So you’ve decided to make the switch to cloud-based email. Congratulations! Now you may want to consider how you’re going to get your data from your current email system into Exchange Online. What are your options?

Because no two organizations are exactly alike, Exchange Online provides multiple options for migrating to the cloud. The option you choose will depend on your organization’s requirements and scenarios. A few critical factors to think about when developing your migration plan are:

• Type of email system that your mailboxes are coming from
• The number of mailboxes your organization wishes to migrate to Exchange Online
• If you want to keep any mailboxes on-premises – either for a period of migration or indefinitely
• Your identity management and provisioning requirements

Here are some questions to help determine your scenario and the best migration option for you. We’ve also recently updated the Exchange Deployment Assistant with questions and instructions to help you get started as well.

Are you migrating from Exchange 5.5, Exchange 2000, or a non-Exchange email system (like Gmail)?

For any IMAP enabled messaging system (including previous versions of Exchange), you can migrate using our IMAP email migration process. This is a simple and low-impact way to migrate your users’ mailbox, email messages and email folders. An important thing to note is that this option does not migrate contacts or calendar items although many of our partners such as Quest or Binary Tree, BitTitan and Messaging Architects offer additional migration tools.

Are you migrating less than 1,000 mailboxes from Exchange 2003, Exchange 2007 or Exchange 2010 and would like to migrate all of your mailboxes in one shot?

If yes, Cutover Exchange Migration is the easiest way to provision cloud-based Exchange Online mailboxes and then migrate mailbox data to the cloud from your on-premises Exchange server. This option migrates your organization’s distribution groups, external contacts, email messages as well as other Exchange mailbox data such as calendar items, contacts and tasks. This allows you to migrate all of your mailboxes at once, such as over a weekend and is ideal for a small to medium sized organizations that desire less complexity and a short migration timeframe. You also do not need to install and configure the Microsoft Online Services Directory Synchronization tool or DirSync in this instance; this option is ideal if you plan on identity management entirely in the cloud. Please note that this method should not be used if you plan to maintain any mailboxes on-premises after the migration.

Are you migrating mailboxes from Exchange 2003 or Exchange 2007 and answer yes to one or more of the following:

• Would you like to maintain mailboxes in your on-premises organization?
• Do you have more than 1,000 mailboxes to migrate?
• Do you have requirements to pilot or stage migrations?
• You do not require calendar free/busy sharing between cloud and on-premises users?

If yes, Staged Exchange Migration may be the best option for you. This option allows your organization to move some mailboxes to the cloud over time while maintaining the rest of your mailboxes in your on-premises environment so you can migrate your mailboxes in discrete batches. You get a unified global address list for both your on-premises and cloud-based mailboxes but need to replicate user objects from your on-premises Active Directory directory service to your Office 365 environment to do so; this means you will need to install and configure the Microsoft Online Services Directory Synchronization tool and keep on managing user attributes in your on-premises Active Directory. For more information, see Plan for User Identity in a Staged Exchange Migration.

Are you migrating mailboxes from Exchange 2003, Exchange 2007, 2010 and either:

• Would like to maintain mailboxes both in the cloud and in your on-premises organization indefinitely
• May want to migrate all mailboxes to the cloud but have a requirement to pilot or stage migrations of mailboxes over an extended period of time
• Have a requirement to have the smoothest possible migration experience including free/busy calendar sharing between cloud and on-premises users, have a single Outlook Web App URL for both on-premises and cloud users?
• Do you wish to centralize control of mail flow so your on-premises organization can control mail flow for both the on-premises and cloud-based organizations?

If so, then a Hybrid deployment is likely the best option for your organization. This enables seamless calendaring between hosted and on-premises users and all email looks and feels internal to the company; recipients on email are resolved as internal, MailTips will work correctly and OOF messages to internal recipients will apply to both on-premises and Exchange Online cloud-based user mailboxes. Human resources teams or your compliance officers can conduct multi-mailbox searches/discovery across both on-premises and Exchange Online mailboxes. You can even move mailboxes back to on-premises if requirements or scenarios change and users’ Outlook profile is preserved so users do not need to resynchronize or create new .OST files.

In the hybrid scenario, an Exchange 2010 SP1 (or higher) server must be deployed on-premises which acts as a gateway to the cloud; larger organizations will typically deploy two of these servers for redundancy. There is no need to upgrade mailboxes to Exchange 2010 prior to moving them to the cloud if you are currently running Exchange 2003 or Exchange 2007. You can migrate and manage on-prem and online users from the same Exchange Management Console or using Remote PowerShell. Setting up a hybrid deployment has more steps to consider than the other options but provides the most flexibility, particularly if your organization intends to maintain mailboxes on-premises and in the cloud for an extended period of time.

