Cutover Timeline

In any migration there are many complex and timely steps that must take place in an orchestrated fashion for a successful switch to Office 365. With a SkyKick SMB or Enterprise migration, most of these are performed by SkyKick automation. This significantly reduces the risks of a migration to Office 365 and is why SkyKick is Microsoft’s recommended migration project automation tool. The automated time-sensitive tasks include:

  • Making public DNS changes to activate mail flow (if an automated DNS option is selected)
  • Switching Outlook to Office 365 with the Outlook Assistant
  • A comprehensive final synchronization of data

SkyKick refers to “Migration Time” or “Cutover” as the moment the first of these steps are initiated, and is the date and time chosen for the Migration Project in the Migration Planner. For full overview of Cutover Timeline, see Visual Cutover Timeline section below.

  • What Happens at Cutover

    At cutover, SkyKick automated technology ensures that everything happens in the right order and at the right time for a successful migration. There are many automated tasks that are initiated at cutover time.

    Local DNS Changes

    Regardless of the DNS Option selected, you will need to make local DNS changes in a timely manner to ensure that Outlook connects to Office 365 correctly.

    Public DNS Changes

    • Fully or Partially Automated DNS Options: Nothing is required by the partner and no SkyKick automation is initiated until approximately 10 minutes after cutover.
    • Manual DNS Options:
    • SkyKick will automatically send an email with directions on making the required public DNS changes. To help you prepare for this task, this same instructional email is sent approximately 8 hours before cutover.


    Based on the Communications Option selected in the Migration Planner, SkyKick technology sends emails to end users with access instructions. This same email is also sent 8 hours earlier to prepare end users for accessing Office 365 at cutover.

    The email sent to the old mailbox at cutover time instructs end users how to log into and use their Office 365 mailbox from that moment on. Users will also receive Office 365 access instructions and links to:

    • Outlook Web Access (OWA)
    • Mobile phone setup instructions
    • Outlook reconfiguration instructions for PC and Mac
    • Instructions on adding other email accounts to Outlook
    • Outlook Assistant download

    Once Final Sync is complete for each mailbox, a Migration Complete email is sent to that mailbox.

    Once all mailboxes have completed Final Sync, a Migration Complete email is sent to the Partner and the point of contact (POC) at the customer.

    Note: All End User Communications, including cutover communications, are dependent on the Communications settings selected in the Migration Planner.

  • What Happens Approximately Ten Minutes after Cutover

    SkyKick automation deliberately starts several actions approximately ten minutes after cutover to orchestrate the steps to ensure a seamless cutover and optimize user experience.

    1. Public DNS Changes: These are coordinated with the Outlook Assistant flip, which allows automated communications to reach the old mailbox and end users to complete work.
    2. Outlook Assistant: A dialog box pops up which allows end users to delay the switch for their mailbox. This is designed to occur simultaneously with public DNS changes.
    3. Data Migration: Data Migration: To allow for DNS propagation and end users to receive communications, and to ensure the most complete data set for Final Sync, the final migration of data also begins about 10 minutes after cutover.

    Public DNS Changes

    • Fully or Partially Automated DNS Options: Fully or Partially Automated DNS Options: SkyKick DNS Sync makes the required public DNS changes.
    • Manual DNS Option:
    • Partner makes public DNS changes.

    Outlook Assistant Process

    SkyKick Outlook Assistant

    1. SkyKick Outlook Assistant Commands are Set
    2. Polling: Outlook Assistant reaches out to SkyKick server for Migration Commands
    3. User is prompted to begin local Outlook migration or wait 10 minutes
    4. Outlook Assistant hard codes Outlook to Office 365, changing the default Outlook profile to a new Office 365 ready profile that it created earlier in the migration process. Autodiscover can overwrite these settings. Therefore make your Autodiscover changes precisely at cutover.
    5. Settings are migrated

    Duration is dependent on machines being on, logged in, unlocked, online; the Outlook Assistant running; the amount of data moved; and bandwidth, etc.

    Note: It may take longer than ten minutes for the Outlook Assistant process to start due to computer status and the last successful Outlook Assistant poll.

    End User Experience

    The Outlook Assistant will pop up and tell users how much time they have before the Outlook changes automatically take effect (typically 3-5 minutes). It will also prompt the users to begin the Outlook migration or delay it in 10 minute increments.

    Data Migration

    Final Sync

    Approximately ten minutes after the scheduled migration time, Server Sync initiates a robust Final Sync process of the customer’s source and destination server mailbox to ensure everything is replicated. Final Sync will mirror any server data and changes into the customer’s new Office 365 mailbox so the migration is seamless from an end user’s perspective.

    Data Sync

    Final Sync copies any new data in the source mailbox. This can take anywhere from a few minutes to a few hours depending on the size of the mailbox, the number of mailboxes, and the processing speed/bandwidth of the source server.

    Completion progress is displayed within the Migration Dashboard. While users have been notified that their new Office 365 mailbox is active while Final Sync is running, it is unlikely that a user will notice any difference between the source and destination mailboxes before the Final Sync completes because Server Sync always starts with the most recent data first.

    Delta Sync

    At the conclusion of the Final Sync process, a Delta Sync is performed. Delta Sync identifies any differences between the source mailbox and the Office 365 mailbox and replicates any changes that occurred or were made in the source mailbox to the Office 365 mailbox. For example, if an email is moved from the Inbox to a personal folder, Delta Sync will replicate that change in Office 365.

    Sweep Sync

    Sweep Sync continues to check the source mailbox for new email every hour for 48 hours after the migration cutover time in case an email is erroneously routed to the old email server. This ensures that no email that can be migrated is ever left behind. This can be extended upon request.

  • Post Migration

    If any end users are not available to participate in the migration prior to the cutover, it does not have to delay the migration project. Those users can still migrate after cutover as soon as source email access is provided, at which time they have the opportunity to download the Outlook Assistant which will launch immediately.

    The next time they check their mail, they will see one of the last emails from SkyKick in their (now inactive) old mailbox. In that email there is a Start button to begin their on-demand migration. Since Server Sync migrates the newest content first, the user will be up and running in no time, and they will continue to see data flow into their new mailbox as they are working in Outlook or OWA.

Visual Cutover Timeline

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