Currently, when “update all” is selected in ESPHome, it reflashes everything. On my system with 39 devices rarely updates all successfully. Attempting to update this week, only 4 devices were updated. If I run “update all” again. It will reflash those 4 devices again even though it knows they are up to date.
ESPHome (and all other addons) are not a part of the WTH. Feel free to make a post there: ESPHome - Home Assistant Community