Hi,
I do have the Attach PDF Invoice plugin running, but also when going to system->emails with the order status emails i added 2 pdf attachments (terms & conditions and return form).
On the mailserver i can see the order created email going through, but the order status email (confirmation email) there is nothing in the logs. I also checked the PHP error.log but there is nothing in there.
Also reset the order status email, so removed changes i made to it to see if there was an issue in that, but that didnt make a difference either.
What i will do is, since the website is live, copy the website to a test site and take the attachments off and see if it goes through.
Im also talking to the cciDeal developer and he said it should work ok, so i think its best to go back to the test site and start adding changes one by one to see where it goes wrong.