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Send File as Email

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When in Adobe, I cannot send a file that I have attached either through hitting the email envelope or by selecting attach to email. When I do this, they email loads with the attachment, but when I hit send, it just disappears into thin air, and I am not sure where it goes. If I start a new email, and then attach the PDF through the email it works, but it doesn't when I use Adobe directly.

Any ideas?

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