Since ArcGIS Enterprise depends heavily on HTTPS communication, users should be able to use OpenSSL natively from within ArcGIS Enterprise. The Let's Encrypt now support wildcard certificates which is easy to implement and handle both single and multi-machine ArcGIS Enterprise setup. OpenSSL is free, open, and as secure as most other cert out there.
Users should be able to install and configure OpenSSL using Let's Encrypt while they install ArcGIS Web Adaptor and bind it with the web server while the installation proceeds. In this way the Web Adaptor can setup the HTTPS connections by itself for the Enterprise so that the 'federation' and 'hosting server configuration' become easier.
- setting up HTTPS shouldn't be this costly and tedious in 2018, while the Enterprise itself takes a lot of effort
- management and troubleshooting becomes easier for the IT department
- its free to obtain and use.