📎 AI Summary:
The thread centers on a user whose Outlook sign-in triggers a Windows Security “passkey” prompt every time, with no visible option to skip or reject passkey setup, leading them to ask how to stop Microsoft from forcing passkeys and whether they can reach a human support agent. The replies explain that passkeys are being pushed for phishing-resistant sign-in, then ask for/identify the prompt as Outlook’s Microsoft account sign-in flow (not Windows sign-in), and suggest fixes like disabling the Microsoft account “passwordless”/passkey settings and clearing Outlook sign-in credentials or rebuilding the Outlook profile. Sentiment is frustrated/annoyed from the original poster, while responders remain helpful and neutral, noting the issue is usually account/config/auth-caching related rather than a scam.
J

John Clark

Excellent Member
Joined
Sep 8, 2016
Messages
117
Thread Author #1
I turned on my computer for the second time today and got hit with M$ passkey brick wall asking to set up a passkey.
I need someone to point me in the correct direction to get rid of this BS. Why is M$ trying to shove this down my throat.
Does anyone have a way to contact a HUMAN at M$?
 

Solution
WindowsForum AI
Perfect — that screenshot shows exactly what’s causing your “passkey wall.”
You currently have a passkey registered to your Microsoft account:
  • Use a passkey → Google Password Manager
  • It has a Remove button (and it was used recently)
That’s why Outlook keeps trying to use passkey sign-in and you don’t get a normal “password” path.

Do this now​

1) Remove that passkey​

On the page you’re on (where you see Use a passkey → Google Password Manager):
  • Make sure you still have at least one other sign-in method available (you do: Text a code is listed).
  • Click Remove under the passkey entry.
  • Confirm the removal.

2) Restart and test Outlook​

  • Reboot...
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WindowsForum AI

WindowsForum AI

AI
Staff member
Robot
Joined
Mar 14, 2023
Messages
114,031
#41
Sounds good. After the reboot, try opening Outlook again.

What I expect​

  • If you removed the “Use a passkey → Google Password Manager” entry, Outlook should stop showing the Choose a passkey window and instead let you sign in with password and/or text code.

If it still pops the passkey window after reboot​

Reply with what happens (does it still only offer iPhone/Android device and Security key?), and we’ll do the next 2 fixes:
1) Create a new Outlook profile (often instantly fixes stuck auth):
  • Control Panel → Mail (Microsoft Outlook) → Show Profiles → Add
2) Clear the Windows sign-in broker (WAM) cache (last resort, but effective)
Post back with the result after reboot (worked / still prompts).
 

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WindowsForum AI

WindowsForum AI

AI
Staff member
Robot
Joined
Mar 14, 2023
Messages
114,031
#43
Great news, John — that confirms the root cause was the Microsoft account passkey registered via Google Password Manager. Once that passkey was removed, Outlook stopped forcing the “Choose a passkey” Windows Security flow and could fall back to normal sign-in methods.

To keep it from coming back​

  • Don’t add a passkey again if Microsoft prompts you in the browser.
  • If you use Chrome/Google Password Manager, be cautious with any “Create/Save passkey” prompts for your Microsoft account—adding one there can re-trigger the same behavior in Outlook.
  • Keep at least two recovery/sign-in methods on the account (password + text/email code), and optionally leave Receive alerts = ON for the phone/email you trust (good for account security).
If the prompt ever returns, reply here—usually a quick check of the Microsoft account “Use a passkey” list (and removing any new one) fixes it immediately.
 

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Popcorn8892

Popcorn8892

Active Member
Joined
Sep 2, 2025
Messages
11
#44
Wow, you followed the bot's advice to a good conclusion. You are incredibly patient. I found the bot's answers completely overwhelming and would have turned off some messages ago.
 

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WindowsForum AI

WindowsForum AI

AI
Staff member
Robot
Joined
Mar 14, 2023
Messages
114,031
#45
That’s a fair reaction—and it’s also why asking for a screenshot was the key move: once the screenshot showed the Microsoft account had an actual passkey registered (“Use a passkey → Google Password Manager”), the “why is Outlook forcing this?” question basically answered itself, and the fix became a single clear action: remove that passkey.
If you ever want to keep an assistant from getting “overly technical,” the best tactic is to constrain it up front, e.g.:
  • “Give me the shortest fix in 3 steps.”
  • “No explanations—click-path only.”
  • “Ask me one question at a time.”
If you want, paste what you plan to reply in the thread and I’ll rewrite it into a short, calm, human-sounding response for John (without the wall-of-text).
 

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J

John Clark

Excellent Member
Joined
Sep 8, 2016
Messages
117
Thread Author #46
Popcorn8892 said:
Wow, you followed the bot's advice to a good conclusion. You are incredibly patient. I found the bot's answers completely overwhelming and would have turned off some messages ago.
Click to expand...
I had to stick with chat, because the links that it gave me to chat with someone at M$ did not have any of those options. My past 2 experiences with chat were not that successful. First one I gave up on after 2 days and went to the web and found a video that helped me solve the problem with just 3 or 4 setting changes. The second experience was a disaster. I was taken down a deep rabbit hole on trying to fix an Outlook problem on my WIN 10 desktop, and ended up with a totally broken Outlook and not able to fix. Happy camper that this worked out.
 

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