Provisioning Office 365

  • 6/30/2015

Objective 1.3: Plan a pilot

This objective deals with planning an Office 365 pilot project. To master this objective you’ll need to understand the steps involved in planning a successful Office 365 pilot project, including determining a cohort of pilot users, determining which workloads should not be migrated to Office 365, leveraging the Office 365 on-ramp tool, having a test plan, and configuring email accounts for pilot users.

Designate pilot users

When selecting users for the Office 365 pilot, you need to ensure that you select a variety of users that represents the organization in its entirety. Part of the reason for the pilot is to identify potential pitfalls. For example, you want to figure out that there’s a particular on-premises requirement for a group of workers in the accounting department before you migrate their workloads to Office 365. Figuring this out beforehand is much better than having to work out how to roll the accounting users back on-premises after the rest of the organization has migrated to Office 365.

The first step in selecting users for a pilot program is to determine how many users you want to include in the pilot program. Successful pilot programs often attempt to use a minimum of 5% of the potential group to be migrated. This 5% of pilot users should meet the following general criteria:

  • Full-time employees of the organization Full-time employees will be working with the new technology during normal work hours. Part-time employees may be more sporadic in their interaction with the technology and may be less able to provide useful feedback across the pilot period.
  • Representative of the organization Pilot users need to be from different parts of the organization. They need to have a mix of age, experience, and seniority.
  • Have been with the organization a minimum of six months This ensures that the pilot users are familiar with normal organizational procedures.
  • Already trained on the software that they will be using For example, if the pilot program involves moving to online mailboxes, pilot users should already be familiar with Outlook. If the pilot program means moving to an online version of SharePoint that the pilot users are already familiar with the on-premises deployment of SharePoint.
  • Willingness to provide feedback One of the most important aspects of a pilot program is hearing what works and what does not. Pilot users who don’t provide both positive and negative feedback aren’t providing you with the information necessary to allow you to determine if a full implementation of Office 365 for your organization will be successful.

Identify workloads that don’t require migration

When planning an Office 365 pilot, an important thing to realize is that not all workloads need to be migrated to Office 365. Implementing Office 365 is not an all-or-nothing proposition. While it’s possible to have all user accounts, Exchange mailboxes, Skype for Business infrastructure, and SharePoint sites hosted in Office 365, it’s also possible to configure a hybrid deployment where these services are both on-premises and in the cloud. For example, you could have a deployment where only a fraction of your organization’s user accounts are native to Office 365, some mailboxes are hosted on-premises, and some are hosted in Office 365 cloud. Your organization’s SharePoint deployment could even be spread across servers in your local datacenter and others in Microsoft datacenters.

As part of your pilot, you should identify which workloads you don’t need to migrate to Office 365. The factors that influence this decision will vary depending on your organization. Factors also vary depending on your region. Most countries/regions don’t have local Microsoft datacenters, which might mean that moving workloads to Office 365 means moving workloads across national/regional borders. For some workload types, this may not present a problem; for other workload types, such as for workloads that deal with confidential medical data, it may not be possible to migrate the workloads across borders without contravening local legislation.

Run the Office 365 on-ramp readiness tool

The Office 365 on-ramp readiness tool allows you to run a set of tests to identify troubleshooting and configuration problems with Office 365. You access the tool either by navigating to or by clicking Check Your Office 365 Configuration With Office 365 Health, Readiness, And Connectivity Checks from the Tools section of the Office 365 Admin Center as shown in Figure 1-25.

Figure 1.25

FIGURE 1-25 Checks

Running the tool involves performing the following steps:

  1. On the Advanced Setup page, shown in Figure 1-26, you can elect either to make your own selections or to have an app run a check to discover what’s installed in your organization’s on-premises environment.

