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Diagnosing Ruby-on-Rails App: LoadError: cannot load such file -- enumerator

I'm trying to install a Ruby app (EasyRedmine) and the installer keeps crashing at various points with the error "LoadError: cannot load such file -- enumerator" I thought the issue was that the enumerator module wasn't loaded, but I wrote a little hello world program that required it and it loaded fine. I'm not very familiar with Ruby myself, so I was hoping someone could help me at least narrow down what module is throwing the error from the stack trace. This is the output I'm seeing:

  STD: LoadError: cannot load such file -- enumerator
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/vpim-13.11.11/lib/vpim/property/recurrence.rb:10:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/vpim-13.11.11/lib/vpim/vevent.rb:20:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/vpim-13.11.11/lib/vpim/icalendar.rb:15:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/vpim-13.11.11/lib/vpim/attachment.rb:10:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/vpim-13.11.11/lib/vpim/vcard.rb:11:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/ruby-msg-1.5.2/lib/mapi/convert/contact.rb:2:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/ruby-msg-1.5.2/lib/mapi/convert.rb:5:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/ruby-msg-1.5.2/lib/mapi.rb:5:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/ruby-msg-1.5.2/lib/mapi/msg.rb:2:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/easy_plugins/easy_extensions/patches/plugins/mapi_patch.rb:1:in `<top (required)>'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:231:in `load'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:231:in `block in register'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:231:in `each'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:231:in `register'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/easy_plugins/easy_extensions/init.rb:1:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:447:in `require_plugin_init_file'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:437:in `load_plugin_init'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:389:in `block in init!'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:388:in `each'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:388:in `init!'
  STD: /tmp/d20220116-64334-1fi5jlq/plugins/easyproject/init.rb:462:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /tmp/d20220116-64334-1fi5jlq/config/initializers/22-change_plugins_order.rb:15:in `load'
  STD: /tmp/d20220116-64334-1fi5jlq/config/initializers/30-redmine.rb:20:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:326:in `load'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:326:in `block in load'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:326:in `load'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/engine.rb:681:in `block in load_config_initializer'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/notifications.rb:205:in `instrument'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/engine.rb:680:in `load_config_initializer'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/engine.rb:634:in `block (2 levels) in <class:Engine>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/engine.rb:633:in `each'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/engine.rb:633:in `block in <class:Engine>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:32:in `instance_exec'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:32:in `run'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:61:in `block in run_initializers'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:50:in `each'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:50:in `tsort_each_child'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/initializable.rb:60:in `run_initializers'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/application.rb:391:in `initialize!'
  STD: /tmp/d20220116-64334-1fi5jlq/config/environment.rb:16:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `block in require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:299:in `load_dependency'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/activesupport-6.1.4.1/lib/active_support/dependencies.rb:332:in `require'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/application.rb:367:in `require_environment!'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/railties-6.1.4.1/lib/rails/application.rb:533:in `block in run_tasks_blocks'
  STD: /usr/local/rvm/gems/ruby-2.7.5/gems/rake-13.0.6/exe/rake:27:in `<top (required)>'
  STD: /usr/local/rvm/gems/ruby-2.7.5/bin/ruby_executable_hooks:22:in `eval'
  STD: /usr/local/rvm/gems/ruby-2.7.5/bin/ruby_executable_hooks:22:in `<main>'
  STD: Tasks: TOP => redmine:plugins:migrate => environment
  STD: (See full trace by running task with --trace)

Easy Redmine version 11plus.3.2 will contains fork of vpim gem. -> It will be released next week

I've had the same error. In my case, I'm using the Docker image included in the package, and the error was that EasyProject doesn't freeze the version of the base image.

The issue is, as Holger mentioned in the coment, that vpim and ruby-msg are not being supported in Ruby 2.7.5. If you change to 2.7.4 it will work.

In Docker version, changing the base image to ruby:2.7.4-slim-buster is enougth.

By the way... I think that should be a good practice to freeze libs and images versions...

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