A cloud-based identity and access management service for securing user authentication and resource access
Thank you for your reply.
1) Why your “What If” tool can’t find Register security information
In your screenshot, the Target resource → Select target type dropdown is set to Cloud apps. In that mode, User actions won’t appear.
Microsoft documents that Target resources can be applications/services OR user actions (for example, “Register security information”).
For your reference: https://learn.microsoft.com/en-us/entra/identity/conditional-access/concept-conditional-access-cloud-apps?tabs=powershell
What to do
Go to Entra admin center → Protection → Conditional Access → What If.
Under Target resource, change Select target type from Cloud apps to User actions.
Then select Register security information.
If you follow those exact steps, the option should appear because it’s the documented way to target combined registration
https://learn.microsoft.com/en-us/entra/identity/authentication/howto-registration-mfa-sspr-combined
2) The correct Conditional Access design for MFA/SSPR registration
Recommended: A dedicated policy targeting the User action
Microsoft’s guidance for securing security info registration is to create a policy that targets User actions → Register security information, then apply the grant control you want (MFA/auth strength, trusted locations, etc.).
Create/confirm this policy (baseline)
Assignments → Users: your test group (plus exclusions for break-glass accounts).
Target resources: User actions → Register security information
Grant: typically Require multifactor authentication (or an authentication strength).
(Optional but common) Locations: exclude trusted locations or require registration only from trusted locations.
Docs:-
https://learn.microsoft.com/en-us/entra/identity/authentication/howto-registration-mfa-sspr-combined
3) Fix your “Block all cloud apps” policy so it stops breaking registration
Because your block policy targets “All cloud apps” + Block access, it can still collide with registration redirects and token issuance that happen as part of the combined flow. Internally, the registration flow relies on Conditional Access evaluation for the registration “action” and can require specific claims to proceed; blocking broadly often results in the type of generic failure you’re seeing.
Safer pattern
Keep your Block all cloud apps policy, but exclude your test users while you validate the registration policy. (Use a temporary exclusion group.)
Turn the block policy Report-only during testing so you can see the impact without hard blocks. Microsoft recommends phased rollout/testing for CA changes.
Ensure you have the dedicated User action: Register security information policy enabled
https://learn.microsoft.com/en-us/entra/identity/conditional-access/plan-conditional-access
4) Use Sign-in logs the right way (your screenshot is showing “Windows 365 Portal”)
Your sign-in log screenshot shows Application: Windows 365 Portal. That may not be the actual registration event for mysignins.microsoft.com/register — it could be a related sign-in (or a different step) rather than the registration “user action” evaluation. The right approach is to find the failed event at the time of the BadRequest and open the Conditional Access tab for that event.
Microsoft’s troubleshooting doc confirms:
You can drill into the event and see which policy applied/failed.
53003 = BlockedByConditionalAccess is a common error for CA blocks.
Use Sign-in diagnostic from the event when needed.
What to do
Entra admin center → Sign-in logs.
Filter by the affected user and the failure time.
Open the relevant failed sign-in and go to the Conditional Access tab.
Identify policies with result Failure and confirm which one is enforcing Block.
https://learn.microsoft.com/en-us/entra/identity/conditional-access/troubleshoot-conditional-access
5) Could Security Defaults be interfering?
Usually, Security Defaults and Conditional Access aren’t meant to run together — Microsoft states you can’t enable security defaults if you have Conditional Access policies enabled, and vice-versa. So in most tenants, if CA policies are active, Security Defaults should already be off (or not enable-able).
Still, it’s worth checking Entra ID → Properties → Manage security defaults, but don’t expect it to be simultaneously enforcing if CA is active