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Office 365 errors and what they mean

Below are possible error messages that may occur with your Office 365 API setup and what you can do to fix them.

Updated yesterday

Please Make sure your Microsoft Office 365 integration is working

Error: Invalid refresh token, please sign in again

Please Make sure your Microsoft Office 365 integration is working

Error: Code: InvalidAuthenticationToken Message: CompactToken Validation failed with reason code: 80049228. Inner error: AdditionalData: date:

Please Make sure your Microsoft Office 365 integration is working

Error: invalid_grant

Please review the list of errors

  1. An unknown error has occurred

Please review the list of errors

  1. The server could not process your request.

The above errors generally indicate that the Office 365 API has not been set up correctly in Azure or SmartDocs. For example, Invalid Grant usually means a permission error where one or more app registration permissions are not enabled.


Recreate the Office 365 API connection

  1. Delete the existing Office 365 API connection in SmartDocs.

  2. Go to Setup > Configuration > Integration.

  3. Recreate the connection using the mailbox credentials that will send emails from SmartDocs.

  4. Use the API Key (Application Client ID) and Account Key (Client Secret) from your Microsoft Azure account.

  5. Test the connection.

If you need to send emails before fixing the API, delete the Office365 API from SmartDocs so the system temporarily reverts to the centralised mailbox (hub.ddslive).

The most common cause of these errors is that the person setting up the integration did not log out of Azure before connecting SmartDocs to Office 365.


Incorrect email address used after reconnecting

If SmartDocs starts sending from your email address instead of the nominated mailbox:

  1. Ensure you logged out of Azure before Step 9 of the setup instructions.

  2. Delete the Office 365 API in SmartDocs.

  3. Ensure you have saved the Application (Client) ID and Client Secret.

  4. Fully log out of Azure—closing the window is not enough.

  5. Reconnect the API again while logged out of Azure.

Tip:
Use an Incognito window when logging into SmartDocs so that the correct Microsoft login screen appears.

A video is provided in the original article showing the correct logout position in Azure.


“I can’t sign into the nominated mailbox”

If you see an error while attempting to give access to the nominated mailbox, check for URL errors in Step 2 of the setup instructions. Ensure there are no spaces or spelling issues.

The article includes:

  • A setup video

  • Step‑by‑step instructions

  • A document containing the full Office 365 setup guide

  • A video on common setup mistakes


MFA considerations

If you enable MFA on your Office365 mailbox, you must reconnect the API Integration in SmartDocs and enter the verification code.

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