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Moving Into Microsoft’s Suite OfficeAdopting Office 365 is an attractive proposition for IT departments. Actually pulling off a successful migration is daunting, yet quite doable.

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The Suite Life

The significant waves made by Office 365 are difficult to ignore, and its myriad ben-efits and application upgrades put pressure on IT departments. Maybe you’re wondering if it’s time for your organization to make the leap.

A successful migration to Microsoft’s cloud-based suite of Office tools means starting in the right place and making a full assessment of your organization’s existing environment. IT should look closely at the business from all angles and then target migration planning to the areas in which 365 will be most involved. Syncing the right technology, identifying patches and assessing mail infrastructure are just some of the essential tasks in preparing for migration.

This three-part guide offers help with this complicated process. First, Microsoft expert

Steve Goodman identifies where IT should begin and how it should work its way through an assessment. He outlines a mail migration, discusses how organizational size plays into the decision-making process and speaks to the intricacies of Office 365.

Next, Neil Hobson touches upon the must-know apps for Office 365. He covers the major applications, and discusses potential complica-tions that may arise when users are accessing Office 365 on mobile devices.

Finally, Goodman writes about how to build a remediation plan and how a pilot program can serve as a dry run prior to implementation. n

Patrick HammondAssociate Features Editor

Data Center and Virtualization Media Group

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Migrating to Office 365

Transitioning to Office 365 (or any new productivity system) can be disruptive to a business for both good and bad reasons. A suc-cessful migration should enhance productiv-ity, whereas a troublesome migration can cause pain for end users and potentially even lead to lost revenue for a business.

This is certainly the case with Office 365, which comprises a number of different inte-grated platforms: Exchange Online, SharePoint Online, OneDrive for Business, Skype for Business Online, Office Pro Plus and Yammer. You should consume all—or at least most—of these services in order to make the investment worthwhile.

STARTING POINT

Most organizations start with Exchange Online and first migrate email to the cloud. This is often done in conjunction with a rollout of

the new Office Pro Plus client. By starting the migration this way, a core business system is moved to the cloud and the business will see an early return on investment (ROI), often with minimal interruption to users.

When creating your adoption plan, be sure that senior executives understand and support the overarching goal. Users also need to be in the loop. This is often best achieved via a series of workshops, all-company meetings and regular, friendly communication. If there are desk visits or a small degree of disruption, it is helpful to keep users informed of the business vision.

Any successful migration requires a thorough understanding of the current environment. With Office 365, this process means gathering information about the number of employees at each site, where specific departments are located within the organization, network links between sites, along with existing firewall and

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supporting proxy server infrastructure.Identity forms the core of the relationship

between the source environment and Office 365. Azure Active Directory, Office 365’s underlying identity service, will have a copy

of on-premises Active Directory accounts. It’s important to carefully examine information about security requirements, such as if multi-factor authentication is needed for external access to email.

The User Principal Name, or the Windows 2000 Account Name in Active Directory, is usually copied to Office 365 and instituted as the login ID. Alternate Login ID is not typi-cally suitable for email migrations. Therefore, you will need to update User Principal Names to use a valid Internet-routable domain name system suffix. The most appropriate option is usually to make the User Principal Name match

the email address.You’ll also need to understand which objects

you want to sync—this decision should be made based on the Organizational Unit and the total sync count. Any errors within the data being synced must be identified using Microsoft’s IDFix tool, which is provided in the Office 365 portal.

MIGRATION PLANNING

For a mail migration, performing an assess-ment of the email environment is a must. In particular, ensure you understand the current Exchange (or third-party) versions and the cor-responding patch level. You should know how Exchange Server is published to the Internet and if valid SSL certificates or pre-authenti-cation are used. All in-use, accepted domains will need to be registered within the Office 365 tenant.

Check the number of mailboxes in use, includ-ing shared mailboxes, for license assessment and migration planning. Understanding how long a migration will take becomes clearer once you know the mailbox size and item counts.

