Local update error caused by outdated pyOpenSSL

[impressiver]

I'm following guides on alternate bootstrap instructions after easy-install failed (I have an unconventional network configuration, so not too surprised). I'm working through the guides in order so I can take notes on speedbumps.

Running local update I ran into an OpenSSL error. It has a simple fix (update pip), but as it might bite others, I'm documenting the error/solution here in case it might help. I can also add a note to the wiki if it's a common issue.

Initial run:

$ sudo ./oakupsrv
Password:
Preparing SSL key
Fetching https://oakota.digistump.com/firmware/firmware_v1.bin
Fetching https://raw.githubusercontent.com/digistump/OakSoftAP/master/config.html

Using another WiFi capable device (NOT this machine) connect to your network, open a browser and go to: http://10.82.81.205:8080 and follow the instructions to update your Oak.

NOTE: You must use the config app at that address, it is configured specifically for this local update. Status messages will print here during the update. Do not close this window until you have finished updating.
2016-04-04 09:01:06 New connection from: 10.82.80.137
2016-04-04 09:01:07 Starting firmware transfer to: 10.82.80.137
2016-04-04 09:01:07 Connection lost to: 10.82.80.137
2016-04-04 09:01:07 Firmware request finished for 10.82.80.137 (Reason: [Failure instance: Traceback: <class 'OpenSSL.SSL.SysCallError'>: (0, None)
twisted/internet/selectreactor.py:149:_doReadOrWrite
twisted/internet/tcp.py:209:doRead
twisted/internet/tcp.py:215:_dataReceived
twisted/protocols/tls.py:422:dataReceived
--- <exception caught here> ---
twisted/protocols/tls.py:360:_flushReceiveBIO
OpenSSL/SSL.py:1320:recv
OpenSSL/SSL.py:1178:_raise_ssl_error
])
2016-04-04 09:01:07 Early termination to: 10.82.80.137 (1024 bytes written, fail count = 1)
2016-04-04 09:01:07 Finishing firmware transfer to: 10.82.80.137 (1 transfers done)

Upgrade/update pip:

$ pip list --outdated
...
pyOpenSSL (0.15.1) - Latest: 16.0.0 [wheel]
...
You are using pip version 8.0.3, however version 8.1.1 is available.
You should consider upgrading via the 'pip install --upgrade pip' command.
$ pip install --upgrade pip          # upgrade pip first
$ pip install --upgrade pyOpenSSL    # upgrade ssl module, and optionally additional outdated modules

Voila! Run the local update server again and the ssl error should be gone.

[impressiver]

As an afterthought, this could happen due to any outdated dependencies, might be a better idea to point to a general "update your pythons" wiki page?