Python pip 8.1.1 upgrade failing

Question

I am currently on pip version 8.1.1 and trying to upgrade a package:

root@NetworkAutomation-1:~# pip3 install -U netmiko  

But I am receiving this error:

Collecting netmiko
  Using cached https://files.pythonhosted.org/packages/26/05/dbe9c97c39f126e7b8dc70cf897dcad557dbd579703f2e3acfd3606d0cee/netmiko-2.4.2-py2.py3-none-any.whl
Collecting paramiko>=2.4.3 (from netmiko)
  Using cached https://files.pythonhosted.org/packages/06/1e/1e08baaaf6c3d3df1459fd85f0e7d2d6aa916f33958f151ee1ecc9800971/paramiko-2.7.1-py2.py3-none-any.whl
Collecting setuptools>=38.4.0 (from netmiko)
  Using cached https://files.pythonhosted.org/packages/f9/d3/955738b20d3832dfa3cd3d9b07e29a8162edb480bf988332f5e6e48ca444/setuptools-44.0.0-py2.py3-none-any.whl
Collecting textfsm (from netmiko)
  Using cached https://files.pythonhosted.org/packages/bd/27/0b149b6da3e47cc8daebace6920093114392171a8f5c24f1f2ad9a9e9c4d/textfsm-1.1.0-py2.py3-none-any.whl
Collecting scp>=0.13.2 (from netmiko)
  Using cached https://files.pythonhosted.org/packages/4d/7a/3d76dc5ad8deea79642f50a572e1c057cb27e8b427f83781a2c05ce4e5b6/scp-0.13.2-py2.py3-none-any.whl
Collecting pyserial (from netmiko)
  Using cached https://files.pythonhosted.org/packages/0d/e4/2a744dd9e3be04a0c0907414e2a01a7c88bb3915cbe3c8cc06e209f59c30/pyserial-3.4-py2.py3-none-any.whl
Collecting cryptography>=2.5 (from paramiko>=2.4.3->netmiko)
  Using cached https://files.pythonhosted.org/packages/be/60/da377e1bed002716fb2d5d1d1cab720f298cb33ecff7bf7adea72788e4e4/cryptography-2.8.tar.gz
Collecting pynacl>=1.0.1 (from paramiko>=2.4.3->netmiko)
  Using cached https://files.pythonhosted.org/packages/61/ab/2ac6dea8489fa713e2b4c6c5b549cc962dd4a842b5998d9e80cf8440b7cd/PyNaCl-1.3.0.tar.gz
    Complete output from command python setup.py egg_info:
    c/_cffi_backend.c:2:20: fatal error: Python.h: No such file or directory
    compilation terminated.
    Traceback (most recent call last):
      File "/usr/lib/python3.5/distutils/unixccompiler.py", line 118, in _compile
        extra_postargs)
      File "/usr/lib/python3.5/distutils/ccompiler.py", line 909, in spawn
        spawn(cmd, dry_run=self.dry_run)
      File "/usr/lib/python3.5/distutils/spawn.py", line 36, in spawn
        _spawn_posix(cmd, search_path, dry_run=dry_run)
      File "/usr/lib/python3.5/distutils/spawn.py", line 159, in _spawn_posix
        % (cmd, exit_status))
    distutils.errors.DistutilsExecError: command 'x86_64-linux-gnu-gcc' failed with exit status 1

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/lib/python3.5/distutils/core.py", line 148, in setup
    dist.run_commands()
  File "/usr/lib/python3.5/distutils/dist.py", line 955, in run_commands
    self.run_command(cmd)
  File "/usr/lib/python3.5/distutils/dist.py", line 974, in run_command
    cmd_obj.run()
  File "/usr/lib/python3/dist-packages/setuptools/command/bdist_egg.py", line 161, in run
    cmd = self.call_command('install_lib', warn_dir=0)
  File "/usr/lib/python3/dist-packages/setuptools/command/bdist_egg.py", line 147, in call_command
    self.run_command(cmdname)
  File "/usr/lib/python3.5/distutils/cmd.py", line 313, in run_command
    self.distribution.run_command(command)
  File "/usr/lib/python3.5/distutils/dist.py", line 974, in run_command
    cmd_obj.run()
  File "/usr/lib/python3/dist-packages/setuptools/command/install_lib.py", line 23, in run
    self.build()
  File "/usr/lib/python3.5/distutils/command/install_lib.py", line 109, in build
    self.run_command('build_ext')
  File "/usr/lib/python3.5/distutils/cmd.py", line 313, in run_command
    self.distribution.run_command(command)
  File "/usr/lib/python3.5/distutils/dist.py", line 974, in run_command
    cmd_obj.run()
  File "/usr/lib/python3/dist-packages/setuptools/command/build_ext.py", line 49, in run
    _build_ext.run(self)
  File "/usr/lib/python3.5/distutils/command/build_ext.py", line 338, in run
    self.build_extensions()
  File "/usr/lib/python3.5/distutils/command/build_ext.py", line 447, in build_extensions
    self._build_extensions_serial()
  File "/usr/lib/python3.5/distutils/command/build_ext.py", line 472, in _build_extensions_serial
    self.build_extension(ext)
  File "/usr/lib/python3/dist-packages/setuptools/command/build_ext.py", line 174, in build_extension
    _build_ext.build_extension(self, ext)
  File "/usr/lib/python3.5/distutils/command/build_ext.py", line 532, in build_extension
    depends=ext.depends)
  File "/usr/lib/python3.5/distutils/ccompiler.py", line 574, in compile
    self._compile(obj, src, ext, cc_args, extra_postargs, pp_opts)
  File "/usr/lib/python3.5/distutils/unixccompiler.py", line 120, in _compile
    raise CompileError(msg)
distutils.errors.CompileError: command 'x86_64-linux-gnu-gcc' failed with exit status 1

