@kyrylo, thank you for reply! There is full exception for me:

Encoding::CompatibilityError: incompatible character encodings: UTF-8 and Windows-1251
from C:/tools/ruby27/lib/ruby/gems/2.7.0/gems/pry-0.13.1/lib/pry/code/code_file.rb:102:in `expand_path'

And:

Encoding::CompatibilityError: incompatible character encodings: IBM866 and UTF-8
from C:/tools/ruby27/lib/ruby/gems/2.7.0/gems/pry-0.13.1/lib/pry/commands/show_info.rb:112:in `+'

Steps to reproduce:

1. Start Windows Sandbox, install Chocolatey and run choco install ruby, gem install pry
2. Create folder and Ruby-file with non-ASCII symbols in path and content:

def тест
end

require 'pry'
Pry.start

3. Run the file and hit show-method тест

The root of the problem is Windows default filesystem, please see below:

C:\Data\Тест>docker run --rm ruby ruby -e "p Dir.pwd.encoding"
#<Encoding:UTF-8>

C:\Data\Тест>ruby -e "p Dir.pwd.encoding"
#<Encoding:Windows-1251>

C:\Data\Тест>docker run --rm ruby ruby -e "p Dir['*'].first.encoding"
#<Encoding:UTF-8>

C:\Data\Тест>ruby -e "p Dir['*'].first.encoding"
#<Encoding:IBM866>

In Ruby we cannot mix non-ASCII symbols with different encodings. So on Windows we should convert non-UTF-8 strings to UTF-8 before first use. This does not affect strings that are already in UTF-8.

I just realized there was several places in code where converting is required too and pushed a new commit. And also another one to fix Rubocop warning.