I was facing same issues. I found a ppa for python 2.5. It is maintained by Felix Krull <https://launchpad.net/%7Efkrull/+archive/deadsnakes>
sudo add-apt-repository ppa:fkrull/deadsnakes sudo apt-get update sudo apt-get install python2.5 After this urllib2.HTTPSHandler errors were gone and was able to launch GAE without any problems. PS - This ppa is not official python repository. Hope this helps.
