Try this condition instead:
* ^X-Spam-Flag:(.*\<)?YES
From: Spam <spam(_at_)ainscough(_dot_)com>
Date: Thu Jun 19, 2003 1:24:07 PM America/Chicago
To: andrew(_at_)ainscough(_dot_)com
Subject: Spam- SPAM TEST
Received: from localhost [127.0.0.1] by server1.arteryserver1.net with
SpamAssassin (2.53 1.174.2.15-2003-03-30-exp); Thu, 19 Jun 2003
18:24:15 +0000
Message-Id: <36F1E1FA-A283-11D7-80F1-0003935804A4(_at_)ainscough(_dot_)com>
X-Spam-Flag: YES
.
.
.
procmail: [7961] Thu Jun 19 18:24:15 2003
procmail: No match on "^X-Spam-Flag:(.*\<)?YES"
Weird.
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