Hi @Rohanathan S ,
I understand that you are trying to enforce MFA using conditional access, but are not receiving the MFA prompt when you pick an account showing "Connected to Windows" to authenticate.
If you received the "Stay signed in?" prompt and chose "Yes", the web browser will remember your information for 90 days. Could you try signing in with a different account and selecting "No" to see if the problem persists?
If this is the first time authenticating and you have already enabled MFA, one thing you can try is disabling and then re-enabling the MFA.
Other possibilities:
The account could be saved in "Work or school" and you may need to sign out under Windows > Settings > Accounts.
If the browser is saving the account information, you can try clearing the information on that browser or signing in with a different one.
If you do not want the option for users to stay signed in, you can set "Show option to remain signed in" to "No." https://learn.microsoft.com/en-us/azure/active-directory/fundamentals/keep-me-signed-in
If none of these scenarios apply to your situation, could you please share some screenshots so that I could better assist?
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