The password and path in bindings is not related to the password and path in Settings->SSL Certificates. 

Thanks Patrick,

Am I confusing myself by having the certificates (.pfx files) in the bindings in the same folder as the SSL Certificates (the .pfx's uploaded from this page)?

Are they both separate entities for different functions within SM?

Yes and no. SmarterMail will create certs with the subject names and ASNs you need, but I haven’t taken the time to look at specifically what certs it creates,  in my example, it has a cert listed in automatic certificates for webmail.mydomain,com, and one for mta-sts.mydomain,com (which I manually configured) and it shows two for mail1.mydomain.com, which is what I use for bindings. I doubt there are two .pfx files for mail1, but I haven’t looked yet. 

All of this is why I continue to use Certify. SM’s internal certificate Ajax client is OK, but it’s not yet ready for prime time IMHO. 

In my other setup, every domain has its own webmail.whateverdonain.com, but for those domains, Mx records are mail1.mymaindomain.com.  I’ve always let Certify handle all the certs, and it handles the IIS bindings for webmail, and it places the .pfx for mail1 in the location and with the right password to satisfy the bindings. It wasn’t easy to set up but it just works and I understand what it’s doing.