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Deciding to use Office 365 Exchange Online for your business emails is one thing. Moving mailboxes from your on-premises Exchange environment to Microsoft´s cloud is another.

Anyone who has performed a migration from a local Exchange Server to Office 365 knows that the process can be a daunting, quite complex undertaking that takes a good deal of proper planning and effort to keep things from going wrong (and avoid blowing IT resources).

Hedge your bets and turn your migration to the online service into one happy experience with a lot less stress and zero downtime with our Office 365 Exchange Online migration checklist (we packed a couple of best practices, too).

First things first - choose the right migration method

Start with the obvious. Before you begin moving your mailboxes to Office 365, assess your existing email environment and distinct business needs to determine which type of migration will be most suited for your organization.

Don’t be intrigued by some of the marketing hype surrounding Exchange Server to Office 365 migrations. There is no one-size-fits-all formula for moving your mailboxes to the cloud in three easy steps that let you take the switch in stride. In reality, only the smallest businesses get off lightly with these simplified migrations.

All Exchange Server migration scenarios are not created equal. In essence, you have to decide between a few possible migration routes from on-premises Exchange to Office 365, depending on how fast you aim to complete the switch, how many users need to be moved, and how ample your IT resources are. Before you jump in at the deep end, have a look at Microsoft’s collection of migration best practices that will give you a leg up.

These are your migration options:


1. Cutover migration. Move all of your mailboxes at the same time. You might want to opt for this “bite the bullet” migration type if you operate less than 2000 mailboxes and want to get things done as quickly as possible. Even though cutover migrations are designed to be easy, they might not always be the best solution as the transition to Office 365 has to be completed in one go. Cutover migrations are battering-ram projects – they can pose considerable challenges even for small organizations as they tend to quickly bring IT departments to their administrative limits. If users tend to have excessively large mailboxes, moving them from an on-premises environment to Exchange Online might take up an unacceptable amount of time to complete. Before you decide for a cutover migration, make sure you have sufficient resources to hand.


2. Hybrid Exchange deployment. If you want to move mailboxes gradually and in small increments over time, a Hybrid Exchange migration might be the best choice as it allows you to integrate your on-premises Exchange environment with Office 365. In principle, a hybrid deployment facilitates the possibility to maintain a mix of on-premises and Office 365 email users for a certain amount of time while getting the look and feel of one unified Exchange environment.

 If you decide for a hybrid deployment, you will need to manage both on-premises mailboxes and those in the cloud, which can quickly put a strain on your IT resources (and get your goat). On the bright side, a hybrid deployment will probably be the most convenient method for users as they can access resources both online and offline with only one set of login credentials via single sign-on while you can easily manage password policies through Active Directory and remain in full control over security (the servers used for single sign-on are managed in your on-premises environment).


3. Staged migration. This type of migration lets you move mailboxes in batches from your local Exchange Server to Office 365 Exchange Online, which makes it your best bet if you have to juggle more than 2000 users and want to scoot them over to cloud-based email as quickly as possible.

 Sounds pretty much like a Hybrid Exchange migration to you? Well, yes and no. While in both cases there will be some mailboxes in your on-premises Exchange organization and some in the cloud, the difference lies in the length of co-existence of the two environments. Contrary to a staged migration where mailboxes are intended to be moved to Exchange Online as quickly as possible, a hybrid deployment is designed for you to simultaneously operate on-premises and online mailboxes for an extended timeframe.


4. IMAP migration. Go for an IMAP migration if you migrate mailboxes from a non-Exchange environment to Exchange Online. In some instances, IMAP migrations serve as a shortcut when moving mailboxes from outdated Exchange Server versions (Exchange 2000 and newer are supported). That sounds good in theory, however in practice you will be able to do only that – as IMAP migrations are incapable of migrating anything other than e-mails, you will lose contacts, calendar entries, and all other tasks during the switch to Office 365 Exchange Online


5. Third Party migration. If you want to migrate emails from platforms like IBM Lotus Notes or Novell GroupWise to Exchange Online, you can resort to a vast number of third-party tools (Binary Tree, BitTitan, Dell, SkyKick, etc.) that provide protocols and best practices to help you migrate mailboxes to Office 365.

In the right ballpark – calculate your time commitment

How long will it take to move your mailboxes to the cloud? The answer is it depends upon a host of factors.

No matter what route to the cloud you take, you will undoubtedly be concerned about any kind of impact on network performance and downtime during the migration, and what you can expect in regard to the data that travels between your on-premises Exchange Server and Office 365 Exchange Online. To ensure a smooth migration that leaves no one frustrated, it is paramount to tally up and accurately calculate the hours your migration project will take.

To reduce costly network downtime, plan carefully as to how and when you will move your mailboxes and how many of them you will move at the same time. Consider the average mailbox size, the number of mailboxes you will migrate, and the overall bandwidth you will have available through your internet connection to accurately estimate the transfer speed you should factor in (other cloud-based Office 365 services such as SharePoint and Lync Server can affect the bandwidth available for your email services).

Microsoft provides a useful overview outlining the average throughput you should expect during an Office 365 migration.

Hardware matters - don’t skimp on infrastructure

Before you can start
moving mailboxes to Office 365, you have to meet a number of infrastructure requirements to make the switch work. In case of a staged migration, you will need two servers – one running Active Directory Federation Services to handle identity management between your on-premises environment, one to facilitate the migration process itself. Both of them need to be suited to accommodate the required workload.

