Windows 11 Passkey and outlook

J

John Clark

Extraordinary Member
Joined
Sep 8, 2016
Messages
101
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
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):
  1. Make sure you still have at least one other sign-in method available (you do: Text a code is listed).
  2. Click Remove under the passkey entry.
  3. Confirm the removal.

2) Restart and test Outlook​

  1. Reboot...
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Yes — if you’re already signed into your @live.com mailbox in a browser, you can use that signed-in session to open the Microsoft Account security page in a new tab and remove the passkey/security key from there.

Remove a passkey / security key (personal Microsoft account)​

Method 1 (direct link — easiest)​

While you’re signed in, click this link (it will open a new tab):
[url unfurl="true"]https://account.live.com/proofs/manage[/url]
  1. On that page, look for a section such as Advanced security options / Security info / Ways to prove who you are.
  2. Find entries named Passkey and/or Security key.
  3. Click the entry → choose Remove (or Delete).
  4. Confirm.
Important: Before you remove anything, make sure you still have at least one other recovery/sign-in method listed (phone number, alternate email, Microsoft Authenticator). Don’t remove your last method.

Method 2 (go through “My Microsoft account” from your email)​

  1. In Outlook.com (your email), click your profile icon (top-right).
  2. Click My Microsoft account (or View account).
  3. Go to Security → then Advanced security options.
  4. Look for Passkey/Security key and remove it.

If you don’t see any passkey/security key listed​

Tell me what you do see on proofs/manage (just the headings like “phone number”, “email”, etc.). If there’s no passkey to remove, then Outlook is being forced into the passkey flow for a different reason (often Windows/Outlook account broker/WAM), and we’ll switch to the next fix.
If you want, paste a screenshot of that proofs/manage page (blur email/phone details) and I’ll point to the exact item to remove.
 
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When I use "url unfurl="true"]https://account.live.com/proofs/manage[/url" I get a web page of Items an have to log in again?
 
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Yes — that’s normal.
Even if you’re already signed into Outlook.com in the browser, when you go to:
[url unfurl="true"]https://account.live.com/proofs/manage[/url]
Microsoft often makes you sign in again (or “confirm it’s really you”) because you’re entering security-sensitive settings (sign-in methods, recovery info, etc.). That extra login is expected.
The key is: when it asks you to sign in again, you must switch that sign-in prompt away from “passkey”.

Do this (in the SAME browser window where your email is already open)​

Method 1 (best): Go through “My Microsoft account” from Outlook.com​

  1. While you’re in your mailbox at Outlook.com, click your profile icon (top-right).
  2. Click My Microsoft account / View account.
  3. Go to Security.
  4. Look for Advanced security options or Security info.
  5. Find Passkey / Security key entries and Remove them.
This route is less likely to throw you onto the wrong sign-in flow.

Method 2: Use the direct link, but switch sign-in method​

  1. Open:
    [Sign in to your Microsoft account](https://account.live.com/proofs/manage)
  2. If it asks you to sign in and immediately pops the “Choose a passkey” window:
    • Click Cancel
    • On the previous Microsoft sign-in screen, look for Sign-in options / Other ways to sign in
    • Choose Password (or Email a code / Text a code)
If you never see “Sign-in options” and it only offers passkey, then your account is effectively being forced to passkey at that moment—at that point the quickest exit is usually a password reset (which re-enables password sign-in cleanly):
[url unfurl="true"]https://account.live.com/password/reset[/url]

After you remove passkeys/security keys​

Then we’ll stop Outlook (desktop) from reusing the stuck method:
  1. Settings → Accounts → Email & accounts
  2. Under Accounts used by other apps, remove the Microsoft account (if listed)
  3. Reboot
  4. Start Outlook and sign in again

Quick question​

When you try to sign in on account.live.com/proofs/manage, do you see any “Sign-in options” link after you hit Cancel on the passkey prompt—yes or no?
That one detail determines whether we can switch to password immediately, or if we need to go straight to password reset/account recovery.
 
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when I sign in i get the message I can't use a personal account. But still in private window.

Also your recommendation to chat with with a human doesn't work. there is no option to chat/callback.
 
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The “you can’t use a personal account” message is the giveaway here: you’re being sent to a work/school (Microsoft Entra) sign-in page, not the personal Microsoft account system your @live.com uses. That’s why it refuses your personal account and why you can’t get to the page where passkeys/security keys are managed.

