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I just got a used bike with a threaded headset. I noticed play so I tried tightening the adjustable race. If I tighten it enough to get rid of the play, the headset becomes totally stuck/unturnable. During the process of tightening, long before the play is gone, I start feeling the headset getting stiff.

Hopefully that was clear enough. I just want to get rid of play and still have a turnable headset, but I'm getting stiffness and play unless I really tighten it, in which case I get no play but absolute stiffness.

I'm new to bikes and haven't tried disassembling it yet, but am up for the challenge if it would help.

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I think you will find either the balls are damaged or maybe the ball races have either corroded or become deformed and are jamming up the bearing when the correct preload (tightened enough to remove play) is applied.

You must, for your own safety, disassemble and check the bearings. It is not unlikely you will find parts that need replacing so do not worry what happens: if the balls fall all over the floor, you needed to do something here anyway.

The situation you currently have is not safe. I have more than one anecdote regarding people who have ignored the state of the headset and had the steering lock up. Neither accident was serious, but it's better not to have to walk home with gorse in your hair.

To disassemble, keep the front wheel in to start. Remove the stem, then, working with the front wheel between your legs for leverage, undo the top nut, remove the washer(s) and loosen the bottom nut which also directly contacts the bearings. Remove the wheel before fully removing the rest of the heaset, then you can drop the fork out of the frame and see what you've got. Depending on the type of headset, it may be easier, faster and cheaper to have a bike shop replace the cups in the frame and start with a whole new headset. There are many that are very cheap and function very well, certainly when new.

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Along with the suggestions provided in the answer by Noise check that the upper and lower head-tube races still fit the frame.

I've seen bicycles where the head tube on the frame became oval shaped and the pressed in head-tube races no longer fit the frame. They flopped around even when the bearings were adjusted correctly.

The head-tube races are pressed into the frame head tube and should not move.

Adjust the bearings as best you can and then try to move your handlebars or fork back and forth. Pay careful attention to what is moving. If the head-tube races (also known as top and bottom cups) move then they are no longer tightly pressed into the frame. You'll need to determine if the frame is damaged or if the head-tube are damaged. Hope it's the head-tube races because they are replaceable.

I don't know of a way to fix frames with ovalized head tubes.

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Thanks @DavidD for providing the excellent picture to show the parts of a headset. I agree with @Noise that you should check the bearings and cones before reassembling the headset. Corrosion and missing bearings will be obvious, but rare for a bike that's been stored in a dry place. Older bikes may have loose bearings but most will have them in a cage to make disassembly/lubrication easier. Speaking of lubrication, if you see that it's dirty while you've got it apart, clean up the bearings and cones with some WD40 and let it dry, then squirt in some bearing grease on the bearings and cones. You'll get years more service if you do this right.

@Leo you didn't say how you were tightening the adjustable race, but I'll assume you were using a single wrench to tighten it because that tightness/immovability is the symptom of adjustable race pressing too hard on the bearings (or the damage @Noise described). You probably needed to tighten it pretty hard to keep it in place.

You need to tighten a headset with two wrenches: a narrow headset wrench that can fit on the adjustable race, and a regular crescent wrench for the locknut. The goal is to get the adjustable race tightened perfectly or just a little too tight, then holding it stationary while tightening the locknut hard against it. It's hard to keep the adjustable race completely stationary, that's why I usually make it a little too tight before I start. It may take a couple tries to get a feel for how much it loosens while tightening the Locknut.

When it's perfectly tightened you should be able to lift the front of the bike slightly and the weight of the front wheel will pull it to one side. If it's too tight it will stay in one place and you may feel some resistance when you steer. If it's too loose you will feel some play in the front fork when you apply the front brake and move the bike forward/backward.

This adjustment is pretty fun to do on your own, but a mechanic can do it in less than a minute with the right tools. Sometimes they won't even charge you. If you do choose to do it yourself, make sure you get the right size headset wrench for your bike. There are a few options.

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After disassembling the headset, I found that the upper bearings were missing entirely! No wonder there was so much play and it was impossible to adjust.

I bought a new bearing, cleaned up and lubed the whole set, and reassembled. The headset is now perfect, super smooth and with no play.

Thank you all for helping!

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