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Hi all. I have a 1999 3500 dually diesel. The prior owner broke off starter bolts, and bugged up the repair. He drilled the bolts out, but didn't do it right. I have since drilled out, did t-serts, and recounted the starter. It worked great for a couple months, and then the starter started to skip. I pulled it off, recounted again, and worked for 2 starts. Skipping again.
Recounted again and now won't catch at all, skipping and grinding.

I have made sure to use the rear brace, OEM knurled bolts, ensured to torque correctly, etc. I'm losing my mind trying to figure out what I can do. Any thoughts on why the starter keeps shifting and skipping would be helpful.

I've never had issues like this before. I have looked, and the flex plate teeth are showing a little wear, but no broken or missing teeth. Do you all think that with all the issues that the teeth may be worn roo much, and a new flexplate is next on the list? How do I stableize the starter more so it stops shifting and kicking out? Is there any aftermarket stabilizer I can add, or any other thoughts?
 

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Hi all. I have a 1999 3500 dually diesel. The prior owner broke off starter bolts, and bugged up the repair. He drilled the bolts out, but didn't do it right. I have since drilled out, did t-serts, and recounted the starter. It worked great for a couple months, and then the starter started to skip. I pulled it off, recounted again, and worked for 2 starts. Skipping again.
Recounted again and now won't catch at all, skipping and grinding.

I have made sure to use the rear brace, OEM knurled bolts, ensured to torque correctly, etc. I'm losing my mind trying to figure out what I can do. Any thoughts on why the starter keeps shifting and skipping would be helpful.

I've never had issues like this before. I have looked, and the flex plate teeth are showing a little wear, but no broken or missing teeth. Do you all think that with all the issues that the teeth may be worn roo much, and a new flexplate is next on the list? How do I stableize the starter more so it stops shifting and kicking out? Is there any aftermarket stabilizer I can add, or any other thoughts?
Welcome to DieselPlace

Sadly, this is a common occurrence with the 6.5L Diesel when it gets neglected.
Check the repaired bolt holes to see if they are stretched out(warbled). You may have to re-drill and install Helicoil inserts
Make sure you are only using the correct OEM starter support bracket and that it is fastened tight.
Make sure to properly torque the starter bolts
 
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You need NEW OEM Knurled bolt everytime it is giving problem.
 

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About 15 years ago my original factory starter, started grinding and wouldn't start the truck, I was new to Diesel at the time and replaced the starter and everything worked fine for about a year. Then the new starter started doing the same thing, turns out the teeth on the fly wheel were worn down and a few teeth missing. Put a new flywheel and starter in haven't had a problem since.

Not a very hard process, took a few hours basic tools, a couple jacks and some wood.
Pulled starter
Removed torque converter cover and bolts between flywheel and torque converter.
Disconnected both driveshafts at the axles and let them lay on the ground, leaving them connected to the transfer case, so there wasn't an oil mess.
Disconnect transmission cooler lines at the transmission.
Removed transmission tail mount.
Support engine at oil pan with a jack.
Position another jack under the transmission in a way that it will be balanced and center lined with the truck so the transmission can roll back on the jack. You only need a couple of inches.
Remove bell housing bolts.
Roll transmission back on jack until you can reach the crank shaft flywheel bolts.
While you're there is a great time to replace rear main seal (cheap and easy), gently pop the old one out, put the new one in position, I used the old seal to gently tap the new one in along the perimeter.
 
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