Best practices for deploying the SkyKick Outlook Assistant

By Joshua Dowdy on Nov 28, 2017

SkyKick regularly updates the Outlook Assistant client and MSIs to work most effectively with Office 365 as it evolves. It is therefore best practice to download and use the most current version for each migration project (rather than using an MSI file saved from a previous migration). This optimizes performance and significantly reduces the potential for issues as the Outlook Assistant performs its various actions across a migration project.

Best Practices for Office 365 Migration Desktop Readiness - deploying the SkyKick Outlook Assistant

The Outlook Assistant ensures every desktop is ready to migrate, and recreates each user's Outlook profile in Office 365 (including address autocomplete, signature blocks, and more), so users feel at home when they get to Office 365. And it gives the Partner the benefit of not having to go desktop to desktop to set up Outlook profiles.

The SkyKick Outlook Assistant is a powerful, yet lightweight client application that:

  • Performs desktop and Outlook readiness checks.
  • Configures Outlook to work with Office 365.
  • Moves local data (i.e. signature blocks and address autocomplete) as required.
  • Recreates the user’s previous Outlook experience as closely as possible post-migration.
  • Collects PC and network data to ensure data can be moved across the network in the allotted project time.

By using Outlook Assistant as part of an email migration, partners do not need to manually configure desktops or handle PST files, resulting in a high quality, more secure migration. Outlook Assistant moves the address autocomplete, re-attaches all PST data stores to the new profile, and sets the default signature for the new profile. For more information, see Outlook Assistant Overview.

Best Practice: Always deploy the most current SkyKick Outlook Assistant

SkyKick regularly updates the Outlook Assistant client and MSIs to work most effectively with Office 365 as it evolves. It is therefore best practice to download and use the most current version for each migration project (rather than using an MSI file saved from a previous migration). This optimizes performance and significantly reduces the potential for issues as the Outlook Assistant performs its various actions across a migration project.

Best Practices by Outlook Assistant deployment option

SkyKick provides several options for deploying the Outlook Assistant. For more information on these options, see Deploying the Outlook Assistant.

End user direct download deployment

No partner action is required. Users will receive an email with a link to directly download the most current version of the Outlook Assistant.

Standard and Silent Group Policy deployments

Download and deploy the most current core Outlook Assistant MSI package for each migration project.

Coming soon: This will be available in the Migration Dashboard->Overview tab->Settings section->Info tab.  

Note: If your customer has a firewall that blocks any action of the Outlook Assistant, specific configurations on the firewall will be required.

Group Policy deployment for Hands-Free Migrations

Due to Microsoft changes to Windows Defender, the following steps must be performed to successfully deploy the Outlook Assistant for a Hands-Free Migration project. This scenario offers the benefit of eliminating most End-User involvement in the migration process. 

  1. Whitelist sklquery.exe before downloading sklquery MSI package(s). For more information, see Instructions for whitelisting the MSIs required for a Hands-Free Migration.
  2. Download and deploy the most current:

Coming soon: These MSI packages will be available in the Migration Dashboard->Overview tab->Settings section->Info tab.

Note: If your customer has a firewall that blocks any action of the Outlook Assistant, specific configurations on the firewall will be required.

For more information, see Recent MSI Updates (November).  

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Topics: MSPs For Partners Office 365 Outlook Assistant