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When you log a multiple-county QSO with N1MM configured for a State QSO Party contest, N1MM logs one QSO per county, but these multiple QSOs are not conveyed to DXKeeper via the N1MM-DXKeeper Gateway for reasons that are presently unknown.
Until the responsible defect is identified and corrected, please do not use the N1MM-DXKeeper Gateway when employing N1MM to participate in a State QSO Party. Instead, at the end of the contest, direct N1MM to export an ADIF file containing the State QSO Party QSOs, and then direct DXKeeper to import this file.
+ AA6YQ comments below
I can't tell you for sure whether N1MM+ emits one <contactinfo> message or four, but from the N1MM+ manual:
"Separate QSOs will appear in your log, one for each county."
If four separate QSOs are logged, it might seem reasonable to expect four <contactinfo> messages in rapid succession, but without setting up a test I cannot be sure about that.
+ The 3 possibilities are
1. N1MM+ only sent 2 <contactinfo> messages (defect in N1MM+)
2. N1MM+ sent 4 <contactinfo> messages, but only 2 of those messages were actually delivered the N1MM_DXKeeper gateway because the UDP protocol that N1MM+ employs to deliver <contactinfo> messages is a "best efforts" protocol, with no guarantee of delivery.
3. N1MM+ sent 4 <contactinfo> messages, and all 4 of those messages were actually delivered to the the N1MM_DXKeeper gateway, but a defect in gateway or DXKeeper resulted only two QSOs being logged.
+ I would be helpful if someone familiar with N1MM+, the N1MM-DXKeeper Gateway, and state QSO parties could attempt to replicate this scenario so that we can determine what's going on, and correct whatever defects we find.