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Calendaring body being ignored of more than one mail sent out via threaded mailer

 
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I'm trying to send a calendaring email to a group of people via a threaded mailer and for some reason I can get the first email coming out with the relevant ics headers seen in MS Outlook 2007 but any subsequent emails are seen as plain text and the calendaring part of the mime message is ignored. Is there anything that I am missing or doing incorrectly? Thanks in advance for any pointers.

The mail Entity that is called by the programme:

and the callable() is section is:
 
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