I looked up the print yesterday and spoke with the plant engineer, been there longer than i have been at Chrysler, and he agrees that the seal goes in like shown in the second image. The trans is vented. This is a seal to keep dirt and water out of the manual shaft to throttle shaft interface, nothing more. It is not a dynamic seal, it is a static seal. Dynamic seals work by pressure or rotation. The tool to install this seal looks something like a sleeve - the sleeve fits between the inner and outer lips of the seal. If you turn the seal over - the tool does not work correctly. So if you are a lazy worker - it is easier for you to use the seal sleeve than to try and install it upside down. These seals usually leak after getting hard from heat aging. Likely - many were replaced in service. Some were installed correctly when the tech paid attention and installed it like the old one was. Some were installed incorrectly when the tech didn't pay attention or didn't understand the purpose of the seal.