In previous posts, I covered a lot of details related to the benefits of moving to Office 365. Of course, few technical solutions consist of only benefits, and there are a few potential issues that I think might be important to keep in mind. In this post, I’ll cover some of the issues that I have run into or think might be an issue for others.

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.

Office 365 Considerations

• Cost: First and foremost (for many people), Office 365 is not free. You can use the Office 365: Compare Plans page to get more details on the available offerings. The Small Business (P1) plan is most appropriate for my purposes, and after the free trial period, it will cost me $6/month ($72/year). That’s infinitely more than “free”, but to me, it’s worth the cost.
• Exchange ActiveSync Support on other devices: Outlook 2013 works great for me, but I found that the built-in Android 4.0 Email application leaves a bit to be desired in the “user experience” department. First, the app is buggy – it took me many tries to just add an account. I was unable to change my password without completely removing the account and re-adding it (no easy task on a touchscreen interface). The e-mail widget doesn’t work on my ASUS Transformer TF101, and the folder management UI is almost as painful as Gmail’s web UI. Of course, there are third-party apps (most are relatively expensive for mobile apps) that fill in some of these gaps.
• Incomplete Migration of application settings: While the majority of commonly-used messaging settings seem to be stored online (and, more importantly, are automatically synchronized between client installations), some are not. For example, I found that some toolbar customizations and Outlook client message settings (I usually change the default reply font and color) do not migrate automatically. It’s not a huge deal, but it would certainly help to have all relevant client settings roam to new computers and devices.
• Outlook Data File Synchronization: The default settings in Outlook 2013 specify that the application should download and cache 12 months of data on the local client (stored, by default, in the user’s profile folder in an OST file). As long as you have enough bandwidth and storage space, you should be fine with those settings. However, features like Windows Search can cause a significant amount of overhead while it indexes your entire offline data store. It’s not a huge deal, but it became readily apparent when my aging laptop temperature started to exceed the 100-plus degree Texas summer heat while performing the initial synchronization.

• Outlook 2013 UI: Overall, I like the new Outlook 2013 UI (especially the default setting on in-line replies from the “Reading” pane). There are some things I don’t like, though. As many people have complained, I find that the overly white/washed-out appearance of the new Office 2013 ribbons and toolbars to be a step backward in usability and aesthetics. Perhaps over time, I’ll get use to the new look. Or, better yet, Microsoft will listen to the feedback and offer some customization options (as they did with Visual Studio 2012). It’s not a deal-breaker, but it might affect some users’ willingness to use the Office 2012 Beta.
• Office Updates: I think most of us who have come to rely on online services have tended to like the idea that new updates and features can be rolled out seamlessly online. In general, being able to use the newest features is a good thing. However, there’s always a chance that an update will make things worse from a usability or functionality perspective. I don’t think it’s an “issue” exactly, but there’s a potential for unwelcome changes to occur. Personally, I’m not worried and will address any problems if/when they arise.
• Preview-related downtime and issues: I did experience the inability to send messages from my Office 365 account for almost an entire week. More details on that issue can be found in a previous post, Cloud Services: The Importance of Technical Support.

Potential Preview Program Pain

The Office 365 Preview is just that – a pre-release version of the final services that Microsoft plans to release. It comes with limited support offerings, and users should expect at least some problems. I’ll probably be ready to sign up as soon as the service goes live, unless anything unexpected comes up before the general availability of the new service.

One important statement in the Microsoft Office Preview FAQ is that existing data (calendars and e-mail) will not be migrated automatically. It reads:

· The Preview is separate from your current Office 365 service and is for temporary use only.

· When the Preview ends, all data in the Preview account will be deleted, including email and calendar data, web sites, and uploaded documents, so be sure to download any information that you need to keep.

It will be inconvenient if I have to back up my entire Exchange mailbox to a .PST file and then re-import it. However, it wouldn’t take a lot of my time and effort to accomplish (now that everything is consolidated and organized as I want it), though it will consume significant Internet bandwidth. Either way, I’m psychologically prepared for the eventual transition.

