I've had this thing, a Craftsman model C909-228200 hanging around for decades, I recall trying it out when it was new and not being particularly impressed. I tried it again today, and although, yes it brings a completely dull drill bit back somewhat, it's sure not like a new bit. There is probably a bit of a learning curve to the process, after all I worked with a guy who just sharpened them by eye, using a bench grinder. I wish I could find the manual, a google search doesn't even find the tool!
Doesn't look like the bit was turned as it was sharpened. Try rotating it while it grinds. Not scientific I know...
The instructions actually warn against rotating the bit. More experimentation os required...
I always wondered about those because the two types I use (Drill Dr. and a Craftsman grinding-wheel fixture) require a good bit of indexing and fixturing before the drill bit goes anywhere near the grinding wheel.
Harbor Freight sells a knockoff of this machine and the users guide is available on their website. It has a small theory and troubleshooting section that might be worth a read. You might also want to check the grinding wheel on your machine. The Drill Dr. wheels can be flipped upside down to expose a fresh grinding surface but I don't know if that's the case with yours.
I think the manual can be downloaded here:
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