support wrote:I'm not sure. Is the problem it is a self-generated certificate? If so, then I would think that you would need to get the certificate added somehow. What happens if you go to the HTTPS address from iOS Safari instead of Indigo Touch? Any way to add the cert there?
The certificate was puchased from godaddy.com. Don't judge, it was cheap.

It requires an intermediate certificate which Mac OS X Server doesn't seem to handle very well. Every time I reboot, it rewrites the apache certificate and looses the intermediate certificate in the process.
The iOS Safari client gives an option to ignore the certificate issues or cancel. Ideally, I'd like Indigo to have the same behavior.