Error generating certificate with Certbot: ACME challenge returning 404

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1

My domain is:
macucotechapi.com

I ran this command:
certbot certonly --manual -d macucotechapi.com

It produced this output:
Certbot failed to authenticate some domains (authenticator: manual).
Domain: macucotechapi.com
Type: unauthorized
Detail: 177.55.104.46: Invalid response from http://macucotechapi.com/.well-known/acme-challenge/X9bAl4Qmjc5vepvFOQIe9Io0iY6R-4obddk4yQ_mwSI: 404

My web server is (include version):
IIS 10

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

My hosting provider, if applicable, is:
Self-hosted (on-premise server)

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

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

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):
Certbot 2.7.3

2

Welcome @VitorHugoFra

The EFF discontinued support for Certbot in Feb of this year. See their announcement here: Certbot Discontinuing Windows Beta Support in 2024

That announcement includes suggested alternatives. The easiest to use is Certify The Web. It has a nice gui and integrates very well with IIS. It is the first one listed in the EFF announcement. Also below

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3

Here is what I see using curl

Simulating the ACME HTTP-01 challenge request,
gets a HTTP Response of HTTP/1.1 307 Temporary Redirect which isn't quite correct.
However we get a redirect from HTTP to HTTPS, which is fine.

$ curl -Ii http://macucotechapi.com/.well-known/acme-challenge/sometestfile
HTTP/1.1 307 Temporary Redirect
Transfer-Encoding: chunked
Location: https://macucotechapi.com/.well-known/acme-challenge/sometestfile
Server: Microsoft-IIS/10.0
Date: Sat, 07 Dec 2024 16:29:01 GMT

Following the redirect to HTTPS I see this which is about what is expected.

$ curl -k -Ii https://macucotechapi.com/.well-known/acme-challenge/sometestfile
HTTP/2 404
server: Microsoft-IIS/10.0
date: Sat, 07 Dec 2024 16:29:42 GMT
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4

image
image1293×648 55.4 KB

recebi esse erro

5

I would say the screen shot you are showing there is an error about what 404 means
image

1 Like
6

Yes, you got one cert but have error on the other. It says it could not use the built-in HTTP Challenge handler. That is probably why the authorization failed.

Questions like these are best posted to the Certify forum.

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