You will either need a self-signed certificate or a CA-signed certificate in order to use HTTPS on your server.
If your certificate is not assigned to you by a certificate authority, then any connection you make will trigger an error in your URLRequest
that you will have to handle. The problem with an untrusted certificate is that a malicious man-in-the-middle could fake data to and from your server with his own self-signed certificate, and possibly pick up authentication credentials or data that he should not have access to.
If you are dealing with any authentication credentials or other private data, I'd recommend just requesting a signed certificate. If you shop around, you can find cheap signed certificates for $10-20 a year, which is a trivial cost to protect your users.
However, if this is just a personal project (the only data you have to worry about is yours), or any data that you will be sending is freely available, a self-signed certificate may be enough.