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My 2000 Caravan's "hey buddy you left your key in the ignition" warning chime doesn't sound when I merely open the door with the key in the slot; I have to wiggle the key. The lock cylinder itself turns smoothly and the other functions seem OK.

Would this be the lock cylinder, the switch - or something that I might have missed?
 

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. . . . My 2000 Caravan's "hey buddy you left your key in the ignition" warning chime doesn't sound when I merely open the door with the key in the slot; I have to wiggle the key. The lock cylinder itself turns smoothly and the other functions seem OK. . . . .
I have noticed the same phenomenon with my 2000 Grand Voyager. Open the driver side door and you do not get the tell tale chime of key-in-lock reminder. If you push inward on the key the chime will sound. This has happened because of overall wear in the key lock, intermediate actuator for steering column lock, and actual ignition switch. Attached image of a typical Chrysler ignition switch arrangement is shown. Yours will not have the resistors but the functionality of how the key-in-lock sensor works is valid.

Ignition Key Lock Actuator Switch.gif

I suppose you could remove the ignition switch and bend the contacts such that they are a little closer and eliminate this intermittent action. Only you can decide if this effort is worthwhile to you.
 

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I had this issue with a couple of later lock units I got out of a junk yard. The ignition lock is an eight cut system, odd number slides on one side even on the other, the slides when lined up properly allow the locking bar to retract. I believe it was on here I posted pictures of the assembly and how it comes apart. If it is only one key that does that, a new key may fix the problem. If not Dorman sells two different ignition locks, one is just a basic lock cylinder with 2 keys and full instructions on rekeying it to your keys, the other is a more complex (and expensive) automatic rekeying cylinder.
 

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I did the slide replacements on my 99 GC and didn't find it all that complex. You just have to make sure you replace them one at a time, clean the spring and the hole, and then put the same letter slide back in the same slot. If not, your key will not work. I noticed this after the second slide I removed. I pulled first one out and noticed that it was NOT the same letter. I put the same letter one in the slot and after I got them all done, reinserted the switch and is worked like a charm. AND the key in ignition feature worked again too!
 

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. . .
I suppose you could remove the ignition switch and bend the contacts such that they are a little closer and eliminate this intermittent action. Only you can decide if this effort is worthwhile to you. . . . .
A "poor boy" fix would be to add a drop of a 2 part epoxy such as J B Weld to the tip of the key. This effectively extends key tip length slightly and cause the key-in-lock sense switch to be activated. See image.

Ignition Key Blank.gif
 

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I agree. The tip of the key pushes a plunger to close the key-in switch. Aftermarket or worn keys might not push far enough.
The older switches could be serviced by bending a contact tang slightly. The newer switches may be more tamper-proof and not really accessible.
The other half of the equation is the drivers door ajar switch staying open (the switch, not the door). If the drivers door always looks closed, the key-in warning won't work. It may be a separate switch than the courtesy lamp switch.
 

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. . . The other half of the equation is the drivers door ajar switch staying open (the switch, not the door). If the drivers door always looks closed, the key-in warning won't work. It may be a separate switch than the courtesy lamp switch. . . .
On my 2000 Grand Voyager there is only one switch integrated into the latch assembly for door ajar and interior courtesy lamp control. When the door is not properly closed and latched, it sends an appropriate signal to the BCM (body control module) and the instrument cluster. The instrument cluster illuminates the DOOR AJAR icon and the BCM activates the chime and interior lamps. There is no separate switch for the courtesy lamp.

Check the ignition key and make sure it is straight. It is possible that someone could have used the key as a pry and the shank could be bent slightly. A slight misalignment could cause the key shank to not push properly on the actuator, through the steering column lock, and into the ignition key switch and close the key-in-lock reminder contacts.
 
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