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Standard MSI Skykick Outlook Assistant Deployment

When migrating via EWS, you can eliminate the need for end-users to install the Skykick Outlook Assistant (SKOA) by using a standard MSI deployment. End-users will still need to sign into SKOA after it is installed, and destination credentials will be required for profile creation. This can be done by end users directly through Password Reception.

Roll-out of new version of SKOA

SkyKick is rolling out a newer version of SKOA. In addition to the requirements listed in the section below, the new version includes the following requirements:

  • Outlook 2016+ x64
  • Windows 10 x64

Note: If a migration is enabled for 8.0, the migration technology will automatically deploy Outlook Assistant 8.0 on any machine that meets the requirements and will deploy Outlook Assistant 7.3 on any machine that does not. See the section below to determine if a migration is enabled for 8.0.

Standard MSI deployment for SKOA on all machines

Requirements and roles 


  • Computers must be domain-joined
  • .NET Framework 4.6+ pre-installed
  • Destination credentials for profile creation

End User action

  • Provide destination credentials
  • Sign in to register the device

Client action

  1. Place migration order
  2. Download Outlook Assistant MSIs
  3. Prepare deployment package
  4. Deploy MSI package (via Group Policy or other tool or process)
  5. Manage end-user progress for sign-in and destination credentials

Step 1: Place migration order

Place a migration order with your sales representative.

Step 2: Download Outlook Assistant MSIs

  1. Get the Outlook Assistant MSI from Big Green IT.
  2. Get the SKOA Core ZIP filemsi.png

Step 3: Prepare deployment package

Extract all files from the Outlook Assistant ZIP file

Important: If you have a mixed environment, you will need to deploy separate packages, based on operating system, one for 32-bit versions of Windows and one for 64-bit versions of Windows.

For PCs running a 64-bit version of Windows, select:

  • outlookassistant
  • mapi64helper

For PCs running a 32-bit version of Windows, select:

  • outlookassistant

Note: If SKOA is installed on a machine, whenever a user with a SAM Account Name logs into that machine, SKOA will attempt to create an Outlook profile for that user. If there are any machines in an organization on which this behavior is not desired (e.g. a machine which many users may log into for a specific task, but on which no user would require an Outlook profile), those machines should be excluded from the deployment process.

Step 4: Deploy MSI package

The MSI package can be deployed via Group Policy or other deployment process or tool (e.g. RMM). If you are using another tool, refer to that tool’s instructions for performing an MSI deployment. For instructions on deploying via Group Policy, see the Standard MSI Deployment via Group Policy section below.

Step 5: Manage end user progress for destination credentials 

Destination credentials are required for Outlook profile creation. Whether end users are providing these via the Password Reception Process or you are providing them manually, ensure this is completed prior to cutover.

Standard MSI deployment via Group Policy

The following instructions are for deploying the MSI package via Group Policy. 3rd party deployment tools can also be used to deploy the MSI package.

Disclaimer: The following instructions and code snippets are provided to help you use Group Policy to perform an MSI deployment. Because Group Policy is not within the scope of a migration project, these instructions represent the extent of help with the deployment process. 

Step 1: Create a shared folder on the Windows Server

Create a shared folder on the Windows Server from which you wish to create the Group Policy.

In order for the MSI installation to work, the MSI needs to be placed in a Shared Folder on the server such that it can be accessed by every user/device. You can use an existing network share, but it is often simpler when troubleshooting if you create a new one.

Once you have established the Shared Folder you will use, follow the following steps to grant access to everyone you wish to provision with the Outlook Assistant.

  1. Right click the folder
  2. Select the Sharing tab
  3. Click Share
  4. Add the names of the Users to whom you wish to grant access, or simply enter “Everyone” to enable the package to be accessible by every user/device (typical). Users only require Read access.skoast2.4.png
  5. Click Share and make a note of the Network Path.
  6. Click Close

Step 2: Configure Group Policy

  1. Open the Group Policy Management console from Administrative Tools menuskoast3.1.png
  2. Once the console opens, expand the navigation tree to the domain for which you would like to deploy SKOA
  3. Right-click the domain and select Create a GPO in this domain and Link it here…   skoast3.3.png
  4. Give the Group Policy any name you please
  5. Once the Group Policy Object has been created, find it in the Group Policy Objects folder, right-click it and select Edit.
  6. Once the Group Policy Management Editor has opened, expand the tree through Computer Configuration->Policies->Software Settings
  7. Right-Click Software installation and select New->Packageskoast3.7.png
  8. Navigate to the Network Address of the Shared Folder you created earlier.

Note: Navigate to the UNC address (generally \\server\path) NOT the local path (e.g. c:\mysharedfolder). For the MSI deployment to be possible the path specified must be a path the device can access over the network, therefore the local path on the server will not work correctly.

  1. Select SKOA MSI you downloaded earlier.

Important: Attempting to install both the _x86 and _x64 versions of sklquery.msi will cause an error. Therefore, if you have a mixed environment, you will need to configure two Group Policy Objects, one for 32-bit versions of Windows and one for 64-bit versions of Windows.

For PCs running a 64-bit version of Windows, select:

  • outlookassistant
  • mapi64helper

For PCs running a 32-bit version of Windows, select:

  • outlookassistant
  1. Click OK
  2. Ensure Assigned is selected as the Deploy Software option and click OK. The Group Policy Object may take a few seconds to create, and you will need to click OK for each MSI you are including in the GPO.
  3. Return to the Group Policy Management console and select your Group Policy Object
    1. In the right pane, under Security Filtering select Authenticated Users and click Remove.skoast3.12a.png
    2. Once Authenticated Users has been removed, click Add.
    3. Type “Domain Computers” and click Check Names. Exclude any computers on which you do not want Outlook profiles created.
    4. Click OK

Note: If you have a mixture of 32 and 64 bit PCs you may need to add each PC Name specifically to the list of objects to which the Group Policy will apply. Alternatively, create an Active Directory Group for 32 and 64 bit PCs respectively. You can then add the relevant group rather than specifying the PCs individually here.

  1. Open a command prompt and type “gpupdate” and press enter to ensure the Group Policies have been updated.
  2. Group Policies can take some time to propagate to each PC. To force a PC to update its Group Policies, you can go to each PC, open a command prompt and type “gpupdate /force” (this will require a reboot). The next time the PC reboots and connects to the Domain, the Group Policy will be enforced.
  3. Once installation is complete, the user will be prompted to sign-in to SKOA using their email credentials as provided via Password Reception or the CSV spreadsheet. The sign-in process is required for SKOA to confirm the identity of the user and connect their identity with the PC.
  4. As part of the sign-in process, the user will be prompted to specify the Outlook data store from which their settings (and data in a POP/IMAP migration) will be migrated.

  5. Once the user has successfully signed-in, SKOA will report back to our Migration Dashboard that it has been installed successfully. We will keep you appraised. 





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