Setting up SkyKick Outlook Assistant (SKOA)

Outlook Assistant: Requirements

Local PC health is essential to the success of the Outlook Assistant. It is recommended that Windows Update be run on all machines prior to the installation of the Outlook Assistant to ensure that the local Office installation is ready to connect to Office 365.

IMPORTANT: If you are upgrading to a newer version of Outlook, the following best practices are recommended.

If users have not been upgraded before order placement, it is best to wait to perform the upgrade until after the migration is complete, unless an upgrade is required for compatibility with Office 365.
If an upgrade is required for Office 365 compatibility and the migration has begun, be sure to remove all previous versions of Outlook.

If using click-to-run, ensure that Outlook is opened and run before for any click-to-run installations of Outlook.

Anti-viruses or firewall settings may need exceptions made for the Outlook Assistant.

Outlook Assistant: Unsupported Scenarios

• Multifactor Authentication (MFA) on the destination Office 365 tenant. MFA (e.g. 2FA) will prevent Outlook profiles from being created in Office 365. If possible delay deployment of MFA or disable it for migrating end users until after the migration is complete. For more information, see the Enable/Enforce Multifactor Authentication for All (Bulk) Users in Office 365 article from Microsoft.
  Running two versions of Outlook side-by-side
• Upgrading Outlook after the Outlook Assistant has been installed
• Terminal Servers/Services (e.g. VDI, RDP, Citrix, etc.)
• Some third-party applications that customize the MAPI properties of Outlook items or add additional, proprietary properties (e.g. MDaemon)
• Mobile Devices (e.g. Android, iOS, etc.)
• Outlook 2003 and 2007. Office 365 does not support Outlook 2003 and 2007. When migrating from these versions of Outlook, the Outlook Assistant provides desktop readiness checks. In the final email, users are given a link to access Office 365 email through Outlook Web Access (OWA). If Outlook 2003 or 2007 is upgraded, the Outlook Assistant will automatically configure the upgraded Outlook to work with Office 365.
• Macs and Outlook for Macs. In the final end user email, Mac users are provided with instructions to setup Outlook, and access Outlook Web Access (OWA).

Important Considerations:

Single User, Multiple Machines

The Outlook Assistant can be installed on multiple machines for a single user. The migration results will depend on the migration type.

Exchange/Google

The Outlook Assistant will create a new outlook profile for each machine on which it is installed. Signature blocks and reattached .PST stores will be confined to the originating machine.

IMAP

Contacts and calendars are migrated to M365 using the Outlook Assistant. The Outlook assistant will migrate the local contacts and calendars to Office 356 from each Outlook profile it is connected to. If identical calendar entries and contacts exist on multiple Outlook profiles across multiple machines, the Outlook Assistant will migrate each data set to Office 365 potentially creating duplicates.

POP3

Local data from the primary data store is imported into the new Outlook profile and then synced to Office 365. If the Outlook Assistant is installed on multiple machines for the same user, duplicate data may be migrated to Office 365 through this process.

Multiple Users on the Same Machine

The Outlook Assistant is designed to migrate one user, using one Outlook profile, on a single machine. However, the Outlook assistant can be used for multiple users on a single machine. If multiple users exist on the same machine, a user will have to sign out of the Outlook Assistant and another user will have to sign into the Outlook Assistant to ensure that each user’s Outlook profile is created correctly. This process can be done during the migration and/or post cutover. To ensure each user on a machine is ready for the migration, it is important to verify the SKOA status for each user on a single machine using the Devices tab of the Migration Dashboard.