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I'm on my 4th big Indian (not counting the '47 Chief I wish I still owned) and all of them have had the same frustrating design flaw...black plastic oil dipstick that is impossible to read in most lighting conditions. My solution for the '14 Vintage and the '16 Chieftan was aftermarket dipsticks with stainless steel rods. Effective but expensive. I bought the '18 Vintage and decided that I would just live with the stock dipstick. Then I got the Challenger in December and discovered that the Mother Ship had not paid any attention to my continuing problem. I considered manufacturing my own stainless dipstick since the Chally is not the same threads nor length as the 111's. No aftermarket stick to be found. The other issue with the oil level check for the Chally is the new procedure of "Start the engine when cold, run for 30 seconds, shut down. Hold bike upright and level, remove dipstick, wipe it off, reinstall by screwing it fully into the crankcase, remove dipstick and read oil level. You may need a flashlight and a helper to accomplish this safely. Then I started thinking "old tech". Remember seeing dipsticks with a tiny hole at the minimum oil level and another one at max oil level? When you pulled that dipstick, the bottom hole was full of oil and the max hole was dry unless you were under or over filled. You already know the answer ... using a #44 drill bit (.0860 inch) or 2mm bit, I drilled holes thru the center of the plastic wand of the Chally dipstick. Screwed it in, took it out. Problem solved. The oil viscosity fills the hole and doesn't drip out while you hold it up to the available light and look for light thru the holes. Bottom hole full, upper hole clear. Then I wondered whether oil level could be checked cold without running the scavenger pump for 30 seconds and with the bike on the sidestand? The answer is of course "yes", but with a caveat. Each bike may be a little different depending on the weight of your oil (15w60 for the Chally unless you are experimenting) and don't forget the break-in oil is 40 weight. The oil weight and temperature at shutdown will also affect the time it takes for the oil to drain from the scavenger sump to the main sump. Just to be safe, let the engine cool overnight and check the oil level on the sidestand before you start or move the bike. My level using this method showed my oil at 30 mm above the full mark. I tried this 3 days in a row and the levels were consistent. If you want to try this, note the level above the full mark for your bike and recheck a few times on different days.
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Caution: If you drill your dipstick, I recommend holes no larger than 2mm. You don't want to weaken the wand and have it break off in the crankcase.
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Awesome! I have one of those steel ones, and I still might do this mod. Great idea!
 

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BAD, you're all ready to start your new venture......BAD....Bad Ass Dipsticks!! Great suggestion. That's why I love this forum....but not more than riding my Challenger!!!
 

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Great idea and easy, inexpensive fix for an issue that impacts all of us! Plus, to accomplish this, I don't have to order anything from Amazon, Indian or eBay...(y)
 
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