Encrypt and Trust Server Certificate doesn't take effect when using SSMS 20 Utility with -S -U flag

Question

Hi, I recently updated SSMS 19 to 20, but I encountered a strange issue. When Using SSMS 20, I have a remembered profile with Encryption set to optional and enabled Trust Server Certificate, and connect will not show certificate not trusted. However, if I use the utility ssms.exe -S <server> -U <user>, this will show certificate not trusted.

I also tried with SSMS 19, seems the above two option takes effect. Is SSMS 20 utility not using the advanced settings anymore?

Answer 1

They reworked the connection dialogue in SSMS 20, and SSMS (like all client APIs), now defaults to requiring an encrypted connection. The regular connection dialogue exposes the encryption options on the front page, but there a couple of places they still have to address.

And one such place is when you use the command line to start SSMS. I have noticed this myself, but I don't think I have come around to bring it up with Microsoft. But they may still have it on their radar.