1) We need to confirm the redirect (1 minute)​

When you get that “can’t use a personal account” page, copy the address from the browser’s address bar and paste just the beginning (you can truncate it after the domain).
  • If it starts with mysignins.microsoft.com or login.microsoftonline.com → that’s work/school sign-in (wrong system for @live.com).
  • For your personal account, you should be on account.live.com / login.live.com / account.microsoft.com.

2) Force a clean personal-account session (do exactly in this order)​

  • Open Edge InPrivate (Ctrl+Shift+N).
  • In that InPrivate window, open this sign-out link:
    [url="https://login.live.com/logout.srf"]Continue[/url]
  • Then manually type (don’t copy forum link text) this into the address bar:
    [url="https://account.live.com/proofs/manage"]Sign in to your Microsoft account[/url]
If step 3 still throws you to a work/school-only page, tell me the exact domain it redirects to (Step 1). At that point the problem is “wrong login endpoint,” not your account settings.

3) About Microsoft “chat/callback” not showing​

Unfortunately, for personal Microsoft account issues, Microsoft often only offers the “sign-in helper / self-help” flow, and live chat/callback options appear only for certain categories/accounts (and can vary by time/region). The official Contact Us page explicitly says it will show self-help first and “additional help” only if available.
For Microsoft-account sign-in problems, Microsoft’s official path is their account help + “Can’t sign in” helper.
Do not call random phone numbers from blogs—a lot of them are scams impersonating Microsoft support.

4) While we’re fixing access: quickest way to get Outlook running (workaround)​

If you just need mail immediately while we sort the passkey loop:
  • Use Outlook on the web (you’re already able to get into your email), or
  • Use a different mail client temporarily.
Then we’ll correct the Outlook desktop sign-in method once we can reach the correct personal security page.

Two questions so I can lock onto the exact fix​

1) When it says you can’t use a personal account, what domain is in the address bar (e.g., mysignins.microsoft.com vs account.live.com)?
2) Are you using Classic Outlook (Office 2021 desktop Outlook) or the New Outlook for Windows?
Reply with those and I’ll give the exact next steps for your specific redirect/Outlook version.
 
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That URL you pasted is the smoking gun:
login.microsoftonline.com/... redirect_uri=[My Account](https://myaccount.microsoft.com/)
That is Microsoft’s work/school (Entra ID) sign-in system, and myaccount.microsoft.com is the “My Account” portal for work or school accounts—so it will reject a personal @live.com account.
What we need is to get you back onto the personal Microsoft account security pages (the ones that live at account.live.com) so you can remove the passkey/security key.

1) Remove any Work/School account hooks from Windows (this often causes the redirect)​

On your PC:
  1. Settings → Accounts → Access work or school
    • If you see anything connected (work/school account, “Connected to…”, “Enroll only in device management”), Disconnect it.
  2. Settings → Accounts → Email & accounts
    • Under Accounts used by other apps, remove any work/school account entries.
Reboot after doing this.
Why: Windows/Office can “helpfully” steer sign-ins into the work/school broker (microsoftonline.com), which then blocks personal accounts.

2) Use the correct personal-account passkey removal page (and don’t use myaccount.microsoft.com)​

After reboot, open Edge InPrivate and go directly to:
[url unfurl="true"]https://account.live.com/proofs/manage[/url]
Microsoft’s own instructions for removing a passkey for a personal Microsoft account are exactly on that page: sign in there → under “Ways to prove who you are” select the passkey → Remove.

If it still tries to force a passkey while signing in​

On the sign-in prompt, look for “Sign-in options” / “Other ways to sign in” and choose Password or Email/SMS code instead of passkey. Microsoft documents that “Sign-in options / Other ways to sign in” is how you switch methods.
If you never get any option except passkey, the fastest way to restore password sign-in is to do a password reset, then try again.

3) After passkey is removed, fix Outlook so it stops looping​

  1. Close Outlook.
  2. Control Panel → Mail (Microsoft Outlook) → Show Profiles → Add
  3. Create a new profile and add the @live.com account again.
(Once the account itself is no longer advertising/forcing passkey, Outlook usually returns to password + verification code.)

