Opening up oil hole on chainsaw bar.

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I've had better luck grinding them out with a dremel than drilling them with a drill.
Some of the oregon bars I have use a tear dropped shaped oil hole and oil very well, I kinda copy it when opening up the oil hole. You can see the shape of the oil hole in the pic below.
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Angle the hole, it helps prevent sawdust/debris from catching and filling the hole up.
I've done that with a Dremel, drilled larger round holes, even cut a small slot in one with a dremel cut off wheel. I haven't had a real problem with clogging just telling the op that it could happen.
 
I've done that with a Dremel, drilled larger round holes, even cut a small slot in one with a dremel cut off wheel. I haven't had a real problem with clogging just telling the op that it could happen.
When the Stihl bars first started to come out with the reduced port hole for the bar oil I used a dremel to open them up, too little oil was getting to the chain through those little restricted holes, I could get a good angle on the diamond burr to allow debris to slide on by and not catch to fill the hole in prematurely. That was about the time the soft metal Husqvarna bars were on the market, my cutting buddy was running a Husky 365 and going through a new bar every month, my bar lasted for the entire 3 month cut and I still run it on a 066.
 
When the Stihl bars first started to come out with the reduced port hole for the bar oil I used a dremel to open them up, too little oil was getting to the chain through those little restricted holes, I could get a good angle on the diamond burr to allow debris to slide on by and not catch to fill the hole in prematurely. That was about the time the soft metal Husqvarna bars were on the market, my cutting buddy was running a Husky 365 and going through a new bar every month, my bar lasted for the entire 3 month cut and I still run it on a 066.

Yes, the older bars had much bigger holes and flowed more oil.
 
Yes, the older bars had much bigger holes and flowed more oil.
Stihl downsized the holes and then painted the bars with a good deal too much paint filling the holes in even more, I had new bars that had holes a 1/16 tip cleaner could not pass through due to paint clogging the hole, these were replaceable sprocket pro bars, some say it was a E PA mandated change to use less oil, all the bar I bought got the holes enlarged..
 
I have heard that good quality masonary bits do a reasonable job.
A masonry bit will cut through hardened steel, but it still takes quite a bit of pressure, and they still don't last long. I've enlarged the holes on some of my Oregon bars. I have to sharpen the bit after every one, but I've had no issues drilling them with a decent cobalt bit. I do like the idea of an angled hole, and I've used my dremel to try and add some angle to the hole after its drilled, but I can't say whether or not the effort has made much difference because I've never really had issues with the hole getting clogged.

One thing I HAVE noticed with my Oregon bars is that the hole is rarely centered (vertically) with the corresponding slot on my Stihl saws. The hole tends to ride a little high. That's what actually prompted me to reach for my dremel to begin with.
 

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