Ensuring a Successful Migration to Office 365

John oversees all services related client activities and is responsible for growing CloudStrategies consulting business. In addition to helping clients migrate from legacy infrastructure into modern cloud infrastructure, John is responsible for setting consulting business strategy, and is actively involved in day to day consulting with hybrid coexistence deployments. John is a US Navy Veteran with more than 20 years of IT infrastructure experience and is an all-around propeller head card-carrying gadget geek.

Lessons Learned for a Streamlined and Successful Migration to O365
Since our beginnings as a company, Cloud Strategies has focused solely on the Microsoft online experience, previously BPOS and now Office 365. Over the past few years there are a number of things we have learned that help to ensure a smooth transition to Office 365 and Exchange online. Many customers think that as long as they can move their mailboxes from point A to point B then the process is done. And while that is certainly the high-level goal, to accomplish this successfully it is almost always more complicated behind the scenes.

Speeding and Automating the Migration to Office 365
At Cloud Strategies we specialize in migrations to Office 365 and Exchange online. What we’ve learned through our years of experience is that speed and automation really matter. The faster you can complete the migration, and the more automated the process steps, the more likely you will deliver a successful project with a happy customer. To enable this automation and migration speed we have started using the E2E Complete product from Binary Tree. They are the well-known experts in the mail migration market and we have already standardized on using their Notes to Exchange migration tool. They bring quality products and expertise to the table, and it only makes sense that their professionalism and expertise translates into the Exchange-to-Exchange migration space as well.   Cloud Strategies Logo

Mail migrations from Exchange on-premises to Exchange Online can utilize the free mail transfer tool from Microsoft included with Office 365, but the inherent limitations often stop us and customers alike from utilizing the built-in tool. I want to start by saying that “if” your Exchange environment meets the requirements, the free tool can get you where you want to go, but often that’s not the case. The first issue is that the Office 365 migration tool works VERY differently from its BPOS counterpart. The new tool requires a totally manual process. It forces you to import user mapping via a spreadsheet, and if you accidently choose the wrong migration type (staged vs. cutover) undoing that mistake is not straightforward. Plus, you can’t easily schedule migrations of staged groups, and the transfer speed is not consistent, or at least not historically.
The thing I like least about the free tool is that RPC over HTTP must be active in your current Exchange environment for the tool to even connect. I personally don’t like having to spend time fixing the old mail system when we are migrating away of it, so unless RPC over HTTP is in place, I just prefer to save time and skip the free tool.
For the low overhead of adding another Virtual Machine to your hybrid setup, E2E Complete brings scheduling automation, tracking and reporting to your migration project, as well as integrated communications to the end users. As long as I have an Exchange 2010 server in the environment, (which is a hybrid coexistence requirement anyway) then I have all the PowerShell cmdlets that I need to make E2E Complete work to my advantage.  
Even though you can schedule the mailbox moves with the coexistence server, the E2E Complete tool scheduler takes a lot of the manual work out of the process and allows much more user friendly batch migrations, making it a faster, easier, and smoother transition from on-premises Exchange to Office 365. Because of the added complexity of the hybrid coexistence environment, Cloud Strategies experience has been that the faster the customer gets out of coexistence, the happier they are with their move to the cloud. Most organizations are working on a razor thin IT staff and IT budget, and adding all the complexity that hybrid coexistence brings can be very frustrating. E2E Complete helps us get customers into the cloud faster so that they can reap the benefits of a simplified IT spend for email. For all future Cloud Strategies migration projects we have standardized on using the E2E Complete tool to help streamline and speed up the migration processing.
Migration Planning and Preparation
It should go without saying that planning is paramount to the success of a migration to Office 365. Although there are no design considerations in Exchange online as the architecture is largely dictated, there are several items that you must plan for to make your transition as smooth as possible.  One of the most important items is DNS.  You must have access to be able to modify your records in a timely manner, so make absolutely certain that you understand DNS and have zone file access to your registrar and/or internal DNS servers. Making Exchange online happy with your DNS settings will make your users happy once the transition is underway.
Another item of great importance is service mail accounts such as pop accounts, copiers, and fax machines.  Almost everyone has them, and there are almost no two that send mail the same way. For these to continue to work in Office 365 they need to be authenticated, secure SMTP accounts that support TLS.  Many older devices do not. The way we manage this is through an SMTP relay cloud-based service or through an on-site SMTP relay like IIS. Be sure to test these accounts before the final cutover to Office 365.
Rooms and Resource calendars are another pre-move consideration. Which ones are used and which ones have data that needs to be translated to the new environment in Office 365. Microsoft’s move tools don’t replicate the data, but if you are using directory sync, mail enabled distribution lists are synced to the cloud, but you will need a plan for high-use shared calendar data.
Public folder information is always an important topic. Microsoft has been trying to move away from public folders for a number of years, and the disposition of this data is no different in Exchange online. Public folders are not supported, but the data can transition nicely to SharePoint online or a shared mail folder. With enough understanding of what the data is and how you plan to use it in the future can greatly ease your move to Exchange online. We highly recommend having public folder data planning done prior to planning any mailbox moves so that the data can be available to users immediately upon their transition to the cloud.
My last bit of advice is to validate your network bandwidth during the planning phase. You must make sure that your ISP connection will be conducive to a move to online services. This can easily be gauged by visiting speedtest.microsoftonline.comand running the tests to see if you need an upgrade to your internet service.
Additionally, be sure to read the service descriptions for the Office 365 online services so that there are no surprises after your move. Understand what Exchange online provides and doesn’t provide. The question about Exchange online being a secure platform is asked of us regularly, and that topic is detailed very well in the online service descriptions and various security white papers that Microsoft provides. Another common complaint is sending limits. Exchange online will only allow a user to send 30 messages per minute, and if submission occurs at a faster rate that user is throttled and messages are queued and delivered at a slower rate.  In an on-site Exchange environment you control the send limit. In Exchange online Microsoft does, so be aware of your current usage and come up with a plan to handle your mass mailings before your move to the cloud.