Technically, the migration server can run on virtual hardware. However, quality is worthwhile. Using a non-physical server for migration can quickly result in considerable performance problems you don’t want to encounter. Steer clear of budget solutions if possible and facilitate physical, enterprise-class hardware as Microsoft recommends especially to larger businesses.

Old becomes new - polish up your Active Directory

For any Windows-centric organization, Active Directory is the backbone and source of all authentication across entities. Before
migrating mailboxes to Exchange Online, it is important that you bring your on-premises directory up to date to properly prepare for cloud or hybrid environments.

Here is why: When you move to Office 365, you are required to link your on-premises Active Directory to Microsoft’s cloud-based directory Azure AD in order to sync between the two environments. It hardly needs mentioning that this can only work well if your local Active Directory is cleaned up and in well-organized shape – something that most older local infrastructures are not.

Vet your organizational readiness

Ready. Set. Go?

You already know that a staged migration is a complex undertaking. If you haven't properly prepared your local Exchange Server deployment, the migration process may fail. To help you succeed, Microsoft provides Office 365 Health, Readiness and Connectivity Checks that allow you to assess whether your organization is ready to migrate - either perform a quick check of key readiness aspects, or use the tool to carry out a comprehensive readiness assessment.

Think about the clients, too

How do you want users to access their mailboxes after the move to
Exchange Online? While you set up your organization for an Office 365 migration, make sure to verify client readiness, too. In case you're planning to connect users to their mailboxes through Outlook Web App, checking up on client readiness is as easy as verifying browser compatibility. If you want users to access their mailboxes via Outlook, carry out a software inventory to ensure compatible versions of Outlook are implemented throughout the organization. Did you know that POP and IMAP connections to Outlook 2003 are not supported with the use of Office 365?

Some more tech facts:

In general, Microsoft recommends to use Outlook 2010 or Outlook 2013 for Office 365 connectivity. Be aware that Outlook 2010 may need to be configured manually in order to connect to mailboxes with the use of Office 365. As such, it might be a smart move to test ahead of time to identify any connectivity problems you could encounter after mailboxes have been migrated.

Test. Test. Test.

You’re almost there.

If you don’t want to leave your mailbox migration to chance, go the extra mile and plan for a pilot migration - it will save you hours of damage control and a whole deal of frustration later on. Ideally, you set up a whole pilot program comprising several stages to verify your migration technique and make sure that all users will be able to work effectively after moving to Exchange Online.

Sounds daunting? It really isn’t.  Consider it nothing more than a migration test – create a few test mailboxes, load them up with messages, calendar entries, and contacts, and move them over to Office 365. If all goes as expected, take your pilot program one step further and migrate a representative sampling of your mailboxes.

While testing, expect bumps along the way – even welcome them. Uncovering problems during the pilot migration will only help ensure a smoother, quicker migration later on. The gist of it? Don’t rush it. After the pilot migration, allow for some time to discover any post migration issues that could jeopardize your migration project as a whole. Make sure all is working fine before moving everyone else.

Don’t migrate in haste

There's no rule dictating you have to perform a staged migration in a rash and close down your
local Exchange Server environment immediately afterwards. Quite the contrary is true. You can keep up co-existence between your on-premises Exchange and Office 365 Exchange Online for as long as you want. Even maintaining both environments for an indefinite amount of time is fine – it’s your call. In fact, it might be a good decision to spend some time getting familiar with Office 365 and its functionalities first before putting your local Exchange Server environment out of operation.

Get the right tools for your switch to Exchange Online

To help you along, Microsoft provides a number of handy
migration tools you should take advantage of to simplify the migration process. Besides the Office 365 Health, Readiness and Connectivity Checks, you can resort to the Microsoft Exchange Server Deployment Assistant, which will ask you questions about your migration and then create a migration plan for you. There are also third-party tools available to start you off – Metalogix Cloud Acceleration Suite for Office 365, Dell Migration Manager for Exchange, Binary Tree E2E Complete, to name a few.

After the migration: Take your emails even one step further with professional corporate email signatures

Emails are at the heart of business communication. Outbound and in-house – the amount of emails sent daily in large corporations is impressive. According to the
Email Stats Report, an employee crafts roughly 40 emails each day. Adding up the numbers, an organization with around 2,000 employees produces up to 80,000 emails in one single day. On a yearly average, that adds up to a striking 20,000,000 emails.

Moving mailboxes to Exchange Online and harness the power of cloud-based emails for users to work more productively is one thing. Making emails stand out to promote your brand is another.

Email signatures are your online business card. Filled with the right information, they not only create a stylistic impression, but also help to popularize your corporate brand.

Don’t leave email signatures to chance. Templafy’s Email Signature feature is the simple, dynamic way to manage email signature design across a multitude of users, business units, locations, and languages. While the current version of the feature is only available for Outlook clients running on Windows, Templafy’s developers are already working eagerly to support email signatures across different devices and platforms to make email signature management even more effortless on an enterprise scale.

Keen to learn more? Click the link below to receive our ultimate guide for enterprise email signature solutions to easily manage email signatures across your organization.

     Download Free Guide     

Enterprise email signature management


Enterprise email signature management

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