Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. crt.sh | example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.
My domain is:ptl-inc.com
I ran this command: "N:create cert with default settings"
Your adss.ptl-inc.com domain is using an Apache server.
I don't know the details of your win-acme request but it needs to setup Apache for the HTTP Challenge of the cert request. Did you instead have it work with your IIS server?
A 404 error means the Let's Encrypt server could not find the file created by win-acme at the system handling HTTP requests to your domain.
Can you clarify what Apache and IIS should be doing for this domain name?
The website is hosted by apache tomcat and im using IIS to reverse-proxy to the server. I am new to most of this and most of the guides show to use IIS to install the cert.
The webserver that answers for http://adss.ptl-inc.com/ (HTTP over TCP port 80) appears to be the apache server, not IIS, as shown by the Server header. It would be a little easier to get your certificate if it was IIS that was reverse proxying back to apache but I assume you have it working the other way around.
To order your cert yo need to validate your domain, and to do that you can use http validation (a special HTTP request to your server). In your case Apache is answering, so you could use the "webroot" method of writing the challenge response files out to the apache htdocs filesystem, however I don't know how that interacts with Tomcat (is tomcat even involved yet? maybe you run the app off a /app etc path?).
Here is win-acme's docs for an Apache example: win-acme
To use it with IIS (if IIS was the thing answering on port 80) you would just use the self-hosting option and select the website or enter the domain name to order the cert for.