Not sure how I would make the connections at outlet #2 and switch to control outlet #2??
Any help appreciated.
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...then you will have to replace the cable between outlet #2 and the switch with some /3 cable. In that case, you would use the red wire between the switch and the outlet, and instead connect the white wire to the neutral side of outlet #2, and leave the white wire unconnected in the switch box (or connected to you smart switch).