I realize it is an issue with "mail" all settings are correct, there is an issue with apple mail sending single page attachments that are pdf files it embeds them if they are single page, if they are more then one page they go out sometimes... Single page emails form Timemaster sit in the outbox and give you the error message I mentioned. It is an apple problem surprised you have not heard this. Was hoping there was a workaround, currently i have to send them from my iPhone with IOS6 since the iPad won't send pdf's. All mail settings are identical, everything else works fine just wont send it out when it comes from Timemaster as a single page pdf.