My rule to turn off my light didn't work last night; how do I debug?

That's fine, but note that it should not have an impact on the outcome--a reboot does not cancel scheduled jobs. (They will be missed if the hub is off at the exact time it was scheduled to run, perhaps because it was rebooting at that moment, this is otherwise not a concern.)

Yes, most apps do not log events. If apps log something, it is generally to "Logs," and normally you have to enable an option in the app to make that happen.

As for why this particular automation isn't working, I don't know. It looks right. You could try creating a new instance and removing this one, just in case something got corrupted, or perhaps you could try a different app in case you've stumbled on an odd bug. What would be good to know is whether the app is executing the command on the device or not, or if the device is indeed having the command run but simply not responding to it. From your logs a couple posts above, I don't see anything to suggest the app is sending the command (this would be an "app:" log, not a "dev:"/device log, and only if the app has logging enabled--which it appears you do?). If it is the latter, that could indeed be a Zigbee network problem, but I'm not sure it looks like that. If it is, there are some diagnostic tools built-in, but the best approach is generally just to make sure you have a good network with enough repeaters and no "problem devices" like many brands of smart bulbs.

Follow-up: I am mostly certain that the problem is with the zigbee communication of the smart outlet, either because the signal strength is bad or because the outlet itself behaves poorly.

I plugged another Sonoff S40 Lite smart outlet (named "Living room outlet") in between my hub and the lamp I'm trying to control. It appears to have become a relay, like you might expect:

Parent child parameters
EzspGetParentChildParametersResponse [childCount=0, parentEui64=0000000000000000, parentNodeId=65535]

Child Data

Neighbor Table Entry
[Living room outlet, 6B5F], LQI:234, age:3, inCost:5, outCost:1
[Family Room lamp, 7BE8], LQI:253, age:3, inCost:3, outCost:0

Route Table Entry
status:Active, age:64, routeRecordState:0, concentratorType:None, [Family Room lamp, 7BE8] via [Living room outlet, 6B5F]
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused
status:Unused

Since that time, the lamp has been more reliable about turning on and off. Unfortunately, I'm not sure whether the problem is "real" or because of hardware glitching, but honestly I'm not sure how to distinguish between the two.

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I would say the problem is real and if i am reading that table right related to the very few devices you have for zigbee to route through. In many cases having several devices for either zwave, or zigbee can enhance routing options and will improve reliability. The moure routing devices you have scattered the better.

That stinks for folks just getting started but is unfortunately a result of using low powered devices with tiny radios and anttennas.

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Right now I only have two Zigbee devices, and they're both routers. Nothing is battery powered yet. I wanted to have a "proof of concept" before doing more.

Given the low power nature of zigbee radios, one might expect automation reliability to improve dramatically with mesh strength. I recently posted an example of how adding properly positioned repeaters was transformational in my automation setup.

Since taking the time to do this, my automations have never failed. Details here:

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I can second that. I didn’t use to think I needed repeaters, but then eventually found that some devices would disconnect so added a bunch of them, and things have improved substantially!

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