G'day edimusrex,

I've never used any of these modules; however, as your question has been sitting there for over 12 hours without a reply, I thought I'd have a look.

In Net::CLI::Interact::Phrasebook, under the PHRASEBOOK FORMAT section, it has:

"Try to make the Prompt as specific as possible, including line-end anchors."

All the examples show that anchor. Here's the first two match examples:

match /\(config[^)]*\)# ?$/
match /> ?$/
[download]

And one further down is very close to your password prompt:

match /[Pp]assword: ?$/
[download]

So instead of

match /User Name/
match /Password/
[download]

maybe try

match /User Name: ?$/
match /Password: ?$/
[download]

You might also want to scrutinise your expected prompts for case and whitespace. For instance, perhaps this would work better for the username prompt:

match /[Uu]ser\s*[Nn]ame:\s*?$/
[download]