Alan,
Since you said it was a QSO party and you had multiple qso's with the same station could it be you worked him on a County Line? If you log a qso and all info is the same, including date and time LOTW will reject as a dupe. You have to change the time of one of the qso's by at least a minute to make LOTW happy.
I don't believe LOTW looks at the County name so that could be the problem. I have worked 3 and 4 county lines in the past and have to fudge the time of the qso to make it go through.
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73
Fred
K2DFC
