MBP 13" doesn't always recognize external monitor
 

for some reason my new 13" (late 2011 model) doesn't want to recognize my external monitor when I plug it in. Sometimes it instantly recognizes it, sometimes I have to completely restart (even after trying to "detect displays").

Any thoughts, i've tried multiple mini-dp to VGA connectors (we have about 5 in the office, all official apple)

Have you done a PRAM or SMC reset? Is your software all up to date? What happens if you go to system prefs -> displays and click the Detect Displays button?