Likely firewall problem + Windows Server 2019

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My domain is: www.iotplayground.tk

I ran this command: Validation from Certify the Web

It produced this output:
2020-05-22 10:34:42.800 -03:00 [INF] Fetching http://www.iotplayground.tk/.well-known/acme-challenge/9OAiIITNtUoPbbg_rtvmFAWrhb7--ZYRn8ptS7WsJ0I: Timeout during connect (likely firewall problem)
2020-05-22 10:34:45.236 -03:00 [INF] Validation of the required challenges did not complete successfully. Fetching http://www.iotplayground.tk/.well-known/acme-challenge/9OAiIITNtUoPbbg_rtvmFAWrhb7--ZYRn8ptS7WsJ0I: Timeout during connect (likely firewall problem)
2020-05-22 10:34:45.237 -03:00 [INF] Validation of the required challenges did not complete successfully. Fetching http://www.iotplayground.tk/.well-known/acme-challenge/9OAiIITNtUoPbbg_rtvmFAWrhb7--ZYRn8ptS7WsJ0I: Timeout during connect (likely firewall problem)
2020-05-22 10:34:45.238 -03:00 [INF] Performing Post-Request (Deployment) Tasks…
2020-05-22 10:34:45.238 -03:00 [INF] Validation of the required challenges did not complete successfully. Fetching http://www.iotplayground.tk/.well-known/acme-challenge/9OAiIITNtUoPbbg_rtvmFAWrhb7--ZYRn8ptS7WsJ0I: Timeout during connect (likely firewall problem)

My web server is (include version): IIS

The operating system my web server runs on is (include version): Windows Server 2019

My hosting provider, if applicable, is: CloudFlare

I can login to a root shell on my machine (yes or no, or I don’t know):
I don’t know

I’m using a control panel to manage my site (no, or provide the name and version of the control panel):
CloudFlare dashboard

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you’re using Certbot): Certify the Web

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HTTP (TCP port 80) needs to reach your server.

It doesn’t, it times out from LE (as seen in your logs).

It times out from where I am:

curl -Iki http://www.iotplayground.tk/
curl: (7) Failed to connect to www.iotplayground.tk port 80: Connection timed out

And it also times out via the LetDebug test:
https://letsdebug.net/www.iotplayground.tk/147311

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