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When The World Held Its Breath: First Lightning

I really do doubt that the Soviets would have been able to make it a surprise attack in 1941. Just too much in the way of German preparation and expectation of the Soviets to strike.

Yeah, given how much the attack would have relied on surprise it doesn't exactly inspire confidence in the chances of success. The Germans reacted with alarm to what appeared to be new Red Army "concentations" that appeared in March although this was only ever a partial mobilisation and defensive in nature, if it wasn't the Germans wouldn't have simply ignored it.

The one thing I would say is that German intelligence appears to have become more brazen as Barbarossa neared; a report on June 13th (a Friday) determined that there seemed to be some Red Army reinforcement of the frontiers going on but this was dismissed as irrelevant, too late in the game. If the Soviets had began their build-up in May and played a very good deception game then I think there's at least a chance they could have caught the Germans off-guard.
 
The one thing I would say is that German intelligence appears to have become more brazen as Barbarossa neared; a report on June 13th (a Friday) determined that there seemed to be some Red Army reinforcement of the frontiers going on but this was dismissed as irrelevant, too late in the game. If the Soviets had began their build-up in May and played a very good deception game then I think there's at least a chance they could have caught the Germans off-guard.

In a sort of 'rolling all 6s' way?
 
What one really needs is for something to cause a distraction at the crucial time. May 1941 involved the Bismark's enterprise, for example. Have Bismark and PE evade Norfolk, Suffolk, and POW after the Hood, and start to cause issues in the Atlantic while the British seek it in the expanse of the Atlantic, and it's possible German eyes will be at least flickering westwards as well as eastwards. The Army will still be looking towards the Soviets, but those higher up the chain might be less focused.

The Iron Guard coup in Romania being a bit more successful might also be an idea - diverting attention and even resources from the Wehrmacht in having to put them down a very short time before Barbarossa
 
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