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Send Email - Can't establish SSL/TLS Connection

Steve Flores

Hello,

When I try to run the email workflow I get the following issue. In the emailsettings.json file I have tried Port 465, 587 and 25. Restarting the application pool each time and all result in the same error. Has anyone dealt with this?

 An error occurred while attempting to establish an SSL or TLS connection.",
        "One possibility is that you are trying to connect to a port which does not support SSL/TLS.",
        "The other possibility is that the SSL certificate presented by the server is not trusted by the system for one or more of the following reasons:",
        "1. The server is using a self-signed certificate which cannot be verified.",
        "2. The local system is missing a Root or Intermediate certificate needed to verify the server's certificate.",
        "3. The certificate presented by the server is expired or invalid.",
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Comments

4 comments

Date Votes
  • Nelson Dobbs

    I had that same issue, I believe the way I fixed it was to go in to IIS on the server and set up the SMTP E-Mail settings there.  I have the Deliver email to SMTP Server filled out with the Server and port 25 with Authentication Settings set to "Not required".  Email address is blank.

    Nelson

    1
  • Steve Flores

    Thank you. I tried the same steps you listed out, but I'm still getting the same error. Still working on trying to figure out the fix. 

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  • Daan Molleman

    I'm having the same issue, so bump

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  • Matthew Poirier
    Edited

    Note that Steve's issue was resolved by setting EnableSSL to false when using port 587 with a Gmail SMTP server:

     { 
 	"EmailSettings": {
      	"Configurations": {
          	"Default": {
              	"Host": "smtp.gmail.com",
              	"Port": 587,
              	"Username": "gmailaccount@gmail.com",
              	"Password": "password",
              	"EnableSSL": false           
              }
          }
      }
  }

    The reason SSL has to be set to false in the above examples is because port 587 does not allow SSL connections - it uses StartTLS. Therefore set EnableSSL to false if using this port. Port 465 on Google SMTP servers support SSL: https://developers.google.com/gmail/imap/imap-smtp 

    Of course, the “ An error occurred while attempting to establish an SSL or TLS connection.” error from mailkit is fairly generic so the above solution may not be applicable to all scenarios.

    For those troubleshooting the different Email Settings please also remember to recycle the Workflow App Pool in IIS (step 5 in our documentation) to ensure changes to the settings are applied.

     

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