binding.pry is often ignored since upgrading to ruby 3.3 + rails 7

Question

I am currently in the process of upgrading my rails 6 app to 7, and when I've run into issues, I have been trying to debug, and keep running into this weird issue where binding.pry does not seem to be stopping execution... For example, I have an active model validation callback which calls a dynamically defined method:

   29     define_method "#{subclass}_include?" do |id|
   30       binding.pry
   31       puts "pry should have been called"
   32       find_by_id(subclass, id).present?
   33     end

And I am trying to trigger this from an rspec spec file:

[1] pry(#<RSpec::ExampleGroups::Share::WhenShareTemplateIdIsNotAValidShareTemplate>)> subject.valid?
pry should have been called
pry should have been called
pry should have been called
NoMethodError: undefined method `find' for "translation missing: en.foo.bar":String

The binding.pry command is getting completely ignored...

*** UPDATE ***

It happened again.. I have an ActiveJob spec which is doing:

after_perform :enqueue_next_job

...

def enqueue_next_job
  self.class.set(:wait_until => 30.seconds.from_now).perform_later
end

running this spec, I see:

     SystemStackError:
       stack level too deep
     # ./app/jobs/my_job.rb:20:in `enqueue_next_job'
     # ./app/jobs/my_job.rb:20:in `enqueue_next_job'
     # ./app/jobs/my_job.rb:20:in `enqueue_next_job'
     # ./app/jobs/my_job.rb:20:in `enqueue_next_job'
     # ..etc (forever)

So I put a pry in my enqueue_next_job:

[1] pry(#<MyJob>)> job = self.class.set(:wait_until => 30.seconds.from_now)
=> #<ActiveJob::ConfiguredJob:0x000000012ff33128 @job_class=MyJob, @options={:wait_until=>Wed, 21 Aug 2024 23:15:51.479173000 UTC +00:00}>
[2] pry(#<MyJob>)> edit job.perform_later

added to the perform_later code:

 14     def perform_later(...)
 15       binding.pry
 16       puts "binding.pry should be happening"
 17       @job_class.new(...).enqueue @options
 18     end

exited, and called perform_later on the job and I get:

[3] pry(#<BulkIndexAssetItemsJob>)> job.perform_later
binding.pry should be happening
binding.pry should be happening
binding.pry should be happening
binding.pry should be happening
binding.pry should be happening
binding.pry should be happening
binding.pry should be happening
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SystemStackError: stack level too deep