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Datto Autotask PSA: How to Troubleshoot MS Exchange Extension Sync Issues

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This article provides troubleshooting steps for resolving synchronization issues between Datto Autotask PSA and Microsoft Exchange.

Environment

  • Datto Autotask PSA
  • Microsoft Exchange Server 2013
  • Microsoft Exchange Server 2016
  • Microsoft Exchange Server 2019
  • Microsoft Office 365

Description

The Microsoft Exchange Integration automatically synchronizes contacts and calendar items between Autotask and the Microsoft Exchange server. There are no add-on components or agents to install. Contacts, appointments, To-Dos and service calls flow from Autotask to Exchange, and appointments scheduled in Exchange flow to Autotask. Items synchronize as follows:


mceclip0.pngFigure 1: Microsoft Exchange - Datto Autotask PSA communication flow

To leverage the Microsoft Exchange Integration, your environment must use Microsoft Exchange 2013, Microsoft Exchange 2016, Microsoft Exchange 2019, or Microsoft Office 365.

NOTE: The following guide does not cover the Public Folder contact synchronization for this extension. See our Datto Autotask PSA: How to Configure Public Folder Access for Office 365 article for this guidance, or consult your Microsoft Exchange administrator for assistance.

Troubleshooting Steps

  1. Have you configured the information on the General tab correctly based on your setup, and can you click "Save" on the page without an error?
    On-premise, Hosted, and Office 365 environments each have different setting requirements for the sync to work. See Configure the MS Exchange Extension in our help documentation.
    1. Yes
      Proceed to step 2
    2. No
      Review the help document linked above and ensure the credentials entered on the page are accurate. Be sure to check for variables such as whether or not the user is using Two-Factor Authentication in their Office/Exchange environment. See Datto Autotask PSA: Can I use Two-Factor (Multi-Factor) Authentication in Office 365 with the MS Exchange Extension? for more information.
      If the credentials are valid for the listed synchronization account, have your user provide the username/password for the user listed and test the credentials with the Microsoft Remote Connectivity Analyzer Tool (external link).
  2. Are you using the credentials on the General tab for synchronizing individual user accounts?
    When you check the box that says Use these credentials for synchronizing individual user accounts under the Synchronization Account section, enabled users do not need to enter a password when they configure their synchronization settings and do not have to worry about updating their password in Autotask (for the integration) when it changes. You must, however, ensure that the synchronization account has read/write access to users' MS Exchange folders, the ability to create public folders, and access to its own mailbox. If you leave this box unchecked, individual credentials will be used for the synchronization. Each user will enter his or her username and password in their User Profile (Home  User Profile Advanced MS Exchange). Exchange account information is encrypted in the Autotask database, but there is no central password management. When users change their usernames or passwords, they will also need to make the change in Autotask for the MS Exchange Extension, or the synchronization will fail.
    1. Yes
      Proceed to step 3
    2. No
      Skip to step 5
  3. Is the synchronization account configured correctly?
    If the Exchange environment is On-premise or Hosted, work with your domain administrator to verify this portion. If you determine that you require Datto Technical Support assistance, please attach screenshots of your configuration. For Office 365, refer to Datto Autotask PSA: How to Configure Impersonation Rights in Office 365.
    1. Yes
      Proceed to step 4
    2. No
      You must make the required changes to ensure impersonation rights have been granted. Once these changes are in place, if the save still fails, proceed to step 4.
  4. Have you tried unchecking the "Use these credentials for synchronizing individual user accounts" checkbox? This control determines if the sync leverages user impersonation or individual credentials.
    1. Yes
      If you are still not able to complete a test save on the General tab of the setup and you have tried all of the steps above, try entering a different username and password for the sync account. If you're not leveraging impersonation rights, this account is only used to test that the Exchange or Office 365 server is reachable via that username and password combination. Note that the user account must be a fully licensed user with a real mailbox in Exchange. If clicking Save on the General tab after performing this step, and the user has this box unchecked, proceed to step 5.
    2. No
      To rule out any configuration issues with the sync account, try leveraging the sync at a user level using their credentials rather than the sync account. If the test connection for a user works with this box unchecked, the behavior indicates a configuration issue in your Exchange or Office 365 environment. Uncheck this box as part of troubleshooting and proceed to step 5.
  5. On the Resources tab, click on the Last Attempted Synchronization date for a resource who is activated. Do the Test Connection and Save buttons return successful as-is with no changes?
    1. Yes
      If you've skipped to this step from step 2, it means the user account you've tested is not currently experiencing a sync issue. If you've arrived at this step by following the steps prior, it is an indication that either the sync account was or is presently misconfigured. Feel free to test with other resources to verify the issue is now fully resolved for all profiles.
    2. No
      Manually type the username, password, and exchange email address for this resource in the user profile window. Autofill or password generator tools can sometimes replace the values entered in this window between a test connection and the save. Using an incognito or private browsing window will often rule this possibility out. If the test continues to fail, proceed to step 6.
  6. Does the resource you are testing have 2FA or multi-factor authentication enabled in their Exchange/Office 365 environment?
    1. Yes
      You must configure an app password to leverage the MS Exchange Integration for this resource. See Datto Autotask PSA: Can I use Two-Factor (Multi-Factor) Authentication in Office 365 with the MS Exchange Extension? for more information.
    2. No
      If the user insists the credentials are valid for the account yet the test is failing, have them provide the username/password/email for the user listed and test the credentials with the Microsoft Remote Connectivity Analyzer Tool (external link). If the tool is unable to run, it means the username/password/email combination is invalid. If the tool can run, please contact Datto Technical Support for further assistance.

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