The bomb was probably triggered by GPS coordinates rather than time. The cargo was scheduled to be delivered a day earlier. If it had been a time bomb, it would have blown up while the guy was taking the nap.
I think Ukrainian special forces have been shutting down rail lines in Crimea for a couple of months. They blow some track and the trains have to stop for a few hours until the track crews get in there and replace the rail. They have probably been doing that for a while to get the Russians used to harassment attacks like that so they didn't think anything else was up.
The Ukrainians probably had a dry run or two to see where on the bridge a train would stop if they blew up tracks fairly close to the exit of the bridge. When they knew the truck was moving towards the bridge, their team blew up the tracks to stop the next train crossing to Crimea. That's the only reason I can think of why the Russians would stop a train on a bridge. A bridge is a choke point and it makes no sense to park a train on a bridge unless the tracks just past the bridge are out.
Some more on Russian logistics situation now that the bridge is disabled. There is also some information about how the rail bridge was built. I think the damaged section is toast. It might be able to handle a few lightly loaded trains, but it's going to start crumbling with regular rail traffic.
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I was thinking about the quality of the new commander in theater. He's known for being a ruthless fighter, but he's never commanded a large operation.
It brings to mind a critique of Irwin Rommel I read several years ago. Rommel was a brilliant division commander, but he fell down on the job in North Africa when he commanded the Afrika Korps. The job of a division commander and a corps commander are different. A division commander is focused on battlefield objectives while a corps commander's job is mostly to ensure each unit has all the supply it needs to get the job. They also have an eagle's view of the battle situation, but their day to day duty is to make sure supply is moving to the right places.
Sergey Surovikin was commander of the Eastern Military District in peacetime. His only experience in high level combat command was in Syria where Russia had 4000 troops committed at their peak. Supplying 4000 troops is very different from supplying 50-150K. Also it appears people hated working under Surovikin. He's notable for being a jerk commander in an army renown for jerk commanders.
Any commander competent with supply would be scrambling right now to ensure forces in the south were getting supply. It appears nothing is being done, Surovikin is just waiting for the Kerch bridge to re-open. Within a week or so the troops in the south are going to hit a supply shortage and even with a maximum effort they may not be able to move in enough supplies to keep the army going.