Currently, it is not possible ipMonitor to send encrypted email alerts over SSL/TLS. We have this on the list for the next release. However, you can use the External Process alert action to leverage a script to perform this action.
Any idea of a timeframe for this support? I'm particularly interested in using port 465 with my Orion alerts.
Unfortunately, we can't give timeframes for feature updates. I'll make sure that the product manager sees this. In the meantime, check out our Advanced Alerts Technical Reference. If might give a workaround.