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I have seen it done, but I try to avoid silicone on tranny gaskets. Too easy to clog things up.
Before you put the pan on, you should hold it against the edge of a bench, and take a hammer and flatten the metal around the bolt holes. Then when installing the pan, tighten the bolts with a ratchet and socket, with your hand over the head of the ratchet. Go around a couple of times like this, and that should be it. Holding you hand over the head of the ratchet will limit the torque you can apply. If you tighten it too much, you just end up bending the pan around the bolt holes again.
After a week of driving you can get under there and check the bolts again, incase the gasket shrinks.
That was the general method I used. Sugged it up pretty good but it looks like it's starting to seep a bit. At this point I worry about overtightening and splitting the gasket - an experience i've unfortunatley been through before.