Put Pry's history in different files (by date).

.pryrc

###################################################################
## History

PRY_CONFIG_DIR = File.expand_path("~/.pry")

Pry.history.loader = proc do |&block|
  Dir["#{PRY_CONFIG_DIR}/history-*.log"].sort_by { |f| File.mtime f }.last(2).each do |fn|
    File.foreach(fn) { |line| block.call(line) }
  end
end
 
# history_file = nil
 
Pry.history.saver = proc do |line|
  if !@history_file
    filename = "#{PRY_CONFIG_DIR}/history-#{Time.now.strftime('%Y-%m-%d')}.log"
    @history_file = File.open(filename, 'a', 0600).tap { |f| f.sync = true }
  end
  @history_file.puts(line)
end