You wrote: "No I don't get a little popup when I go to save as PDF."
Those do appear to be popup windows. Mine just happen to be smaller. The size is manually adjustable by dragging the edge. Yours are just expanded more and bigger than mine. They overlie the main TurboTax screen. The size will vary from person to person.
The first image you posted (2020) doesn't have the little "options" symbol in the top right corner like mine does. Your second image (2019) does have the little "options" symbol in the top right corner. I don't know why your 2020 image is different. My 2019 and 2020 windows look the same and can be sorted; i.e., I can sort by either Name or Date Modified and can click again to change the direction to make the newest appear at the top.
My 2019 and 2020 "Save As" windows both look like your second image, and are the same as my image I originally posted above. The only difference is that mine are black. Both of mine have the little "options" symbol in the top right corner. I cannot tell any difference between my 2019 and 2020 Explorer windows. I can't reproduce anything that looks like the first image (2020) you posted. The top and bottom area of your 2020 screen looks different than the top and bottom areas of your 2019 screen and different from either of mine. And the left column directory tree looks like an old version of Explorer with "+" symbols to expand folders.
Since we're both using Windows 10, I don't know why your 2019 and 2020 would be different from each other, while mine aren't. So let's be sure we are both producing them the same way.
There are at least 3 ways to save a PDF in the TurboTax Program. How are you doing it? Here are some examples. When you try the 3 methods, do you get any difference among them, or do all of them produce the same result as your image 1, which you can't sort?
Method 1
With the 2020 return open, go to top left corner and click FILE, then in the dropdown choose "Save to PDF."
Then in the popup windows that allows you to choose what to include, click the button "Save as PDF."
Method 2
With the 2020 return open, go to the top left corner and click FILE, and in the dropdown choose "Print."
Then in the popup window that allows you to choose what to include, click the button "Save as PDF."
Method 3
Go into Forms Mode and pull up the Form 1040 or any form.
Then at the bottom of the screen choose the PRINT button.
Then in the popup window that allows you to choose what to include, click the button "Save as PDF."
All 3 methods produce the same end result for me, like the Explorer image I posted, and all can be sorted in either direction; i.e., one can reverse the sorting direction by clicking the column header again.