4) About “chat/callback”: why you’re not seeing it​

For Microsoft personal account sign-in/security issues, Microsoft often routes you to the sign-in helper first, and “Contact Support” options may only appear in some cases. Microsoft states this directly on their passkey support page (it points to the sign-in helper tool and then “Contact Support” if available).

One question (so I can give the exact next move)​

After you disconnect anything under Access work or school and reboot, when you open:
[Sign in to your Microsoft account](https://account.live.com/proofs/manage)
does the address bar stay on account.live.com, or does it still jump to login.microsoftonline.com?
If it still jumps, tell me what (if anything) is listed under Settings → Accounts → Access work or school right now (just the headings—no personal info).
 
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Ignore
 
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If you’re on Windows 11 Pro, Settings absolutely has an “Accounts” section—so what’s happening is almost always one of these:
  • you’re not in the Windows 11 Settings app (you’re in Control Panel), or
  • the left navigation is collapsed/hidden because the window is narrow, or
  • you’re being blocked by a policy/corrupted Settings page (less common).

1) Open the exact Accounts pages directly (bypasses the menus)​

Do this:
  1. Press Win + R
  2. Paste each line below one at a time and press Enter:
ms-settings:yourinfo
ms-settings:emailandaccounts
ms-settings:workplace
ms-settings:signinoptions
These open the same pages as Settings → Accounts → (Your info / Email & accounts / Access work or school / Sign-in options) without you needing to find “Accounts” in the menu.
What I need you to check:
  • On ms-settings:workplace (Access work or school): do you see anything listed as connected? If yes, disconnect it.
  • On ms-settings:emailandaccounts (Email & accounts): under Accounts used by other apps, is your Microsoft account listed? If yes, remove it.
Then reboot and try Outlook again.

2) If those Run commands don’t open anything (or say the app can’t open)​

That indicates the Settings app/URI handlers are broken or restricted. Tell me exactly what happens when you run ms-settings:workplace (error message or nothing).

3) Quick sanity check: make sure you’re in the real Settings app​

Press Win + I (that is guaranteed to open Settings).
  • If you don’t see the left navigation, maximize the Settings window, or look for the three-line (hamburger) menu at top-left and click it.
  • In the Settings search box, type work or school and click Access work or school from results.

4) Why we’re doing this​

Your earlier link shows you’re being routed to login.microsoftonline.com → myaccount.microsoft.com, which is work/school sign-in, not personal @live.com. Disconnecting anything under Access work or school and removing “accounts used by other apps” often stops Windows/Office from forcing that work/school sign-in broker and lets Outlook use the normal personal Microsoft sign-in again.

Two questions (so I can pick the next exact step)​

1) What happens when you run: ms-settings:workplace (does it open? what does it show?)
2) Are you using Classic Outlook 2021 (the desktop Outlook that comes with Office 2021), or New Outlook?
Reply with those and we’ll get you out of the passkey loop without setting up a passkey.
 
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Do not have anything listed in Work & School account.
Do not have option "Email & accounts" or "Accounts used by other apps" under Account .
 
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You’re not crazy—what you’re seeing is Outlook/Windows picking passkey (WebAuthn) as the only sign-in method, and your browser getting shoved to the work/school sign-in system (login.microsoftonline.com), which will always reject a @live.com account. The easiest way out is to reset the Windows “broker” sign-in cache that Outlook uses, and (if possible) remove any passkey/security key from the personal Microsoft account once you can reach the right page.
Below is the “get Outlook working again” path that doesn’t require you to set up a passkey.

1) Open the missing Windows pages directly (bypasses the Settings menu)​

Even if you can’t see “Email & accounts” in Settings, these pages can be opened directly.
  1. Press Win + R
  2. Run these one at a time:
ms-settings:emailandaccounts
ms-settings:workplace
ms-settings:signinoptions
If ms-settings:emailandaccounts opens, look for Accounts used by other apps (or similar wording) and remove your Microsoft account entry (if present), then reboot.
If these commands do not open or error out, tell me the exact message you get—then we’ll repair the Settings app/URI handler.

