Can You Really Replace Microsoft Exchange with Google Apps Premier?

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The come-on is enticing: Replace that expensive, high-maintenance Microsoft Exchange platform -- and maybe some of your other Microsoft software -- with Google's Apps Premier service for a low, low price of $50 per user per year.

Google will host your email, calendars, documents, and more in their cloud. You can get at everything through a Web browser using the well-regarded Gmail interface, and you may be able to keep using your own client software, even Outlook. Google promises 99.9 percent uptime, and its support includes telephone access to real people. SSL encryption is required to be on, and Google uses the services of its Postini unit to provide malware protection. Google Apps Premier also supports shared contact lists and more sophisticated contact migration, such as LDAP synchronization.

[ The InfoWorld Test Center reveals whether Microsoft's Office for Web apps has what it takes. | Discover J. Peter Bruzzese's 8 key tips for moving to Exchange 2010. ]

Sounds good, but can Google Apps Premier really deliver on what businesses need?

Whatever you're paying for Exchange and other Microsoft servers, I guarantee it's more than what Google Apps Premier costs, but that's not the only issue. A major platform change is disruptive, and you may have come to rely on Exchange features that either have no equivalent in Google Apps or will require some conversion work.

This was the quandary I faced for my own small business and personal domain. Only a few people use it, but we all love Outlook and the power we get from our hosted Exchange server at AppRiver. Although I'm very happy with AppRiver and I'm paying a fair price, I need to save some money -- just like a lot of larger companies.

So I gave it a shot. Here's what I found and what you need to know before you make your decision.

Mobile Support is Equivalent

Google has a plug-in for BlackBerry Enterprise Server, but it doesn't run BlackBerry Enterprise Server. You'll need to run BES yourself or find a provider that will host it with the plug-in.

Google does offer Microsoft ActiveSync support, which iPhones, Palm Pres, Windows Mobile, and some Android smartphones use to enforce security and access policies. It worked well on my Droid device.

When it comes to mobile, you won't save any effort with Google Apps, though you get the same capabilities as you would with Exchange -- including the burden of dealing with BES yourself.

Migration Testing is Incomplete, Slow

I have just two real users on my domain, but I made sure to learn and test at least some of the tools for larger organizations. Google has put together a wide variety of options for migrating your email installation from Exchange (and from Lotus Notes, which I did not test) to Google Apps Premier. If you have more than a handful of users, your main migration tool from Exchange will be Google Apps Migration for Microsoft Exchange (GAMME), which performs bulk migrations of users from the Exchange Server to Google Apps through an intermediary system running the migration app.

The Administration Guide for GAMME made a great impression on me. Google has the approach to this exactly right. The guide stresses the importance of pilot migrations and phasing in the actual transfer, and provides extensive guidance for this approach. In fact you'd be nuts to try this without a test migration. Even I did one for my puny domain. Fortunately, you can test Google Apps Premier for free for 30 days.

The tricky part is that you can't change the MX records on your mail domain until you do the real migration. Because the test users won't have their real email domain in their address (otherwise, their email is down while you are testing), testing can be awkward. For example, I had to use the test account, but my normal mail comes in to I finessed the mismatch by forwarding to and using a reply-to on the .net address, but that of course means testing under abnormal conditions.

When it came time to do my actual GAMME migration, parts of it failed, returning errors that Google's support staff wasn't entirely able to explain. On Google's advice, I switched to the command-line version of GAMME to specify particular parameters. It still didn't work quite right, but running it twice migrated all my data.

GAMME is a slow process. As the docs recommend, you want to shut off email for a weekend -- maybe a long weekend -- when running it. You could scale the performance and decrease the total downtime by running multiple GAMME systems to port different groups or users, or perhaps in different virtual machines on the same computer, or even different sessions on a Terminal Server.

For smaller installations or special cases, GAMMO (Google Apps Migration for Microsoft Outlook) migrates a single Outlook user profile from a client to Google Apps. This tool worked flawlessly for me.

You Have a Choice of Email Clients -- Which You'll Appreciate

After the migration is complete, you have some choices for how to handle email: You can work in Gmail or you can work in Outlook, using GASMO (Google Apps Sync for Microsoft Outlook). This tool has a pretty bad reputation, but it works surprisingly well for me. Google also supports IMAP.

Half of the users in my installation (that would be my wife) were adamant about keeping Outlook. GASMO is both a local MAPI provider and a tool for creating Outlook profiles for synchronizing the Outlook account with a Google Apps account. There is a slow, one-time process to synchronize the Google Apps mail, contacts, and calendar data with the Outlook equivalents. It took many hours each time I ran it, but the further you get from that initial sync, the faster Outlook feels -- as fast as with Exchange, I'd say.

Folders Don't Work the Way You're Used To

Unlike most conventional mail clients, Gmail doesn't have hierarchical folders, but instead uses labels. You can work on all messages with a particular label and treat them as if they were in a folder. Labels don't have a hierarchy as such, but a message can have more than one label and thus appear in both label views.

To map labels into Outlook's hierarchical folders, GASMO turns folder locations into fake hierarchical labels: A message in the InfoWorld folder will have a label of Inbox\InfoWorld. This makes it possible for a message to appear in more than one folder in Outlook. If you delete one of the messages, all the instances are deleted, which is not what you'd expect if you're Outlook-oriented.

The messiness of the hierarchical labels could make it difficult to get used to Gmail after a migration; you start getting a lot of backward slashes in label names to simulate folder hierarchy, rather than the clean names of Exchange folders. If you decide you want to use the Gmail interface instead of GASMO, you may find it worthwhile to restructure your labels to the friendlier, folder-style names it supports.

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