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Use crashdetect.dll and check your server log for warning or error. And we would appreciate if you post here your onplayerpickuppickup or checkpoint or something related to that object when you pick it up.
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-d 3 in pawn.cfg for more debug info with crashdetect plugin
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create pawn.cfg in server\pawno and inside type -d 3
then run samp-server.exe again and post the errors
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This has happend me before, it was a very long time ago, but I think it has to do with the pickup(s).
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Crashdetect works only for server crashes and run time errors. It won't work for client crashes like your case.
However, crashdetect found a run time error 4 and that should be fixed. It should say more details (amx backtrace) about it and those can help us to get it fixed.