Help! Can I upgrade my OS? in Troubleshooting Posted June 21, 2018 I am a long time but small time user of Vectorworks. I decided I could not justify upgrading beyond 2014 because of cost and I was comfortable with the capabilities of the software. Now, I am finding that issues outside of Vectorworks 2014 are pushing me to upgrade my Mac OS from 10.8.5 Mouuntain Lion. Can anyone tell me the latest Mac OS version that will run Vectorworks 2014. Thanks in Advance.