I have a strange issue after the 1 August when all was fine and working as normal on August 1st and prior that date. I have been using it since the beginning of the year without any issues even on switching to Sonoma 16.4 or other windows or parallels update. The context: I have a Windows 11 Arm 64 updated to date, Parallels updated to date and Sonoma 14.6.1 update after August 1st. Apple M2 ARM Third party app Certificate with two factor authenticator from windows Authenticator app on mobile phone. The certificate its not expired or the webpage is not having issues with it. Tested/Working on Windows PC all ok. ( do not ask questions about the expired certificate or the webpage not working. Its all fine on that side, more in the details) The issue: - I have a Certificate that is installed on Windows by a third party app that is also the authority for that certificate used in some important relation with the financial authority in Romania. That certificate worked perfect prior August 1st and on August 15 I noticed that its no longer working. Not using it every day I was not able to point exactly the day of changes. - On Edge browser or Chrome browser the Popup for the selection of the certificate appears I select it then the web page says the certificate is not being present and fail the login. ---- This site can't provide a secure connection confirmare-doc.certsign.ro didn't accept your login certificate, or one may not have been provided. Try contacting the system admin. ERR_BAD_SSL_CLIENT_AUTH_CERT ---- The Observed mechanics: - I don't know what was the setup prior August 1st cause I was not aware of any issues. The certificate works like this. After you select it from browser popup the Third Party app displays a Popup to enter the 2FA code generated by Authenticator App (Microsoft). After that the page logins ok. -After August 1st that third party certificate app popup for the code no longer appears. - The browser popup for the certificate appears ok and the certificate is installed ok and available in windows certmgr. (as it was before) The Workaround: (Suggested by the Certificate and App creators.) I have to run Edge browser on Windows 11 Arm 64 on Parallels, select IE mode compatibility from browser Edge menu.( this way i return to very old stuff ). In this mode the pop-up for the Third party certificate app is working and it is showing up to enter the 2FA code. The secured page loads OK and all is fine. They say the IE uses an old security protocol that apparently its not affected. ( fun fact they don't know either why it was working prior August 1st) My Conclusions: The Third party certificate app works but not as it was prior August 1st. The probable issues: - The browser is not able to send the Certificate to the webpage or send it in a wrong way. - The Third Party certificate application is not able to intercept the Certificate request from the browser - The third party certificate app is not able to communicate outside via a secured channel when Chrome/Edge is used. Not that probable due to the fact the app works when in IE compatibile mode on EDGE, and also worked before. - The Parallels handles the secure channel in a wrong way - The Sonoma update 14.6.1 handles something wrong - The Windows 11 Arm 64 version somehow messed up something in their updates. (someone suggested the fact that they ar now available on Qualcomm laptops makes that a problem with compatibility and there is a chance they messed up Apples M2 Arm)