I run seamless RW on a Mac Studio M2 Max with OS Venture and a planning to upgrade to OS Sonoma, but could there be issues with RW Classic and Stacks?
Maybe it’s a question that I have to direct to Stack developers?
No issues with RWC on Sonoma, although I’ve been reading the latest macOS 14.4 release has been causing some big issues like Java not working, some USB hubs breaking (not working), and a big one "macOS Sonoma 14.4 Bug ‘Destroys Saved Versions in iCloud Drive’…
So maybe waiting until the next patch release of Sonoma would be good if any of those things are important for you 
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Hi, I run Sonoma latest release on M2 ultra with RW classic, stacks 5, foundry 3 : no problem until now 
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Hi Dang
Java isn’t a part of MacOS so I don’t see there could be a issue a bout that?
I’ll wait until I see fit to update, because now I’m very confident about Ventura.
But nice with your input
Apple just released a point release that fixes the things that 14.4 broke. 
Sonoma has been pretty stable from my experience. I think with the most current version now is a good time to update, especially since you have a beast of a machine (Mac Studio M2 Max) that can handle it.
One thing I recently learned, you can create a new Volume on your SSD and install another version of macOS (instead of using partitions). It used to be slightly more difficult with partitions, but since Apple started using APFS, the process of installing two versions of macOS on your machine is easier now.
Good for testing a new macOS version before committing anyway.