I change the fluid and filter in my automatic transmission every 30,000 miles. The pan gasket is rubber. The recommendation is apply grease to the pan under the gasket. This is supposed to hold the gasket in place. Usually it does, although the process always makes me nervous about the gasket moving and causing a leak. It finally happened. The gasket slipped out of place somehow just about as you see it here. I lost several quarts of oil on the garage floor.
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Step 1: A Resolution of the Problem
Cut some card stock about 1 x 1 1/2 inches. Make as many as you have transmission pan bolts.
Step 2: Make a Sandwich With Two Pieces of Wood
Use two pieces of scrap wood to make a sandwich with the card stock.
Step 3: Clamp the Sandwich
You will be drilling a hole through the card stock. That means drilling through the wood, too. The wood sandwich gives you the best chance for a clean hole in the card stock.
Step 4: Drill
Select a bit a little smaller than the transmission pan bolts. Drill through the top piece of wood and the card stock. You will probably drill into some of the bottom piece of wood, too.
Step 5: Slice With a Scissors
Slice from the edge of the card stock to the hole with a scissors.
Step 6: Use the Card Stock to Retain the Bolts
Insert the bolts through the pan holes and the gasket holes. Slip a piece of card stock over the bolts to hold them in place.
If I were to do it again, I would push the bolts only half of their length through the card stock retainers. When I was positioning the pan, some of the bolts pushed out as I threaded their neighbor into the transmission. Still, enough of the gasket was securely in its proper place that I had no problems from a bolt or two dropping out.
Step 7: Start Bolting the Pan to the Transmission
The card stock keeps the bolts in place, which keeps the gasket in place. When starting the bolts into the transmission case threads, try to keep the card stock from rotating inside the transmission. When all of the bolts are started, pull the card stock pieces off of the bolts and throw them into a waste container. Double check to be sure the gasket is still in place. Work your way around the bolts and tighten each two or three times in a rotation to take up any compression of the gasket.