Drag and Drop images from Messages app to Windows

After upgrading to Monterrey I can no longer drag and drop images from the Mac Messages app to Windows. I get an error message, "The file <file name> can not be copied. Do you want to skip it?" I can drag and drop from Windows to the Messages app.

Copying and pasting from Messages to Windows does not work either. No error message, the image just does not copy and paste. However, after copying and pasting without the image actually copying I can then then drag and drop the same image from Messages to Windows and it will copy.

Dragging/dropping and copying/pasting works normally from every other app as far as I can tell- just not Messages app. Jams up my workflow to not be able to do this.

 

Hello, The Parallels Tools need to be installed in the Virtual Machine and the Isolate Mac from Windows option disabled in the Security Pane. Kindly refer to this link - Unable to copy and paste in Parallels Desktop for the same. Thanks.