Hi Tim,
As Rachael stated there is a ulp you can use to create tapered (fillet/teardrop) entries into vias and pads.
I would not, however, recommend the teardrop script that ships with Eagle. The included ulp is very outdated, is not undoable, and does not create curved traces. There is an updated version that can teardrop the board and also undo it later down the line. t's still a good idea to back up before hand, but this way you won't have to go all the way back, or worse yet, ripup all of the segments in order to get back to a non teardropped board. (I recently had to clean up a board from a contractor who ran the included script many times. I had to ripup thousands of overlapping traces because of it)
Download the attached zip and add to your ulp path (or place it in a good place and add the directory to the ulp directories setting).
TEARDROP.ulp is used to create the teardrops, and CLEANWIRE.ulp is used to remove them.

I still don't understand why Eagle had not updated and included the new version. It was uploaded all the way back in 2013.
Best Regards,
Cameron
Eagle Library Resources
Kudos are much appreciated if the information I have shared is helpful to you and/or others.
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