all i can say is shop around

some of the prices are from $10 - $100+ for the same thing

Just make sure you don't buy SSL certificates from Symantec.... 

jarledb:

 

Just make sure you don't buy SSL certificates from Symantec.... 

 

DigiCert buying Symantec PKI solutions today.

Question is then: Is DigiCert swallowing a poison pill by taking over Symantecs SSL business? The certificates from Symantec will stop working in Google Chrome in a not too distant future.

I usually just use SSLs.com. Good prices for wildcard and EV certs if required too.

I recently started using LetsEncrypt and I'm totally happy.  The only downside was that I had to add an HTTP site just for the verification process.

I couple of notes to clarify/correct what some have said already. LetEncrypt works fine with IIS (I used it specifically for Exchange) and the renewal process not only "can be" automated, it is by default.

This is the Guide that got me started: https://github.com/Lone-Coder/letsencrypt-win-simple/wiki/Create-a-SAN-certificate-for-Microsoft-Exchange-2016,-2013-&-2010.

jarledb:

 

.......The certificates from Symantec will stop working in Google Chrome in a not too distant future.

 

nope, only old certs .
All you need do is to get the cert reissued (that should be free)