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CRM emails getting stuck in the outlook queue

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I am hoping someone can shed some light... we are using CRM 2011 on premise and it is using exchange web services to integrate with Outlook  to thread mail. Quite frequently messages are getting stuck in the inbox (even though they say sent in CRM) and it causes a huge backlog. So my questions are: If one email does not get processed in a thread of 20... does it stop all 19 following emails from getting processed? it seems like it does but want to know for sure how the threading works. 2) what could be stopping these emails from processing? I can't find a pattern other than potentially it may be due to the pdf attachments? but why?

any expertise would be greatly appreciated.


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