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.

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.

In my previous post, Reasons for Moving from Gmail/POP to Office 365, I described many of the limitations of my Outlook/POP/Gmail approach to managing e-mail. In this post, I’ll talk about the reasons I decided to take the plunge and move to the Office 365 Preview.

Based on the issues I had with my older configuration, I decided to look into Outlook.com and Office 365 as a solution. Here’s a list of the primary benefits. For the most part, these improvements directly address the problems listed earlier.

Note: Some of the following also applies to Microsoft’s free e-mail offering, Outlook.com, but this section focuses on Microsoft’s hosted Exchange / Office 365 service offering.

Office 365 Messaging Benefits

• Improved Web/Client Interface: Though I occasionally used the Gmail web-based interface, I could never stand to use it for more than just the most basic messaging tasks. The process of organizing, replying to, and sending messages was too cumbersome for me. I tend to format my messages with tables and other options where needed, and that was just too clumsy for me to perform via the web interface. I know that a lot of people like Google’s approach to a conversation-based views and the use of labels instead of folders, but I found the process of organizing e-mail to be so tedious that I wouldn’t do it. Instead, I always used the full Microsoft Outlook client wherever possible. Though that required other services to back up the local .PST file, I was able to use a much better user interface. The updates to Outlook.com and Office 365 changes all that for me – I can now use drag-and-drop and familiar keyboard shortcuts to create and manage messages. It also manages my Contacts and Calendar without the use of other integration methods. And, with the ability to perform on-demand installations of Outlook directly from the Office 365 Admin page, I can make sure that I get the full Outlook client installed and configured on my frequently-used Windows machines.
• Elimination of PST File Synchronization: With Office 365, all of my data is stored online and there’s no need to synchronize and backup separate .PST files. I can now keep Outlook 2013 open all day, every day, on several different computers and mobile devices and I never have to worry about missing any changes.
• Efficient Local Storage: While cloud-based access has been reliable for me in the past, for performance, backup, and peace of mind, I prefer to have a local cache of my data. Outlook 2013 uses a more efficient, compressed .OST file format that keeps all e-mail synchronized locally on my machine. Outlook 2013 provides some great improvement for Cached Exchange Mode though .OST file improvements. You can now specify how much data is cached locally, and the .OST file sizes benefit from compression (in my tests, I got around a 50% reduction in storage space when I compared similar .OST and .PST files). For more information, see What’s New in Outlook 2013.
• Consolidation / Historical Data: With Office 365’s generous storage space (25GB per user, in my plan), I was able to transfer all of my historical e-mail to a single hosted Exchange account. I no longer have a need to archive data in separate PST files or periodically strip out attachments. By default, Outlook will cache one year of data locally. That’s probably plenty for most users. On my primary computer, I chose to download the entire list of messages for easy indexed searching.
• Better support for mobile devices: While IMAP (and, to a lesser extent, POP) are acceptable options for accessing e-mail on multiple devices, it can be a tedious and error-prone chore to keep track of folder structure, calendar items, contacts, and changes from multiple devices (especially those that are occasionally disconnected from the server). With Gmail, I relied on the Gmail Notifier and Google Calendar Sync applications (both of which are years-old and poorly supported) to try to keep things in sync. With Exchange Active Sync, all of this works flawlessly (so far) on my Android Phone (Motorola Droid), Android Tablet (ASUS Transformer TF101) and Windows-based machines.
• Attachment Archival: With the storage space offered by Office 365, I no longer need to worry about archiving off attachments to keep my .PST file small enough for frequent backups. No need to remove attachments due to unlimited storage space.
• “Automatic” backups: An obvious benefit of having all of my messages stored online is that there’s less of a need for local backups. I still periodically export my data store to a .PST file, but that’s a quick and simple operation.
• On-demand / Streaming installations: The ability to automatically download, install, and configure an instance of Office 2013 in a matter of a couple of clicks is really powerful. Occasionally, I’ll be working in a VM or on-site on a client’s computer, and the ability to use a full-fledged e-mail client is excellent.
• Spam / Junk-Mail Filtering: Over the years, I have received as many as 24,000 spam messages per month. Thanks to Gmail’s excellent spam filtering, only an extremely small number of bad messages would get through. So far, Office 365’s spam filtering has seemed to work fairly well, though I’ll need more time to evaluate how it compares. I do like the ability to quickly and easily allow or block specific senders, though.
• Push-Based Notifications: In my POP-based approach for receiving messages, I had configured Outlook to regularly poll for messages. It worked fine, but there was a potential delay of a few minutes before I received messages. Unfortunately, that little delay is often enough for some of clients to start to panic when they don’t get a (really) quick response to an issue. With Exchange-based messaging, I can get near-instant notifications to my desktop, laptop, tablet, and mobile devices.

