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Specifying pry directly works for me (gem "pry", github: 'pry/pry') but when you use pry from github master, guard will break due to changes in Pry.config.history -- see #953
See related issues deivid-rodriguez/pry-byebug#221 pry/pry#1871
When running Guard on Ruby 2.7, it shows this warning:
Pry unfortunately hasn't had a release in a long time, but this has been fixed in pry master.
Specifying pry directly has no effect because Guard adds Pry as a runtime dependency https://github.com/guard/guard/blob/master/guard.gemspec#L25
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