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Rails 7.0 to 8.1 in 8 pull requests, dual booting through every version in between, and the client's verdict was that nothing ever broke. go.fastruby.io/3pc #RailsUpgrade

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The part of dual booting I'd copy: keep config.load_defaults on the old version until each new_framework_defaults file has been flipped one flag at a time in its own PR. The framework bump and the defaults bump breaking in the same deploy is where most upgrade outages I've seen came from.