When you connect the adapter before connecting the power supply it blocks the start
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Oh so it's a problem of the TTL
Yes EXACTLY, mine is a CH340 the first usb serial I snapped on Amazon a while ago, and it works great with my Tasmota/ESPHome crappy devices
And this is the reason it should be at 5 seconds for the boot time, otherwise it's almost impossible to get there on time (and still on 5 secs it's pretty tricky if I don't put the USB on time)
By the way @hecatae also reported this behavior a time ago for a similar router. He did a even more trickier stunt to fool the issue: he disconnected GND and plugged it back after powering the router. I found that just not plugin the USB was simpler. Now here you have the solution to the issue
PS: Maybe I can snap a FT232RL that I find on Amazon relatively cheap also, may it work better?