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strategy for upgrading "core" development gems?



Hi,

I looked into upgrading webmock to a more recent version. The current
version in Debian is 1.22.6-1, with a number of versions released since
then[1]. I tried to package version 3.0.1, but unfortunately, there has
been some incompatible changes, and the following
reverse-build-dependencies fail to build with 3.0.1:

[1] https://rubygems.org/gems/webmock/versions

berkshelf
gist
ruby-flowdock
ruby-gemnasium-gitlab-service
ruby-influxdb
ruby-license-finder
ruby-mixlib-install
ruby-omniauth-crowd
ruby-rest-client
ruby-ridley
(out of 31 reverse b-deps, it's not too bad)

I wonder what we would do about such "core" development packages. Upgrading the
leaf packages first does not work because newer versions tend to require newer
core packages, so it's a chicken-and-egg problem.

One possible strategy could be to:
- upload the new version of webmock to unstable
- with a versioned Breaks: on the broken packages (so that it does not migrate to testing)
- file RC bugs given those packages now FTBFS in unstable

According to a crude hack, our top 40 packages in terms of reverse b-deps are:
gem2deb 1113
rake 505
ruby-rspec 403
ruby-minitest 114
ruby-test-unit 76
ruby-rack 74
ruby-mocha 66
ruby-json 54
rails 54
ruby-nokogiri 53
ruby-multi-json 41
ruby-rack-test 38
ruby-ronn 36
ruby-sqlite3 34
bundler 33
ruby-webmock 32
ruby-rspec-its 31
ruby-fog 28
asciidoctor 27
ruby-http 25
ruby-simplecov 24
ruby-fog-core 24
ruby-faraday 24
ruby-coveralls 23
ruby-omniauth 22
ruby-shoulda 21
ruby-addressable 21
ruby-thor 20
ruby-mime 20
ruby-mime-types 19
ruby-i18n 19
ruby-timecop 17
ruby-sinatra 17
ruby-tilt 15
ruby-fog-json 15
ruby-ffi 15
ruby-eventmachine 15
ruby-builder 15
ruby-build 15

And the DMD status page for those would be:
https://udd.debian.org/dmd/?email1=&nosponsor1=on&email2=&nosponsor2=on&email3=&packages=gem2deb+rake+ruby-rspec+ruby-minitest+ruby-test-unit+ruby-rack+ruby-mocha+ruby-json+rails+ruby-nokogiri+ruby-multi-json+ruby-rack-test+ruby-ronn+ruby-sqlite3+bundler+ruby-webmock+ruby-rspec-its+ruby-fog+asciidoctor+ruby-http+ruby-simplecov+ruby-fog-core+ruby-faraday+ruby-coveralls+ruby-omniauth+ruby-shoulda+ruby-addressable+ruby-thor+ruby-mime+ruby-mime-types+ruby-i18n+ruby-timecop+ruby-sinatra+ruby-tilt+ruby-fog-json+ruby-ffi+ruby-eventmachine+ruby-builder+ruby-build&ignpackages=&format=html#todo

Lucas


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