New book downloaded from Amazon to Kindle not showing in Calibre

[JohnnyBook]

Back Story/rant if you want to read it:

Got a 7th Gen Paperwhite, that I normally keep in airplane mode. (Amazon screwed me over several times with updates that "upgraded" my paid "add free" Kindle with updates that switched it to "adds included". Each time I had to spend time on hold to finally get someone to "turn off the adds" on my Kindle. The last time I connected (a few years ago) I got stuck with the "Home/Library" update, and just gave up. But switched the Kindle to Airplane Mode permanently.)

So for years I just downloaded any purchases to my computer or Kindle PC and sideloaded them. Until.... they made purchases downloadable to Kindle only. Since then I have stopped buying books on Amazon and bought them elsewhere or did without. (Didn't want another unwanted update jammed into my kindle. BUT,

I bought a book back in August but never downloaded in until now. Today I connected the Kindle online and sent the book to my Kindle and when it was done, back in airplane mode.

Book is on my kindle and I can read it. Connected the Kindle to my computer but Calibre does not show the book as on the device.

Any ideas why Calibre cant see the new book on the device? Every other book I have downloaded to my kindle from Amazon is visible.