[lammbo]

Under the Site properties in SecureClient there is a reuse credentials for multiple gateways (I know, not exactly 100% for this scenario). I want to say that this option takes care of the continual prompting if you're using OM. (Note that I am in Traditional mode, so this MAY behave differently if you are running Simplified)

If memory serves me, I think that a few years ago, a director at our UK office complained of the same issue while on trains and this fixed it. I may be confusing different cases though, so try for yourself.

As far as security issues go, since you still have to enter credentials on the initial connection, I have no hangups with re-using the credentials, as some of us do. If you have a security officer at your company, you should probably check in about this before deploying globally.