Hi @HappyTeacher_63
Thanks for the update and for testing this out so thoroughly. That's a great question to bring back to your class.
Here's the short version of what's happening: Set Page Boxes only changes the page's outer boundary, not the size of the content sitting on it. When you set the page to 8.5 × 11, Acrobat resized the "canvas," but the JPG itself is still the same physical size it was before, just now centered on a bigger sheet. That's the tiny image you're seeing in normal document view.
Print Preview is a different story. By default, Acrobat's print settings scale a page's content to fit the paper size you're printing to (this is normally a helpful thing, it's why oversized or undersized pages still print sensibly). So what you're seeing in Print Preview is Acrobat temporarily stretching that small image up to fill a letter sheet for printing purposes. It's not a preview of what's actually stored in the PDF, it's a preview of what will physically print. If you saved or exported instead of printing, the file itself would still have that small image.
So for your class: the image's true size on the page never changed, you were just looking at two different things (the stored page content vs. a print-time scaling adjustment).
To actually make the JPG fill the letter page for real, a couple of options:
Resize it directly on the page, go to Tools > Edit PDF > Edit, click the image, and drag a corner handle to enlarge it (hold Shift to keep it proportional). Steps here: Edit images or objects in a PDF.
Convert the image at the right size before combining, this is probably the cleaner one to demonstrate to a class: instead of dragging the JPG straight into Combine Files, right-click it in Windows and choose Print, select the "Adobe PDF" printer, and pick Letter as the paper size with "Fit" scaling. That produces a properly Letter-sized PDF page from the image before it goes into your combined file, so you skip this mismatch entirely.
Great instinct to check Print Preview and notice the difference.
Hope this information will help
~Amal