I will admit to not testing the "forced" upgrade aspect of this, but I did download and install the upgraded iSkoot for my Nokia N95 this morning. While there is some information floating around in the clear, at least in my case, none of it was personally identifyable.
The vast majority of the communication between the iSkoot client and server now uses TCP port 443 and is encrypted with SSL. Visual inspection of the packet traces confirm that it's SSL traffic. No personal information in the clear anymore.
Nice job, iSkoot. Considering I zero-dayed you on a weekend, you did a great job of getting it fixed!