Hi Sage,
  First let me say that probably no one out there knows less about this than me. I just keep hammerin' at it because I love a challenge, am eager to learn and am a glutton for punishment.

As far as the arcs go, even after removing the extra entities one chain would not pocket so I converted the arcs and it pocketed fine. Dont know why and cannot explain it. Others have posted that saving the file as R12, (which it was) does this autimatically.

I can only tell you HOW I made it work. As is true with MOST of my solutions, I have virtually no knowledge of WHY.

"Quirky"........"Flakey"......could probably come up with a few more...but if we can find a way to muddle through, you still cant beat the price.

And I like your Lead-in trick....that will go in my toolbox as well, thanks

Regards,
RC

Overloaded:
 I think what you did requires some more explaination. I took the file you sent and I see now that your conversion fom arcs to curves (or whatever) has made separate chains, each with about 29 separate entities, for the very small curves in the corners of the end shapes. So how did you select the whole shape as an outline to create a pocket?
 Also: forgetting the corner ones, I picked one of the rectangles to pocket. When I try to do the pocket I get the same results, i.e the software inserts an offset (as seen in the list) instead of a pocket. I tried the zoom trick - no help. Did you send an old  file with the extra lines in it?

Sage

Each shape is a chain....many entities in each chain. I just select the chain and then pocket.
I may have gotten the files mixed up, did a lot of changing. Will send you another in a min.
RC

BTW
I don't see where you pulled that convert menu from I'm using Acad 2002.

I'll wait for the file. In the one you sent there are may chains making the corner shape. It needs to be all one chain to be ale to pick it as an outline and to pocket it.

Sage

Try this one Sage. It works OK here.
RC

Thanks. See my note above. I guess we're both on line at the same time.

Sage

Yeah...you gotta watch those edits.

I'm using AutoSketch..from Autodesk.

I select the curve, then right click in the box surrounding it and get the menu.

In the last dxf, I set them all to polylines and it is OK here. That also eliminates all of the dinky entities in the curve.

See pic.

RC

Ok I tried it and initially I still had multiple chains for the end shape. I changed my connection tolerance to .001 and then I had one chain for the whole shape. So far so good. This is another one to try to remember. I always forget.
 But still when I pocket it I get an offset instead of a pocket. See attached screen grabs.

Man this is tedious.

Sage

OK Sage, Try this one here.
Let me know...then I gotta go to work..(and take it easy fir a while )
RC

Ok, so I decided to step back a bit. I created a very simple rectangle with Acad 2002 rectangle feature. I saved it as a version R12 dxf. It's attached below. When I pocket it with a 1/16 cutter you can see that it does pocket but it seems to give up early on the pocket - at least from what I can perceive from the screen shot. It should continue the spiral right out to the edge.
 Yet another issue to fugure out I guess.

Sage