I got the private message, but I'll post here as well. Essentials is a complicated build of Windows Server, so the first step is to make sure that your IIS is working in general. Do you have a https://your.site.here/remote page working?
Make sure IIS is working, Then follow the instructions (here's the raw view: https://raw.githubusercontent.com/megahambone/PlexConnect/master/README.md)
A lot of the install is the same as plexconnect out of the box, but it gets tricky after the fact.
Basically, you're setting up an IIS reverse proxy - so you need to ensure IIS is working. Then, you need to set plexconnect to work on non-standard ports (because 80 and 443 are owned by IIS) - I took 8090 and 8091. Then, because the request hits IIS first instead of plexconnect, you have to have the certificate there too. The IIS reverse proxy is bound to listen to the site you set up (I used secure.marketwatch.com) - it listens on 80 and 443, and forwards the request to 8090 and 8091 so that plexconnect can do its thing.
Because of the complexity of the whole picture, telling me that it doesn't work isn't really a good starting point. You've got IIS to check, so look at your IIS logs. You have ARR to check, you have plexconnect to check, you have split dns to check. Also, the fact that plexconnect isn't starting tells me that there's a port conflict, so that makes me wonder if you set the http/https to 8090 and 8091 on the application. If it is starting, I misunderstood.
If it's strictly an HTTPS issue - did you double-check that the certificate was added to the essentials box? Did you use mmc and edit the local certificate store to add the certificates, as described? Once you did that, did you insure that the IIS binding for your site refers to that certificate?
Also, did you install the certificate on the appletv? I didn't put that in the steps - but you will need to load the certificate on the atv as with a vanilla install.
I can't stress the complexity enough. Basically, plexconnect is awesome - but it has built-in dns and webserver components which won't work on an essentials box, so you need to disable plexconnect's dns and use the essentials dns instead - you do this by adding new zones. You can test this out by adding a zone, doing a ipconfig /flushdns and then pinging the zone (ping secure.marketwatch.com) - this should return the internal address of the essentials box. Then the webserver stuff - you can't turn it off, but you can change to ports that aren't being used and proxy back instead.
I don't know what to tell you, but I'll try to help - we just need to pinpoint the issue a little more clearly.
