Hi,
Yes it is possible. See our changelog here: https://boxcryptor.desk.com/customer/portal/articles/1188696-boxcryptor-2-0-for-windows-changelog)
Added: When creating a file or folder in a plain text folder a dialog pops up asking the user if he wants to encrypt the file or folder (This dialog can be disabled by adding '"dontConfirmPlaintextOperation": true' in %LOCALAPPDATA%\Boxcryptor\volume.db)
When disabled, files or folders created in an unencrypted folder will also be unencrypted and files or folders created in an encrypted folder will also be encrypted.
Best regards,
Robert
PS: We will add a "Do not show again" checkbox to the message box in a future release.