The biggest problem that I see with Microsoft 365 login is that the user has gotten confused as to what password they should be using. Maybe they have a corporate login for Microsoft 365. But it says Microsoft account when the login screen comes up, so they enter their personal login. Then they go back and forth entering corporate in the personal spaces and personal in the corporate spaces hoping for the best. At some point they give up and change their password. In this article I’m going to highlight some of the scenarios that cause login issues and offer a few solutions and troubleshooting tips.

Microsoft 365 troubleshooters

I enter my email--the same one I used for this account, and it just kicks me back to the previous "sign in to get started with Word" box! I have tried signing in with a different email, in case that was somehow the issue. I have tried entering my phone number, zilch. No matter what I do, I just go in circles with those two sign in boxes. Microsoft 365 is a vital tool for many businesses, and login issues can significantly disrupt day-to-day operations.

Understanding The Root Causes Of Microsoft 365 Login Issues

Some older operating systems, such as Windows 7 SP1, Windows Server 2008 R2, and Windows Server 2012, require an update to enable TLS 1.2 by default. This article will help you troubleshoot sign in issues when activating Microsoft 365 Apps. After you run any troubleshooter, Get Help provides details on any findings and suggestions for possible remedies. If one of these resolves your problem, close the app and continue working.

Recover your account

I have encountered some people who have constant problems logging into Microsoft/Office 365. Most often it’s been a user misunderstanding, which means they enter panic mode and start clicking and resetting passwords in a desperate attempt to get the prompts to go away. No one should have to go through that type of frustration and aggravation.

Sign in issues when activating Microsoft 365 Apps

• It will analyze every function of your Office 365 environment and make the necessary changes to get things working again.
• I open word, the pop up with "Sign in to get started with Word" opens.
• You can also allow Microsoft 365 to bypass the proxy server by creating a PAC file.
• Many IT people then created an app password for Outlook to use.
• For more information, see End of support resources for Office.
• Each firewall will have a different method to enable access to these URIs.

For a long time, Outlook required an app password because it didn’t understand multi-factor authentication. Those days are long gone but if you Outlook not syncing emails were an early adopter of Microsoft/Office 365 then Outlook might not be enabled for modern authentication. Which means that after you’ve enabled MFA, Outlook will start repeatedly prompting for credentials. Many IT people then created an app password for Outlook to use.

Microsoft 365 uninstall troubleshooter

When you launch the tool you’ll be asked to pick the issue that applies most closely to what you are experiencing. Because this tool is very thorough expect it to take minutes to run, sometimes even longer. It’s possible that login prompts are an indication of corruption in the application. Gone are the days where this is an hours-long process. The solution to this is to train the users to glance at this bottom right corner of Outlook from time to time.



Use the MIcrosoft 365 inventory scan troubleshooter to generate either a normal or full scan report of your computer and installed Microsoft 365 applications. To do this, open Credential Manager from Control Panel by just typing the word Credential after hitting the Windows key. Notice everything that references Microsoft online, and all those "msteams" items, too. If you’d like to chat with us about how MS 365 can benefit your business, get in touch.