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I am working with several websites that runs on IIS and accessible locally only.

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I have SSL on main website from Let's Encrypt for *.domain.com Those currently runs on different ports. 443, 45455. Etc Unfortunately, the company who services network is a pain in my ass and most of the times I must do everything by myself.

I would like to have three wildcards for each website so SSL would work on them too.

Let’s say: local.domain.com, dev.domain.com, etc

I have full control on server where websites running from and limited access where AD is installed. Currently all traffic is redirected to domain.com. What would be the best approach to achieve what I want interacting with main server as less as possible. Note that I had experience with networks in the past but my skills are quite rusty since I am not working with network for some time.

Justas
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    Server administration is off topic here, and if you selected the right tag you should know that Windows Server 2008 reached end of life a long while ago. – Lex Li Aug 28 '23 at 15:25
  • Are you trying to set up an SSL certificate for a subdomain of your main domain that is currently running on a different port? Did you generate a wildcard SSL certificate? Obtain a wildcard SSL certificate for all the subdomains you need (e.g. local.domain.com, dev.domain.com) using a certificate authority such as Let's Encrypt. – YurongDai Aug 29 '23 at 03:13

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