SkyKick Outlook Assistant

Outlook Assistant Overview

 

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.

Note: The Outlook Assistant is not available with a Data-Only Migration.

By using Outlook Assistant as part of a SkyKick 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. The end goal is to mirror a user’s Outlook environment prior to the migration as closely as possible.

  • 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: Outlook upgrades should be performed at least 72 hours post migration. Upgrading Outlook installations on workstations after the Outlook Assistant has been installed may cause the Outlook Assistant's processes to fail at cutover time.

    Other requirements include:

    • Windows XP SP3, Vista, 7, 8, and 10
    • Office 365 supported versions of Outlook (currently Outlook 2007-2016) on Windows (no thin clients or terminal servers).
    • .Net Framework 4.0
    • Local Administrator rights to download and install the Outlook Assistant.
    • Office 365 license type that supports client-level Exchange access.

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

    Unsupported Scenarios

    • 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.)
    • Mobile Devices (e.g. Android, iOS, etc.)
    • Outlook 2003. Office 365 does not support Outlook 2003. When migrating from Outlook 2003, 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 below is upgraded to Outlook 2007+, 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).
  • Installation

    The SkyKick Outlook Assistant is typically installed by users several days in advance of the migration, and runs silently in the Windows System Tray until the migration time when it finalizes the migration and sets up the user's PC.

    If an end user hasn’t downloaded the Outlook Assistant prior to the migration date, one of the last emails in Outlook will have a simple call to action to download the Outlook Assistant. Once they download the Outlook Assistant, it will immediately set up their new Outlook profile while data syncs in the background.

    If an end user cannot use the Outlook Assistant, email communications will be provided with manual Outlook setup instructions. Office 365 login credentials and instructions will also be provided so they can use the Outlook Web Application.

    For more information on the end user experience, see Outlook Assistant End User Experience.

    Note: The Outlook Assistant's Client app will run under the identity of the currently logged in user and must be able to communicate with migsvc.skykick.com and *.loggly.com on ports 80 and 443. The Outlook Assistant's Windows Service will run under the identity of the Network Service and must be able to communicate with migsvc.skykick.com and *.loggly.com on ports 80 and 443.

    The Outlook Assistant can also be installed via Group Policy. Additionally, with a Hands-Free Migration, users will not need to interact with the Outlook Assistant at all. For more information, see Installing and Managing the Outlook Assistant.

  • Before Migration

    Partners should review Alerts daily in advance of the migration date to ensure a seamless migration experience.

    Before the Migration Date, the Outlook Assistant will:

    • Perform desktop and Outlook readiness checks to analyze the following.
      • OS version
      • Outlook version
      • Windows Update/Outlook readiness for Office 365
      • Hard drive size and available space
      • Outlook email protocol selected
      • Size of data stores (PST files to be migrated)
      • Network bandwidth upload speed
      • Active Directory usage.
    • Perform Auto-patching of Outlook as required.
    • Alert you to any local issue through the Alerts section of the SkyKick Portal. The most common issue detected by the Outlook Assistant is outdated Outlook installations needing Service Packs or patches.

    Retry Profile Creation

    Standard Profile Creation Retry Workflow

    As part of its standard workflow, the Outlook Assistant is often able to resolve errors automatically. Many errors are transient and often resolved with a retry of the operation at a later time. When profile creation fails, the next retry is set for 4 hours later. If the failure occurs within 6 hours before or after cutover, the next retry will occur 39 minutes later. Beyond 24 hours after cutover, there are no profile creation retries.

    Note: Profile creation for Outlook 2016 will not be attempted until after cutover has occurred and the autodiscover path is verified.

    In the event an Outlook profile creation fails and the Outlook Assistant is unable to resolve the error automatically, an alert or notification will appear in the Migration Dashboard and manual troubleshooting of the desktop is required.

    Profile Creation Troubleshooting

    In order to expedite the troubleshooting process, the Recreate profile button enables you to force the Outlook Assistant to retry its operation sooner than the standard schedule. This allows you to quickly determine if the troubleshooting steps resolve the issue.

