Google Apps Sync

Used to be I always worked in a corporate environment where someone else was responsible for providing email with Microsoft Exchange and everyone used Microsoft Outlook.  Email was not my problem, life was good.

Now I have my own business and I manage email for clients with limited resources.  Life, or at least email, is a lot messier.

Common options these days are

  • Run your own Microsoft Exchange on Windows Server.
  • Use a hosted Exchange solution, eg. from Rackspace.
  • Use Google Apps.

My experience with Google Apps Sync has not been as seamless as I had hoped for: calendars didn’t seem to sync quite right, and including iPhones with ActiveSync just made it worse.  Then there was all the confusion around Apps Sync wanting to remove emails from in-boxes over 2-4 GB – maybe justifiable but it just didn’t work in the same way as Exchange, and sometimes trying to introduce change in an organization is simply not worth it.  My client is now happy with hosted exchange from Rackspace: not as cheap as Google Apps, but cheaper for a mid-sized organization than administering email in-house.

Thunderbird and Lightning, DavMail & Exchange

Thunderbird is a cross platform email client, Lightning is a calendering add-on.  Lightning will be integrated into Thunderbird 3.  Thunderbird installation is straightforward, Lightning is installed from Thunderbird’s ‘Tools/Add-ons’ menu.

DavMail is an Exchange gateway that wraps standard protocols like IMAP around the proprietary interfaces to Exchange.  DavMail setup is straightforward, following the instructions on it’s website, all I had to provide was the OWA URL.

To configure IMAP in Thunderbird all I had to do was specify a server name of localhost and port of 1143, not 143.  To configure CalDAV I specified a CalDAV location of http://localhost:1080/users/[email protected]/calendar   To configure SMTP for outgoing mail I specified localhost port 1025, not 25.

I couldn’t figure out how to use DavMail LDAP, the documentation is too cryptic. Instead I configured a Thunderbird address book to directly access Active Directory, which works only locally on the LAN.  With the address book available autocompletion works also. 

Trying to replicate the directory for offline access did not work for me, however.  This is supposed to be fixed in a later release.  To work around not having the Exchange address book offline I installed Email Address Crawler which instantly scooped every to or from address from my existing mails into an address book.   I took this home and it worked as expected: I could send and receive mails and had a limited address book.

Having proven this configuration under Windows I installed Ubuntu in a VM and used Synaptic to install Thunderbird. Lightning and DavMail are downloaded and installed the same way as on Windows.  I did, however, run into a defect and workaround installing Lightning.

This solution seems to work OK, but I noticed some issues with the HTML email editor. This is improved in Thunderbird 3, which went into its fourth beta release a few days ago.

Email Strategy

Should you upgrade Microsoft Exchange or switch to an alternative? It depends what you want. In addition to hosting your own solution it is now possible to outsource to a SaaS provider, providing management and investors are comfortable with the idea. Requirements to consider:

  • Compatibility with Microsoft Outlook. All mail servers support IMAP and POP to access and download mail, but fewer solutions support Microsoft’s various proprietary protocol and extensions (eg. MAPI/RPC) used by more advanced features of Outlook. Open source implementations are still a work in progress.
  • Storage management. Traditionally mail servers have supported a mailbox of up to 1-2GB, but what happens when a user accumulates more than that?
  • Spam filtering and support for e-discovery. Postini addresses this well upstream from your corporate mail server and eliminates this as an issue.
  • Smartphone integration. More proprietary protocols are used to synchronize smartphones using Windows ME or Blackberry OS.
  • Cost.

Solutions to consider:

  • Google. Google offers a hosted solution with IMAP. Premier edition offers 25GB storage and 99.9% uptime (=8-9 hours/year downtime) for $50/yr.
  • Yahoo Zimbra. Competing solutions similar to Zimbra include Zarafa, Axigen and Scalix (fka. HP OpenMail). Zimbra gets the best reviews, however.
  • MailStreet and Apptix have received good reviews for providing hosted Microsoft Exchange email services. MailStreet charges around $8/mo. including Outlook licence and 2GB storage.

Looking into the future Open-Xchange is closest to providing an open source solution including MAPI/RPC.