In a standard migration scenario, end users will need to perform various actions, based on how the Outlook Assistant is being deployed.

NOTE: If the Outlook Assistant is installed via Group Policy, the end user does not perform the installation steps described below.

For optimal user experience, it is recommended that you download the Office 365 Migration End-User Experience with Outlook Assistant PDF from SkyKick and share with your POC. (You must login to your SkyKick Dashboard to access this material.)

Password Reception Page and Skykick Outlook Assistant Installation

On placing the migration order with SkyKick the Migration Application will send each migrating user an email with a link to download Outlook Assistant from a partner-branded page. Easy, consumer-targeted instructions provide guidance along the way. The Password Reception Process simplifies and streamlines the end-user experience by only requesting what is specifically required from each user, based on the migration scenario and configuration. For more information, refer to the Filling out the Password Reception Page and Downloading SkyKick Outlook Assistant (SKOA) article. 

Outlook Assistant Status and Actions Before Cutover 

Once the Outlook Assistant is installed either by the end user or via MSI, a Welcome screen will appear and the Outlook Assistant will automatically progress through its stages, as indicated by a progress bar.

Sign In

Once installed the Outlook Assistant will prompt the end user to sign into the device with their destination credentials as provided to the SkyKick migration application. This authenticates them and binds the Outlook Assistant application to the workstation.

If sign in is unsuccessful, the reason for the failure will appear. Until the end user successfully signs in, there will be no indication of this in the Migration Dashboard.

Below are some examples: 

Password authentication failed: This is often due to an inaccurately typed password. If this occurs, the end user should select Show Password to ensure accurate entry.

Email was not found in the migration order: If the email address provided does not match an email address in the migration plan, the end user is instructed to report this.

Server unavailable: If the server is unavailable, it is typically due to a firewall or source server issue. However, in case this is a transient interruption, the user is instructed to try later before reporting the issue.

Preparing

Once the end user is signed in, the Outlook Assistant will perform the following readiness actions, and will request end user input if needed (e.g. selecting primary data store if more than one profile is detected).

• Outlook version: For updating to Outlook version supported by Office 365, see the How to install the latest applicable updates for Microsoft Outlook article from Microsoft.
• Outlook profile: If an end user has more than one email data store, the Outlook Assistant will prompt them to select the primary data store where their email is saved.
• Password verification: If the provided password does not match what is in the Migration Plan, there will be a device error reported on the Devices tab of the Migration Dashboard, along with troubleshooting steps, and options to resolve the issue directly.
• Autodiscover path validation: Ensures connectivity to Office 365 account.
• Profile creation for Office 365: Creates new Outlook profile that will be connected to Office 365.

NOTES:

• The screen below may appear on a user’s desktop upon fresh login. If this occurs, users can minimize or close the window.
• Several functions on the Preparing tab cannot be performed until cutover
• In an Office 365 to Office 365 migration more of these functions need to be performed at cutover due to their reliance on vanity domain verification. This may result in a longer time to complete after cutover.
  

Outlook Assistant Actions at Cutover

Switch

At cutover, the Outlook Assistant will automatically switch each end user’s Outlook profile, restart Outlook, and connect their profile to the new Office 365 account.

1. The end users will be notified that the switch to Office 365 will begin shortly. If they are busy, they will have the option to Delay 10 minutes. If they choose to delay, they will be prompted every 10 minutes until they choose to Switch Now.
   
   IMPORTANT CONSIDERATIONS:
   • If the PC is turned off or locked, the end user will be prompted to migrate upon next login.
     If the PC is not connected to the internet, the end user will be prompted to migrate as soon as connectivity returns.
   • If the end user has not downloaded the Outlook Assistant prior to cutover, one of the last emails in their old mailbox will have a simple call to action to submit credentials and download the Outlook Assistant. Once installed, it will immediately begin its processes while data syncs in the background.
   • In rare cases during Outlook profile creation, Windows or Outlook may prompt the end user to perform an action (e.g. entering credentials). If the user responds to the prompt within the 10-minute time frame, there will be no impact on Outlook profile creation. However, if there is no response, the Outlook profile will not be created. If this occurs, profile creation must be retried by going to the Devices tab in the Migration Dashboard, selecting the user, and clicking Retry Profile Creation.
2. The Outlook Assistant will close Outlook if it is open and begin to list all the actions being performed. Depending on the amount of data and the processing speed of the PC, the local migration can take anywhere from a few minutes to a few hours. During this process, end users can access their mailbox through Outlook Web Access (OWA).
   
3. The Outlook Assistant will open the new profile and connect it to Office 365. Outlook will begin rebuilding its .OST by downloading mail from Office 365. The duration of the .OST-building process is determined by available bandwidth and mailbox size.
4. Once complete, Outlook will be configured and operational with Office 365, and the end user will be informed that the switch is complete

Unsuccessful Switch

If the switch to Office 365 is not successful, more information will be provided. This information will also be reported on the Devices tab of the Migration Dashboard, along with troubleshooting steps and actions to resolve.

Examples include:

• Unsuccessful transfer of Autocompletes
  
• Unsuccessful migration of local data
  

More Information Menu

End users can open the drop-down menu at any time to get more information about the Outlook Assistant and its actions.

Show Switching Results

This option is available after cutover, and provides the complete results from the switching process.

If an end user signs out of the application, the device will no longer connect to the Migration Application. For the Outlook Assistant to perform any future actions, the end user will need to open the System Tray, select the Outlook Assistant and sign in.