>> On Jul 24, 2018, at 4:36 AM, Nick Coghlan <ncogh...@gmail.com> wrote:
>> 
>> However, there *are* folks that have been working on allowing
>> applications to be defined primarily as Python projects, and then have
>> the creation of wrapper native installers be a pushbutton exercise,
>> rather than requiring careful human handholding.
> 
> But it sounds like they also want to be able to install/remove/upgrade
> *parts* of the Python project, for their plugin support.
That’s correct. We currently have 18 official plugins for Certbot with plans to 
add more and a few dozen third-party plugins.
> Do any of these tools allow that?
This is a good question. If we went with something like dh-virtualenv or 
packaged virtualenvs with fpm, would we be able to have separate packages for 
our plugins that installed things in the same virtualenv? I haven’t looked into 
this yet, but I wouldn’t expect this to work.
> That's the thing that really made me think about conda.
My biggest concern with conda right now is I believe we (or our users) would be 
on their own for setting up a cron job or systemd timer for renewal. Is this 
correct?

> On Jul 24, 2018, at 11:20 PM, Chris Jerdonek <chris.jerdo...@gmail.com> wrote:
> 
> Just to be clear, I wasn't meaning to promote or recommend the Docker
> option I described.
Sure! After reading your 2nd email describing how this would work in more 
detail, I think this would require a pretty major rewrite to how Certbot 
currently works. Given the other downsides, I’m not sure this is the best 
approach for us, but I appreciate you throwing out the idea regardless just in 
case it was!

> On Jul 26, 2018, at 3:20 AM, Ben Finney via Distutils-SIG 
> <distutils-sig@python.org> wrote:
> Just focus on Certbot, and cheer from the sidelines as the OS distributions
> do the work of third party packages.
> 
> Yes, that's a different set of problems (for example, keeping Certbot
> compatible with those versions of the libraries the OS repositories
> provide).
We’ve done the work to maintain compatibility with the older versions of our 
dependencies available in the official OS repos where we are packaged. The 
source of our problems with official OS packaging is described below and in the 
Google Doc linked in my initial email.

> On Jul 28, 2018, at 8:53 AM, matt...@woodcraft.me.uk wrote:
> 
> I wouldn't be too put off by the idea of Debian politics. Certbot should be a 
> good fit for stable-updates:

We thought so too and getting updates like this was our main packaging plan 
when we launched in 2015. Unfortunately, it hasn’t gone well and is the main 
reason we’re seeking our own solution. Perhaps we did something incorrectly, 
but as Nathaniel pointed out, Certbot is broken in Debian Stretch and has been 
since January. The same and many other problems affect the packages in Ubuntu 
Xenial. We’ve also struggled to find people to help maintain our PPA for older, 
non-EOL’d versions of Ubuntu.

If anyone reading this would like to help us solve these problems or know 
someone who would, please reach out off-list. While these packages exist in OS 
repos, some users will continue to use them regardless of the alternative 
packaging approach we take. Unless the current issues are resolved and we’re 
confident new ones in the future will be fixed quickly as well, I think we need 
to offer alternative packaging so we can provide our users some means of 
getting a working version of Certbot.

> On Jul 28, 2018, at 12:00 PM, Wes Turner <wes.tur...@gmail.com> wrote:
> 
> Took a minute more to read the gdoc link.

Wes Turner, while I don’t have any specific questions or comments right now, 
thank you very much for all the ideas and links.
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