I have this old awl that I need to put the finest point possible on for a project but I've never sharpened anything pointed before. I have a whetstone set and a file for knives and garden tools but the stone is way too fine grit and the file seems to just flatten the thing further. 

Advice, gentlemen?

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you need to turn it as you sharpen. I find with rounded/pointed tools, sometimes it's easier to move the stone/file in a rocking motion (held in right hand, on top of the tool tip, held in left), rather than trying the way you would with a knife. 

Hey man. I found this for you.  I hope it helps.

http://www.howtohistory.com/2010/05/how-to-sharpen-a-leather-awl/

What sort of awl is it?  There are a number of different types, going from the very plain scratch awl (more or less conical  point), to chisel-point brad awl (for starting nails), to fancier leatherworking tools, and so on.

For the conical ones, e.g. the scratch awl or marking awl, some leatherworking awls, you can keep the stone fixed, or use a belt-sander or grinding wheel, but the important thing is to orient the long axis of the awl at 90-degrees to your sharpening motion, and to turn the awl as you sharpen.  If you do this with even pressure, you won't create facets.  Another technique, I believe already suggested, is to fix the awl in a vise (or your hand, though I prefer using a vise), and move the stone in a curved motion.  I've always had better luck with fixing the stone and turning the awl.

For a chisel point brad awl, you want the flattened facets - it should look like a double-bevel chisel.  The purpose of that awl is to sit down precisely, and then be twisted in the wood to make an indentation in which to start brads.  You sharpen that just like a carving chisel, with the bevels more or less symmetric and meeting in the middle.

Leather tools can be more individual, and I'm afraid I don't have a lot of experience with any of them other than the simple, conical pointed awl.

I use a fine wet stone to deburr my awls then I use a rouge machine to polish them sharp.  This will help it make smoother, cleaners holes too. 

Owls need sharpening?
Their beaks already look pretty sharp to me.

Thanks everyone! I finally got it done, though there is a learning curve. Dino, it's a straight awl for starting nails. In the end I just held it against a file and turned, then switched to a whetstone for finishing touches.

Have you ever looked into using a bradawl to start nails?  If you use it right, it prevents splitting. 

Here's a link: http://en.wikipedia.org/wiki/Bradawl

Looks like a great idea though I'm not going to be using this particular one for nails.

I was taught to turn the nail around and give it a light tap to put a dent in the timber then turn the nail around the right way then nail home , should stop the wood from splitting .
What are you useing your awl for ?

That sort of makes it behave like a brad awl.  The idea is to cut the wood fibers with the awl (or with the facets at the point of the nail, as you've described), so you're not just wedging them apart with the nail (which causes splitting). 

Punching pilot holes in vellum. I'm sewing together a handwritten parchment scroll.

Very cool!

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