PDF Sync Issue Between Mac and Windows Using FreeFileSync 13.7

[Gnbnico]

Hello,
When I print an email from Gmail using the browser on my Mac, I can't synchronize the resulting PDF with FreeFileSync anymore. Everything used to work perfectly, but now I'm encountering an issue.

Here’s my workflow:

I print the PDF from my Mac using the default print settings of the browser (Edge and Brave) and save it to a folder on Google Drive using the Google app installed on macOS.
On my Windows PC, I open FreeFileSync and synchronize the Google Drive folder (via the Google Drive app installed on the PC) to an internal hard drive.
This process has worked smoothly until today. Now, FreeFileSync no longer creates the file and keeps asking me to synchronize it again. Oddly, if I print the same email from Windows using "Foxit Reader PDF Print," everything works fine.

This function is essential for my backup and archiving workflow, so I'd really appreciate any help.

I'm using:

macOS Monterey 12.8.8
Windows 10 PRO 10.0.19045 Build 19045
FreeFileSync version 13.7 on the PC
Any advice or insights would be greatly appreciated!

Thank you!

[xCSxXenon]

What do the logs say?

[Gnbnico]

Hi, thank you for your reply. After furthe investigations I think FreeFileSync is not responsible for the issue. If I save an email as a PDF on my Mac and upload it to Google Drive via the app, everything works fine on Mac. The same PDF appears on Windows through the Drive app: here I can open the PDF, but I can't copy it: if I copy it to the desktop, it shows up but disappears after a few seconds. If I "cut" or move it, it appears but then vanishes for good. I think I should ask to Google, not here. Any comments are welcome, thank you

[xCSxXenon]

Interesting... I wonder if it relates to file-streaming.
You mentioned you use the Google Drive app for Windows, have you tried with the native GDrive integration in FFS instead?