    In most cases the Outlook Assistant will poll (check-in) to the Migration App web service every two minutes to request the next command. Clicking the Recreate profile button will instruct the Outlook Assistant to reattempt to create an Outlook Profile when it next polls the Migration App web service instead of waiting the standard interval of either 4 hours or 39 minutes, depending on the proximity to cutover.

    To retry profile creation:

    1. Go to the Email Accounts tab in the Migration Tracker
    2. In the user detail view, click the Recreate profile button

    You will then be informed of the time of the next scheduled poll, at which time the profile creation will be retried.

At Migration

Regardless of the installation scenario, the Outlook Assistant will automatically switch the Outlook profile, restart Outlook, and connect to the user’s new Office 365 account. This process starts about 10 minutes after cutover and takes a few minutes to complete.

  1. The Outlook Assistant will close Outlook (if it is currently open) and begin transferring local data to the new Office 365 profile according to the migration type. For more information, see What We Migrate.
  2. A dialogue box with a status bar will appear on the screen detailing the status of the transfer of local data. During this transfer, Outlook will not be usable, but Outlook Web Access (OWA) can be used during this time. Once completed, Outlook will reopen to the new Office 365 profile.
  3. Outlook syncs with Office 365. During this time, Outlook will begin downloading data from the mailbox and rebuilding the local .OST. Depending on the size of the migration, this may impact local bandwidth.
  4. There are generally few new Alerts in the Partner Portal because all the prior readiness work should have already identified any desktop issues. However, the best practice is to check for any last minute alerts.
  5. Users show up to work the next day, and their Outlook is now configured and operational with Office 365.

End User Scenarios

  • If the user is working at their PC, they will be asked if they want to delay the migration an additional 10 minutes in order to finish up any last minute tasks.
  • If the PC is turned off or is not connected to the internet, then this action will occur as soon as connectivity returns.
  • If the user is away but not logged out, the Outlook Assistant will proceed as long as the PC is unlocked and the user is signed in.
  • SkyKick Outlook Assistant and POP3 / IMAP Migrations

    In the case of POP3/IMAP migrations, data is stored locally on the PC. Outlook Assistant performs a local migration of the primary data store to the new Outlook profile and Outlook syncs that data to Office 365. All offline PSTs are also re-attached to the new profile.

 

Installing and Managing the Outlook Assistant

Note: The Outlook Assistant is only available through the SMB and Enterprise Migration Suites, can only be installed on PCs running Outlook 2007 or later, and is not supported in thin-client (Terminal Services) environments.

The 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, recreates the user’s previous Outlook experience, and collects PC and network data to ensure data can be moved across the network in the allotted project time.

For more general information on the Outlook Assistant, see Outlook Assistant Overview.

There are two ways to install/deploy the Outlook Assistant:

  • End-User Self-Service
  • MSI push/silent install

Before Installation

Outlook upgrades should be performed at least 72 hours post migration. Upgrading Outlook installations on workstations after the Outlook Assistant has been installed may cause the Outlook Assistant's processes to fail at cutover time.

  • End-User Self-Service Installation and Deployment

    The Self-Service installation method is the most technically simple mechanism of installing the Outlook Assistant across the customer's organization. Each End-User downloads and installs the Outlook Assistant by providing their credentials to the Migration Application, via Password Reception.

    This installation is automatic and the default mechanism recommended by the Migration Application.

    For more on the end user experience, see Outlook Assistant End User Experience.

    End-User Self-Service Installation Process

    The following is the default self-service process. The actual steps may vary based on customizations that are made in the Migration Planner.

    1. User receives an email with their unique Password Reception URL to ensure that the Password Reception Page and the Outlook Assistant can correctly identify the user.

      Note: Do not share a download of the Outlook Assistant between different users. The download and installation process is unique to each user.

    2. User clicks the link in the email, opens the Password Reception Page and provides any necessary information and credentials to the Migration Application.
    3. At the end of the Password Reception process the Outlook Assistant download begins automatically.

