Weird issue with Alexa voice commands after Home Assistant VM starts

When my host PC first boots up; and, my Home Assistant VM automatically/immediately starts up
afterward… everything works perfectly. However, if I add an extra 30-second delay (or more) before automatically starting HA, everything works EXCEPT I can’t control any of my HA devices through Alexa. If I ask Alexa to turn on the light, she will respond with:

xxxx isn’t responding, please check its network connection and power supply

Oddly, I don’t see any errors or warnings in the HA log. If I didn’t use voice commands, I wouldn’t even know there is an issue.

Does anyone have any idea what’s causing this weird behavior? I would like to have the flexibility to start my HA VM anytime I want (instead of immediately after my PC reboots). I have no idea what to even try to narrow down the source of the issue.