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 154, in save_modules
    yield saved
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 195, in setup_context
    yield
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 243, in run_setup
    DirectorySandbox(setup_dir).run(runner)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 273, in run
    return func()
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 242, in runner
    _execfile(setup_script, ns)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 46, in _execfile
    exec(code, globals, locals)
  File "/tmp/easy_install-473w7z52/cffi-1.13.2/setup.py", line 248, in <module>
    "Programming Language :: Python :: Implementation :: PyPy",
  File "/usr/lib/python3.5/distutils/core.py", line 163, in setup
    raise SystemExit("error: " + str(msg))
SystemExit: error: command 'x86_64-linux-gnu-gcc' failed with exit status 1

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 1087, in run_setup
    run_setup(setup_script, args)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 246, in run_setup
    raise
  File "/usr/lib/python3.5/contextlib.py", line 77, in __exit__
    self.gen.throw(type, value, traceback)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 195, in setup_context
    yield
  File "/usr/lib/python3.5/contextlib.py", line 77, in __exit__
    self.gen.throw(type, value, traceback)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 166, in save_modules
    saved_exc.resume()
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 141, in resume
    six.reraise(type, exc, self._tb)
  File "/usr/lib/python3/dist-packages/pkg_resources/_vendor/six.py", line 685, in reraise
    raise value.with_traceback(tb)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 154, in save_modules
    yield saved
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 195, in setup_context
    yield
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 243, in run_setup
    DirectorySandbox(setup_dir).run(runner)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 273, in run
    return func()
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 242, in runner
    _execfile(setup_script, ns)
  File "/usr/lib/python3/dist-packages/setuptools/sandbox.py", line 46, in _execfile
    exec(code, globals, locals)
  File "/tmp/easy_install-473w7z52/cffi-1.13.2/setup.py", line 248, in <module>
    "Programming Language :: Python :: Implementation :: PyPy",
  File "/usr/lib/python3.5/distutils/core.py", line 163, in setup
    raise SystemExit("error: " + str(msg))
SystemExit: error: command 'x86_64-linux-gnu-gcc' failed with exit status 1

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<string>", line 1, in <module>
  File "/tmp/pip-build-d9hokmzc/pynacl/setup.py", line 255, in <module>
    "Programming Language :: Python :: 3.7",
  File "/usr/lib/python3.5/distutils/core.py", line 108, in setup
    _setup_distribution = dist = klass(attrs)
  File "/usr/lib/python3/dist-packages/setuptools/dist.py", line 269, in __init__
    self.fetch_build_eggs(attrs['setup_requires'])
  File "/usr/lib/python3/dist-packages/setuptools/dist.py", line 313, in fetch_build_eggs
    replace_conflicting=True,
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 826, in resolve
    dist = best[req.key] = env.best_match(req, ws, installer)
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 1092, in best_match
    return self.obtain(req, installer)
  File "/usr/lib/python3/dist-packages/pkg_resources/__init__.py", line 1104, in obtain
    return installer(requirement)
  File "/usr/lib/python3/dist-packages/setuptools/dist.py", line 380, in fetch_build_egg
    return cmd.easy_install(req)
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 663, in easy_install
    return self.install_item(spec, dist.location, tmpdir, deps)
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 693, in install_item
    dists = self.install_eggs(spec, download, tmpdir)
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 873, in install_eggs
    return self.build_and_install(setup_script, setup_base)
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 1101, in build_and_install
    self.run_setup(setup_script, setup_base, args)
  File "/usr/lib/python3/dist-packages/setuptools/command/easy_install.py", line 1089, in run_setup
    raise DistutilsError("Setup script exited with %s" % (v.args[0],))
distutils.errors.DistutilsError: Setup script exited with error: command 'x86_64-linux-gnu-gcc' failed with exit status 1

----------------------------------------
Command "python setup.py egg_info" failed with error code 1 in /tmp/pip-build-d9hokmzc/pynacl/
You are using pip version 8.1.1, however version 19.3.1 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.
root@NetworkAutomation-1:~# 

Answer 1

it seems like your gcc is not working not configured correctly.

command 'x86_64-linux-gnu-gcc' failed with exit status 1

Please make sure that your gcc is up to date. If this is not working out try to run pip in verbose mode with the --verbose flag. May you can figure out the error in that way otherwise you need to figure out what does the gcc error causes.

Answer 2

You output clearly says:

c/_cffi_backend.c:2:20: fatal error: Python.h: No such file or directory

You have to do this:

sudo apt-get install python-dev   # for python2.x installs
sudo apt-get install python3-dev  # for python3.x installs

or refer to this link for other OS beside Ubuntu: fatal error: Python.h: No such file or directory