Hard to find updated information on the web about this so thought I would post for anyone searching for an answer. I have run Quicken Classic for Windows on my Intel iMac via Parallels for 7 years and decided to upgrade to a new Macbook Pro M3 Max (16/40, 48GB). I am successfully running Quicken Classic Premiere for Windows (R53.16) on the MBP using Parallels 19.1.1 (4 CPUs/8GB RAM) with Windows 11 Pro. No major issues except Quicken occasionally shuts down when backing up a data file and the PDF printer drivers I used on my Imac (Big Sur) were better than the new Microsoft Print to PDF driver (can't scale the output down), but I think this is a Sonoma thing and not an Apple Silicon thing. The software is snappy, even when using a very large (540MB) QIF data file. Windows memory usage of the VM is hovering at ~ 50% (3.7GB) while Windows CPU usage is ~ 3% with occasional spikes up into the 30%s. Mac Memory usage is about 32GB, with a few apps open plus Chrome with 20 tabs. Mac CPU usage is <5%. The MBP is running at about 100 degrees F and the fans are not spinning. Parallels now makes it very easy to install a full Windows 11 instance (no more having to get an unsupported Developers copy). Total time to set up Parallels, Win11 and Quicken was less than 30 minutes. I'm glad I got a 48GB machine. 36GB would probably be fine, less than that would be tight. I think any of the M3 processors would be fine but the base M3 tops out at 24GB.