Hi,
I understand you're looking for some more documentation on how to setup Jira to use SSL. For an nginx reverse proxy setup, I'd recommend Configure Jira server to run behind a NGINX reverse proxy. While it is based for an http proxy, it does have some additional details about setting up SSL on the proxy itself and how to go about that.
Additionally, there is more information if you want to try to run Jira's Tomcat using SSL in Running Jira applications over SSL or HTTPS.
As for which one to choose, well, that really depends. I'd say that using a separate machine with nginx could certainly afford you a greater level of security, but the use of a reverse proxy does seem to complicate the setup when compared to running SSL directly in Tomcat. Setting up Tomcat to use SSL directly might be easier to do, with less overhead, but I think having the additional layer in a reverse proxy is a better option in most cases.
Let me know if you run into any problems with either setup.
Cheers,
Andy
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