"You've Got Mail!" - Now how do you move it?

By William Mabley on July, 22 2016

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William Mabley

Mail.pngToday’s Microsoft Office 365 platform is one of the most sophisticated and comprehensive Cloud computing Software as a Service (SaaS) offerings in the world. It offers significant advantages and benefits to its users: low-cost, increased collaboration; security; and dependability. As Cloud adoption rates continue to rise (just ask Google), more and more companies are looking for ways to take advantage of the Cloud. 

It starts with mail

If you were to poll a random group of people, they would likely agree that email started in the 1990’s with the iconic AOL alert “You’ve got mail.” Most people forget – or perhaps never knew – that email actually first came into use in the 1960’s at select educational institutions and government bodies. Since then we’ve seen the adoption of email spread to every corner of the globe. After launching their first online email platform in the early 2000's, Microsoft quickly became a leader in providing email solutions for the modern enterprise. Today, Exchange Online has become one of the biggest reasons for shifting from on-premises Microsoft servers to the Office 365 Cloud services. 

So, your organization is ready to move from on-premises email to O365. You likely have many questions about what’s required to actually migrate your current mailboxes to Exchange Online. Let’s look at a few of those questions.

How do I get started?

Migrating your mail to the Cloud is not a small project and, too often, companies underestimate the complexity (and the time) required to do it properly. There are many important considerations to address before your migration. In an earlier blog post, we looked at the top 10 considerations for migrating to the Cloud, which may be helpful to you. These considerations need to be addressed before you migrate and then you need to be prepared for after you have migrated.

What should a migration plan include?

You need to make sure your migration plan explicitly addresses three “prep” tasks:

  • Costs: You want to make sure that you understand the upfront costs to migrate to the Cloud, as well as the cost model and your expected savings once the mailboxes are hosted in the Cloud.
  • Security and Compliance: When it comes to security and the Cloud, the costs of not having planned adequately could be catastrophic, so make sure you ask the hard questions before you migrate so you are as prepared as possible. You want to make sure you understand data classification and related sensitivity level, and compliance/regulatory requirements. You also want to ensure you’ve developed a process for ongoing vulnerability testing.
  • Organization Infrastructure: If you haven’t done so already, you want to accurately assess the current state of your overall infrastructure and how it’s performing. Are there changes coming in the near term? In the long term? Having a baseline for performance of the current infrastructure will help you plan effectively (and measure improvements post migration), and keeping a line of sight on planned changes will make sure that you don’t unintentionally create rework later.

Can I do the migration myself? 

This is a good question and the answer varies depending on an organization’s maturity, priorities, and objectives. Our clients benefit from our involvement with the migration because we’ve done it before and they have not. This experience translates into practical advice that ultimately avoids critical deployment mistakes that result in a lot of rework and/or service interruptions. Migration partners not only can ensure a smooth transfer of all mailboxes, but can also provide strategic insights into what is coming in the future – helping you make the most out of every IT dollar. 

What skills do we need to do the migration?

As you build your migration team, be sure you have access to the following expertise and experience: Exchange, Office 365, archives, security, DNS, storage, firewalls, proxies, networking, Autodiscover, Active Directory, AD FS, DirSync, PowerShell, client app packaging, pushing out policies to endpoint clients, managing mobile devices, and ActiveSync policies.

What happens after we’ve migrated?

It’s a lot of work to get to get your mail migrated – but the reality is, once it’s migrated, it’s only the beginning. You need to prepare your users for the differences between the platforms but, perhaps even more importantly, you need to prepare your users so they become accustomed to frequent improvements (through releases from Microsoft) to the tools they are using.

Microsoft has traditionally had a three-year dev cycle (Exchange 2000, 2003, 2007, 2010, 2013, and 2016). Using agile design principles, Microsoft is moving to a three-month dev cycle with their product teams, developing first for O365, and later releasing the features in the boxed product. This means that things change just about as fast as you can learn how they work. Reports, portals, features, whole services – everything changes. It takes a huge investment of time to keep on top of developments and even more time to test all the new features before they become available to end users. But the last thing you want is to be caught unaware. This is another area where having a partner can be very helpful.  You may want to consider a partner to help you manage the service so you are not caught off-guard by updates and, similarly, you are maximizing your investment in Office 365.  


Office 365 migrations are not simple cookie cutter processes that someone can just "wing" over a weekend. They are complicated migrations that require expertise and need to be well planned.

If you’re interested in learning more about O365 Migration, check out our resource page.


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