Check the number of mailboxes in use, including shared mail- boxes, for license assessment and migration planning.

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If your organization uses many public fold-ers, then you need to understand whether you can migrate to another platform, such as Share-Point. Another option may be to move the functions to shared mailboxes. Public folder co-existence is available but ideally avoided.

Third-party systems are often the Achilles heel of mail migrations because they may need upgrades either before or after a migration. These include unified messaging integration with an IP-PBX, anti-spam systems, journal-ing and archive systems, fax software, signature software or client-side add-ins.

Client versions are equally important. As of early 2015, a fully patched Office 2007 client was the practical bare minimum for con-nection to Office 365. A fully patched copy of Office 2010 works well, and Office 2013 or higher provides the best experience and all new features.

You will also need to understand the mobile estate that’s in use within the organization, including ActiveSync clients and mobile device management products. Mobile devices will often need reconfiguration—and possibly replacement—at the time of migration.

DECIDING ON THE BEST APPROACH

The two best migration approaches are using hybrid technologies or relying on a third-party migration tool. The other Exchange options, staged and cutover, are only suitable for smaller organizations. Internet Message Access Proto-col (IMAP) works, but it is very limited unless you run a simple open-source mailer.

n A hybrid migration effectively extends the on-premises Exchange organization into Office 365. This enables secure mail flow, native sharing and full-fidelity mailbox moves, the latter of which allows the pre-staging of data, automatic client reconfiguration and retention of the offline cache. A hybrid migra-tion requires the most preparation, but for larger or complicated organizations it has the biggest payoff. Hybrid works with Exchange 2010 and 2013, and a hybrid “bridge” server can be installed into Exchange 2003 and 2007 environments.

n A third-party migration using products such as BitTitan’s MigrationWiz, BinaryTree’s E2E Complete, and Refresh IT tools is the best

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experience for organizations that do not have the time to implement—or cannot imple-ment—a hybrid migration. These tools provide similar pre-staging technologies and in some cases can accelerate the process by migrating recent data first and then legacy data after the user switches. These tools usually include cli-ent reconfiguration and automation technolo-gies. Third-party tools work with all common Exchange versions and a wide range of third-party mail servers like Lotus Notes or Google Mail.

n Cutover migrations work for smaller com-panies, as directory sync is available and the entire organization is switched in a single operation. On the day of the move, every cli-ent must be visited and reconfigured, and all users must be provided a new password with which to access Office 365. Cutover works with Exchange 2003 to 2013.

n A staged migration—another good choice for small organizations—makes use of the same Directory Sync technologies used in a hybrid

migration, but copies data with Outlook Any-where. A staged migration is a one-shot migra-tion per user. After each batch, single users are visited and the client is reconfigured.

IMAP migrations are great for open source mail servers, such as UW-IMAPD, Dovecot and other similar systems that provide a rudimen-tary experience. Like staged migrations, a batch is created and mail is copied in a single run. When a third-party tool is not available, IMAP can be used to migrate mail from other third-party systems that support the technology, such as Lotus Notes.

If you’re using a third-party archiving or journal system like Symantec Enterprise Vault, then a third-party archive migration tool is often required. Archive migration tools from companies including BitTitan, Transvault, SimplyMigrate, Archive360 and QuadroTech take some of the pain out of extracting data from the source archive and loading it into Office 365. In addition, these tools often clean up the “short cut” stub data to ensure that the mailbox is clean and functional for the user. —Steve Goodman

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Must-Know Apps for Office 365 and Exchange

With an increasing number of avail-able apps for Office 365, it can be difficult for organizations to determine which ones should be deployed and used in conjunction with the software. The answer varies, but Exchange administrators must know which apps are used and how they work with their organi-zation’s systems. If your organization uses cloud services such as Office 365 or Azure Rights Management, take the time to research the apps that are likely to be of value in your organization.

