I think I am getting more and more used to listening to American speakers but sometimes I find it hard to understand British speakers, especially when they talk really fast. It's mainly the accent and pronunciation of native speakers that makes it difficult or easy to understand.
Also, unknown words or phrases trips me up sometimes. When I hear something I don't understand, I try to guess what the speaker said and then I miss what he/she says next because I am too distracted trying to figure out the word/phrase I didn't understand.
The easiest to understand is someone I am talking to face to face, mainly because there is no distortion. Next is listening to someone speak, maybe in a movie or a TV show or podcast, with headphones on. Third in the list is watching movies, TV shows without headphones. The TV or computer speakers tend to distort the sound a bit and sometimes it can get difficult to understand. The most difficult to understand is on the phone, especially when the transmission isn't very clear.