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I have the 2014 Overland and can not find the oil filter. I like to service my own vehicles. Also, like to know another Oil besides the Pennzoil that is recommended.
 

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Just performed my first oil change on my 2014 Overland Diesel. The oil filter is found under the engine cover on the drivers side (cover snaps onto four ball studs on top of engine - gently pull up to unclip). (The oil filter is removed from the top of the engine, and does not look like a typical steel can filter - it looks more like a miniature shop vac filter). The filter is expensive at the dealer (list $55), and includes one small o-ring installed and one large o-ring loose). The oil filter is inside a plastic cylindrical housing with a 1+1/16" (27mm) hex drive molded into the filter cover. Home Depot sells the 1+1/16" socket separately for $3 (1/2" drive). I detached the large airbox tube over the oil filter (flat blade screwdriver or external hex to undo hose clamps at each end), and used a ratchet and extension to unthread the filter cover. Note that the filter is clipped into the cover, so it would be better to hold the filter cover over the lower housing to drain off more of the oil before removing from engine bay. You will need to firmly pull the filter to unclip it from the filter cover (the better drained the filter cover is the less oil will splash when it is unclipped from the filter cover). You will need a turkey baster to suck the remaining oil from the lower oil filter housing. The drain plug is 13mm drive. It takes a long time to fully drain the oil. I have heard that you should not restart until 30 minutes after oil fill, which I obeyed. (I'm curious how that would work at a quick oil change place). Once everything is back together you will need to reset the oil life gauge (push ignition button twice with no feet on either pedal (to ignition on - without engine start), then within 10 seconds slowly and fully depress and release gas pedal three times, then push ignition button again with no pedal activation, to off position (repeat if it does not work). I found I needed to depress and release four times (instead of three) for it to work. I used the recommended Pennzoil Ultra Euro L 5W30 Synthetic Low Ash oil. I have under 6,000 miles and was at 1% oil life by the gauge. I see a Technical Service Bulletin on WK2Jeeps.com to correct the oil life gauge from showing too low oil life (I didn't mind doing my first oil change early).
 

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Had the same issue with oil life being shorter than necessary. The dealer did the software upgrade per TSB and now get close to 10,000 miles.
 
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