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1.
A number of small fails performed in quick succession, creating a chain of fails.
Matthew slipped on the wet deck at the front of his house, which caused him to fall down the stairs onto the pavement, landing in a pile of dog faeces that his pet left there. Chainfail!
av rad rad robotankin' 27. april 2009
 
2.
As Defined By Paul L. and Ryan S. (Definitely not Coop)
Based On Actual Events

The act of failing that effects multiple persons in a chain effect, whereas the fail is directed at one person but is applicable to surrounding bystanders

Ryan: "Hey guys, do you wanna go to the bar tonight? *pause* oh! thats right you guys aren't 21 wow! chain fail!!"

Group: "wow you're an ass"
av failsquad 12. april 2008