So the problem is actually not that tricky to understand. This might sound a bit like flames towards Adobe, but I assure you, it's not just them. There's so many moving parts in developing a propriety system of creating documents. It's a wonder any of it works! So, here it is:
Adobe creates a public key and a private key for your document. It then ecrypts it using those keys.
But who else has those keys??? Well, if you don't send the keys with the attachment, mail won't be able to encrypt it. Thus, the issue is with the keychain and mail not sending that public key with each new email. ONLY the email with the encrypted pdf has the keys attached.
It's implemented poorly. Adobe Acrobat should be completly in charge of encrypting and decrypting the message. NOT mail. It's a poor design that interferes with the way that Apple Mail works.
Making things worse, if you look on Apple's Support page, they point at Adobe. If you look on Adobe's site, they point at Apple. The truth is, Adobe made a system that works for the ONE DOCUMENT THAT YOU WANT TO SEND and no others. Apple's mail system has the ability to encrypt using keys, but not when it's intended for ONLY one recipient.
IMO, both parties are to blame. Apple already encrypts messages sent from mail and shouldn't allow 3rd parties to create and implement their own methods of encryption in Mail. Adobe is kinda shortsighted for using an encryption method that HARDCORE interferes with a Mail program that A LOT of people use. I'm sure it's a bug that's so far down the list of things to fix, that Adobe hasn't looked at it in YEARS. ...OR... and this is probably more likely, they hired someone not versed in the Apple Ecosystem to set up an encryption scheme in Acrobat, figured out how to implement it using the keychain, was able to prove that it works, and then the contract to code it was fulfilled. The coder was probably paid on fivr, and sucked at keeping documentation so no one at Adobe has any idea how to fix it.
That said, coders are people too. We all make mistakes. This one just affects those of us that use Apple Mail regularly.
The way to fix the problem is to create a new email FROM the address that's causing the problem.
On the far right side of the subject line, there's a lock looking icon that shows encrypted to not. (for the record, this shouldn't exist - Apple needs to remove this) Turn this button thingy into an X. Your message will not try to encrypt using Adobe's encryption keys now. It will, however, use the Apple Mail internal encryption which works just fine and is equally secure. If your messages STILL won't send, hit the deny button, quit Mail, open it up again, and ensure that encrypt button has the x in it.
PS - Adobe, if you're reading this, please remove Acrobats ability to encrypt the messages in the mail app. Package the PDF with the public keys, and send that in some super secret package with the recievers keys pre-installed in acrobat. There's no need to perform this trick in the Mail app. I'll send the report in the apple support forums as well. Apple should prevent third parties from doing this!
>>if you want to find the quickest and easiest way to perform a task for your company, find the laziest person you can to figout out how to complete said task<<
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