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2022-11-28 09:55:25 Info : Failed to send to: (StartTlsFailed 220 220 2.0.0 SMTP server ready) will retry 4 for Automation O365 Helpdesk Automation

By @mmerlino
    2022-11-28 15:36:56.538Z


    I'm getting the error message:

    2022-11-28 09:55:25 Info : Failed to send to: (StartTlsFailed 220 220 2.0.0 SMTP server ready) will retry 4 for Automation O365 Helpdesk Automation.

    When Think Automation tries to process an e-mail.

    Anyone else evert see this?

    • 6 replies
    1. D
      Daniel Horton @daniel.horton
        2022-11-28 15:43:14.511Z

        Hi mmerlino,

        Yes, this is a product issue due to a component bug found with SMTP outbound messaging and we have resolved it in our next release, though a fix is available through our Pre-Release version.

        To update to the pre-release go into the ThinkAutomation Studio and follow these steps:

        1. File -> Server Settings -> Customer Participation
        2. Then tick 'Include Pre-Release Updates'
        3. Now Click OK
        4. Then go to File -> Check for Updates
        5. Update to 898.2
        6. Review the behaviour again for SMTP email

        This will resolve the issue and you may turn off the Custom Participation option if you wish to only receive future public builds.

        1. M
          In reply tommerlino:
            2022-11-28 16:23:59.641Z

            Hello Support,

            So I ran the update process as per the below e-mail. After the update we rebooted the server as well.

            We are still getting StartTlsFailed 220 220 2.0.0 SMTP server ready) error messages.

            Please advise.


            1. D
              In reply tommerlino:
              Daniel Horton @daniel.horton
                2022-11-28 16:50:24.253Z

                Okay, this could be a secondary issue with Microsoft's recent removal of Basic Authentication. You would need an App Password for the mailbox in question to be configured to allow you to continue using SMTP with Basic Authentication. You are no longer able to use the account's username + password combination for authentication due to the wide spread changes at Microsoft for their new Two Factor Authentication requirements introduced in October 2022.

                Additionally to that it is also possible that Microsoft have switched off your SMTP protocol for particular accounts if you have not used it. That would also need to be checked to ensure that it is still enabled.

                Unfortunately that is a wide-spread issue that Microsoft have recently introduced and can be confused with the behaviour we had in a previous ThinkAutomation version. Though the solution previously provided is necessary for ThinkAuotmation to support the use of App Passwords against an Office 365 SMTP account.

                Thank you

                1. M@mmerlino
                    2022-11-28 19:51:56.061Z


                    We ran into this issue last month. There was no place to enter an App Passsword in Think Automation. If we setup the App Password, where do we enter in T.A ?

                    Please advise

                    1. In reply todaniel.horton:
                        2022-11-28 20:39:01.097Z

                        We are waiting on approval to increase our level of support.

                        In the meantime, is there anything else that can be suggested? I’ve opened a ticket with Microsoft and they are not seeing an issue in O365. I’ve also opened a ticket with our Ticketing System partner to see if the issue is on their side and they do not see and issue on their side as well.

                        The feeling from both partners is that the issue is with Think Automation. We have tried to adjust settings, but nothing is working at the moment.

                        Think Automation is currently not processing any of our tickets and we are updating existing tickets and entering new ones.

                        If there is anything that can be suggested while we wait for approval, it would be appreciated.


                      • D
                        In reply tommerlino:
                        Daniel Horton @daniel.horton
                          2022-11-28 21:05:15.599Z

                          Hi Mark,

                          The App Password for the account simply goes into the standard password field. This is the same as all other App Password using technologies via Basic Authentication.

                          Apologies if you feel that the problem is on our side. As stated there was a known issue with a component that we have rectified but unfortunately we do not control any changes to your Office 365 account and we are aware that these types of issues have occurred on Microsoft Office 365 over the past month or longer as Microsoft's changes start to take effect to their users.

                          So that you are aware one manner to test your account is to use the Powershell command let called Send-Message. There is a sample here that can be used and you can supply your App Password against it in the password field when prompted - This uses similar methods to ThinkAutomation so is a good test to attempt on the same machine as ThinkAutomation. I find it is best to use the Powershell ISE as you can paste in the entire script and run it as a single operation vs line by line.