Hi roee84,
I'm a privacy researcher and looking into the issue of deadlocks of on-demand VPNs in captive networks. I can fully reproduce the issue and think this is a relevant issue since captive networks are fairly wide spread, especially in unecrypted Wi-Fis where one would really need on-demand VPNs.
Did you come up with a solution or any additional information on the matter? I would really much appreciate hearing from you.
Cheers, cburkert