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Establish a list of common problems with a Gitpod installation and ways of checking automatically. The preflights will likely be a good part of that.
A discussion with Barry @ Replicated as to his recommendations/what other Replicated user do may be a good initial step
Suggestions
Most common (current) issue is Check EKS guide for registry validity #8855. Suggest writing a collector to look for relevant log in pod and then create analyzer to suggest possible resolutions. Typically, these have x509 in the errors
Had someone recently who had problems due to only setting up DNS/certs for $DOMAIN - add DNS check for $DOMAIN, *.$DOMAIN and *.ws.$DOMAIN