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Thanks for all the advice. I think I now know why the flashing is somewhat raised in this section. We recently had our house painted. The painter layed his ladder against this exact section of gutter. I think the pressure on the gutter pushed up the flashing. I'll take a crack at repaining this...

I noticed the other day when we had a big rain, run-off from the roof was going over the gutter. This weekend I took a look at that section of the gutter and noticed the shingles are kind of bending upward - almost like a ramp for the water to fly over the gutter. I also noticed the flashing was...