I started looking into updating pip to the current release because I knew it would take awhile and we need to do it at some point. Merging our changes into the new upstream release turned out to be somewhat less challenging that I had feared (alternately it wasn't and I messed it up). I've pushed the results of that effort to salsa.
The next step is to deal with all the packages that pip vendors and we unvendor. There are quite a few packages that need updating to a sufficient version for the new pip: Needs packaging: pep517 Needs upgrade: CacheControl contextlib2 distro ipaddress (python2 only) msgpack packaging progress pyparsing pytoml idna urllib3 I'm not going to be able to deal with all that by myself, so this is a request for team members to step up and look at updating these packages. I have not checked which of these are DPMT maintained, so in some cases the action may be to work with the maintainer to update their package. I would suggest that people who decide to work on one of the above reply to this message so we don't end up with people doing duplicate works. Thanks, Scott K Here's the full list: appdirs==1.4.3 have 1.4.3 CacheControl==0.12.6 have 11.7.2 colorama==0.4.3 have 0.4.3 contextlib2==0.6.0 have 0.5.5 distlib==0.3.0 have 0.3.0 distro==1.4.0 have 1.3.0 html5lib==1.0.1 have 1.0.1 ipaddress==1.0.23 have 1.0.17 # Only needed on 2.6 and 2.7 msgpack==0.6.2 have 0.5.6 packaging==20.1 have 19.1.2 pep517==0.7.0 Missing (not packaged) progress==1.5 have 1.2 pyparsing==2.4.6 have 2.4.2 pytoml==0.1.21 have 0.1.2 requests==2.22.0 have 2.22.0 certifi==2019.11.28 have 2019.11.28 chardet==3.0.4 have 3.0.4 idna==2.8 have 2.6 urllib3==1.25.7 have 1.25.6 retrying==1.3.3 have 1.3.3 setuptools==44.0.0 have 44.0.0 six==1.14.0 have 1.14.0 webencodings==0.5.1 have 0.5.1
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