Generally speaking, the CLI works with standard https sites like Cloud. However, you may have an internal site or other that runs into various HTTPS/SSL problems. The most common cause is using self-signed certificates. They can be solved, but, each requires some problem determination and finding the solution that works for you. The CLI is implemented in Java and some of the resolutions have to do with telling Java how to work with the security involved with the system you are trying to access in a proper way. This describes some of the common problem symptoms and links to help resolve. Often using Google with your error is the best way to find some help in this area.
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