Said It Here

Fixing security token enrollment errors for non-technical users

Asking standard employees to manually navigate certificate tools, templates, and provisioning slots turns simple token setups into 30-minute helpdesk calls. Additionally, strict configurations cause sign-ins to fail with error messages stating that the passkey does not meet the criteria set by the admin.

Overview
People affected5 accounts across 1 forum
Workarounds found8 items attempted
Community agreement20 total upvotes

What people tried

Every workaround mentioned in the threads below. We haven’t tested any of them — and nobody here is claiming they worked.

Found another way around this?

Share your steps and trade-offs so fellow engineers don't have to reinvent the wheel. No account required.

  1. 1
    Purchasing expensive commercial Certificate Management Systems
    Did this help you?
  2. 2
    Writing custom internal enrollment tools
    Did this help you?
  3. 3
    Check Conditional Access policy configuration for MFA
    Did this help you?
  4. 4
    Verify device requirements like PIN or Face ID settings
    Did this help you?
  5. 5
    Using device-bound passkeys instead of synced passkeys
    Did this help you?
  6. 6
    Sticking to traditional authentication methods until synced enterprise deployment matures
    Did this help you?
  7. 7
    Treating Temporary Access Pass (TAP) as the bootstrap method and enforcing phishing-resistant MFA only after enrollment finishes.
    Did this help you?
  8. 8
    Using an Azure app or group automation to temporarily exclude onboarding users from Conditional Access policies requiring authentication strength, then removing the exclusion after a set number of days.
    Did this help you?
Tried another approach not listed above?+ Share your workaround ↑

In their words

Unedited, grouped by where they were said, most upvoted first within each place, each linked to the thread it came from.

r/sysadmin5 people · September 2026

“Asking standard employees to navigate certmgr.msc, pick the right AD CS template, and properly provision Slot 9A usually results in a 30-minute helpdesk call.”source ↗

Legal2k · r/sysadmin · 14 upvotes

“Windows hello pops saying it's required to save passkeys on this device > Next > then it runs into a failure and the whole thing breaks.”source ↗

“Essentially the above flow works, but it's not very pretty. It requires that i inform my endusers with a very clear instructruction during the setup”source ↗

denstorepingvin · r/sysadmin · 5 upvotes

“I am getting a “Your sign in was successful but this passkey does not meet the criteria set by your admin” error message.”source ↗

evil-scholar · r/sysadmin · 2 upvotes

“Trying to force everything during Autopilot made the flow way too fragile”source ↗

Current_Package8576 · r/sysadmin · 1 upvotes

“What app are you using / recommending to deploy synced passkeys.”source ↗

“Microsoft authenticator passkeys seem to be device bound which i can for-see being a pain”source ↗

Longjumping-Time2076 · r/sysadmin

Where this came up

People with this problem also raised