Do you really need a technical background or some sort of college training to find the File > Save As > PDF option?
Window management in Windows GUI:
1. Usage of File Menu and/or Ribbon Menu
2. Knowledge of Word's PDF integration
File System knowledge:
1. What a "file" is
2. What "file formats" are
3. What a PDF is
4. That a word document can be saved or printed as a PDF
Etc etc etc
I work with non-technical folks all the time and printing/saving as PDF comes up often.
Usually in most cases I can install a PDF printer and let them "print to PDF" and they can understand it, but before they know the process, they look at me like I'm speaking Latin when I try to describe what files are, what PDFs are, what conversion is, what the file menu is used for, etc.
HN readers who don't work with non-technical users may not realize just how lost and unable to explore many people are, particularly when they didn't grow up with computers. There's also a huge problem with "dialog blindness."
If you have an understanding of how "computers" (hardware, OS, apps, websites, doesn't matter it's all the same mystery box) work then you can explore with less fear. I deal with people in their 20s and 30s who don't grasp that a "scanner XYZ not found" error may mean that they should look for a way to select a scanner. Many of my older end users are clearly using a lot of software entirely by rote, though it's definitely not limited to them.
Can probably go to 55-58 for people who have degrees; ie people who used computers during Uni education.
If you're older you've probably had 20 years with computers in the workplace save for some niches, seems long enough to learn to use a simple point-click menu.
None of that means that he actually understands what is happening behind the scenes. Odds are good that his college exposure to computers was limited to Hollerith cards used for registration.
Put differently, Manafort is from the generation that indents in word processors by hitting space 4-5 times.
He knew enough to attach the file to an e-mail and send it to someone else asking for a PDF version. So the only piece of missing knowledge here appears to be finding the option in word's menus.
"On February 11, 2011, another trader, Trader E, wrote to Trader C: 'shall we spoof.' Trader C responded: 'sure.'
...
Even the most minimalist 2018-era bank compliance program would at least teach traders not to use the word 'spoof' in a recorded electronic chat, but a decade ago our primitive forebears did not quite understand the problem."
https://www.bloomberg.com/view/articles/2018-01-31/sergeant-...
I'm having trouble buying any other explanation than, "This absurdly overcomplicated workflow introduced by conventional office software not designed to cover its tracks didn't cover its own tracks" as plausible.