Middleware is sometimes not found when defined in the traefik service's docker labels

Does it make sense?

Hi, yes, that absolutely makes sense.
From this, I understand the following:

healthcheck enabled AND failing -> its configuration is ignored -> middleware truly not defined -> 404
healthcheck enabled AND healthy -> configuration NOT ignored -> middleware truly defined -> A-OK

With that in mind, I see how this really is a different problem that is indeed unrelated to the original observation. Well, mostly unrelated: The case "healthcheck enabled AND healthy", while not 404ing, still prints the missing middleware errors. This, I believe, has the same root cause as the original issue?