`bundler (= 2.5.1)` required by `user-specified dependency` / undefined method `request' for nil:NilClass (NoMethodError)

[pboling]

I have a gem that supports Ruby 2.7+.

I want to update the lockfile to be using the latest version of bundler that still supports Ruby 2.7, but I seem to have broken my RubyGems / Bundler install completely.

I am using Ruby 2.7.8 (which I know is no longer supported, so not sure what to do here)

This is the end result:

❯ bundle update --bundler
Fetching gem metadata from https://rubygems.org/.
Updating bundler to 2.5.1.
Fetching bundler 2.5.1
Installing bundler 2.5.1
Traceback (most recent call last):
        15: from /Users/pboling/.asdf/installs/ruby/2.7.8/bin/bundle:25:in `<main>'
        14: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `activate_bin_path'
        13: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `synchronize'
        12: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:286:in `block in activate_bin_path'
        11: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:229:in `finish_resolve'
        10: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:425:in `resolve_current'
         9: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:413:in `resolve'
         8: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:191:in `resolve'
         7: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolver.rb:43:in `resolve'
         6: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:182:in `resolve'
         5: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:254:in `process_topmost_state'
         4: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:682:in `attempt_to_activate'
         3: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:297:in `unwind_for_conflict'
         2: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:297:in `tap'
         1: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:299:in `block in unwind_for_conflict'
/Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:317:in `raise_error_unless_state': Unable to satisfy the following requirements: (Gem::Resolver::Molinillo::VersionConflict)

- `bundler (= 2.5.1)` required by `user-specified dependency`
        13: from /Users/pboling/.asdf/installs/ruby/2.7.8/bin/bundle:25:in `<main>'
        12: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `activate_bin_path'
        11: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `synchronize'
        10: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:286:in `block in activate_bin_path'
         9: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:229:in `finish_resolve'
         8: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:425:in `resolve_current'
         7: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:413:in `resolve'
         6: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:192:in `resolve'
         5: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `rescue in resolve'
         4: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `raise'
         3: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `exception'
         2: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/exceptions.rb:55:in `initialize'
         1: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/exceptions.rb:61:in `conflicting_dependencies'
/Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/conflict.rb:48:in `conflicting_dependencies': undefined method `request' for nil:NilClass (NoMethodError)

And here is how I ended up there:

❯ gem update --system
Updating rubygems-update
Fetching rubygems-update-3.5.1.gem
ERROR:  Error installing rubygems-update:
        There are no versions of rubygems-update (= 3.5.1) compatible with your Ruby & RubyGems
        rubygems-update requires Ruby version >= 3.0.0. The current ruby version is 2.7.8.225.
Installing RubyGems 3.4.21
  Successfully built RubyGem
  Name: bundler
  Version: 2.4.21
  File: bundler-2.4.21.gem
Bundler 2.4.21 installed
RubyGems 3.4.21 installed
Regenerating binstubs
Regenerating plugins
# ...

I thought, that's strange, I know there is one more point release after that which still supports Ruby 2.7, and sure enough, when I ran another command it installed:

❯ gem -v
3.4.21
❯ gem install rubygems-update -v 3.4.22
Fetching rubygems-update-3.4.22.gem
Successfully installed rubygems-update-3.4.22
1 gem installed

A new release of RubyGems is available: 3.4.21 → 3.5.1!
Run `gem update --system 3.5.1` to update your installation.

That post install note is not applicable to Ruby 2.7, so I didn't try doing it. Instead I ran the normal next step, update_rubygems:

❯ update_rubygems

  Successfully built RubyGem
  Name: bundler
  Version: 2.4.22
  File: bundler-2.4.22.gem
Bundler 2.4.22 installed
RubyGems 3.4.22 installed
Regenerating binstubs
Regenerating plugins
# ...

Now I get the error at the top for every bundle command (e.g. bundle -v, and bundle install):

❯ bundle -v
Traceback (most recent call last):
        15: from /Users/pboling/.asdf/installs/ruby/2.7.8/bin/bundle:25:in `<main>'
        14: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `activate_bin_path'
        13: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `synchronize'
        12: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:286:in `block in activate_bin_path'
        11: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:229:in `finish_resolve'
        10: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:425:in `resolve_current'
         9: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:413:in `resolve'
         8: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:191:in `resolve'
         7: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolver.rb:43:in `resolve'
         6: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:182:in `resolve'
         5: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:254:in `process_topmost_state'
         4: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:682:in `attempt_to_activate'
         3: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:297:in `unwind_for_conflict'
         2: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:297:in `tap'
         1: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:299:in `block in unwind_for_conflict'
/Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/molinillo/lib/molinillo/resolution.rb:317:in `raise_error_unless_state': Unable to satisfy the following requirements: (Gem::Resolver::Molinillo::VersionConflict)