Requirements for Medium and Large Size Migration Projects
The requirements for a move to the cloud are certainly varied based on your customer’s specific needs, but there are some constants. For simple migrations (all users in the cloud with no site AD syncing to the cloud) all that’s required is Outlook 2007 SP2 or Outlook 2010 for installed clients, or a supported browser. Use the following link to view the service description for Exchange online.
For customers that want to maintain users in on-premises Active Directory and have all their Exchange mailboxes in the cloud, there is an additional requirement for the directory sync software that you can read about in the following articles.
If your on-premises Active Directory has fewer than 50,000 objects, you can deploy directory synchronization with Microsoft SQL Server 2008 Express. However, if your on-premises Active Directory has over 50,000 objects, you must deploy directory synchronization with a full instance of SQL Server.

For customers that want to utilize Single Sign-on and full hybrid coexistence with Exchange Online the requirements are significantly more stringent. At a bare minimum 4 additional servers are needed, 6 are recommended. Microsoft recommends Active Directory Federation Services 2.0 with a primary ADFS server and a secondary ADFS server configured in a load-balanced fashion. Additionally a primary and backup ADFS proxy should also be configured in a load-balanced setup. Add to those a member server for directory synchronization and an Exchange 2010 server for the hybrid coexistence server. All of these can be virtualized, and there are a number of ways that these roles can be played by existing servers, but we won’t go into that in this article.

This brief article is hardly a catch all for Office 365 preparedness, but hopefully it will help point you in the right direction for planning your own Office 365 transition. I cannot stress enough the importance of proactive IT staff planning and user communications. Project management can often be overlooked in IT, and it shouldn’t be. Setting the proper expectations in conjunction with the steps outlined above will go a long way in making your transition a success. And if you want to perform the fastest migration possible, I highly recommend using the E2E Complete tool from Binary Tree.
Before you start down this path you should really contact a partner like Cloud Strategies that has experience moving organization to Office 365. Some additional, useful links to help you prepare for your upcoming migration to Office 365 are below.