Yesterday I was trying to create new device in my ESPhome network. Like I always do, create new device in ESPHome, choose appropriate device (in my case D1mini, which is ESP 8266) and try to upload .bin to the device via web.esphome.io. Now I have new ESPHome so I must fiddle around to get my .bin file but I made it. Go to the web.esphome, try to connect my device in pop-up window but after I click connect it says Failed to execute 'open' on 'SerialPort': Failed to open serial port. After a few tries I give up and reach for another device, ESP32-12. Make a new code in ESPhome, connect device in web.esphome pop-up and upload my .bin file. After that I reboot device but ESPHome says it's offline. I have move back to web.esphome to erase and put in "prepare for first use". I have manage to do that and I was able to see all my SSID in reach but wasnt able to connect to them (I have same SSID's for years and build numerous ESPhome devices and connect to them).
So I switch to ESP32 S2 mini board which I use few month ago. Make a new code and .bin file, press boot + reset on ESP32 S2, connect to device in pop-up window, load .bin and when I try to upload it says - Failed to initialize. I have tried to put this board in "prepare for first use" but there is also message that Failed to initialize.
So now I have three different devices of which two of them can't upload anything and one is able to upload but WiFi can't connect 
No code, no compile logs, scant run log entries, no idea. Is your wiring correct?
Like it was before. I use one micro USB cable and one USB C cable, every one in his USB port. In device manager was COM port every time I connect any of all three board
Have you tried pressing the boot button when starting install like it says when it fails?
UPDATE: partially solved 
Use same cables and same devices on HA server and flash all devices. And they all connect to HA like it is supposed to.
For now, that will be the way to add new devices in my ESPHome
Are you uploading from the same device your bin file is compiled and stored on using the web installer?
Yes I can also confirm the tried and true method of compile and upload to update from the HomeAssistant server still works.