Additional Options

Beyond those options, we have a number of partners such as Quest or Binary Tree, BitTitan and Messaging Architects who offer other rich migration tools and support, particularly if you are migrating from other email systems such as Novell GroupWise or IBM Lotus Notes and Domino. To check out a complete list of our partners, please visit our website.

Summary

We provide several different migration options because organizations differ greatly in size and requirements; it’s not a one-size-fits-all world and we would like you to help pick the solution that works best for your business. We’ve had a number of businesses successfully transition to the cloud – on their terms. http://www.youtube.com/user/MSExchangeTeam#p/u/8/nVOzQwVeA7Y

Optional Quiz

Now let’s take a little quiz see what these options look like applied towards real world scenarios.

Question 1

Tailspin Toys is a business that has 120 employees across Washington and California and currently manage their own Exchange 2003 environment that physically resides in a shared datacenter space. Their existing email environment is working well although their hardware warranty is going to expire very soon so their CIO Sanjay Jacob would like to use this as an opportunity to move to cloud-based email with Exchange Online. Sanjay noticed that they have an all-company retreat planned next month over a long weekend and would like to have all of their mailboxes migrated to Exchange Online by the time Tailspin Toys’ employees arrive back to work on Monday. What migration option is most suitable for Tailspin Toys?

a) IMAP Migration

b) Cutover Exchange Migration

c) Hybrid Deployment

Question 2

Lucerne Publishing is based in Toronto, Canada with 2,507 employees worldwide; each employee has their own email mailbox. Lucerne is currently on Exchange 2007 and is excited to move to the cloud as quickly as possible. However, their CTO Allison Brown would like for her IT staff and a few corporate executives to be part of a pilot and have their mailboxes moved first before eventually moving all of their mailboxes to the cloud in batches based on each office. There is not a lot of cross-office collaboration at Lucerne; employees work with teams within the same department and office location. Allison’s migration project management team needs to create a migration project plan based on what migration option they choose. Which option would you recommend?

a) Cutover Exchange Migration

b) Hybrid Deployment

c) Staged Exchange Migration

Question 3

Fourth Coffee is the world’s fastest growing retailer of coffee beans with thousands of coffee shops and retail stores around the world. Over the last decade, they have expanded their business into restaurants and cafes and manufacturing their own line of coffee-makers. They currently have 7,100 full-time employees with mailboxes and a mix of Exchange 2003, Exchange 2007 and Exchange 2010 mailboxes due to some mergers and acquisitions they have had in the past and would like to migrate mailboxes to Exchange Online in order to simplify and streamline their email services and would like to move to the cloud with the least possible impact or changes to end users. End users at the corporate offices all over the world collaborate very closely with each other; due to the nature of their global business, they also have strict compliance requirements which necessitate policies to centralize management and control of their mail flow including use of MailTips to provide warning messages for softer policy requirements and protection of some emails using Windows Rights Management Services so messages on new initiatives cannot be forwarded outside of the company. What migration option would be most suitable for Fourth Coffee?

a) IMAP Migration

b) Staged Exchange Migration

c) Hybrid Deployment

Answers

1. Answer: If you selected B, you’re correct. Tailspin toys is under 1000 seats, is currently using Exchange 2003 for their messaging system and their CIO wants to migrate all of their mailboxes at once. Both IMAP migration and hybrid deployment could feasibly work but cutover is probably the simplest for them to set up, migrates entire mailbox contents including calendar items and contacts and is ideal for a quick migration.
   
2. Answer: If you selected C, you’re correct. Lucerne Publishing has more than 1,000 mailboxes and wants to pilot migrations, so Cutover Exchange Migration isn’t an option. Hybrid and staged Exchange migrations are both viable options. Since it appears that the office-by-office nature of the migration will allow Lucerne to live without cross-premises free/busy sharing, staged Exchange migration will get the company to the cloud with the least effort. Hybrid deployment is still an option but may not be necessary.
   
3. Answer: If you have selected C, you’re correct. Staged Exchange Migration and Hybrid Deployment are other possible options. We do not know if they have requirements on timeframe for deployment or migration – perhaps they would like to migrate to the cloud very quickly or might have mailboxes for their corporate mailboxes managed on-premises indefinitely while migrating mailboxes for employees at their retail stores, shops and manufacturing to the cloud. However, we do know that they would like minimal user impact, their users all over the world work very closely together and they have some compliance or governance requirements which require them to centralize mail flow and have both on-prem and online users ‘look internal’ in terms of MailTips and IRM-protected messages. These requirements can only be fully addressed with a hybrid deployment.