Hi, we've been seeing occurrences of this issue from time to time in Sonoma, Sequoia, and Tahoe. From our observations, it seems that the issue is rare, but certain devices can reproduce it relatively consistently on boot. A pattern hasn't been established between these devices yet. As posted by @Appleaholic above, when we try to call NEVPNConnection's startVPNTunnel() from within a do-catch statement, no error is thrown. However, the VPN never enters a Connecting/Connected state. Is there any way that startVPNTunnel() can fail, without an error being thrown?

Sorry for the delayed response! We opted to wait for the release of Tahoe to see if the issue would be resolved there, before creating a bug report. Thanks for the suggestion, and no worries about not wanting to dive into an essay on the issue here! A bug report has now been opened under: FB20282285. In case it helps any future readers, WWDC 2017 Session 701 can still be found here, and is indeed a good watch: https://devstreaming-cdn.apple.com/videos/wwdc/2017/701jvytnoey2yc7222/701/701_hd_your_apps_and_evolving_network_security_standards.mp4 (Or to download: https://devstreaming-cdn.apple.com/videos/wwdc/2017/701jvytnoey2yc7222/701/701_hd_your_apps_and_evolving_network_security_standards.mp4?dl=1) Thanks for the help!