Ron Hardin wrote:
My gutter is coming down at one end - three consecutive nails have worked
themselves out over 40 years, I guess.

I climbed up there to hammer them back in, but they show almost no resistance
to hammering - you could just push them back in the holes by hand.

Obviously they will not stay.

Are there various diameter gutter nails, and I just have to go up one size?

Wrap them in something like friction tape and them hammer them back?

Glue of some sort to encourage them to stay put?

What's the drill for this?

Ron,

There are gutter screws:

http://www.gutterworks.com/gutterscrews.html

Never tried but I had heard of them.

Frank