That is an incredibly ancient pip. Your best bet would be to uninstall the system package, and install it via pip's own instructions: https://pip.pypa.io/en/stable/installing/ Note that you should run the install as the root user.

alas (

python get-pip.py

> Retrying (Retry(total=4, connect=None, read=None, redirect=None)) after connection broken by 'ConnectTimeoutError(vendor.requests.packages.urllib3.connection.verifiedhttpsconnection object="" at="" 0x7f9d7ac582d0="">, 'Connection to pypi.python.org timed out. (connect timeout=15)')': /simple/pip/vendor.requests.packages.urllib3.connection.verifiedhttpsconnection>
Previously, there was a version 8 pip - and it had the same error

Paste the output of 'mtr -rwb pypi.python.org' here.

mtr -rwb pypi.python.org

> Start: Thu Feb 16 07:46:04 2017

HOST: debian Loss% Snt Last Avg Best Wrst StDev

1.|– 2a01:7e00::8678:acff:fe0d:8f41 0.0% 10 0.9 1.0 0.9 1.1 0.0

2.|-- 2a01:7e00:7777:2::1 10.0% 10 0.9 1.2 0.8 2.3 0.0

3.|-- unknown.r00.londen10.uk.bb.gin.ntt.net (2001:728:0:5000::ebd) 0.0% 10 1.2 1.3 1.2 1.4 0.0

4.|-- ae-13.r24.londen12.uk.bb.gin.ntt.net (2001:728:0:2000::6a) 0.0% 10 0.8 1.0 0.7 2.1 0.3

5.|-- ae-1.r04.londen05.uk.bb.gin.ntt.net (2001:728:0:2000::5e) 0.0% 10 1.2 1.3 1.1 2.2 0.0

6.|-- ae-5.r03.londen05.uk.bb.gin.ntt.net (2001:728:0:2000::115) 0.0% 10 1.5 1.4 1.2 1.7 0.0

7.|-- 2001:978:2:21::7c:2 0.0% 10 1.1 1.1 1.0 1.3 0.0

8.|-- 2a04:4e42:4::223 0.0% 10 0.9 1.0 0.9 1.6 0.0

That's odd. Try 'mtr -4rwb pypi.python.org'

mtr -4rwb pypi.python.org

> Start: Thu Feb 16 07:54:44 2017

HOST: debian Loss% Snt Last Avg Best Wrst StDev

1.|– router1-lon.linode.com (212.111.33.229) 0.0% 10 0.6 0.8 0.6 1.8 0.0

2.|-- switch-lonr1.linode.com (109.74.207.4) 0.0% 10 1.0 0.8 0.7 1.0 0.0

3.|-- rpc2-lon1.linode.com (109.74.207.8) 0.0% 10 0.9 1.1 0.7 2.1 0.5

4.|-- ip81-60.fastly-gw2.lonap.net (5.57.81.60) 0.0% 10 1.1 0.9 0.8 1.3 0.0

5.|-- 151.101.16.223

Hmpf. Let's try these:

tcptraceroute pypi.python.org 443
tcptraceroute6 pypi.python.org 443

Put the results in a code block, instead of a quote block, so phpBB won't replace letters with smilies

````
tcptraceroute pypi.python.org 443

traceroute to pypi.python.org (151.101.16.223), 30 hops max, 60 byte packets
1 * * *
2 * * *
3 * * *
4 * * *
5 * * *
6 * * *
7 * * *
8 * * *
9 * * *
10 * * *
11 * * *
12 * * *
13 * * *
14 * * *
15 * * *
16 * * *
17 * * *
18 * * *
19 * * *
20 * * *
21 * * *
22 * * *
23 * * *
24 * * *
25 * * *
26 * * *
27 * * *
28 * * *
29 * * *
30 * * *

````

That explains a lot. Paste the output of 'iptables-save' (this one has to be run as root, and will not error if it is not (annoyingly)).

````
iptables-save

Generated by iptables-save v1.4.21 on Thu Feb 16 08:37:44 2017

*security
:INPUT ACCEPT [11294:2634117]
:FORWARD ACCEPT [0:0]
:OUTPUT ACCEPT [11244:1402248]
COMMIT

Completed on Thu Feb 16 08:37:44 2017

Generated by iptables-save v1.4.21 on Thu Feb 16 08:37:44 2017

*raw
:PREROUTING ACCEPT [11307:2638329]
:OUTPUT ACCEPT [11251:1403048]
COMMIT

Completed on Thu Feb 16 08:37:44 2017

Generated by iptables-save v1.4.21 on Thu Feb 16 08:37:44 2017

*nat
:PREROUTING ACCEPT [2489:140268]
:INPUT ACCEPT [2476:136056]
:OUTPUT ACCEPT [875:69751]
:POSTROUTING ACCEPT [875:69751]
COMMIT

Completed on Thu Feb 16 08:37:44 2017

Generated by iptables-save v1.4.21 on Thu Feb 16 08:37:44 2017

*mangle
:PREROUTING ACCEPT [11307:2638329]
:INPUT ACCEPT [11294:2634117]
:FORWARD ACCEPT [0:0]
:OUTPUT ACCEPT [11253:1403288]
:POSTROUTING ACCEPT [11253:1403288]
COMMIT

Completed on Thu Feb 16 08:37:44 2017

Generated by iptables-save v1.4.21 on Thu Feb 16 08:37:44 2017

*filter
:INPUT ACCEPT [11294:2634117]
:FORWARD ACCEPT [0:0]
:OUTPUT ACCEPT [11253:1403288]
COMMIT

Completed on Thu Feb 16 08:37:44 2017

````