I'm using a macOS Catalina vm guest for heavy application testing. Since some Parallels Desktop releases back (I think 16) the Apple macOs Update inside this guest isn't working properly. I found a description of the problem in the knowledge base https://kb.parallels.com/124705 There it is stated that you should reset the machine to overcome the problem. Well, it doesn't help me at all. The catalina guest won't update. The update process just stucks forever although you can interact with the vm normally. Resetting or not. If I am trying to list the macOS software updates with the help of the command line and softwareupdate tool : sudo softwareupdate -l I won't even get anything back in stdout. Very strange. Host HW is an Intel Apple Mac Book Pro 16'' (2019) running macOS Monterey 12.6.1. / CPU 2.3 GHz 8-core Intel Core i9 / 16 GB RAM/ 1 TB SSD Parallels Desktop 18 Pro for Mac - Version 18.0.3 (53079) Someone came across the same problem? Maybe similar problems with Big Sur/Monterey guests? Any help is appreciated. Thanks.