Email and Microsoft Office are likely the first two applications that come to mind. Most end users can’t operate without email, so a mail app that connects to an Exchange Online mailbox is something many consider essential. For Win-dows Phone users, Outlook Mobile is already included and allows for Exchange ActiveSync connectivity to Exchange Online. Microsoft offers an Outlook Web App (OWA) for Office

365 that provides iPhone and iPad users with mobile functionality, such as offline access to mailbox items.

Most end users will also want to view Office documents on mobile devices. To facilitate this, there are versions of Microsoft Office available for a number of device platforms. Office Mobile is built into the Windows Phone operating system and allows users to view and edit Word, Excel and PowerPoint files. A version of Office Mobile is also available for Android users.

For Apple devices, Microsoft offers Office for iPad and Office for iPhone, complete with indi-vidual Word, Excel and PowerPoint apps. As an Exchange admin, be sure you understand the core Office apps your end users have, and also related apps such as OneNote and OneDrive for Business. End users may be storing files in multiple locations, which makes the latter group of apps all the more important.

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For organizations using Lync Online in Office 365, there are apps for Lync 2010 and Lync 2013 on Windows Phone, Android, iPhone and iPad. These apps bring Lync features such as instant messaging and audio conferencing to the mobile device.

Not only will systems admins likely want to use the Lync app as part of their day-to-day duties, but they’ll also want to be aware of any functionality restrictions applicable in some countries. More information on these apps can be found on the Office on Microsoft’s Mobile Devices site.

There are apps for Office 365 that appear within existing products such as Outlook or OWA. Exchange Online comes with five apps

that are enabled by default and available to all end users. The Bing Maps app, for example, displays in Outlook or OWA the map location of physical addresses that appear in email. To find these apps, Exchange admins can launch the Exchange Admin Center, navigate to the Organization pane and then click the Apps tab. The Action Items, Bing Maps, My Tem-plates, Suggested Meetings and Unsubscribe features are then revealed.

In addition to Office 365, an organization can deploy other cloud services, such as Azure Rights Management. If this is the case, con-sider the Rights Management sharing app that’s available for Android, iOS and Windows Phone mobile platforms. This mobile app allows end users to view protected files, as well as protect pictures they might want to share. If they want to protect files other than pictures, they’ll need the Rights Management Services app for Windows. These apps can be down-loaded from the Microsoft Rights Management portal. —Neil Hobson

In addition to Office 365, an org-anization can choose to deploy other cloud services, such as Azure Rights Management.

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Remediation and Transitioning to Office 365 Services

Once an IT shop has assessed its current environment in preparation for an Office 365 migration, a clear remediation plan is required. This should cover areas that are required to prepare the source environment for the imple-mentation, based on the chosen migration approach—hybrid, third-party, staged, IMAP or cutover.

There are numerous areas that typically require remediation. These include patch-ing the Exchange environment, updating User Principal Names in Active Directory, imple-menting corrections recommended by the Microsoft IDFix tool, replacing or obtaining additional SSL certificates, updating Proxy Server exclusions, modification of firewall rules, acquisition and implementation of band-width upgrades, correction of DNS entries and patching of Office clients.

The assessment should provide a list of accepted domains that must be registered

within Office 365. The first tasks therefore should be to verify the domains and add them to Office 365. At this stage, no MX records are likely to be switched.

If you plan to use the cutover migration approach, then you will use a CSV file to cre-ate an import file instead of relying on direc-tory sync tools. After the cutover migration completes, you could choose to implement the identity management tool set.

Other migrations typically require a little more preparation, although third-party tools do make this optional. Identity management implementation usually starts with installation of Windows Azure AD Sync Tool (DirSync) or, for multi-forest environments, Azure AD Sync Services (AADS)—these copy and link user accounts from AD to Azure AD in Office 365, and may also copy the hash of passwords. DirSync with Password Hash Sync meets requirements for many organizations and is a

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simple installation that allows the sign-on with the same password as used with AD.

