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Migrate Exchange to Office 365 with these tips

Check this list of common issues that can occur during an Exchange migration to steer the organization away from potential mishaps during the messaging platform's relocation.

As several Microsoft server products are on the verge of losing support, some organizations will likely migrate Exchange to Office 365 or make another messaging platform transition.

In January 2020, both Exchange Server 2010 and Windows Server 2008 will move out of extended support, which will spur some Exchange administrators to prepare for an on-premises upgrade or a move to Exchange Online.

Editor’s note: A Sept. 16 blog on the Exchange Team site indicated Microsoft would push the extended support of Exchange Server 2010 from Jan. 14, 2020 to Oct. 13, 2020 "to give Exchange Server 2010 customers more time to complete their migrations. This extension also aligns with the end of support for Office 2010 and SharePoint Server 2010."
Administrators who run Exchange Server 2010 workloads on Windows Server 2008 will need to make adjustments due to the Jan. 14, 2020, end-of-life for that server operating system.

A migration to the cloud might not intimidate experienced admins, but there are sure to be a fair amount of surprises and hidden pitfalls on this journey. Administrators should check this list to circumvent email disruptions, which can befall some Exchange migration projects.

Get updated to avoid compatibility issues

To migrate Exchange to Office 365 or Exchange Server 2019, administrators must first check the version of Microsoft Office and Outlook they use. Older Office suites, such as Office 2007 and 2010, will work with Office 365 to some degree, but newer functionality, such as focused emails and Office Groups, will not.

Organizations on Outlook versions prior to 2013 may find they suffer from connectivity and security errors when connecting to Office 365 or Exchange Online services. To be safe, these organizations should upgrade Office prior to a migration.

To migrate Exchange to Office 365 or Exchange Server 2019, administrators must first check the version of Microsoft Office and Outlook they use.

A migration also requires the latest patches and security updates. Administrators must apply these updates or make other technical changes, such as adjusting the Active Directory (AD) functional level to Windows 2008 R2, if they plan to use Azure AD Connect with password write-back. Failing this, an Exchange hybrid installation cannot proceed because the systems will not meet Microsoft's minimum requirements.

Don't overlook third-party and VoIP integrations

Administrators must check for any potential incompatibility of Exchange Online with third-party applications, such as Mitel and Cisco, prior to migrating Exchange to Office 365. Most modern applications use Exchange Web Services to communicate with Exchange objects, but Office 365 introduces a number of new capabilities and security requirements, such as a unified API across all Office 365 workloads and the use of the latest token-based security for communication between voice over IP (VoIP) and Exchange Unified Messaging.

Several third-party vendors retuned their applications to make them compatible with Exchange Online. Exchange administrators must inventory any third-party applications in use, check their compatibility and plan their transition.

Think about the existing unified communications arrangement

Organizations that rely on integrated email and phone system functionality will likely have to adapt during an Exchange migration. These changes relate to the voicemail-to-email function, also known as voicemail transcription.

Microsoft has made significant improvements to its Unified Messaging features as part of the shift from Skype for Business to Microsoft Teams. Microsoft touts some of these new enhancements in Cloud Voicemail, the successor to Exchange Unified Messaging, including deposit function and voicemail answering, voicemail retrieval via Skype for Business Online or the Outlook client, and voicemail management through the Office 365 portal.

But these changes have affected customers who integrated VoIP and Exchange. Exchange administrators must ensure that their current VoIP platform supports Exchange Online and prepare for the transition with that vendor.

Plan for the licenses and time you need

Microsoft licensing is notoriously difficult to understand, and Exchange administrators will have to work hard to find the right Office 365 licenses. Further sowing this confusion, Microsoft continually develops new products and bundles them with existing offerings. It's imperative for administrators to understand exactly what offerings they need based on business demands.

For example, organizations with several field workers that just need email might only require a cheaper Office 365 F1 license at $4 a month compared to the E1 plan which is $8 a month but offers more services and storage space. In many cases, organizations spend more on licensing for users who do not require advanced functionality.

Timing is key during a migration effort

It might come as a surprise that Microsoft regulates bandwidth during a migration from Exchange to Office 365. This throttling of the mailbox replication service affects all Office 365 migrations, including the cutover, staged and hybrid Exchange migrations. Because throttling controls the speed at which mailboxes migrate online, IT must ensure that they manage their migration batches properly and plan their timeline based on the performance of the initial batches.

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