what is the cassette, what are the shifters and what is the deraileur?

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36 kona qualifiers 2006-'23 - 3 Kona Podiums - 4 OA IM AG wins - 5 IM AG wins - 18 70.3 AG wins
I ka nana no a 'ike -- by observing, one learns | Kulia i ka nu'u -- strive for excellence
Garmin Glycogen Use App | Garmin Fat Use App

Answer Mark's questions as well as:

How old is the chain? Is the chain new but the cassette old or vice versa? Is the chain new and the jockey wheels old or vice versa?

Stuff like this can be a bit of a mystery until you get ALL the info! :)

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Steve Fleck @stevefleck | Blog

The jockey pulley should not be greased, a drop or two of chain lube should suffice.

If the problem is with only the bottom pulley it sounds as though the pulleys are worn.

They will wear to the point they do not have anything to "grab" the chain

Order they appropriate jockey pulleys for your deraileur.

cassette is shimano 9spd, shifters and deraileur are 105s

The chain is probably close to needing replacement but I had my bike in about a month ago and the guys at the shop thought it was ok at the time. Both the cassette and and the jockey wheels are older than the chain. I should probably also mention that the skipping started this morning: I shifted into the big ring and my chain jumped the big ring, I put the chain back on and the skipping started then.

Sounds like a possible stiff / damaged link onthe train

nothing's jumping out.

Got a local expert mechanic you could take it too? I can't recall hearing the chain jumping the second pulley.

Best of luck... please let us know what you find out.

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36 kona qualifiers 2006-'23 - 3 Kona Podiums - 4 OA IM AG wins - 5 IM AG wins - 18 70.3 AG wins
I ka nana no a 'ike -- by observing, one learns | Kulia i ka nu'u -- strive for excellence
Garmin Glycogen Use App | Garmin Fat Use App

Yup, this is the problem. I actually went to measure the chain to see if it needed replacing and I saw the culprit link which was bent, sure enough, when I turned the crank with my hand that link would cause the chain to skip on the jockey wheel. BTW, the chain looks like it needs replacing anyway.

Thanks all.

-Dan