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Hey Markm,
Looking at the description given above, I believe you are referring to the MS Outlook Send & Track feature as described in this help article: https://helpx.adobe.com/acrobat/using/adobe-send-for-outlook.html
Is this error appears only when attaching a specific file or any file size which is 100 MB or larger than that?
It could be a possibility that file size has been exceeded and that causes the trouble. Try with a different file which is smaller in size.
Thanks,
Akanchha