LetsEncrypt encryption on port 80

According to this page, it’s only possible to configure a Let’s Encrypt Certificate on servers that are publicly accessible on port 80.


Is this limitation still present and I assume it’s a Lets Encrypt limitation of their certificate issuing process? It say “Configure” - is it possible to get the certificate working on port 80 and then switch to another port? Not ideal but my server isn’t heavily used so a bit of downtime is acceptable each 90 days.

I’m just a lone guy running SimpleHelp on my own server where I also run a web server on port 80. So SimpleHelp is on port 8008.

Another question (that I’ve had for a long time), is that can IIS work as some kind of proxy service in front of SimpleHelp? So IIS can listen on port 80 but redirect everything SimpleHelp on port 8008? My knowledge of IIS and web servers never went this deep.


If you can’t get LetsEncrypt working, another possible solution that will work is to find a dirt cheap SSL certificate from a company such as SSLS.com.

Here is a link: https://www.ssls.com/ssl-certificates/comodo-positivessl

In this case if you purchase for 1 year its $5.50 or if you purchase for 5 years its $17.20 total.

@Rob_Nicholson - This is in the spec for LetsEncrypt, and not a function that Simple-Help has control over.

It seems as though if you have 2 servers behind one ip that both need to accept traffic on port 80 then you need a “reverse proxy”. This would allow to route traffic based on host name, so port 80 traffic bound for yourshserver.com would go to your simple-help server, and traffic bound for yourwebserver.com would go there.

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Indeed I have - three in fact: IIS web server, SimpleHelp web server and Spiceworks help desk. Thanks for the heads up about reverse proxy. Know the phrase but never implemented one.

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