    Figure 1.26

    FIGURE 1-26 Advanced Setup

  2. If you choose the Make My Own Selections option, you’ll be presented with the following options show in in Figure 1-27:

    • Create new user accounts in Office 365
    • Sync users and passwords from an on-premises directory
    • Authenticate users with single sign-on
    • Use the free domain
    • Add or buy your own domain
    • Add a domain you already use on-premises
    • Migrate from a system that supports IMAP
    • No migration or users will move their own email
    • Cutover migration from Exchange 2003, Exchange Server 2007, or Exchange Server 2010
    • Staged migration from Exchange 2003 or Exchange 2007
    • Hybrid environment with Exchange Server 2007 or later
    Figure 1.27

    FIGURE 1-27 Select My Own Setup

Depending on your selections, you’ll be provided with advice and tools about how to perform each step of the Office 365 deployment process. Much of the advice provided by the on-ramp readiness tool mirrors what is provided in the links to Office 365 documentation in this Exam Ref.

Create a test plan or use case

Creating a test plan or use case involves developing a formal process to describe how the pilot will proceed and how the results of the pilot will be assessed. The test plan should involve the following general phases:

  • Deploying the Office 365 tenancy that will be used for the pilot
  • Create user accounts for pilot users
  • Configure active use of email for pilot users
  • Deploy Office 365 ProPlus software
  • Enable pilot user access to Office 365 services
  • Solicit pilot user feedback about the experience

Each organization’s plans will be slightly different. You need to ensure that pilot user feedback is recorded so that you can use it when evaluating how decisions made in the planning phase stack up against real-world outcomes, allowing you to make adjustments to the deployment phase.

Connect existing email accounts for pilot users

It is possible to migrate the email accounts of a small number of users from your on-premises environment to Office 365 while keeping the majority of your existing mailboxes in the on-premises mail solution. The method for doing this is termed simple domain sharing for SMTP email addresses as shown in Figure 1-28.

Figure 1.28

FIGURE 1-28 Mail flow

For example:

  • Your organization has provisioned the Office 365 tenancy.
  • Your organization has its own on-premises mail solution. It uses the email suffix.
  • You set the domain as an Internal Relay domain as shown in Figure 1-29.

    Figure 1.29

    FIGURE 1-29 Internal Relay

  • Configure the on-premises mail solution to configure mail forwarding of each pilot user account to the mail domain. For example, the on-premises mailbox for the email account should forward all incoming email to
  • Configure each pilot user’s account in Office 365 to use the on-premises DNS zone mail domain. For example, Don Funk’s Office 365 user account should be configured with a reply-to address of
  • You can migrate the contents of pilot users’ on-premises mailboxes using Exchange Admin Center.

Service descriptions

Office 365 is made up of multiple separate services. Service descriptions provide information about what the service does. The service descriptions for these Office 365 services are as follows:

Objective summary

  • Pilot users should provide a representative sample of your organization.
  • Not all workloads can be or should be migrated to Office 365. Use the pilot phase to determine which workloads you will not migrate.
  • The Office 365 on-ramp readiness tool provides advice for migrating to Office 365.
  • A test plan or use case is a document that provides information on each phase of the migration process.
  • You can configure pilot users with Office 365 mailboxes through the configuration of SPF records, accepted domains, and email forwarding.
  • Office 365 service descriptions provide precise information about Office 365 service functionality.

Objective review

Answer the following questions to test your knowledge of the information in this objective. You can find the answers to these questions and explanations of why each answer choice is correct or incorrect in the “Answers” section at the end of the chapter.

  1. Your organization has 200 users. What’s the minimum number that should be involved in the Office 365 pilot?

    1. 2
    2. 5
    3. 10
    4. 1
  2. Which Office 365 service provides spam filtering?

    1. Exchange Online Protection
    2. Exchange Online Archiving
    3. SharePoint Online
    4. OneDrive for Business
  3. You are configuring a custom domain as part of an Office 365 pilot. You want to host some, but not all, pilot user email accounts in Office 365. Which setting should you configure for the custom domain?

    1. Authoritative
    2. Internal Relay
    3. External Relay
    4. Remote Domain
  4. The current SPF record for your organization’s custom DNS zone is configured as “v=spf1 mx ~all.” What should be the value of the SPF record if you want to have some pilot users use Office 365 as the mailbox for email sent to their email address?

    1. “v=spf1 txt ~all”
    2. “v=spf1 txt ~all”
    3. “v=spf1 mx ~all”
    4. “v=spf1 mx ~all”