OK, well, answered my own question. First, after poking around on the server I noticed the attachments were correctly downloaded and placed in the c:\arcgisserver\arcgisoutput folder. So I went into server manager and noticed it had two arcgisoutput folders listed, one on the c: drive and one on the e: drive. Probably my error on install/re-install over the years.The service actually pointed to the correct arcgisoutput folder where the pdf's were waiting so I investigated further and in IIS the virtual folder was pointing to the other, incorrect arcgisoutput folder. I pointed IIS to the correct arcgisoutput folder and like magic the pdfs open when I click their name in the popup. Keith