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Deploying the Outlook Assistant


Required Information

Outlook Assistant requirements and capabilities

For Outlook Assistant general information and requirements, see Outlook Assistant Overview.

Destination credentials required for Outlook profile creation

The Outlook Assistant requires destination credentials to create the Outlook profile connected to Office 365. For more information, see User Credentials.

Three Options for Deploying the Outlook Assistant

There are three primary ways to install and deploy the Outlook Assistant.

The right method for each migration depends on a variety of factors. The decision flow chart and table below provide the information required to select the right deployment method for each project.

Decision flow chart


  1. If users do not have admin rights and you do not want to deploy the Skykick Outlook Assistant (SKOA) via MSI, you can arrange for someone with admin rights to download and install SKOA on the users’ behalf.

Decision table


End User Direct Download

Standard MSI

Silent MSI


End users must have admin rights to their machine

Destination credentials for profile creation

Computers must be domain-joined

.NET Framework 4.6+ pre-installed

Destination credentials for profile creation

Computers must be domain-joined

.NET Framework 4.6+ pre-installed

Destination credentials for profile creation

SAM Account Names must be provided

End User Action

Download and install application

Sign in to register the device

Provide destination credentials*

Sign in to register the device

Provide destination credentials*

Provide destination credentials*

Partner Action

Manage end user progress for installation, sign-in, and destination credentials

Download SKOA MSIs

Create deployment package

Manage end user progress for sign-in and destination credentials

Download SKOA MSIs

Create deployment package

Manage end user progress for destination credentials or provide manually

Provide SAM Account Names for device registration

*These can be manually provided by the partner to remove end user requirement

Recommended Information

Microsoft Announces Temporary Mailbox Error

A Temporary Mailbox Error announced by Microsoft may impact users when upgrading to Outlook 2016+ or migrating to Office 365. See Your mailbox has been temporarily moved to Microsoft Exchange server

Microsoft recently announced a fix for this issue in build (16.0.7766.2060). However, users are still reporting incidents of this error, even after updating Outlook to the recent build. We will continue to investigate the error, and will keep you informed of what we discover. Please let us know what you experience in the field, as this will help us monitor the issue.

  1. Review the following Microsoft articles in order to be prepared to address these Outlook 2016+ issues that may arise:
  2. Update Outlook 2016 with the most recent build (16.0.7766.2060) For information, see March 14, 2017, update for Outlook 2016 (KB3085429).
  3. For additional best practices, see Microsoft Announces Issues with Outlook 2016

Microsoft Direct Connect feature may prematurely connect Outlook to Office 365

SkyKick has identified the root cause of an issue related to a new Microsoft feature called Direct Connect. Some users have reported that they have stopped receiving new email in their Outlook profile. Customers with Outlook 2016, who are not yet active in Office 365, but have mailboxes provisioned in Office 365, may automatically connect to Office 365 before DNS cutover. When this occurs, emails continue to flow to the source, but because Outlook is connected to Office 365, the user will not receive them in their Outlook profile. For more information and troubleshooting, see Microsoft Direct Connect error may prematurely connect Outlook 2016+ to Office 365.


Impact of Outlook version upgrades on Outlook profiles

When an Outlook version upgrade is performed some components of the previous Outlook profile may not appear in the new Outlook profile. 

Upgrades required for Office 365 compatibility

If a user’s current Outlook version is not compatible with Office 365, it is best to perform the upgrade and remove all previous versions before installing the Outlook Assistant.

If the Outlook Assistant has already been installed, follow these steps:

  1. Install the upgrade
  2. Remove all previous versions
  3. Let Big Green IT know which user and which device. Big Green will Retry Gather PC Info.

Non-required upgrades

If there are Outlook version upgrades you would like to perform for users whose current Outlook version is compatible with Office 365, it is best to wait to perform the upgrade until after the migration is complete.

Additional Considerations

Single User, Multiple Machines

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


SKOA 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.


Contacts and calendars are migrated to Office 365 using SKOA. SKOA 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, SKOA will migrate each data set to Office 365 potentially creating duplicates.


Local data from the primary data store is imported into the new Outlook profile and then synced to Office 365. If SKOA 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

SKOA is designed to migrate one user, using one Outlook profile, on a single machine. However, SKOA 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 SKOA and another user will have to sign into SKOA 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, Big Green IT will verify the SKOA status for each user on a single machine using the Devices tab of the Migration Dashboard.





Check out our resources below for more information on Azure and Office 365