I think Kamailio has generic code in the core parser to handle multiple header values in a header. That is a generic construct in the SIP protocol (probably inherited from SMTP).
I think it is indeed a bug that the Diversion module does not support this. While waiting for someone to patch I'm pretty sure you can implement what you need with some clever code and transformations.

The discussion about Diversion and History-Info is a separate issue, not related to this bug - in my view.

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