When you say "out the back", do you mean that the wires are pushed into the back of the outlet? If so...this is a 'back stabbed' outlet....and a good chance a source of your problems.
And on the second outlet, the wires are attached to the side screw as well as back stabbed?
It sounds like you should be changing all of your outlets to pigtails....
This is not the best picture...but should give you an idea of how it should look........and no, your wires should not be this long....most of mine are long because I still have drywall to do and I find it's easier for things to stick out like that so I can drywall around them.