Microsoft's Exchange Server may be the king of corporate email, but it has plenty of detractors, especially among smaller companies that find managing the software and dealing with email backups to be a huge hassle.
Meanwhile, Microsoft's Outlook email client has its issues — sluggish performance, a user interface that isn't especially user-friendly and ever-increasing complexity. But it maintains a devoted following among the tens of millions of business workers who practically live in the software while on the job.
Not surprisingly, there is no shortage of alternatives that let users get rid of Exchange Server in their datacentre while keeping Outlook on the front end. They range from open-source Exchange clones to web-hosted Exchange offerings from Microsoft and countless other service providers.
"If you're able to replace the back-end mail servers so no end-users notice, then IT gets a less expensive email infrastructure but doesn't have to deal with angry users set in their ways," says Guy Creese, an analyst at Burton Group in Midvale, Utah.
Google's Gmail service joined the list of alternatives last year, after Google added support for the Internet Message Access Protocol. IMAP enables rapid synchronisation of messages between Gmail and desktop email clients such as Outlook, and between the mail server and various end-user devices. And Gmail is free for some users and inexpensive for others.
"Many of my customers with under 50 employees don't even need Exchange, so I see a lot of growth in Outlook-to-Gmail," says Ronnie Mansoor, CEO of Implicit, a developer of Outlook add-on software.
However, Google didn't go all the way with its IMAP support: Users still can't download their Gmail contact lists or calendars into their Outlook email clients.
Now a vendor named Cemaphore Systems is publicly releasing a beta version of a tool that lets users synchronise their email, contacts and calendars between Outlook and Gmail. That could make it possible for companies to use Gmail as an inexpensive disaster recovery backup to Exchange Server, or perhaps to dump Exchange altogether.
Cemaphore is taking sign-ups from users who want to test its new MailShadow for Google Apps software, known informally as MailShadowG. The company said that a commercial release is expected to ship during the third quarter.
Unveiled several months ago, MailShadowG has already achieved some early-adopter praise. In March, blogger Robert Scoble raved that during a demo by Cemaphore, MailShadowG synchronised his email and calendar between Outlook and Gmail in a matter of seconds. "Google's synchroniser sucks compared to Cemaphore's," he wrote. "It's slow and buggy".
"Google may sync every 30 or 60 minutes. We're firing as the events fire," Cemaphore CEO Tyrone Pike said in a recent interview. "That's why we call ours a continuity product, not a sync product."
Pike also claims that MailShadowG doesn't create multiple versions of the same calendar event, a problem with some calendar synchronisation software. "Our algorithm is very immune to that," he says.
Cemaphore, which was founded in 2002, is no fresh start-up. According to Pike, the company already has about 100 corporate customers and 70,000 licensed seats for a non-Google MailShadow product that can be used to replicate Exchange messages for business continuity purposes and during upgrades from one version of Exchange Server to another.
But being in beta, MailShadowG isn't perfect. For example, some testers with large Exchange email boxes have had problems during the initial upload of their directories into Gmail, Pike says, although he blames that on Google. "Their view is this could be a spam or denial-of-service attack," he explained. "So they throttle you down." Subsequent synchronisations shouldn't suffer from that problem, he says.
The bigger problem is how to preserve Outlook and Exchange data as it is imported into Gmail. Created in an era when spreadsheets were still king, Outlook uses copious hard-coded data fields. Gmail, by contrast, was developed after the rise of search engines. Google's software has far fewer structured fields because it assumes that "if you need to find something, you're going to search for it, not do a column sort", Pike says.
For instance, Outlook uses first and last name fields, while Gmail just has one field for both. Or take the recurring meetings function — Pike says Gmail has "very limited" support for that compared to the combination of Exchange and Outlook.
Such differences are big enough that they pose some problems for MailShadowG, he admits. "For the things that really matter, we do 95% well," Pike said. "But this isn't a 1:1 solution."
Pike claims that data will never simply be "obliterated" by MailShadowG during the import process. If the software can't find an equivalent field in Gmail for one in Outlook and Exchange, it will move data to a general notes field, he says. Pike also expects Google to partly fix the problem by eventually letting Gmail users create their own data fields.
Still, data fidelity is a big enough issue at this point that Pike isn't pushing MailShadowG as a way to help Gmail replace Exchange, but instead as a way to help it back up the Microsoft technology. "We've told people that you really have to think of this as a continuity solution," he says. "If you're going to make a full migration, you're going to need to run the two in parallel for a long time."
Gartner analyst Matt Cain agrees. "I don't think that in this case Outlook would be the front end of Gmail," he says. But he does expect MailShadowG to catch on among individual employees seeking a way to back up their Exchange work email and contacts, even if their companies frown on that information "being stored outside the official e-mail system".
Pike sees another, and bigger, reason why Gmail won't be replacing Exchange at the email back end anytime soon: its still-spotty support for BlackBerry devices, Windows Mobile smart phones and Apple's iPhone. "Google's BlackBerry sync is not an enterprise product," he says.
MailShadowG doesn't support smart phone synchronisation yet, either, although Pike says he is "very interested in providing" it if Google doesn't step up to the plate.