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I am trying to send multiple docuemments and can not get it to work
As per the description above, I can understand that you are facing issue while sending files via Adobe Send, Is that correct?
Please try to send the files from online account https://cloud.acrobat.com/send
You may also refer to Adobe Send FAQ Link: https://forums.adobe.com/docs/DOC-4472
Let us know how it goes.