this may be my problem... from the docs: "Note: If you did not set a custom connection string, stopping and restarting a session will reset it's connection string."
Do you have any content around how you manage your holesail connections?
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You can setup a custom connection string to avoid that, holesail --live <port> --connector "any random stuff that is secure"
Future version will have a --preserve flag to keep the connection string same when the server restarts.