      Note: If the user does not download or otherwise fails to complete the installation of the Outlook Assistant, the Migration Application will send them ongoing reminders until the installation is complete.

      If the user failed to download the Outlook Assistant, simply revisiting the Password Reception page will allow the user to download the Outlook Assistant. The end user may be prompted to re-enter their credentials on the Password Reception page if they password has become invalid.

    4. Once downloaded the Outlook Assistant begins to install.

      Note: The installation of the Outlook Assistant requires the End-User to have Administrator permissions on their PC. If the user does not have Administrator permissions, deployment via MSI (see below) is recommended.

    5. Once installation is complete, the user will be prompted to sign-in to the Outlook Assistant using their email credentials as provided via Password Reception. The sign-in process is required for the Outlook Assistant to confirm the identity of the user and connect their identity with the PC. In order for the sign-in process to work, the user will need to have completed Password Reception correctly before installation and provide the same credentials as were provided via Password Reception.
    6. 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.
    7. Once the user has successfully signed-in, the Outlook Assistant will report back to the Migration Dashboard that it has been installed successfully.

    Note: If you’d like to avoid end users having to install or authenticate Outlook Assistant to the machine with their email credentials, you can perform a Hands-Free Migration. For more information, see Hands-Free Migrations.

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 Office 365 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, 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 Email Accounts tab of the Migration Tracker

Troubleshooting and Uninstall Options

Troubleshooting

Partners should review Alerts daily in advance of the migration date to ensure a seamless migration experience.

SkyKick Support can help partners with remote troubleshooting for issues and alerts related to SkyKick technology. If you encounter an alert or issue related to the Outlook Assistant, please contact SkyKick Support so we can help you perform any necessary troubleshooting.

Retry Profile Creation

Standard Profile Creation Retry Workflow

As part of its standard workflow, the Outlook Assistant is often able to resolve errors automatically. Many errors are transient and often resolved with a retry of the operation at a later time. When profile creation fails, the next retry is set for 4 hours later. If the failure occurs within 6 hours before or after cutover, the next retry will occur 39 minutes later. Beyond 24 hours after cutover, there are no profile creation retries.

Note: Profile creation for Outlook 2016 will not be attempted until after cutover has occurred and the autodiscover path is verified.

In the event an Outlook profile creation fails and the Outlook Assistant is unable to resolve the error automatically, an alert or notification will appear in the Migration Dashboard and manual troubleshooting of the desktop is required.

Profile Creation Troubleshooting

In order to expedite the troubleshooting process, the Recreate profile button enables you to force the Outlook Assistant to retry its operation sooner than the standard schedule. This allows you to quickly determine if the troubleshooting steps resolve the issue.

In most cases the Outlook Assistant will poll (check-in) to the Migration App web service every two minutes to request the next command. Clicking the Recreate profile button will instruct the Outlook Assistant to reattempt to create an Outlook Profile when it next polls the Migration App web service instead of waiting the standard interval of either 4 hours or 39 minutes, depending on the proximity to cutover.

To retry profile creation:

  1. Go to the Email Accounts tab in the Migration Tracker
  2. In the user detail view, click the Recreate profile button

You will then be informed of the time of the next scheduled poll, at which time the profile creation will be retried.

Uninstall Option 1: Uninstall Button

You can uninstall the Outlook Assistant on every device in the migration with a single button that becomes available 24 hours after cutover.

To uninstall the Outlook Assistant from every device:

  1. Go to the Partner Portal
  2. Click the Uninstall all SKOA devices button
  3. Review the information in the pop-up window
  4. Click Submit to proceed

The next time the Outlook Assistant checks-in, it will be given the uninstall command.

Uninstall Option 2: End User Uninstall

The application can also be uninstalled by the end user or the SkyKick partner using the Control Panel -> Add/Remove Programs interface or can be uninstalled by Group Policy. Within seven days of the cutover, partners may also contact SkyKick Support to uninstall all polling Outlook Assistants if they were not deployed via Group Policy.

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