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Email Sending Failed : SMTP connect failed ()

Original Question or Issue:

Receiving an 'Email Sending Failed : SMTP connect failed () ' error in the Admin Portal while setting up XOAUTH2 for Email

Environment:

  • Product - FileCloud Server
  • Version - 23.1
  • Platform - Any

Steps to Reproduce:

From the Admin Portal > Settings > Email page:

  • Set 'Email type' as SMTP
  • Set 'SMTP AUTH Type' to XOAUTH2
  • Fill in the required fields using FileCloud's Email Settings support documentation below:

https://docs.filecloud.com/fcdoc/latest/server/filecloud-administrator-guide/filecloud-site-setup/email-settings

Error or Log Message:

Email Sending Failed : SMTP connect failed ()

Defect or Enhancement Number:

 

Cause:

Confirmed as a Microsoft-related issue in this particular scenario

Resolution or Workaround:

  • Open up a private/incognito browser
  • Log into the Admin Portal as the superadmin user, and not an elevated admin user
    • (NOTE: If the superadmin password was forgotten, it can be reset)
  • Open up Dev Tools in the Web Browser (F12) > Network Tab > Record Network Log
  • Navigate to Settings > Email and press the 'Generate oAuth Token' button
    • Check which Microsoft Account the login prompt displays (this should be the mailbox configured for all FileCloud email fields and the one Azure granted SMTP permissions to)
    • If the wrong Account is displaying in the log-in prompt, it can be changed before moving forward
    • Ensure the correct credentials are being used

Notes:

  • The associated HAR file can be downloaded from the web browser if all else fails after running through the workflow
  • FileCloud Server Logs in DEV mode can also be generated by first visiting the Admin Portal > Settings > Server page, and setting the 'Log Level' to DEV
    • Reproduce the issue
  • Then to download the newest logs, from the Admin Portal you can navigate to System > Checks > 'Generate Logs' button
  • The FileCloud Server logs will also be available in these locations:
    • Windows: C:\xampp\htdocs\scratch\logs\log_YYYY-MM-DD.txt
    • Linux: /var/www/html/scratch/logs/log_YYYY-MM-DD.txt
  • Email Settings Support Documentation:

https://docs.filecloud.com/fcdoc/latest/server/filecloud-administrator-guide/filecloud-site-setup/email-settings