The biggest trouble I ran into while pumping breastmilk was not having any free hands.  This was troublesome for two reasons.  One - this prevented me from being able to feed Melody AND pump at the same time.  This was an issue only at night because I did that feeding alone, and I was ready to go back to sleep!  Prior to my pumping bra, it was taking me 15 minutes to prep for feeding and pumping, 30 minutes to feed, and 30 minutes to pump.  Then I had to clean up, change Melody, put her to bed, then go to bed myself. That was over 90 minutes!  The second reason was that my hands would get super tired from holding the breast shields in place while pumping. I sometimes would slide my bra over the bottom of the shields, but it would still leak.