At this point, I temporary opened perms to any valid account to that directory with a chmod -R ugo+rwx /usr/lib/python2.7 and tried again. All my pi home directories are permed properly and it looks like root owns the install in /usr/local (which would make sense). I got further, but then it tossed an error that it couldn't create another new file: /usr/local/lib/python2.7/dist-packages/Werkzeug-0.8.3.egg-info. That also did not work, so I went ahead and created werkzeug directory in that location /usr/lib/python2.7/dist-packages and made sure staff group had permissions to that new directory. Regarding number two, initially it complained that it couldn't created werkzeug directory under there, so I went ahead and added the pi account to the staff group since that had group ownership of the area. It did not like my perms on /usr/lib/python2.7/dist-packages. I was able to get by this by simply passing the command to trust the cert like this: pip install -trusted-host install It looks like you may need to add the subject alternate name from the looks of it to me. Pip did not like the SSL cert for the url. I'm a pretty long-term linux user and python dabbler, so I'm trying to troubleshoot myself to give you all I can. I followed the manual instructions for a latest install (not from source) and I've had two problems so far. The error had to do with a dependency not being available, but the prompt to reload the page covered the message so I can't post it here. It kept indicating it had completed, but it had actually failed. I had some trouble with 1.3.7 upgrade through the web interface.
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