How to upgrade all TLS in pipeline to 1.2?

Question

We have a virtual machine running Windows Server 2019.

Until recently, emails have been sent OK. However, since TLS 1.0 / TLS 1.1 has become obsolete on 5th June, the emails have stopped working.

We are using TwillioSnedGrid as the SMTP facilitator for our VM hosted on Azure. We have modifed the E-mail settings in the Report Server Configuration Manager on our virtual machine from smtp.sendgrid.net to tls12.smtp.sendgrid.net, and have prooved emails can be sent using the api key configuration using TELNET. However when sending emails from our reporting server web interface, the emails do not send.

It could be that there is some configuration somewhere that is stil using the obsolete TLS version, however we have been unable to determine if this is the case.

Any advise greatly appreciated!

Best regards,

Luke

Answer 1

@Iwan S Jones

I understand that you are facing issues with sending emails from your reporting server web interface after the TLS 1.0 / TLS 1.1 became obsolete. I can help you with that.

It's good to know that you have already modified the E-mail settings in the Report Server Configuration Manager on your virtual machine from smtp.sendgrid.net to tls12.smtp.sendgrid.net and have proved that emails can be sent using the api key configuration using TELNET.

To troubleshoot the issue, I would suggest you check the following:

Check if the reporting server web interface is using the updated E-mail settings. You can verify this by checking the configuration settings in the reporting server web interface.

Check if there are any other applications or services that are still using the obsolete TLS version. You can use tools like Qualys SSL Labs or Fiddler to identify which TLS version is being used by the clients connecting to your application1.

Check if there are any firewall rules or network policies that are blocking the traffic. You can check the firewall logs to see if there are any blocks or drops.

If you have checked the above and still facing the issue, let me know and we can work with you directly to troubleshoot.

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