In testing, even though the Mac is checking in it is not pulling application, package receipts etc into jamf pro. Also the machine name isn't DEP - (Serial number) on the Mac. It supposed to report as L(Serial Number) back to jamf pro. This has always worked up until the Catalina Mac. See image.
@NealIV 10.19.0 is Catalina compatible, so that's not it.
Are you using SSL inspection on your network? If so, macOS Catalina changes the server used for the initial APNS communication to init.push.apple.com. If you don't follow changes to Apple's Use Apple products on enterprise networks KB article on what servers need to be on an exception list for SSL inspection you may have courier.push.apple.com as an exception. That works through macOS Mojave, but as of macOS Catalina you need to change it to .push.apple.com to accommodate that initial connection to init.push.apple.com.