Are rolling updates possible with managed VMs?

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We began using managed VMs over the sandboxed environment and experienced that even though multiple instances of the application were running, the platform didn't roll them out in a rolling fashion so we hit 503s on a regular base while deploying.

Are we missing something in terms of health checks or the like?

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PrecariousJimi On

Managed VMs (Flex environment) does not yet support full rolling updates. The recommended way would be to always deploy into a new incremental version, ensure that new version is serving fine and then start ramping up production traffic to it using traffic splitting feature.