8 factors to consider when migrating from Windows Server 2003 to Office 365

 In Cloud, Microsoft, Office 365, Software, Volume Licensing

The retirement of Windows Server 2003 is closer than many think. If you haven’t started planning for your migration yet, now’s the time. For both those yet to start and those already underway, we’ve been presenting the options for migration from Win2k3, including Windows Server 2012 and Microsoft Azure. In this final post, we’ll cover everything you need to know about licensing Office 365 (O365), Microsoft’s cloud solution.

O365 provides a number of flexible and cost-effective licensing and purchasing options for migrating Exchange and/or SharePoint to Microsoft’s SaaS offering. If you’re evaluating Office 365, ask yourself the following eight questions in order to make an informed decision on your strategy moving forward.


1. What enterprise products am I licensed for?

As part of an O365 migration strategy, it’s important to understand how you are currently licensed for your core Microsoft desktop and server technologies, which are now offered in Office 365. There are both licensing and cost implications to transitioning to O365, so being able to identify your current license footprint for the Office Suite, Exchange, SharePoint, and Lync will provide additional knowledge needed to make an informed decision.

2. What licensing programs am I buying under?

As important as identifying your current license footprint is determining what licensing vehicle(s) you’re procuring these licenses under. Certain programs like the Enterprise Agreement (EA) provide for a transition path to O365, whereas others like Select Plus or Open Business don’t afford the same level of flexibility. Having a clear picture of the transition is imperative in understanding your cost and licensing options.

3. Am I licensed for the Client Access License (CAL) Suite?

The CAL Suite, which is offered as either Core CAL or Enterprise CAL, includes the key workloads that make up O365. With the exception of the Office productivity suite, the CAL workloads like Exchange, SharePoint, and Lync will transition to O365. The ability to transition to O365 depends in large part on how the CAL workloads are licensed, as there are both licensing and cost implications that you’ll need to evaluate as part of the process.

4. When is my current volume license agreement up for renewal?

Microsoft offers various programs to license O365 services. The most common program is the EA, which is designed for organizations with a minimum of 250 users. Ideally, a transition to O365 should align with an organization’s agreement end date, as it provides the most flexibility to reset license counts, cost structure, payment method, and contract terms. In August 2014, Microsoft changed the pricing for certain O365 SKUs, which impacts certain organizations looking to move to O365. Understanding when your current agreement is up for renewal will be imperative in the decision-making process before transitioning to O365.

5. What is my timeline for migrating to O365?

Having a migration plan is equally important as understanding the licensing issues and costs. As you evaluate the licensing costs in moving to O365, there will undoubtedly be cost considerations for the migration and deployment of O365 services. Microsoft offers various programs to help alleviate these migration costs; however, it is still important to have a plan in place. Without one, you might find yourself the owner of unintended subscription shelf-ware.

6. What service plans am I looking at, and should I mix plans based on user requirements?

O365 is not necessarily an all-or-nothing proposition. Depending on the service plans, agreement type, and program requirements, organizations will have flexibility in how they license their users in the cloud. For example, some organizations looking to migrate to Exchange simply want to license Exchange Online instead of the entire O365 suite of services. Furthermore, the option to license Exchange Online in two different plans, depending on feature requirements, provides an added layer of flexibility in service costs and matching features and functionality to user requirements. The ability for an organization to right size their user profiles based on service needs provides additional licensing elasticity and cost savings.

7. Do I want to move to O365 through a transition or add-on?

There are multiple methods by which organizations can procure O365, but the two most common are the transition and add-on processes. The O365 transition allows an organization to move to O365 services either mid-term or at renewal based on your current license footprint. This transition path takes the form of multiple licensing and cost options, so understanding what you have and when you want to get there is imperative to making an informed decision. Another less complex option is via the O365 Add-on. This option was introduced in August 2013 and provides some organizations with a flexible, cost effective Office 365 purchase option.

8. What are my costs?

The licensing costs to move to O365 depend on the answers to the questions above. Factors including the licenses you have now, your timeline for migration to O365, and which method you choose to procure the services will all play a role in the licensing costs incurred. The benefit of O365 is its flexibility. However, the complexity in licensing means it’s important to answer these questions in a timely manner to help with a smooth migration to the O365 plan and service of your choice.

Working with an experienced partner like SHI to help navigate these licensing considerations will be integral to an organization’s decision-making process. Windows Server 2003 end of support goes into effect July 14, 2015. Reach out to your SHI Account Executive today to start the conversation about migration.

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