Office 365 Migration Considerations (Part 1)

If you would like to read the next part of this article series please go to Office 365 Migration Considerations (Part 2).

Office 365 is a cloud-based service that businesses can use to provide their users with the Microsoft Office experience without the need of locally deploying Office on each user’s computer or device. To learn more about the various business and technical considerations around migrating your organization’s users to Office 365, I’m going to pick the brains of Kelsey Epps, a Technical Consultant with Concepps Group and a Microsoft MVP for Office365 who runs a blog called the Office 365 Technical Support Blog.

Mitch: Kelsey, I understand that one of the first things that organizations often ask concerning Office 365 is the following: Is my data secure in the cloud? Can you give us some insight into this issue?

Kelsey: Data security is a huge concern when moving into the cloud. This rings true, not just for Office 365, but for all cloud offerings from all companies. I find that Microsoft does the best job at eliminating concerns that my clients and potential clients have. Microsoft has a dedicated team and website to deal with such concerns. I am finding more and more that it’s not just big businesses and government that are concerned, it’s the little guys too; including myself. Microsoft adheres to the strictest compliance measures; “world-class industry standards, including ISO 27001, EU Model clauses, HIPAA BAA, and FISMA, and it is verified by third-party auditors”. They take data security really seriously, as they should; they have to as there are many eyes on them. A good place to learn more about how Microsoft addresses security and privacy for Office 365 customers is the Microsoft Trust Center.

Mitch: I agree, the Trust Center really shows how serious and committed Microsoft is towards ensuring the security and privacy of their customers’ data. But before they take the plunge and move over to Office 365, another concern I’ve often heard from businesses is in the area of availability. What sort of service level agreement (SLA) for uptime does Microsoft guarantee for Office 365?

Kelsey: Microsoft has a ‘financially-backed 99.9% uptime guarantee’. This means that they guarantee three nines uptime (roughly 43 minutes downtime per month). If they fail at keeping this SLA, then the SLA states that you can be financially compensated by Microsoft. The specifics of the SLA are publicly available, with individual SLAs for Exchange, SharePoint and Lync. The SLAs read as a standard industry SLA should; scheduled maintenance and factors outside their control is not considered downtime. Microsoft has been really up front and honest with their service disruptions. They have a Service Health section in the admin portal that shows current status and planned maintenance. See the Service Level Agreements at

Mitch: OK let’s say that I’m satisfied with the security and SLA of Office 365 and I’m ready to buy into one of their plans. Why is it important for me to choose the correct Office 365 plan from the start?

Kelsey: I can’t stress the importance enough about reviewing all the plans (and features of) before you sign up for the trial. Do not assume that you can just swap between the plans once the tenant account is created. You cannot migrate between an Office 365 Small Business and an Office 365 Enterprise Plan. I have seen a lot customer grief, where people have signed up for the Enterprise plan, then rolled it out to a pilot group of users, then tried to swap to a Small Business plan once the trial period is over. Once a tenant account has been created in the Small business or Enterprise service line, you can upgrade/downgrade licenses within the same service line. This means that you can move from an Enterprise Plan 1 to an Enterprise Plan 3, or you can have a mixture of users on different licenses (within the same service line).

From the Office 365 for business FAQ:

How do I switch between plans?

You cannot migrate between an Office 365 Small Business and an Office 365 Enterprise plan. In order to change from a Small Business plan to an Enterprise plan or vice versa, you must first cancel your account with the plan you currently have, and then sign up for a different one. You can migrate your account within plan families, for example, from Small Business to Small Business Premium, or from one Enterprise plan to another.

Working with an Office 365 cloud partner, like myself, we can review the pros and cons of the two mail service lines, Small Business and Enterprise. There are a number of key differences in the service lines and those differences are make or break choices, that will point you down one path or another. Microsoft has a great BLOG post (Office 365 – Comparing P, M and E plans) that details all the features of all the plans and I use this as a guide to help my customers make the right decision.

Mitch: Can you quickly describe a few scenarios where an Enterprise plan might be preferable to a Business plan?

