What caused amusement to me was an inspection of the headers, it looked to me as if part of the reason for the looping was that the email was regard as spam, the report started off as (34 lines 1321 bytes) as the following spamassassin report:
Content analysis details: (-3.9 points, 5.0 required)
pts rule name description
---- ---------------------- --------------------------------------------------
-2.6 BAYES_00 BODY: Bayesian spam probability is 0 to 1%
[score: 0.0000]
-1.3 AWL AWL: From: address is in the auto white-list
but 80+ messages later (706 lines 18625 bytes)
Content analysis details: (-0.4 points, 5.0 required)
pts rule name description
---- ---------------------- --------------------------------------------------
0.1 FORGED_RCVD_HELO Received: contains a forged HELO
2.5 HEAD_LONG Message headers are very long
0.5 DATE_IN_PAST_03_06 Date: is 3 to 6 hours before Received: date
0.0 UNPARSEABLE_RELAY Informational: message has unparseable relay lines
-2.6 BAYES_00 BODY: Bayesian spam probability is 0 to 1%
[score: 0.0000]
-1.0 AWL AWL: From: address is in the auto white-list
so the more it looped and the spammier it got and more likely it was to loop....as it says
Message headers are very long
hmmmm
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