Off the top of my head and in no particular order…
- Was the PDF extension appended to the file name?
- How was the PDF created? Print to PDF, Direct PDF output of an application (if so what application)?
- Did you attach the original PDF to the second message or did you re-create the PDF file before you re-sent it?
- Have you considered submitting the invoice as the text of the email rather than as an attachment?
- Assuming you are sending this via Mail, are you sure "Send Windows friendly attachments" is turned on?
- Did you use 16 bit characters/fonts in the invoice or did you stick with the standard 8 bit fonts and character set? {*]By any chance was the invoice a scanned image and if so had it been edited in a PDF editor?