JOB-172614 Update pry to allow unblock Ruby 4.0

[leehoworko]

The current version of pry has a dependency on the readline gem which is a default gem in Ruby < 4. With the release of Ruby 4.0, the readline gem has been "promoted" to become a bundled gem because Ruby is swapping to use reline in it's place -- a Ruby only rewrite to avoid requiring the readline binary.

How this matters for us, pry ~> 0.15 depends on readline. So to get to Ruby 4 we have two options: explicity include readline in the Gemfile, or update pry to a version that depends on reline. This is the second approach

• pry changelog
• The pry-byebug issue that led me this way
• Ruby docs mentioning this gem

Note

Upgrading Pry to 0.16 drops support for Ruby 2.6