2) Reset the Windows sign-in broker cache (this is the big hammer that often fixes the passkey loop)​

This does not delete mail. It will sign you out of Microsoft apps and make them ask you to sign in again.
  1. Close Outlook and all Office apps.
  2. Open Task Manager and end tasks for:
    • Outlook.exe
    • anything named Microsoft AAD / Broker / Account if you see it
  3. Delete (or rename) these folders:
A) AAD Broker token cache
%LOCALAPPDATA%\Packages\Microsoft.AAD.BrokerPlugin_cw5n1h2txyewy\AC\TokenBroker
B) OneAuth + Identity cache
Code: 
%LOCALAPPDATA%\Microsoft\OneAuth
%LOCALAPPDATA%\Microsoft\IdentityCache
  1. Reboot
  2. Launch Outlook and try signing in again.
Why this helps: Outlook uses the Windows “broker” to sign in. If that broker gets stuck preferring passkey-only, clearing these caches often restores normal “password / code” sign-in options.

3) Make sure you’re using the personal Microsoft security page (not work/school)​

This matters because you previously pasted a login.microsoftonline.com URL (work/school). For a @live.com account you want the live.com security site.
Open this in Edge InPrivate:
[url unfurl="true"]https://login.live.com/logout.srf[/url]
Then open:
[url unfurl="true"]https://account.live.com/proofs/manage[/url]
If it still kicks you to login.microsoftonline.com, paste the new redirected URL again (just like you did before). That redirect usually means something on the PC/session is forcing the work/school identity system.

4) Tell me one detail so I can give the exact next step​

Are you using Classic Outlook 2021 (the traditional desktop Outlook) or the New Outlook app?
  • If it’s New Outlook, there’s an additional cache location (WebView2) that can be cleared.
  • If it’s Classic Outlook 2021, the broker-cache reset above is usually the right move.

What I’d do next​

Please try Step 2 (broker cache reset) first and report what changes—specifically whether Outlook now shows any “Sign-in options” besides passkey. If it still insists on passkey-only after the reboot, we’ll switch to a workaround to get mail working (Outlook on the web / alternate client) while we untangle the account-side passkey registration.
 
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OK I'm into Security and it has a listing "email" etc.
There is a listing for "Use Passkey" "google Password manager" see picture
 

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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):
  1. Make sure you still have at least one other sign-in method available (you do: Text a code is listed).
  2. Click Remove under the passkey entry.
  3. Confirm the removal.

2) Restart and test Outlook​

  1. Reboot the PC (or at minimum fully close Outlook and any “Microsoft sign-in” windows).
  2. Open Outlook again.
  3. It should stop forcing the “Choose a passkey” window and fall back to password/code.

If Outlook still tries to use passkey after removal (cache stuck)​

Do these cleanup steps:

A) Remove cached sign-in tokens by creating a new Outlook profile​

  1. Close Outlook
  2. Control Panel → Mail (Microsoft Outlook)
  3. Show Profiles → Add
  4. Create a new profile and add your @live.com account
  5. Open Outlook using the new profile

B) (Optional) Clear the Windows sign-in broker cache (WAM)​

If it still loops, tell me and I’ll walk you through the exact folders to clear (it’s safe, but it signs Microsoft apps out).

Important note​

Removing the passkey from your Microsoft account does not remove your ability to sign in; it simply removes that passkey method. Since you have “Text a code” and likely a password, you’re covered.
After you click Remove, reply back and tell me:
  • Does Outlook open normally, or does it still pop the passkey prompt?
 
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Solution
Under text a code, is "Receve alerts" on or off
 
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“Receive alerts” under Text a code is basically “use this phone/email method for security notifications / verification prompts.” It’s not the passkey itself, and it won’t cause the passkey pop‑up in Outlook.

What you should set it to​

  • If you want Microsoft to be able to send you verification/security notices at that number/address, leave Receive alerts = ON.
  • If you don’t want Microsoft sending alerts there, set it OFF.
Either way, you can still use “Text a code” for sign-in verification as long as the method remains listed.

What matters for your Outlook problem​

The key action is still:
  • Remove the “Use a passkey → Google Password Manager” entry.
After you remove the passkey:
  1. Reboot (or fully close Outlook + sign-in windows)
  2. Open Outlook and confirm the passkey prompt is gone.
If you remove the passkey and Outlook still asks, tell me and we’ll clear the Outlook/WAM sign-in cache.
 
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Re booting lets see if it works
 
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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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