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I'm trying to somehow generate some SSL certificates using Certify The Web / IIS but every time (and with every certificate authority) I just get a timeout:

Timeout during connect (likely firewall problem)

I have absolutely no clue what could cause this! curling the domain (http://my.domain.ch/.well-known/acme-challenge/yodT8bocZCWbfCvwcUemr90z94wvbD063ytCcPWg1Vo) works perfectly. Tried it from several machines internal and external. Even with my mobile etc. What could cause the authorities to not be able to call my webservice?

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  • How 'external' were those external machines actually? Same ISP or different ISP? Is it a locally hosted server or is it a dedicated/VPS server? Commented Dec 17, 2024 at 10:07
  • Could it be the outbound connection from your webserver host which is timing out? What happens when you try running 'curl' to an external address? Commented Dec 17, 2024 at 12:22

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Thank you so much for your support guys! A geo blocking turned out to be the issue! I just tried it from different German ISPs! Using an Azure server located it the US I could reproduce the issue.

I asked the provider to allow (in my case)

Let's Encrypt acme-v02.api.letsencrypt.org acme-staging-v02.api.letsencrypt.org Buypass Go SSL IPv4: 185.62.160.0/22 IPv6: 2a03:520::/29

and everything is working as expected.

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