Questor: I've had problems like that on humid days or days when it was so hot that the air was thick. But, years ago I developed a technique to assure that all the powder dropped into the case.
Now, I have both a Dillon 550B as well as an older Rock Crusher. I have an old Lyman powder measure that is probably older than I am and the technique I use is as follows - I double tap everything in the powder dispensing process. That means that when I drop the handle on the powder measure to fill the interal cavity with powder, I let the handle drop twice (or tap it twice) to make certain the cavity is both filled and 'tamped'. Then, when I dispense the powder to the case, I double tap the handle against the body of the measure to make certain everything drops out. That seems to work for me even when it is really hot and humid.
I have found that once I get the powder measure regulated to as close to the charge I want as it will throw, I will be only .1 - .2 grains weight off on any charge I randomly measure, which is pretty ok for just 'fun fodder'. For hunting or carry stuff, I measure out each charge. HTH. Mikey.