@Aravot 

Can you send a snapshot of how the Control with a Switch is configured?

@Carl 

Please see screengrab.

@Aravot 

Thank you and to be clear these two smart actions are marked as active?  I ask because I have had customers who have setup multiple smart actions and assumed all were automaically active, but only 3 can be active.  

Just want to rule it out because of that. 

@Carl , if by active you mean smart action enabled, yes.

What do you mean by 3 can be active, do you mean if we have 15 smart actions only 3 can be active, if so this is not good, I am just starting with Kasa and already have about 7 to 8 actions in mind, please confirm as I don't want to spend $300 to $400 chaning hardware to find out it will not work.

@Aravot 

Yes at this time, and since the feature was added Smart Actions is limited to 3 active at one time.  As you have seen several devices can be linked to a single smart action.  For example with the "Control with Smart Switch"  you can have several "action" devices when the a smart switch is triggered.  

With the Garage Test; The Outside Up and Outside Down, are these seperate switches or status of the same switch?  

@Carl ,

Outside Up and Outside Down are separate switches (HS210), bottom of the stairs & top of the stairs and garage test is HS200 switch, the names are for testing before I went out and purchased more, but it seems I will be looking at other solution since 3 active smart actions is not enough unless you have plan to expand to 20+ active actions.

@Aravot 

Okay so then the two HS210s are controlling the same lights?  My understanding is that only one HS210 is active when using both on the same lights.  This is because only one switch has constant power, whichever is the switch on the line side.  The other switch should not be on network and acts more or less as a dummy switch.  If both are one and the HS210 you have set to the smart action is the one that is acting as the "dummy" switch that could be the case.  Can you confrim if they are the same circuit?