Failed to install v2.6.0 on OSX using Python 2.7.10

[dugjason]

➜  ~  sudo pip install datasift --upgrade
The directory '/Users/jason/Library/Caches/pip/http' or its parent directory is not owned by the current user and the cache has been disabled. Please check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
The directory '/Users/jason/Library/Caches/pip' or its parent directory is not owned by the current user and caching wheels has been disabled. check the permissions and owner of that directory. If executing pip with sudo, you may want sudo's -H flag.
Collecting datasift
  Downloading datasift-2.6.0.tar.gz
Requirement already up-to-date: requests<3.0.0,>=2.8.0 in /Library/Python/2.7/site-packages (from datasift)
Requirement already up-to-date: autobahn<0.10.0,>=0.9.4 in /Library/Python/2.7/site-packages (from datasift)
Collecting six<2.0.0,>=1.6.0 (from datasift)
  Downloading six-1.10.0-py2.py3-none-any.whl
Collecting twisted<16.0.0,>=14.0.0 (from datasift)
Collecting pyopenssl<0.16.0,>=0.15.1 (from datasift)
  Downloading pyOpenSSL-0.15.1-py2.py3-none-any.whl (102kB)
    100% |████████████████████████████████| 106kB 1.3MB/s
Collecting python-dateutil<3,>=2.1 (from datasift)
  Downloading python_dateutil-2.4.2-py2.py3-none-any.whl (188kB)
    100% |████████████████████████████████| 192kB 1.3MB/s
Requirement already up-to-date: service-identity>=14.0.0 in /Library/Python/2.7/site-packages (from datasift)
Requirement already up-to-date: requests-futures>=0.9.5 in /Library/Python/2.7/site-packages (from datasift)
Collecting ndg-httpsclient>=0.4.0 (from datasift)
  Downloading ndg_httpsclient-0.4.0.tar.gz
Collecting zope.interface>=3.6.0 (from twisted<16.0.0,>=14.0.0->datasift)
Collecting cryptography>=0.7 (from pyopenssl<0.16.0,>=0.15.1->datasift)
  Downloading cryptography-1.1.1-cp27-none-macosx_10_6_intel.whl (1.3MB)
    100% |████████████████████████████████| 1.3MB 359kB/s
Requirement already up-to-date: characteristic>=14.0.0 in /Library/Python/2.7/site-packages (from service-identity>=14.0.0->datasift)
Collecting pyasn1-modules (from service-identity>=14.0.0->datasift)
  Downloading pyasn1_modules-0.0.8-py2.py3-none-any.whl
Collecting pyasn1 (from service-identity>=14.0.0->datasift)
  Downloading pyasn1-0.1.9-py2.py3-none-any.whl
Requirement already up-to-date: futures>=2.1.3 in /Library/Python/2.7/site-packages (from requests-futures>=0.9.5->datasift)
Collecting setuptools (from zope.interface>=3.6.0->twisted<16.0.0,>=14.0.0->datasift)
  Downloading setuptools-18.6.1-py2.py3-none-any.whl (462kB)
    100% |████████████████████████████████| 462kB 1.0MB/s
Collecting enum34 (from cryptography>=0.7->pyopenssl<0.16.0,>=0.15.1->datasift)
Collecting ipaddress (from cryptography>=0.7->pyopenssl<0.16.0,>=0.15.1->datasift)
  Downloading ipaddress-1.0.15-py27-none-any.whl
Collecting idna>=2.0 (from cryptography>=0.7->pyopenssl<0.16.0,>=0.15.1->datasift)
  Downloading idna-2.0-py2.py3-none-any.whl (61kB)
    100% |████████████████████████████████| 61kB 2.4MB/s
Collecting cffi>=1.1.0 (from cryptography>=0.7->pyopenssl<0.16.0,>=0.15.1->datasift)
  Downloading cffi-1.3.1-cp27-none-macosx_10_10_intel.whl (192kB)
    100% |████████████████████████████████| 196kB 1.8MB/s
Collecting pycparser (from cffi>=1.1.0->cryptography>=0.7->pyopenssl<0.16.0,>=0.15.1->datasift)
Installing collected packages: six, setuptools, zope.interface, twisted, enum34, ipaddress, pyasn1, idna, pycparser, cffi, cryptography, pyopenssl, python-dateutil, ndg-httpsclient, datasift, pyasn1-modules
  Found existing installation: six 1.6.1
    Uninstalling six-1.6.1:
      Successfully uninstalled six-1.6.1
  Found existing installation: setuptools 18.0.1
    Uninstalling setuptools-18.0.1:
      Successfully uninstalled setuptools-18.0.1
  Found existing installation: zope.interface 4.1.2
    Uninstalling zope.interface-4.1.2:
      Successfully uninstalled zope.interface-4.1.2
  Found existing installation: Twisted 14.0.2
    Uninstalling Twisted-14.0.2:
      Successfully uninstalled Twisted-14.0.2
  Found existing installation: pyasn1 0.1.8
    Uninstalling pyasn1-0.1.8:
      Successfully uninstalled pyasn1-0.1.8
  Found existing installation: pyOpenSSL 0.13.1
    DEPRECATION: Uninstalling a distutils installed project (pyopenssl) has been deprecated and will be removed in a future version. This is due to the fact that uninstalling a distutils project will only partially uninstall the project.
    Uninstalling pyOpenSSL-0.13.1:
Exception:
Traceback (most recent call last):
  File "/Library/Python/2.7/site-packages/pip/basecommand.py", line 211, in main
    status = self.run(options, args)
  File "/Library/Python/2.7/site-packages/pip/commands/install.py", line 311, in run
    root=options.root_path,
  File "/Library/Python/2.7/site-packages/pip/req/req_set.py", line 640, in install
    requirement.uninstall(auto_confirm=True)
  File "/Library/Python/2.7/site-packages/pip/req/req_install.py", line 716, in uninstall
    paths_to_remove.remove(auto_confirm)
  File "/Library/Python/2.7/site-packages/pip/req/req_uninstall.py", line 125, in remove
    renames(path, new_path)
  File "/Library/Python/2.7/site-packages/pip/utils/__init__.py", line 315, in renames
    shutil.move(old, new)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 302, in move
    copy2(src, real_dst)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 131, in copy2
    copystat(src, dst)
  File "/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/shutil.py", line 103, in copystat
    os.chflags(dst, st.st_flags)
OSError: [Errno 1] Operation not permitted: '/tmp/pip-awPwpa-uninstall/System/Library/Frameworks/Python.framework/Versions/2.7/Extras/lib/python/pyOpenSSL-0.13.1-py2.7.egg-info'

[andimiller]

This appears to be related to El Capitan using pyopenssl 0.13 for parts of OS X, I'd recommend using a virtual environment so you can install newer packages without breaking your OS

[dugjason]

Thanks @andimiller. Confirming that installing Python 2.7.10 using pyenv works for me