You seem to be using an ancient version of pry-byebug, the latest as of this writing is 3.2.0 but you're using 1.3.3. If you update your gems there's a good chance the problem will go away.
UPDATE
After further research it looks like pry-remote and pry-byebug do not work well together on Ruby 2.x.
However, there is a bit of code a coder posted, most of the comments are in Japanese, but they claim it makes pry-remote work. I'm including their code below (I've translated the Japanese as well):
module ObjectUtils
# remote parameter is the ip address, default port is 9876
def pry!(remote=nil, port=9876)
$LOAD_PATH.unshift "#{ENV['RUBY_PATH']}/debuger"
require 'pry'
return if __callee__ == :pry1 and !Pry.instance_variable_get(:@pry_is_start)
Pry.instance_variable_set(:@pry_is_start, true)
# if defined? Pry and defined? PryStackExplorer and Pry.config.hooks.hook_exists? :after_session, :delete_frame_manager
# Pry.config.hooks.delete_hook :when_started, :save_caller_bindings
# Pry.config.hooks.delete_hook :after_session, :delete_frame_manager
# end
if remote or ENV['USE_PRY_REMOTE']
if defined? PryNav
if defined? ActionDispatch # rails application.
if Pry.initial_session?
warn '[0m[33mloading pry remote ...[0m'
binding.of_caller(1).remote_pry(remote, port)
end
else
binding.of_caller(1).remote_pry(remote, port)
end
else
require_remote_debugger
binding.of_caller(1).remote_pry(remote, port)
`notify-send -t 5000 -- "exiting pry remote ..."` if find_executable 'notify-send'
end
else
# if these constants are defined then you're already in a debugger session
if defined? PryByebug or defined? PryDebugger or defined? PryNav
if defined? ActionDispatch # rails application.
if Pry.initial_session?
# When sending a new request, it will reset Pry.initial_sesssion? It is true.
# This ensures that, in the same request the debugger will be activated once.
# Only on the next request will it be reinitialized
warn '[1m[33mloading debugger ...[0m'
binding.of_caller(1).pry
end
else
binding.of_caller(1).pry
end
else
require_debugger
binding.of_caller(1).pry
end
end
end
def require_debugger
case RbConfig::CONFIG['ruby_version']
when '2.0.0'...'3.0.0'
require 'pry-byebug'
when '1.9.0'...'2.0.0'
require 'pry-debugger'
end
# to make sure the debugger is loaded
warn '[1m[33mloading debugger ...[0m'
require 'ap'; AwesomePrint.pry!
rescue LoadError
require 'pry-nav'
warn '[1m[33mloading debugger ...[0m'
end
def require_remote_debugger
require 'pry-remote'
require 'pry-nav'
warn '[0m[33mloading pry remote ...[0m'
`notify-send -t 10000 -- "loading pry remote ..."` if system 'which notify-send &>/dev/null'
require 'ap'; AwesomePrint.pry!
end
end
Kernel.send(:include, ObjectUtils)
Object.send(:include, Kernel)
You'll need to call these methods, and might need to tweak them for your usage.
References
