Category: SmarterMail

Migrating SmarterMail 5.5 to 8.0 and IIS7

Like any good SysAdmin, I have a private hosted server on which I run my own mailsever and websites, and generally use as a bit of a sandbox for testing stuff out. Judge me if you will.

My particular server is a VPS hosted by the awesome folks at KickAssVPS (they seriously do btw), and I recently decided it was overdue for an upgrade from Server 2003 to Server 2008. No worries – just a case of migrating some websites from IIS6 to IIS7 (sadly not IIS7.5 – R2 not available at KickAss yet). What I hadn’t planned on was finding out my mailserver software was 3 major versions old – SmarterMail 5.5 to be precise – and version 8 had just dropped that week. Too good to pass that up. Shiny!! Must have!

So, now I’m migrating from Server 2003 to Server 2008, IIS6 to IIS7, .NET2 to .NET4, and SmarterMail itself from 5.5 to 8.0. I’ll admit I started to wonder if I’d just made a foolish mistake.

Migration attempts 1 and 2 were a nightmare. Mail service refused to start, webmail couldn’t connect to services, and general hair-pulling ensued. Google unfortunately didn’t have the answers – seemed nobody had tried this particular array of upgrades in one go before. I was in no-mans land. It’s lonely there.

But eventually, I figured it out. If you’re curious, here’s how…

There is a minor but crucial step missing in these instructions (or was when I wrote this – SmarterMail tell me they’re updating them soon). By default, your application pool will be set to run under .NET2. Change this to .NET4 or you’ll get an error popup in IIS about “configuration section ‘system.web.extensions’ cannot be read because it is missing a section declaration” (because the ‘.extensions’ bit is new in .NET4). Like I said, minor but oh so crucial.
  • Stop the SmarterMail service on both servers
  • Copy the following XML files from the SmarterMail program folder on the old server to the same place on the new server: (assumes x64 OS)
C:Program Files (x86)SmarterToolsSmarterMailServicemailconfig.xml
C:Program Files (x86)SmarterToolsSmarterMailServicedomainlist.xml
C:Program Files (x86)SmarterToolsSmarterMailServicegreylistbypass.xml
C:Program Files (x86)SmarterToolsSmarterMailServicegreylist.dat
  • Copy the contents of the entire mailbox folder located (by default) at C:SmarterMailDomains to the same place on the new server.
  • Recursively delete all copies of mailbox.cfg from the C:SmarterMailDomains folder (“del /S mailbox.cfg” will do the trick). Restart the SmarterMail service on the new server.
  • This resolves a problem whereby large numbers of emails show in webmail as ‘email no longer exists on server’. The mailbox.cfg file gets rebuilt automatically when you login to webmail, so don’t panic about deleting it.
  • Restart the SmarterMail service on the new server.
  • Retrieve beer from fridge
  • Open beer and enjoy.

Bare in mind this doesn’t take into account your need to plan your MX record cutover process. If you’re managing a mail server, I’d expect you to understand how that bit works without having to explain it.

SmarterMail 8 is a massive improvement by the way. Faster, much sexier to look at, and just generally betterer.


JB / The Daywalker

Ginger IT dude hanging out down in New Zealand, playing with technology since ages ago.

Currently Service Delivery Manager at Silicon Systems, formerly Skype for Business MVP, and generally into all things Microsoft (and a few things that aren’t).

When I’m not nerding out on technology, you can find me running ultramarathons, brewing beer, or in my woodshop building something.

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