Kelsey: The Enterprise service line is the Cadillac of the Office 365 service lines. Some of the main features that it has, that you can get in the Small Business service lines are:

  • Microsoft Office 365 Admin Center
  • Windows PowerShell Support
  • Single sign on with ADFS and Directory Synchronization
  • Exchange Hybrid Deployments (users on premise and in the cloud)
  • Exchange Unified Messaging
  • Exchange Admin Center
  • Lync Hybrid Deployments (users on premise and in the cloud)
  • Lynd Admin Center
  • Enhanced support model with service requests
  • SharePoint Admin Center
  • Multiple site collections in SharePoint online
  • BCS features for SharePoint Online
  • Insights Features for SharePoint

Enterprise plans also have many add on features; CRM Online, Visio Pro, Project Online and Project Pro

A complete list of all the features of the Enterprise plan can be found here.

Mitch: Let’s say I’ve got a small company with only ten employees and I want to migrate them to Office 365. What is the best way to migrate the email accounts of these employees from my current ISP’s POP3 mail platform?

Kelsey: We must first choose the correct service line. Since the company has ten employees, they fall between two service lines (Small Business and Midsize Business). Looking at the chart below, if we plan for growth, you can choose between the two plans. We would sit down and chose the right plan and then create the tenant account.

  • P = Small Business Premium (Designed for 1-10 users, maximum of 25 users)
  • M = Office 365 Midsize Business (Designed for 11-250 users, maximum of 300 users)

I am a planner and a documenter. I would create a complete migration plan, document the end solution and get the business leaders to sign off on the plan. This is a small migration, it can be done with no outages and with very little user interruption. While the old POP3 email is still up and running, we can setup Office 365. During an agreed time, we can then change the MX record to point at Office 365. A user visit would swap the users to Office 365 and transfer their email.

Let’s assume that they chose the Office 365 Small Business Premium subscription and let’s assume they are running Office 2007 (using Outlook to connect to the POP3 email provider).

Migration plan:

  1. Sign up for the tenant account
  2. Add and verify the external domain
  3. Add all DNS records to the public DNS provider (except the MX record)
  4. Add all DNS records to the private DNS provider
  5. Provision and license all the user accounts and document the temporary passwords
  6. Complete the Exchange setup (Distribution lists, external contacts, delegate permissions, meeting rooms, etc…)
  7. Client Desktop Setup (this can be done with a visit to all users or a well-documented procedure with the help of the local IT person)
    • Assist the users with logging in to the Office 365 Portal
    • Change their passwords
    • Download and install Office 2013 — This will upgrade the current Office version and leave the current POP3 account in place.
    • Download and install the Desktop Applications
    • Configure Outlook so that the Office 365 is another mail account on the same Outlook Profile.

Setting it up like this maintains the connection to the POP3 account and gives us access to the Office 365 account. It will also eliminate any connection or setup issues on the morning of the switch over. Since the MX record is still pointed at the POP3 provider, email is still delivered there.

  1. Switch the MX record to point at Office 365 (Friday 5PM)
    • I like to do this on a Friday night and let the MX replicate over the weekend
    • DNS replication can take up to 72 hours
    • If any email is sent over the weekend, it will get delivered to either the POP3 or Office 365, depending on what MX gets resolved
  2. Outlook Reconfiguration (Monday 8AM)
    • Remove the POP3 connection, thus making the Office 365 connection the primary (noting where the PST file is stored — POP3 will always be delivered to a PST file in Outlook)
    • Verify the PST file is removed from the Outlook profile
    • Launch Outlook, logging into Office 365
    • Import the PST file into Office 365, using Outlook import feature

Since we have setup Outlook to have the Office 365 connection and POP3 connection in the same profile; users that are waiting to be reconfigured to Office 365 only, still have access to their email. Business leaders really like this since there is no downtime.

  1. Sign the users into Lync
  2. Assist the users with mobile device setup
  3. Migration completed

I also like to offer the company a brief training session on Outlook/Exchange features and how to use Lync. Most small businesses, using a POP3 solutions, have never had the ability to book meetings, check calendars and have delegate access.

(to be continued in the next article in this series)

If you would like to read the next part of this article series please go to Office 365 Migration Considerations (Part 2).

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