Surely the trains would be specially constructed to perform this procedure reliably, and it would be entirely automated. This doesn't seem like it should be a hard problem if the system is engineered from the beginning to handle it.
It's quite hard to control exact speed of a train (at such high speed), even without any atmospheric effects and with ideal adhesion conditions that never change. I can imagine it in like 50 kph, when the worst thing to expect is a derailment, some deformation zones blasted, and few non-fatal wounds. But every problem rises at least exponentially with the speed.
But if that's the case then it still seems like the original problem of running two trains right alongside each other, on different tracks, for several minutes while people cross from one to another, and with the consequence of any error being passengers getting sliced in half, would be even harder.
Maybe the coupling mechanism could be something long that extends from the back of the train. The cars can connect can over a wide range of distance, kind of like a runway. The connection is made with a friction clutch that can be applied gradually and eased off if something goes wrong. The coupling also has a drive to pull the cars together after they are securely linked.
They could always slow down to make the link too.
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ICE train in Germany got derailed by few sheep two years ago…