In previous posts, I covered the reasons I wanted to move to Office 365, including the potential benefits of the transition. In this post, I’ll discuss the changes and steps that were required to make the transition.

Note: This post is part of a series on my move from Gmail to Office 365. To see a complete list of related posts, see Summary: Moving to Office 365.

Configuration Changes

Prior to signing up for the Office 365 Preview, I came up with a list of steps and requirements that I’d need to perform in order to fully migrate from Gmail. The list (which is not necessary in order) included:

• DNS Hosting: While there are other options, the Office 365 Small Business (P) plan recommends that users have Microsoft manage their DNS settings. This was actually a fairly easy change for me, as all I had to do was have my domain host point to Microsoft’s name servers. There was an initial step of proving that I owned my domain (by creating a temporary DNS MX record), but the step-by-step setup wizard walked me through it all. I was even able to add a few aliases that I use for my web site (this blog) and for a few other dev/test services. The process might seem more complicated for people who aren’t used to administering their own domains, but it was definitely as simple as I would have expected. For those that want to continue to manage their own domains, there are ways to add the required Office 365 DNS records manually.
• Transfer of Organized E-Mail, Calendars, and Contacts: I needed a method to retain my current folder structure and details from my Hotmail account (which was quite small), as well as for my archived data. I considered the use of TrueSwitch, but I would have had issues with merging and managing the folder structure. I decided that the best approach would be using drag-and-drop through the Outlook client interface. This allowed me to merge calendars, contacts, and (of course) e-mail messages. This was also the primary reason that I decided against using Outlook.com (which is free) and signed up for the Office 365 Preview.
• Client Synchronization: For the most part, I’m connected to the Internet all day, every day (that’s one of the many benefits of working primarily from home). I decided to store all data online and use local .OST files to cache data locally when using Outlook. That provides access to my message store on any device (including through web browsers), while maintaining local performance and the ability to occasionally work offline. Connecting to my new account from Outlook was quick and easy using auto discovery features, but my Android devices were a little more complicated and required me to access the Office 365 Admin Help.

Limitations of Outlook.com vs. Office 365

For the vast majority of online users, I think that many of the free e-mail offerings (Gmail, Hotmail/Outlook.com, Yahoo Mail, etc.) are perfectly usable. Typically, you’ll choose a service based on cost (or lack thereof), performance, reliability, storage space, and the usability of its web interface. That was my initial approach, but I realized that there were some limitations of Outlook.com that prevented me from moving to Microsoft’s free service. They are:

• Uploading Archived Messages: I have been using the Outlook client on my computers for at least the last 10 years, and I have amassed a huge collection of historical messages. Every once in a while, it can be helpful to resurrect a discussion from years ago. Or, more commonly, I just want to look back through some past messages to reminisce. I wanted my new e-mail account to include an automated way to upload my archive, including all old contacts, calendar items, and folder structure. There are two major approaches: First, I could open my current and archive e-mail .pst files and drag and drop the contents to my new mailbox. Or, I could use Outlook’s “Import .PST File” feature to load the data from my local storage files. Outlook.com does not support these methods, while Office 365 supports both approaches (through the use of the Outlook 2013 client). Outlook 2013 also allowed me to merge all of my archived folders with my current ones relatively easily.
• Retaining Folder Structure: The ability to use the TrueSwitch seemed, at first, to be the ideal solution. I could just enter my login information and have the service automatically transfer my messages from Gmail to Outlook.com. The problem, however, was that I’d just end up with one huge folder filled with a tremendous amount of unstructured, unsorted data.

If I didn’t have the above requirements (or, if I were willing to start from scratch with a new e-mail account), I probably would have opted for Outlook.com. Office 365 does provide the benefit of providing excellent pricing for up to 5 installations of the full Office applications, though, so it’s still a compelling subscription offering. And, I haven’t yet experimented with SharePoint and Lync, both of which are included.

I was pleasantly surprised to find that Exchange Active Sync (EAS) is well-supported on many devices and applications, including the stock Android Email application. For more details, see Information about Exchange ActiveSync.

Update (09/23/2012): While I was unable to find an official statement from Microsoft, it does appear that it might be possible to copy messages and folders in the release (RTM) version of Outlook 2013.  I’ll try to post an update here if/when that becomes supported.

Backing Up a Gmail Account

Part of the migration process for me was making sure that, after everything was transferred successfully, that I’d be able to create a full backup of my Gmail content. It’s not that I’m worried about Gmail going away anytime in the foreseeable future. While I had the vast majority of this content organized in Outlook, I periodically deleted attachments from my messages. And, there’s always the chance that I accidentally deleted something important. My Gmail account isn’t going away, and I can always search for content through the web interface. However, I like the convenience and usability of having an indexed .PST file and raw messages if I ever needed them while offline.

Fortunately, there are a few methods you can use to easily download and install your entire Gmail (or other POP/IMAP-based account):

• IMAP E-Mail Clients: Use any e-mail client (like Outlook) to download and save all your messages. I enabled IMAP for my Gmail account, chose to synchronize all mail (it took about 4 hours to synchronize ~55,000 messages), and then exported the results to a .PST file. I now have an archive that I can save off to local or online storage for posterity.
• Backup Utilities: Gmail Backup is a free program that can individually download all your messages and save each in individual .eml files. The files can be opened in Microsoft Outlook or other compatible e-mail programs. I have also used the free Gmvault application in the past. While it worked fine, the resulting downloaded files (which are in text format) were far from ideal.
• Scripting / Enterprise Tools: There are, of course, other approaches for migrating e-mail. I only had a couple of accounts to consolidate, so I took the above approaches. Exchange Server admins and others who need to migrate multiple message stores can use the Windows PowerShell cmdlets for Office 365 or third-party upload tools.

Summary

In this post, I covered a summary of the steps required to move to Office 365 and to back up a Gmail account. I didn’t spend a lot of time on technical steps, because those are well-explained on other sites. Feel free to leave any questions or comments if you have them! Next stop: Potential Office 365 Issues.