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The 1st time, it tries to cast the observation context to a MongoHandlerContext (and succeeds), but the 2nd time, which is executed in the context of the commit of the transaction, this cast fails with an exception
java.lang.ClassCastException: class org.springframework.http.server.observation.ServerRequestObservationContext cannot be cast to class org.springframework.data.mongodb.observability.MongoHandlerContext
This seems to be on purpose, at least according to this comment, which is what causes the MongoHandlerContext to never be created.
Should there be a bit of defensive code to avoid force casting the context into a MongoHandlerContext?