That is very odd. I have a production SSL site that I have been running for months without an issue. Even my development server (which runs trunk, but as of a week ago...haven't updated in a while) runs SSL only and it can run for weeks at a time.
I guess the usual questions apply: what version of web2py? Also, I don't know if it matters, but with my command on the development server, I run with --no-cron (because I use the system's cron) and -l '/dev/null' to prevent logs from conflicting with other web2py instances that I run. So my command looks like this: python web2py.py -i 0.0.0.0 -a password -c my.crt -k my.key --no-cron -l '/dev/null' I also run on Ubuntu Server 10.04 using the web2py trunk. So maybe this is a problem specific to the Rocket implementation on Windows? Or even the binary version of web2py?