Sounds good. How do I sign up?

That concludes the “short list” of potential benefits of my e-mail migration hopes and wishes. In the next post, I’ll provide details on how I migrated to the Office 365 Preview.

For the last five years, I’ve relying on a fairly typical e-mail approach: A Gmail account that I occasionally manage online, but most commonly access through the use of Outlook via POP. I also used a custom domain name so I can have a permanent e-mail address. I documented the setup in an earlier blog post, My E-Mail Setup: Outlook + Gmail + a Personal E-Mail Address.

For a free online e-mail implementation, that approach has worked well for several years. But it left many everyday annoyances. Over the last couple of weeks, after Microsoft’s release of its Office 2013 Preview and Office 365 Preview (both available in free evaluation versions), I decided to re-examine my current setup. I have a lot of information related to the reasons for the move, steps in the migration, and pros/cons of the Office 365 approach. To keep things manageable, I have split the content into several posts. My hope is that the information in these posts will help others who are considering a move to Office 365 or a different hosted e-mail solution.

In this post, I’ll start with a quick overview of what prompted the move for me.

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.

User Profile: About Me

First, a basic background on me and my e-mail needs: I’m an independent IT consultant that does most of my work from home. Occasionally, I travel and visit client sites, and need the ability to access at least my most recent messages. I use multiple devices (an Android phone, an Android tablet, a Windows notebook, and multiple Windows desktops and servers).

I have about 10 years of e-mail stored in Microsoft Outlook .pst files. In the past, I’ve been diligent about periodically removed all attachments from my messages using various scripts, macros, and utilities to lower the PST file size (that makes online backups quicker and more efficient). For me, one of the most important promises of cloud-based solutions is for small businesses like mine to be able to access infrastructure components (like Exchange and SharePoint services) that are typically reserved for larger organizations.

Issues with Gmail, POP, and Outlook

OK, back to the show: My original Gmail/POP/Outlook configuration worked pretty well, but there was clearly room for improvement. Specifically, here’s a list of some of the issues and considerations I had in mind when deciding to migrate:

• Message and Folder Organization: I have never liked the Gmail approach of using labels rather than folders. While folders were available (and accessible using IMAP), I strongly preferred using the Outlook client’s UI for managing my messages. I’m used to drag-and-drop, familiar keyboard shortcuts, and efficient ways of keeping my Inbox clean. I have always found the use of the Gmail web interface to be clunky, time-consuming, and outdated (even though it’s arguably one of the best web-based interfaces).
• Multiple sets of rules (Outlook and Gmail): I have been using the same e-mail address for about 7 years, and I make little effort to try to conceal it (it’s Anil@AnilDesai.net, in case you’re wondering. 🙂 ). One way I maintain sanity is to try to keep my Inbox down to just a few messages at a time. In order to do that, I use rules to transfer messages like newsletters, common feedback and online notifications. The main goal for me is to make sure that I limit interruptions that are received in my Inbox. Newsletters, notices, and other information are automatically moved to other folders. With the Gmail/Outlook implementation, I actually setup rules on both the Gmail web site (to avoid having a large number of unread messages) and in Outlook. It took some effort to keep these rules in sync.
• E-Mail Addresses: I use a custom domain name (AnilDesai.net), and have used one e-mail address (Anil@AnilDesai.net) for almost all communicates over the last five years. While Gmail allowed me to change the reply-to address on my messages, Outlook has a nasty habit of adding an “on behalf of” to the From address. So, my message typically appear as being sent from “Anil.Desai1@gmail.com on behalf of Anil@AnilDesai.net”. Sending, receiving, and replying to the messages works as expected, but I found that even technical people seem to be confused by it. So many of my clients and users tend to respond manually to both my Gmail and custom domain addresses, and I can’t seem to train them out of it.   Note: Apparently, Microsoft is aware of the feedback.  From the Outlook Blog post titled, “Upgrade from Gmail to Outlook.com in 5 easy steps”

A side note on "Sent on behalf"

You may notice that messages you send using your Gmail address will be sent "on behalf of" your Gmail account. This means that Outlook is actually sending the email, but setting the "From:" address to be your Gmail address. The From: header in most email clients will look something like this:

From: myname@outlook.com on behalf of Dick Craddock (myname@gmail.com)

We’ve gotten feedback from some of you that you don’t like the "on behalf of header" and so we’re working to change this – stay tuned!

• Syncing Calendars and Contacts: For many years, I’ve relied on a few utilities to keep my online data in-sync with my Outlook client. That includes the use of the Gmail Notifier application and Google Calendar Sync, both of which seem to have been abandoned many years ago my Google itself. The utilities would often crash, and had to be run regularly in order to keep data in sync. Google is clearly focus on its own paid service, Google Apps for Business.
• Offline Access: Gmail offers the ability to cache messages and to work offline by using its Gmail Offline Chrome Browser Extension, but the experience for me was rather clumsy. For one thing, I had trouble getting my Sent Items to be stored properly in Outlook, and I was stuck with using the clunky web-based interface. It worked, just not well enough for me to like using it.
• Managing Multiple E-Mail Addresses: While I prefer to keep things simple, having multiple e-mail addresses is often unavoidable. For now, I have three (one Gmail, one Outlook.com, and one Office 365). I tend to use only my custom domain name for all messages, regardless of which account I’m actually using. Microsoft, Google, and other online messaging providers are very generous in allowing you to “pull” (via POP/IMAP) or push (via forwarding) messages between accounts. However, I found that, when forwarding to Gmail, everything would just be lumped into my default Inbox, prompting me to eventually reorganize the messages in Outlook. It was manageable, but definitely tedious and labor-intensive.

Don’t get me wrong: The solution did work, overall. It just left a lot to be desired (details are later in this series of posts).

Issues with Gmail and IMAP

One potential solution to some of the above is to use IMAP (instead of POP) with Gmail. While the concept of accessing e-mail via IMAP makes sense, I found that it didn’t actually meet my needs for real multi-device management of messaging. First, there’s a fairly long list of Gmail IMAP Issues available that lists some of the problems I ran into. My main hesitation is the number and frequency of reports people have posted regarding problems with sending, receiving, and organizing their messages. On numerous occasions, I have had to “trick” Outlook into sending the messages by reordering, deleting, or copying messages from my Outbox to other folders. Also, the folder management structure didn’t seem to be nearly as flexible as that of a standard Outlook PST file.

Without going into too much detail, I found that using POP and local Outlook .PST files worked best. I tend to use my primary desktop computer for at least 90% of my work, so for others that are more mobile (and that don’t have access to other methods), IMAP might make sense.

The End (of the Beginning)

OK, so hopefully the stage is set: The characters (me) have their motivation (to address the aforementioned technical and usability issues). In my next post, I’ll cover Office 365: Benefits and Features.