CRM 2011 Outlook Client Mail Merge Issue

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A user is having an issue completing a mail merge with the CRM 2011 Outlook client. She is able to download the template from CRM and open it with word, and all of the recipient information populates the appropriate forms in word. However, when she completes the mail merge, only a few of the messages show up as sent in the sent items folder in outlook. This does not seem to be an issue with any of the contacts, since the workaround is to complete the mail merge multiple times until all of the messages are sent. Sometimes all of the messages send properly, yet other times only one or two messages will send. Any help or insight is appreciated.

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