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Buildr's packaging tasks are built such if you write

packages.first.enhance do |task|
  puts File.exist?(task.name)
end

it will print false (That is, your code is executed before the package is actually created.) This is so that you can enhance the task to, e.g., add or remove files from archive.

This is different from how enhance usually behaves — usually the enhance block is executed after the existing defined behavior of the task. If you want the normal behavior, enhance twice:

packages.first.enhance do |task|
  task.enhance do
    puts File.exist?(task.name) # prints true
  end
end