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Keychain not found alert after OneDrive Desktop and Documents sync enforced

  • March 25, 2026
  • 7 replies
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howie_isaacks
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I am seeing a Keychain not found alert after I recently started enforcing OneDrive Desktop and Documents sync. This just happened on my newly enrolled test Mac after I registered platform single sign-on. The alert appeared as I was logging in to OneDrive. There is actually an entry in Keychain. I looked up the ID shown in the screenshot. Reset to Defaults is NOT the right choice. I found that unlinking the Mac from OneDrive and then signing in again helps, but this prompt came up as I was in the process of logging in. We use platform single sign-on so there is no password prompt. Has anyone else seen this and solved it?

 

Best answer by angelohuang

One other angle that’s bitten us with PSSO/password changes is the login keychain password not matching the current user password (which can trigger weird “keychain not found”/unlock prompts during first token writes).

 

If you want a quick checklist, this walks through the “why” + the clean fixes (change login keychain password vs create a new login keychain): [Change your keychain password to match with your login password](https://help.swif.ai/en/articles/8578787-change-your-keychain-password-to-match-with-your-login-password)

 

In practice: get the login keychain into a known-good state *before* the first OneDrive sign-in after enabling KFM/PSSO, then test again.

    7 replies

    A
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    • angelohuang
    • New Contributor
    • March 26, 2026

    I’ve seen similar “keychain not found” / keychain-item prompts pop up right after enabling passwordless-ish flows (Platform SSO + app sign-in) where the user’s login keychain ends up out of sync / partially initialized.

     

    Two quick things I’d try on a test Mac:

    1) Open Keychain Access → select the login keychain → run “Change Password for Keychain ‘login’…” and set it to the user’s current login password.

    2) If the login keychain won’t unlock cleanly, create a fresh login keychain (Keychain Access → Settings/Preferences → Reset My Default Keychain) and re-auth apps (OneDrive, etc.).

     

    Step-by-step (with screenshots) here: Change your keychain password to match with your login password

     

    If unlink/relink fixes it, that still smells like OneDrive is hitting a keychain state issue during the first token write — so getting the login keychain into a known-good state before the first OneDrive sign-in tends to reduce the weird prompts.

    howie_isaacks
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    • howie_isaacks
    • Author
    • Esteemed Contributor
    • March 27, 2026

    I’ve seen similar “keychain not found” / keychain-item prompts pop up right after enabling passwordless-ish flows (Platform SSO + app sign-in) where the user’s login keychain ends up out of sync / partially initialized.

     

    Two quick things I’d try on a test Mac:

    1) Open Keychain Access → select the login keychain → run “Change Password for Keychain ‘login’…” and set it to the user’s current login password.

    2) If the login keychain won’t unlock cleanly, create a fresh login keychain (Keychain Access → Settings/Preferences → Reset My Default Keychain) and re-auth apps (OneDrive, etc.).

     

    Step-by-step (with screenshots) here: Change your keychain password to match with your login password

     

    If unlink/relink fixes it, that still smells like OneDrive is hitting a keychain state issue during the first token write — so getting the login keychain into a known-good state before the first OneDrive sign-in tends to reduce the weird prompts.

    Thanks for your suggestions. I will try these. While researching this I did run across mention of this being a possible PSSO issue.

    A
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    • angelohuang
    • New Contributor
    • Answer
    • March 29, 2026

    One other angle that’s bitten us with PSSO/password changes is the login keychain password not matching the current user password (which can trigger weird “keychain not found”/unlock prompts during first token writes).

     

    If you want a quick checklist, this walks through the “why” + the clean fixes (change login keychain password vs create a new login keychain): [Change your keychain password to match with your login password](https://help.swif.ai/en/articles/8578787-change-your-keychain-password-to-match-with-your-login-password)

     

    In practice: get the login keychain into a known-good state *before* the first OneDrive sign-in after enabling KFM/PSSO, then test again.

    howie_isaacks
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    • howie_isaacks
    • Author
    • Esteemed Contributor
    • March 30, 2026

    One other angle that’s bitten us with PSSO/password changes is the login keychain password not matching the current user password (which can trigger weird “keychain not found”/unlock prompts during first token writes).

     

    If you want a quick checklist, this walks through the “why” + the clean fixes (change login keychain password vs create a new login keychain): [Change your keychain password to match with your login password](https://help.swif.ai/en/articles/8578787-change-your-keychain-password-to-match-with-your-login-password)

     

    In practice: get the login keychain into a known-good state *before* the first OneDrive sign-in after enabling KFM/PSSO, then test again.

    This happened on my freshly erased and reinstalled test Mac. I registered platform single sign-on and then logged into OneDrive.

    howie_isaacks
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    • howie_isaacks
    • Author
    • Esteemed Contributor
    • April 7, 2026

    Someone in the Mac Admins Platform Single Sign-on Slack channel suggested using Secure Enclave with Platform Single Sign-on. I switched my test Mac to Secure Enclave and the alerts have not appeared again. I will be moving everyone from using password sync to Secure Enclave soon and this is another reason to move forward with that ASAP. This issue starts on my test Mac after I setup PSSO with password sync and then login to OneDrive.

    howie_isaacks
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    • howie_isaacks
    • Author
    • Esteemed Contributor
    • April 10, 2026

    One other angle that’s bitten us with PSSO/password changes is the login keychain password not matching the current user password (which can trigger weird “keychain not found”/unlock prompts during first token writes).

     

    If you want a quick checklist, this walks through the “why” + the clean fixes (change login keychain password vs create a new login keychain): [Change your keychain password to match with your login password](https://help.swif.ai/en/articles/8578787-change-your-keychain-password-to-match-with-your-login-password)

     

    In practice: get the login keychain into a known-good state *before* the first OneDrive sign-in after enabling KFM/PSSO, then test again.

    I’m marking this as the best answer. This backs up what I found doing research on the issue. I found that using PSSO using Secure Enclave fixes the issue. Now I have even more incentive to move everyone off of password sync to Secure Enclave.

    howie_isaacks
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    • howie_isaacks
    • Author
    • Esteemed Contributor
    • April 17, 2026

    The recent OneDrive update appears to have cured this. PSSO using Secure Enclave definitely did make the alerts stop. When I recently erased and reinstalled my test Mac to test changes I had made with the PreStage and Setup Your Mac, I registered PSSO using password sync, then logged into OneDrive. I expected the alerts to appear again. They didn't. On closer inspection I noticed that my test Mac had a newer version of OneDrive than what was installed on my production Mac. As this update gradually gets installed on all my Macs, the problem appears to be solved. I am still going to move everyone to Secure Enclave.

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