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I would like to start a small discussion about overwatch tactics. I will start the discussion with a question if you charge one unit with 2 separate units is the unit being charge allowed to overwatch the second unit?

sure. but only the second unit. Charges dealt with one at a time, so you get one overwatch per defender.

Not. Quite:

Charges are dealt in order. Meaning you charge with the first unit, and the defender can choose wether to over watch or not.

If the defender chooses not to over watch, and the first unit makes it in to base contact, the defender can not over watch the second unit as it is now locked in combat.

If the defender chose not to over watch the first unit and they failed thier charge range, it can then over watch the second unit if it chooses.

So yes, the order you charge into battle can matter a lot.

There is a small wording hole but Steel-W0lf is right. Wording hole is in the BRB not his example.

My group before everyone changed duty stations always believed you declared all charges and the overwatch was just picked from available targets...which is totally wrong. Course, 11 against 1 are pretty difficult to convince, so i just went with it since it hurt them more than me as an ork player anyway.
Im not sure how they all got the same impression from it, but to me the lack of a paragraph stating the unit being charged chooses which unit to fire at if there are multiple units sets it in stone to me that they are not simo. It is rather weirdly worded how you declare charges, least to me it is, but like i said no paragraph talking about multiple targets tells me the option will never arise no matter what.

Not only this, but at the end of the charge sub phase,after the rules tell the defender to fire over watch. I believe the rules then tell you to go back and start the process over for other units charging.

But now when you get to the "over watch" part of the sub phase, the unit being charged is already in base 2 base contact and can't fire.