So, I use PlusNet as my ISP. I have an email address with them where they send updates about my account. It's also been used in the past to sign up to various things that I haven't bothered to update to a new email address. PlusNet's email servers do not require authentication to send email from my home connection, which is fair enough really. But they also don't support SSL for authentication from my connection. So my username and password (which is unique to this account) has to be sent in plain text, now as this is to my ISP over my ISP connection (and I trust my own network) it's not the end of the world. However, I also have a shiny smart phone, and that allows me to connect to my own email server, over SSL (that until recently wasn't as secure as it should be) as it should be when connecting over the internet, from untrusted, or unknown networks. It also allows me to use multiple different email inboxes at once. So I could add my PlusNet email address. They even have a handy guide on setting up email on android phones. And that's where the problems start. That guide sets up email without SSL, or TLS, but it requires username and password authentication. So I'd only be able to use it on my home network. What happens if I forget to turn email sync off? My details would be put at risk!
So what should a good sysadmin do? Should I leave the ISP email only on my home PC? Should I take the risk and add the email to my phone anyway?
Well as a paranoid sysadmin I wasn't willing to take the risk. And that was that. But frankly that was annoying me, so I decided to set up an SSL terminator for my ISP email using my own SSL cert. So I can get my email, from my ISP confident in the knowledge that only my ISP can intercept the username and password pair that I use with my ISP. I use non-standard ports for the ISP connections, and listen using stunnel. This would be a problem if I was supporting users as it would add a level of complexity to the instructions I'd have to give them, but as I only have to support myself I can cope.