I don't have much experience with Expect.pm, but given what I've read above, your command is redirecting output to a file, and it seems that Expect is never seeing the prompt it's expecting because that's been redirected to the file. 
my $exp = Expect->spawn("/usr/bin/python /opt/vtools/Scripts/reportcon
+solidator.py /opt/vtools/Healthcheck/$dDate > /opt/vtools/HealthRepor
+t.out") or die "Cannot spawn \n";

[download]
and 
spawn id(3): Does `'
match:
  pattern #1: -re `Do you want to unpack these archive files for proce
+ssing? [Y/N]: '? No.

[download]

In reply to Re: Perl Expect not matching by Paladin
in thread Perl Expect not matching by rayvn11

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.