The following script works for me: 
#!/usr/bin/perl

use strict;
use warnings;

use Net::OpenSSH;
use Expect;

my $host = $ARGV[0];
my $pass1 = $ARGV[1];
my $pass2 = $ARGV[2];

my $ssh = Net::OpenSSH->new($host, passwd => $pass1);
$ssh->error and die "unable to connect to remote host: " . $ssh->error
+;

my ( $pty, $pid ) = $ssh->open2pty("sudo -kp 'configtest:' bash 2>&1")
    or return "failed to attempt sudo bash: $!\n";

my $expect = Expect->init($pty);

$expect->expect(2,
        [ qr/configtest:/ => sub { my $expect =shift; $expect->send($p
+ass2 . "\n"); exp_continue;} ],
        [ qr/Sorry/     => sub { my $expect=shift; print "Failed\n"; e
+xp_continue; } ],
        );

$expect->interact();

[download]
Can you try it?

Which OpenSSH version and OS are you using?

In reply to Re: Losing my mind with Net::OpenSSH and Expect by salva
in thread Losing my mind with Net::OpenSSH and Expect by rastoboy

Title:
Use:  <p> text here (a paragraph) </p>
and:  <code> code here </code>
to format your post, it's "PerlMonks-approved HTML":


  • Posts are HTML formatted. Put <p> </p> tags around your paragraphs. Put <code> </code> tags around your code and data!
  • Titles consisting of a single word are discouraged, and in most cases are disallowed outright.
  • Read Where should I post X? if you're not absolutely sure you're posting in the right place.
  • Please read these before you post! —
  • Posts may use any of the Perl Monks Approved HTML tags:
    a, abbr, b, big, blockquote, br, caption, center, col, colgroup, dd, del, details, div, dl, dt, em, font, h1, h2, h3, h4, h5, h6, hr, i, ins, li, ol, p, pre, readmore, small, span, spoiler, strike, strong, sub, summary, sup, table, tbody, td, tfoot, th, thead, tr, tt, u, ul, wbr
  • You may need to use entities for some characters, as follows. (Exception: Within code tags, you can put the characters literally.)
            For:     Use:
    & &amp;
    < &lt;
    > &gt;
    [ &#91;
    ] &#93;
  • Link using PerlMonks shortcuts! What shortcuts can I use for linking?
  • See Writeup Formatting Tips and other pages linked from there for more info.