Microsoft 365 Office Outlook sign in issues. Anyone here a tech who can give me a hand?

Hey all I use Micosoft Office 365 outlook email and calender to run my business across several devices and platforms.

I constantly have sign in issues. Microsoft will just sign you out and wont take your password. Then it will take the password on one device but not the next. At least once a week I burn a few hours dealing with this problem. To be honest I barely have free time anymore and I just don’t have time for this bull shit every week. I really hate microsoft and wouldn’t use anything they make if I didn’t have too.

Microsoft doesn’t have a number you can call to help you with anything and their online help site is useless.

I am hoping someone here can help me solve this problem or can put me in touch with someone who can. Any help would be appreciated.



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I can’t offer much help with the issue but we use it also for our business on laptop(s), tablet and phones with no issues. None of the devices are Apple products.

I’m so cheap I still use 2007


I use it on apple iPhone and iPad, Mac, Samsun Galaxy tablets and some Microsoft 11 based laptops.

It’s weird it will suddenly just ask for the password and won’t accept it. You reset it and it won’t take the new password. Or it takes the password on one device and not the other. Just odd

lol that made me laugh.

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It’s possible that you have a password for your Office (the apps) subscription and you have a different password for your Outlook subscription (the email provider). It’s easy to get turned around when you’re being prompted by Microsoft with similar login windows.

The new office 365 forces you to use the same Microsoft password for all apps under office 365 and outlook is one of those apps.

The problem seems to be associated with the calendar function. But that could be more coincidence

There are variations of Microsoft 365 that are Apps only.
So, if your subscription is for the whole office and mail is hosted onmicrosoft, then…

The only way to make sense of passwords not working is:
A. You’re providing the wrong credentials when you’re prompted.
B. The device is losing connectivity and it’s unable to authenticate against Microsoft’s servers.

Are you being prompted for credentials because you’re opening another user’s account for access to their calendar?

All my devices are linked to the same Microsoft office 365 account. They all use the same login. All devices save the password. All devices are used almost daily and everything will work fine for days.

Then for no reason Microsoft asks all device to authenticate and will no longer accept the password.

It sometime will accept on one or two devices but not all.

You’re forced to use the forgot password function and go through the steps multiple times on each device before it will work properly again. This process takes an hour plus to resolve each time. Then a few days to a week later it does it again.

Extremely frustrating

I have a well known 3rd party software that I need to perform my business.

This software uses outlook and calendar to sync appointments and manage sales across all devices.

I believe this software, calendar or outlook it’s self are some how corrupting the Microsoft authentication and then locking me out of office on all devices.

Just a guess but I can’t seem to solve this and I’m hoping someone has seen it and knows how to solve it.

Father in law had a similar problem not too long ago, though not sure it’s related.

This helped solve it …

I do not think this is the same problem.

I’m getting a Microsoft sign in. So my 365, Outlook and everything associated won’t work.

Basically Microsoft suddenly decides my password and login aren’t good anymore. But oddly it will accept it on some devices when the authentication is the same.

I get this… but it won’t accept the login credentials.

However this gives me some ideas on things I can check so thank you.

I just fixed the same issue with my iPhone toady. Got it set up on facial recognition now → takes a massive truckload of handsome to unlock my phone.

it was rejecting passwords and forcing me to create new…not remember…then repeat cycle.

I figured it was an apple software thing?

I think I may have solved it.

I had to sign out of every software that uses it. On every device. Reset the password and then sign back in. Hopefully this solves it. Seems to be working right now.

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