No shame in asking! Thanks so much for raising the question!
I'm not 100% sure I'm following, though - where did you get the .crt and .jks files?
It sounds like it may be helpful to have an overview of SSL / HTTPS. This one looks decent:
Basically, it sounds like you need to create a key / cert. You can create one yourself (this is called a "self-signed certificate"). However, this basically amounts to "I promise I'm trustworthy!" As a result, browsers fittingly complain that this type of certificate is not secure.
The better approach is:
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If your server is behind a firewall or on a company VPN, then the company probably has what is called a certificate authority. This is a digital entity / service that vouches for websites (a trustworthy entity that says "I know this individual. You can trust them."). Your IT team should be able to provide you with the .crt and .key files
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If your server has a domain on the open internet, there are certificate authorities that exist on the web. In this case, you have to buy a certificate (the article shares a few places that you can do that). Usually, the service that sold your domain (i.e. Namecheap) can provide such a service.
As @jcblum said, though, definitely feel free to ping support@rstudio.com . Even during the Pro trial, you have full access to the RStudio support team. Also feel free to post here, though! This has the benefit of being a shared resource that others can access if they run into the same issue 