When I extract PDFs from a portfolio in bulk not all files are extracted

I figured out what is going on here, at least in my configuration. The problem happens when you are dealing with a portfolio generated from conversations spread across different outlook-folders.

Let me explain in more detail. My problem originated in the manner in which I had emails grouped in conversations and their folder locations in outlook. I inadvertently had conversations spread across different folders. It turns out you can have conversations spread over different folders in outlook but outlook will allow you to view all the emails in the conversation regardless of location. It sort of tricks you into thinking you know where your emails are located. But in fairness to outlook, the ones in a different folder will be grayed out.

When such a conversation is exported with PDFMaker (adobe add-in for outlook), the generated portfolio will have all the emails, but you will only be able to extract those emails that were in the initial outlook-folder that you were trying to export.  Apparently, when the portfolio is generated, PDFMaker will only make enough names for the emails that are actually in the folder you are trying to export. Later, when you are extracting in bulk the pdfs from the portfolio, the adobe program assigns those names to the items in the portfolio. If there are more items then pdfs, which happens when emails in a conversation are spread across different outlook-folders, then there will be duplicate names and extracted pdfs will be overwritten.  

When I made sure to move all the emails in conversations into the same outlook folder that I was trying to export, then after I generated a portfolio, I was able to extract all the individual pdf's correctly. Yeah, it was a subtle bug for a non-programmer like me and I nearly went bananas figuring that out.

I hope that helps someone.