IMPLEMENTATION STEPS

For organizations that require true single sign-on or integration with on-premises multifac-tor authentication systems, Active Directory Federation Services (ADFS), a component of Windows 2012 R2, is used in conjunction with Windows 2012 Web Application Proxy in the DMZ. ADFS can then be federated with Office 365, meaning all password requests are redi-rected to on-premises ADFS servers.

When migrating email, the implementa-tion steps depend on the specific migration approach.

A hybrid environment will need either an Exchange 2010 Client Access and Hub Trans-port server or Exchange 2013 Client Access and Mailbox server—if neither are currently installed in an Internet-facing site. This does mean that enabling hybrid for Exchange 2010/2013 is simple, but enabling hybrid for older organizations is similar to the first steps of an Exchange migration. Assuming

prerequisites such as firewall rules have been configured, the Hybrid Configuration Wizard implements all necessary connectors required for mail flow, mailbox moves and sharing.

A staged or cutover migration requires Out-look Anywhere to be configured and enabled externally, along with valid SSL certificates. An IMAP or staged migration also requires mail routing to be configured. This allows the accepted domains to be shared between on-premises and Office 365. At a minimum, an Outbound Connector is required in Office 365 to route email for the shared domain to on-premises.

Third-party tools differ, but most use either Outlook Anywhere or Exchange Web Services. Prerequisite configuration is similar to a staged migration when routing mail for co-existence is configured, but each tool has a different approach when performing the configuration. As an example, BitTitan MigrationWiz works best with a service account in both the source and target that can use impersonation to access mailboxes. A connector is created with creden-tials specified for both environments, and then accounts to migrate are added.

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ENABLING SERVICES

After configuration of base services and asso-ciated basic testing has been performed, other required services should be enabled. Office 365 Multi-Factor Authentication is provided with SKUs such as E3 and ensures that a physical device and password are required. Office 365 Mobile Device Management, which is based on Microsoft InTune, is also worthy of con-sideration. Office 365 MDM can monitor email profiles and Office 365 applications on mobile devices.

The actual transition, after thorough testing, should be straightforward. After basic test-ing, a technical pilot with users typically from the IT and Office 365 project team should be conducted. Obvious issues need to be identi-fied and corrected at this stage. In conjunction with wider communications planning, the pilot

group should be identified. This group should be a dry run of real migrations and include real-world users.

A successful pilot should then lead into the creation of schedules (and associated migration batches) for the transition of users to Office 365. This schedule should be clearly com-municated by the project team and take into account available resources to assist users with any desk-side reconfiguration needed. The migration often starts with smaller batches. As confidence grows, so does the pace of migra-tion. Be prepared to think on your feet through the migration and have the confidence to push forward when necessary, but also halt to deal with issues. Some issues, like sharing problems when users are split between the cloud and on-premises are best dealt with by moving the on-premises users to Office 365. —Steve Goodman

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ABOUT THE

AUTHORS

STEVE GOODMAN, an Exchange MVP, works as a tech- nical architect for one of the U.K.’s leading Microsoft Gold partners. Goodman has worked in the IT industry for 16 years and has worked extensively with Microsoft Exchange. He is the author of the book iPhone with Exchange 2010:

Business Integration and Deployment, co-hosts The UC Architects podcast covering Exchange and Lync, and regu-larly blogs about Exchange Server, Office 365 and Power-Shell at www.stevieg.org.

NEIL HOBSON is a U.K.-based Microsoft consultant with a background in the design, implementation and support of infrastructure systems covering Active Directory, Windows Server, Exchange and Lync. He is currently focused on Office 365 in technologies such as Exchange Online, Lync Online, SharePoint Online, Yammer and Office ProPlus. He is also focused on the associated areas of identity, networking, migration and service integration. Hobson is a member of the Chartered Institute for IT (MBCS) and held Microsoft MVP for Exchange Server status from 2003 to 2010.

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