Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.



Skykick Outlook Assistant Overview

The SkyKick Outlook Assistant (SKOA) 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, clients do not need to manually configure desktops or handle PST files, resulting in a high quality, more secure migration. SKOA 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.

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” message when an Office 365 user opens Outlook

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.

Recommended Action:

Before this error occurs:

  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. For information, see Latest updates for versions of Outlook that use Windows Installer (MSI).
  3. For additional best practices, see Microsoft Announces Issues with Outlook 2016

Password Changes and Password Expiration Policies

If passwords are changed during a migration, it can delay the migration. Emails are sent to inform end users to not change their passwords. However, if a client has a password expiration policy, the timing of it could impact the migration. The following are recommended best practices to reduce the likelihood of password changes during the migration for such customers.

  • Request that the customer disable the password expiration policy and remind users not to proactively change their passwords until the migration is complete.
  • If disabling the password expiration policy is not an option, request that the client have all users change their passwords before placing the migration order and instruct them to not proactively change their passwords before the migration is complete. This will be successful as long as the migration is completed within the password expiration period.

  • Requirements

    Local PC health is essential to the success of SKOA. It is recommended that Windows Update be run on all machines prior to the installation of SKOA to ensure that the local Office installation is ready to connect to Office 365.

    Important: If you are upgrading to a newer version of Outlook, the following best practices are recommended.

    • If users have not been upgraded before order placement, it is best to wait to perform the upgrade until after the migration is complete, unless an upgrade is required for compatibility with Office 365.
    • If an upgrade is required for Office 365 compatibility and the migration has begun, be sure to remove all previous versions of Outlook.
    • If using click-to-run, ensure that Outlook is opened and run before for any click-to-run installations of Outlook.
    • Anti-viruses or firewall settings may need exceptions made for the Outlook Assistant.

    Destination primary SMTP address requirement

    SKOA requires the primary SMTP address of the destination mailbox to be on the vanity domain in Office 365 to create a new Outlook profile. The migration application will move the users it created to the vanity domain once the vanity domain has been verified in Office 365. If there are any users not created by the application, ensure those users’ primary SMTP address is on the vanity domain in the destination Office 365 tenant.

    Other requirements include:

    • Windows 7, 8, and 10
    • Office 365 supported versions of Outlook on Windows (no thin clients).  
      • Outlook 2010 – 14.0.7164.5002 Service Pack 2 (KB2687455) and the December 8, 2015 update (KB2760779) or higher
      • Outlook 2013 – 15.0.4779.1002 Service Pack 1 (KB2850036) and the December 8, 2015 update (KB3121650) or higher
      • Outlook 2016 – Subscription: 16.0.6568.20xx or MSI: 16.0.4312.1001 (KB2920684 & KB4011626) or higher
      • Outlook 2019
    • .Net Framework 4.6
    • Local Administrator rights to download and install SKOA.
    • Office 365 license type that supports client-level Exchange access.

    Note: Standalone versions of Outlook available in the Microsoft Store are not supported.

    Note on Windows XP: Windows XP is no longer supported as it is no longer a supported Microsoft operating system.

    Unsupported Scenarios

    • Multifactor Authentication (MFA) on the destination Office 365 tenant. MFA (e.g. 2FA) will prevent Outlook profiles from being created in Office 365. If possible delay deployment of MFA or disable it for migrating end users until after the migration is complete. For more information, see Enable/Enforce Multifactor Authentication for All (Bulk) Users in Office 365.
    • Running two versions of Outlook side-by-side
    • Upgrading Outlook after SKOA has been installed
    • Terminal Servers/Services (e.g. VDI, RDP, Citrix, etc.)
    • Some third-party applications that customize the MAPI properties of Outlook items or add additional, proprietary properties (e.g. MDaemon)
    • Mobile Devices (e.g. Android, iOS, etc.)
    • Outlook 2003 and 2007. Office 365 does not support Outlook 2003 and 2007. When migrating from these versions of Outlook, SKOA 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 2007 is upgraded, SKOA 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

    SKOA 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 SKOA prior to the migration date, one of the last emails in Outlook will have a simple call to action to download SKOA. Once they download SKOA, it will immediately set up their new Outlook profile while data syncs in the background.

    If an end user cannot use SKOA, 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 SKOA app will run under the identity of the currently logged in user and must be able to communicate with migsvc.skykick.com on ports 80 and 443. SKOA’s Windows Service will run under the identity of the Network Service and must be able to communicate with migsvc.skykick.com on ports 80 and 443.

    The Outlook Assistant can also be installed via Group Policy. 

  • Before Migration

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

    Before the Migration Date, SKOA will perform the following.

    Desktop and Outlook readiness checks to analyze:

    • 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

    The most common issue detected by SKOA is outdated Outlook installations needing Service Packs or patches.

  • At Migration

    Standard Profile Creation Retry Workflow

    As part of its standard workflow, SKOA 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.

    In the event an Outlook profile creation fails and SKOA is unable to resolve the error automatically, an error will be indicated along with a link to troubleshooting information.

    Profile Creation Troubleshooting

    In order to expedite the troubleshooting process, the Retry profile creation button enables you to force SKOA 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 SKOA will poll (check-in) to the Migration App web service every two minutes to request the next command. Clicking the Retry profile creation button will instruct SKOA 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.

    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. 
    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 at this point because all the prior readiness work should have already identified any desktop issues. 
    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 user is away but not logged out, SKOA will proceed as long as the PC is unlocked and the user is signed in.

    SKOA only operates when a computer is in an unlocked state. If the computer is off, not connected to the internet, or locked at cutover, SKOA will wait until the computer is on, connected, and unlocked to initiate its processes. If this is the status of a small number of computers, the impact on the customer may be minimal.

    However, the impact may be more significant if:

    • A large number of devices are turned on and unlocked simultaneously (e.g. Monday morning)
    • It is a migration from POP3 (requiring SKOA to sync email data at cutover)
    • The customer has limited bandwidth

    Therefore, if the cutover is scheduled during non-business hours, it is recommended that end users either leave their workstations on and unlocked or stagger their logins when business hours resume. By taking laptops home and having them on, unlocked, and connected to the internet at cutover, users can also reduce the impact on bandwidth.

    Note: 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, let Big Green know and we will initiate a Retry profile creation.

  • 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.

  • SkyKick Outlook Assistant and POP3 / IMAP Migrations

    In the case of POP3/IMAP migrations, data is stored locally on the PC. SKOA 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.

    If a data store is configured to utilize MAPI connections, it must be saved as a local PST file and identified as the primary data store for SKOA to migrate the data.

  • Storage, Transfer, and Encryption of Data

    SKOA stores, sends, and receives some user data as part of the migration process. Data that is sent or received is encrypted via SSL. 

  • Uninstall Options

    Option 1: Uninstall Button

    You can now uninstall SKOA on every device in the migration that becomes available when the migration is “complete” (5 days after cutover) and remains functional for at least 15 days. Let Big Green know if you would like this to occur.

    Option 2: End User Uninstall

    The application can also be uninstalled by the end user using the Control Panel -> Add/Remove Programs interface or can be uninstalled by Group Policy. Help us help you

Our passion at Big Green IT is empowering clients to be more successful in the cloud. That includes providing the most accurate, helpful information and instructions on using our platform. Please let us know how we’re doing and/or how we can continue to improve.





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