+ AA6YQ comments below
Recently I've had this problem. For instance a new DXCC contact on 30M with Cypress was not indicated in the download summary.
+ Neither the "Sync LoTW QSOs" operation nor the "Sync LoTW QSLs" operation would report a new contact. Only new confirmations that would advance your progress towards your indicated DXCC objectives.
Where would you suggest where I start to look?
+ In the "DXCC Bands & Modes" panel on DXKeeper's Configuration window's Awards tab, is the 30m box checked?
+ Filter the Log Page Display to contain all of your logged QSOs with Cypress by typing 5B into the Filter panel at the bottom of DXKeeper's Main window's "Log QSOs" tab, and then click the Filter panel's DXCC button. How many of those logged QSOs were made on 30m? Of those 30m QSOs, are any of them confirmed via QSL card or LoTW?