.

Outlook Keeps Asking for Password? Fix Persistent Prompts (2025 Guide)

On managed devices, broken work account tokens cause Outlook loops. If all else fails, or the issue persists despite taking the recommended course of action, open a support request. For more information, see how to get support for Microsoft Entra ID. If you need more specifics to research, you can use the sign-in error code for further research. If you need to reset your Microsoft account password because you forgot it, see Reset your Microsoft account password instead.



For example, some networks may have firewalls or proxies that block certain websites or features, or some devices may have hardware or software issues that affect your login process. To rule out these possibilities, try using a different network or device to log in to the website. For example, you can try using your mobile data instead of your Wi-Fi, or using your smartphone instead of your laptop.





Another potential cause of login issues is that your browser or system may be outdated or incompatible with the website you are trying to access. To address this issue, updating your browser and system can help fix any bugs, improve Fix Outlook and Office 365 Errors 2025 your security, and enhance your compatibility. To do so, open your browser and go to the help or about menu to check if there is an update available and install it. Then, open your system settings and go to the update or security menu to check if there are any updates available. Install them if necessary and restart both your browser and system. Login issues can be frustrating and time-consuming for both customers and customer support agents.