PDF is damaged Cannot Open

I create a lot of PDF's and then email them to our sales people. I use accounting software called Account Edge. The software emails invoices and purchased fine. I am unable to email paychecks straight from the software, so I simply print, and create a PDF to be emailed through adobe. The pdf is saved in a folder and then I email it out. The issue is, some associates are unable to open the attachment. They say it shows as damaged or cannot open. Is there some type of fix that I don't know about, or a better way to do this?

1. I assume you have some PDF documents you have been keeping a long time. Look at their modification date. Is it what you'd expect (years ago) or is it all the same, recent?
2. Has a TXT file appeared in the same folder as the PDFs?

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