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I asked around internally, and one of our engineers had a good thought. Are you running each venv install and pulumi up in separate jobs? If you are, you might be losing the local download cache between each job, which can make it take that long. A quick SO post that might help if that's the case: https://stackoverflow.com/questions/62420695/how-to-cache-pip-packages-within-azure-pipelines

Thanks Laura. Yes we are running them as separate jobs. We are now working to convert to a combination of Docker + cache@2 to attempt to speed things up.