Deploy not working when two web sites running HTTPS Windows 2016 IIS 8 with Require Server Name Indication

I’m wanting a deployment solution for this configuration. I’m very new to Octopus Deploy. I’m an independent .NET C# developer. I have a client running a web app in Amazon AWS on Windows 2016 server and IIS 8 with two websites that each have their own SSL certificates. One is for staging and one is production. The HTTPS binding for each Require Server Name Indication is true. I have set up the Octopus server on my remote Window 2016 server on AWS. I have installed and setup Tenticles on the client server. I have configured a deployment to the test website but I don’t really know how to configure it. My install caused the test web to break and nothing seems to have been deployed. The Require Server Name is removed from the production web. I have to remove the test web, recreate, add the HTTPS binding with Require Server Name Indication, and modify the Require Server Name Indication on the production web (set it to true again).

Can you point me to what I might be doing wrong?

Hi Larry,

Thanks for getting in touch. This is the first time I’ve heard of this issue so I’d like to get a bit more information so I can investigate further. Can you tell me which version of Octopus you’re using and can you provide the full deployment task log? You can learn more about accessing your log files at the following URL.

With this additional info, we should be able to figure out what is happening.

Looking forward to your reply.



I finally had time to really work on this and it seems that my configuration was totally wrong. Of course this was because I hadn’t taken the time to study and understand the documentation. I am now able to successfully deploy. :slight_smile:

Hi Larry,

Thanks for following-up to let me know you got it working. I’m happy to hear that it works well with Windows Server 2016!

Happy deployments! :slight_smile: