Can’t update and connect to acme-v02.api.letsencrypt.org / no ping / no tracert

While we wait for an answer could you show result of this curl. Only need the beginning lines through "Server Certificate" display (maybe 25 lines) if it works. This is google CA's ACME endpoint and also uses an IP starting with 172 although not the exact same range as Let's Encrypt. If it fails too might be narrow the problem.

curl -v4 https://dv.acme-v02.api.pki.goog/directory

Are you willing to try a different Certificate Authority? The BuyPass CA is easy to request certs. I think you just add this to your win-acme command

--baseuri https://api.buypass.com/acme/directory

Having two IPv4 network attached, one private other with public IP space and default routes with equal weights does not look stable configuration to me.

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You probably need to use the register command before actually trying a different CA. But, it looks like maybe a comms problem reaching BuyPass too.

I see the curl to the google CA ACME API worked but uses a much different IP than it does from my region (this is not unusual). The good news is you can reach the google API so you should be able to get a cert from them (needs EAB). To test connection to their "172" range IP you could try this. It is just to gather info to better isolate the comms problem

curl --connect-to ::172.253.115.139:443 https://dv.acme-v02.api.pki.goog/directory

And, to just test connection to buypass API

curl https://api.buypass.com/acme/directory

If this curl works you should also be able to get a cert from them. They do not require EAB config so is usually easy to register the ACME account. If it fails show output of this

nslookup api.buypass.com

Unfortunately all attempts (curl and nslookup) have failed.
Look screenshoot, please:
https://cdn.imgchest. com/files/pyvdcl9axdy.jpg
It says "Could not connect to server" and "DNS request timeout"

Do you know the reason why your system is having two network connections?
One is 45.133.235.126 the other one is 192.168.137.122.
I would try to disable one interface and make a trial.

I don't understand why you have two default gateways:
image

The problem was solved by disabling the second network interface, which apparently blocked DNS requests. Thanks to everyone who helped.