- `bundler (= 2.5.1)` required by `user-specified dependency`
        13: from /Users/pboling/.asdf/installs/ruby/2.7.8/bin/bundle:25:in `<main>'
        12: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `activate_bin_path'
        11: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:284:in `synchronize'
        10: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:286:in `block in activate_bin_path'
         9: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems.rb:229:in `finish_resolve'
         8: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:425:in `resolve_current'
         7: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/request_set.rb:413:in `resolve'
         6: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:192:in `resolve'
         5: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `rescue in resolve'
         4: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `raise'
         3: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver.rb:194:in `exception'
         2: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/exceptions.rb:55:in `initialize'
         1: from /Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/exceptions.rb:61:in `conflicting_dependencies'
/Users/pboling/.asdf/installs/ruby/2.7.8/lib/ruby/site_ruby/2.7.0/rubygems/resolver/conflict.rb:48:in `conflicting_dependencies': undefined method `request' for nil:NilClass (NoMethodError)

[pboling]

Uninstalling bundler seems to have worked... but also why did RubyGems allow bundler 2.5.1 to install on Ruby 2.7 at all?

❯ gem uninstall bundler
Gem bundler-2.4.22 cannot be uninstalled because it is a default gem

Select gem to uninstall:
 1. bundler-1.17.3
 2. bundler-2.5.1
 3. All versions
> 2
Successfully uninstalled bundler-2.5.1
WARN: Unresolved or ambiguous specs during Gem::Specification.reset:
      stringio (>= 0)
      Available/installed versions of this gem:
      - 3.1.0
      - 0.1.0
WARN: Clearing out unresolved specs. Try 'gem cleanup <gem>'
Please report a bug if this causes problems.

Now I can run bundle commands again!

So, I think the bug here is that bundler 2.5.1 is not restricted to Ruby >= 3.0?

[pboling]

As an aside, bundle update did update the bundler version in the lockfile to the correct 2.4.22, while bundle update --bundler broke bundler completely by installing version 2.5.1 which doesn't work on Ruby 2.7...

[deivid-rodriguez]

What was your RubyGems version originally before running gem update --system? I'm trying to reproduce on a printing ruby 2.7.8, but I'm not being able to.

[deivid-rodriguez]

This is the error I'm getting:

$ gem update --system                      
Updating rubygems-update
ERROR:  Error installing rubygems-update:
	There are no versions of rubygems-update (= 3.5.1) compatible with your Ruby & RubyGems
	rubygems-update requires Ruby version >= 3.0.0. The current ruby version is 2.7.8.225.
ERROR:  While executing gem ... (NoMethodError)
    undefined method `version' for nil:NilClass

But that's non-destructive and my installation is fine after seeing it.

[pboling]

I think what caused the problem is: bundle update --bundler. I'll make a repro repo.

[deivid-rodriguez]

Thanks! I forgot to mention that I couldn't repro any errors when running bundle update --bundler either, so a repro will be super useful 👍.

[deivid-rodriguez]

@pboling I can repro now!

[pboling]

I wish I knew for certain what version I started with, but I'd guess that it was very recent. It is difficult to keep track of because I use so many versions of Ruby on my machine. I do know that I upgraded RubyGems in every installed Ruby on this computer within the last 3 months after the last bugfix we worked through together.

Perhaps RubyGems could print the current version as it begins the update rubygems process?

[deivid-rodriguez]

Yeah, I tried starting with RubyGems 3.4.21 and it reproduced. Basically it needs to be higher than RubyGems 3.3.0 because those versions are the ones where bundler can upgrade itself through bundle update --bundler (previously it would only be able to update the lockfile to the latest installed version, but was not able to install the latest version available remotely and upgrade the lockfile to use that).

In any case, fix is #7310. However, since this happens while upgrading Bundler, there's no way we can't stop other Ruby 2.7 users from hitting this, since the way to get the fix would be to run bundle update --bundler, which is exactly what's broken 😞.

[pboling]

For future reference - Anyone wanting to continue to support Ruby 2.7 builds in their CI will want to do something like this in their pipeline:

# Because we support EOL Ruby still...
- gem install rubygems-update -v 3.4.22
# Actually updates both RubyGems and Bundler!
- update_rubygems > /dev/null 2>&1