Why do I have to login to login.microsoftonline.com twice?

I just reread your response...

We appreciate your patience and understanding as we continue to balance user convenience with the need for strong protection. If you’d like, we can help check if any settings can be adjusted to improve your sign-in experience while still maintaining security.

You don't have my patience, nor my understanding. You are not balancing convenience with strong protection... at all. As another user has said, making me use my EXACT SAME LOGIN INFO on the EXACT SAME URL adds zero protection. All you are doing is making my experience more frustrating, more difficult, and more annoying, with no more protection for me.

Your suggestion is all about me taking more time and doing more work, to somehow work around your horrible design decision. THIS, THIS is what people hate about Microsoft. You make horrible decisions - decisions that make user's lives worse, not better. When people ask you to change them in order to make their lives better you respond exactly as you have - more work, more wasted time for the user. Nowhere in your response do I detect even a hint of actual EMPATHY...

We sincerely apologize for the inconvenience of having to log in twice. This experience is not ideal, and we truly understand how disruptive it can be to your workflow. 

That said, this additional authentication step is in place to help protect your sensitive information and minimize the risk of your account being accessed by unauthorized actors

Microsoft knows best. It is so far above us that we dare not question its choices. Microsoft certainly will not reconsider any of those choices. It's challenges are so vast and important that listening to us is not something we should expect or even deign to entertain. Ours is only to give - give our patience, give our understanding, give our time, more and more of our time.

I don't blame you, Hendrix-C, I blame Microsoft. Microsoft has worked very, very hard to earn its "Arrogant Bast***s" culture, and it has certainly earned it well over the past several decades. You are merely reinforcing that incredibly well earned culture.

The usual Microsoft response to user pain with Microsoft products = "you need to do more work because we can do no wrong."

1. Use a Single Browser Profile

• I am

1. Check with IT About Conditional Access

• I am the admin. I have done nothing and made no changes. I used to only have to log in once. Now, you have changed something that makes me log in twice. CHANGE IT BACK

1. Try Microsoft Edge

• No. You inflicted that piece of **** browser on us for so long, it's not even an option, and never will be.

1. Stay Signed In

• I always check "Keep me signed in". None of the above was even remotely helpful.

What has changed that now requires me to log in twice? Please change it back.

Protection? If someone else knows your information enough to sign in once, they also know it to sign in twice. This ridiculous pain-in-the-**** extra step does NOT protect people. In fact, whenever this happens, I fear that someone HAS hacked my computer and is requiring me to do it again, so they can monitor my password.

Not to mention, how many people actually NEED extra protection. I have never had anyone get into my accounts. The problem that is most prevalent, is spam emails that trick the account holder. NOT the step of accessing your account in the first place.

So, like the previous person wrote. STOP IT!

Hi Tim, 

Thank you for posting in the Microsoft Community.

Please understand that our initial response does not always resolve the issue immediately. However, with your help and more detailed information, we can work together to find a solution.

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Thank you very much for your understanding and your cooperation. 

Best Regards,  
Hendrix-C - MSFT | Microsoft Community Support Specialist

Hi Tim, 

Thank you for reaching out to Microsoft Community Support.  

We sincerely apologize for the inconvenience of having to log in twice. This experience is not ideal, and we truly understand how disruptive it can be to your workflow. 

That said, this additional authentication step is in place to help protect your sensitive information and minimize the risk of your account being accessed by unauthorized actors. It’s part of Microsoft’s layered approach to security, especially in environments where multiple apps or contexts are involved. 

We appreciate your patience and understanding as we continue to balance user convenience with the need for strong protection. If you’d like, we can help check if any settings can be adjusted to improve your sign-in experience while still maintaining security. 

Based on your requirements, there are a few methods you change it into try this work around to improve your sign-in experience while still maintaining security. Here are some possible solutions to fix this issue: 

1. Use a Single Browser Profile

• If you’re switching between profiles or containers (e.g., in Edge or Chrome), session tokens won’t carry over. Stick to one profile for all Microsoft 365 apps.

1. Check with IT About Conditional Access

• Ask your admin if there are policies requiring re-authentication between apps. They may be able to adjust session lifetimes or app trust levels.

1. Try Microsoft Edge

• Edge is optimized for Microsoft 365 and may handle token sharing more gracefully than other browsers.

1. Stay Signed In

• When prompted, always check “Keep me signed in” to extend your session and reduce repeated prompts.

Try these workarounds and let us know if it's helpful with your concern. Please don’t hesitate to reach out again if you need further assistance.      

Thank you very much for your understanding and your cooperation.    

Best Regards,  

Hendrix-C - MSFT | Microsoft Community Support Specialist