gistfile1.py

prompt_test = True

@click.group()
@click.option('--mode', is_flag=True)
def cli(mode):
    prompt_test = True if mode else False
    print "prompt_test value in cli: %s" % prompt_test

@cli.command()
@click.option('--name',
              prompt=prompt_test,
              required=True
              )
def test(name):
    print "prompt_test value in test: %s" % prompt_test
    print "test %s" % name

if __name__ == '__main__':
    cli()

# Ok
# $ python __test_click --mode test
# prompt_test value in cli: True
# Name: aaa
# prompt_test value in test: True
# test aaa

# Not ok
# $ python __test_click.py test  
# prompt_test value in cli: False <-- Looks good!
# Name: aaa                       <-- Unexpected prompting?
# prompt_test value in test: True <-- Why?
# test aaa

# Not ok
# $ python __test_click.py test --name aaa
# prompt_test value in cli: False  <-- Ok
# prompt_test value in test: True  <-- Why? 
# test aaa