After the send

The library keeps the reading, not just the file.

The Windows page says the app adds personal documents, web content, and other files to your library. Archived documents can be downloaded again on a Kindle or with the free Kindle app on iOS or Android. That wording is in the 1.1.1.260 package description.

Whispersync of notes, highlights, bookmarks, and last page read is available on archived personal documents converted into Kindle format. Files that stay in the original form, or that were sent before 11 November 2022, do not get every newer markup feature.

Amazon help says documents sent through Send to Kindle are protected with end-to-end encryption and that the service reaches your library and Kindle app at no additional cost. You must be signed in.

SurfaceWhat you can do with notes
Kindle ScribeHandwritten sticky notes, text notes, active canvas, highlights, and direct writing on print-format PDFs.
Other Kindle e-readersHighlights and text notes.
Kindle for PC and MacText notes and highlights. This reading app is separate from Send to Kindle for PC.
Kindle for WebPersonal documents are not supported yet.

Handwriting is not supported on PDFs loaded by USB, on documents sent before 11 November 2022, or in EPUB comics, manga, and children books. The send gestures themselves are on the guide.