Good morning Jamie, after a Homey restart, some groups fail to synchronize their state with their respective devices.
I’ll try to provide you with as much information as possible to help you understand the problem. I hope everything is clear. I apologize if there are any grammatical errors, but I’m not good at writing in English 
I have a group of lights called “Faretti Bagno” that contains 4 Philips Hue bulbs [Faretto Bagno 1, Faretto Bagno 2, Faretto Bagno 3, Faretto Bagno 4].
The group is set to “on if any devices are on,” but after the Homey restart, the group stopped synchronizing with some of its devices.
For example, in the last test I performed, if I turn on “Faretto Bagno 1” or “Faretto Bagno 4,” the group that contains them doesn’t change its state. The “Faretti Bagno” group only synchronizes its state with “Faretto Bagno 2” and not with the other devices. It seems as if it has lost the registration for some events.
The issue doesn’t occur for all groups; some of them work perfectly. After that, I restarted the app, and all groups responded correctly to state changes.
Afterward, I conducted another test.
I disabled the Group app and restarted Homey. I waited for all the apps to initialize properly and then launched Group.
In this scenario, all the groups worked correctly, and it was not necessary to restart the app.
I’m using an HP2019 with version 8.1.4.
I’m also using version 3.2.4 of the app, and I recreated all my groups with this latest version.
Before running the test, I made sure that all apps were correctly launched.
I generated a report regarding this issue: 2fec177a-0e6f-4139-a796-01d0b46b5eda
If you need any further information, feel free to ask. Thank you! 