So I saw a posting over at the WHS forum recommending this, and I thought I'd give it a try. Unfortunately, at the present time it doesn't seem like it can do what I want, but I figured I'd be nice and give a few feedbacks on some snags I hit.
1. ST needs to work on the documentation a bit. There's some stuff that was present on the setup screen that didn't have a corresponding entry in the help system, although nothing critical. One thing that did jump at me was that the IIS integration help had an entry on Win2k3 on Pools, but the corresponding entry in the IIS path page did not. Although I'm not sure why a new pool is required, I just followed the direction on creating a new SmarterMail pool and extending the timeout, and assigned it to my virtual path entry.
2. By default the shortcut placed on the desktop refer to a URL file that accesses 127.0.0.1. Unfortunately, the default install of WHS does not include that in the Local Intranet, but does include both http://localhost and https://localhost. I don't know if this is a default on the IE ESC or not, but until I manually changed the URL to localhost (plus updating it to point to the virtual path), I can't use the login page because it uses javascript to validate the input. This goes for the other products as well.
3. Unfortunately, the reason that I wanted to use SmarterMail was for the WM5 calendar/contact syncing, and someone else posted that they are unable to use SSL in the Sync forum, and it does seem that this isn't supported. WHS gives a trusted signed cert from GoDaddy on xxx.homeserver.com, but that WM5 isn't able to use https://xxx.homeserver.com/Mail as the path to connect to SmarterMail to sync. However, the cert does come up as untrusted on PocketIE (GoDaddy's root cert isn't installed?!), so it's possible it's still a trusted/untrusted issue with certs. As my ISP blocks Port 80, I guess theoretically I could go back to using SmarterMail's webserver and/or using an additional site with a different port to get around that, but I was kind of hoping to use https just in case my IP changed and I was hitting someone else's machine with my username/password combo, at least it'd give me a warning that the SSL cert doesn't match or something instead of plain-texting my u/p. And then there's the issue with punching a hole through UPnP instead of relying on WHS to do it for me (kinda figured that one out).
4. There is no program icon installed on the WM5 Sync - I had to go manually through the File Manager and start the program that way. This was using SmarterMailSyncForSmartphone.CAB dated July 2, 2007. As for the program, a bit more detailed log might be useful, as well as sycning-on-schedule for those with unlimited data plans. This was on a Motorola Q.
5. This isn't an issue persay, more like a feature request. Although I realize that SmarterMail Free is the same as the Enterprise, just limited to one domain+10 users, there are too many stuff lying around that doesn't pertain to someone who's using it for one or two domain. A simpler setup screen for those using it for a single domain might make the product a bit easier to install, and I'm sure that includes those who paid for the Pro version as well.
6. On the same line, I'm sure there are users who already have some other e-mail setup that they are using but want the product to do shared calendaring or contact management. I would like to see a setup catered more towards that instead of requiring everyone to jump through the hoop of creating a e-mail server just to use in a different manner.
7. I know that the product can tie into AD for users and groups, but I was wondering if it could do NTLM or Passport auth without use of AD. At least the admin acct should be using the same Administrator username/password of the server via NTLM, or maybe there could be an option to use it like that. I do worry about security, and having another set of username/password or even worse having some security hole from which someone could sniff out u/p that exists on SmarterMail (which in turn would be mapped to their domain logon) isn't something that I want to be worried about.
8. And one thing I forgot, after the install I told SmarterMail to use D:\SmarterMail for the logs and everything, since C:\ only has 20G and is liable to get completely wiped due to how WHS is. It didn't create the directory and kept complaining in C:\SmarterMail\Logs about how it was unable to open D:\... Not sure why that bug appeared, but the first thing I did after install was to transplant it into IIS virtual path, then I started the config. Once I copied everything from C:\SmarterMail to D:\SmarterMail, it stopped complaining to log every 2 min.
Anyway, overall it looks to be a very interesting product, and I'm sure I'll be able to recommend the product to a few people who wants to use it as an e-mail server, especially considering the price-point.
-- Starfox