We use exactly that setup. Plesk 12, SM 14.xxx, on a windows 2008 Server. It all works well so far that we have seen. No real show stopper issues between the two.
There are a few quirks though. some I have been asking and yet to have anyone answer - plesk or smartytools
For instance. when we set up a new domain in plesk :
It creates the DNS entries. then interfaces to smartermail and creates the email accounts.
"Something" does not properly BIND the "mail." to the domain for the location to access web based mail. And, I can not find any setting anywhere to define that option.
So, for instance, we want "mail.HawaiianHope.org" to be our webmail location. When first creating the domain, even though we had the DNS defined, that location was not created. However.... "webmail.HawaiianHope.org" WAS created but we never defined "webmail." anywhere in our system that i am aware of. (it took us 3 days to discover this too)
It (something) does this for every domain we create. We have to manually go into the server DNS and BIND "mail." to the domain and remove "webmail." from the domain BINDing. easily done, but its a pain in the ass to have to manually babysit "automation" products.
I have been asking both smartermail and plesk for about 2 months now which product is responsible for creating "webmail." or where i can define the setting, and neither company has responded yet.
But overall, the 2 products work VERY well with each other (my opinion).
On a separate note about plesk.
While i like the product it also has some items that i think needs adjusting.
Here is a link to a posting i made there :
Not sure how (WSP) 2.0 works, BUT,
In a control panel, if you create a user account and then multiple domains for the account, this is what I am expecting to see :
but with plesk this is what it does.
Giving root access to the first domain created grants full access to every other domain in the account, they are not managed independently
www.HawaiianHope.org - Providing technology services to non profit organizations, homeless shelters, clean and sober houses and prisoner reentry programs. To date we have given away over 1,000 free computers.