I jailbreaked (not for pirates) my iPad 4 (iOS 8.1) several weeks ago and found it unable to ssh email@example.com via Prompt 1 or 2 on iPad. Even I cannot connect via LAN IP (e.g. 192.186.X.X). However, there's no problem if I ssh root@LAN IP on my iPhone or Mac in the same LAN.
By the way, I was able to ssh root@localhost on jailbreaked iPad when it was running iOS 6.1. It is also okay if I have already ssh logged in to iPad on my Mac, and ssh firstname.lastname@example.org again.
The output of netstat on iPad:
Surface-Pro:~ root# netstat -an|grep .22 tcp4 0 28 172.22.29.64.22 172.22.26.158.47927 ESTABLISHED tcp4 0 0 172.22.29.64.50293 184.108.40.206.5223 ESTABLISHED tcp4 0 0 *.22
Does anyone know the reason that iPad cannot connect to itself in apps? (Maybe sandbox/containers model has been changed since iOS 8?)