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Does your truck not have the factory gauge? If it does you might consider a scangaugeII as the second gauge. It's nice to have both to monitor when you're doing serious hauling or extended trips in the mountain passes.
I have the factory gauge along with an Autometer in the quad pod, but I find I use the scangauge more than the others for trans temp.
I think it's a good option for you to look into. They are not very expensive considering how many items it can monitor/access for you. The trick is finding a good strategic spot to mount it so you can see it easily. It's also painfully simple to hook up,,, it plugs into your OBDII port.
If you do a search here on FTE you'll find many posts about the unit.
Rick...
These are older photos of mine installed at the bottom of the dash. I now have a second cable running up to the top of the dash where it's much better for taking quick glaces at. I usually put it back to the lower point if I'm driving at night and don't want any visible lights on my dash.
barthel .. I have the same truck that you do. HAMMER65 is correct about the location of the test port. Your truck should definately have a drain plug for the TC. Look at the bottom of your tranny in the front under where the TC is .. there should be a rubber plug there .. pry out the rubber plug .. after the plug is out put a socket on the crank pulley and turn it slowly while having someone look in the hole until you see the drain plug. As far as the stock tranny cooler goes .. I have the stock one on my truck .. I dont have a factory gauge for tranny temp in my truck either. I purchased an aftermarket tranny temp gauge from glowshift. I pull a 20 ft flat trailer with my jeep cherokee and quads on it quite often. My tranny temp never goes over like 150 or 160. Now your trailer is heavier than mine but as long as your tranny dont go over around 220 for extended periods of time you should be ok. When im not pulling my trailer my temp dont go over 140 in the summer. If the temp outside is lower than like 40 then my gauge dont move at all .. it rests on the pin and the starting temp on the gauge is 100. Hope this helps.