Keep failing Cert registration

Harpalus · November 28, 2020, 1:19am

My domain is:

I ran this command:
certbot certonly --webroot

It produced this output:
Domain: www.fileit.org
Type: unauthorized
Detail: Invalid response from
http://www.fileit.org/.well-known/acme-challenge/P5C-0MvdPFB63VYV0tRxvyuKPZk8
EPwad3G2wKAPsQ8

My web server is (include version):
IIS 8.5

The operating system my web server runs on is (include version):
Windows Server 2012R2

My hosting provider, if applicable, is:
Locally hosted

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):

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):
1.9.0

The website is running from c:\inetpub\wwwroot and the command creates the certbot folders:
C:\inetpub\wwwroot\.well-known\acme-challenge

rg305 · November 28, 2020, 1:06am

Try creating a test challenge file and see if it can be reached from the Internet.
echo success > C:\inetpub\wwwroot\.well-known\acme-challenge\test-1234

Then:
http://www.fileit.org/.well-known/acme-challenge/test-1234

Also, the IIS version is 8.5

Harpalus · November 28, 2020, 1:18am

https://www.fileit.org/.well-known/acme-challenge/test1234.txt

rg305 · November 28, 2020, 1:20am

Please remove the .txt extension from the file.
In order to best simulate an actual challenge file, it can't have any extension at all.

Harpalus · November 28, 2020, 1:20am

Thanks for your help. I guess it thinks it's a directory now

rg305 · November 28, 2020, 1:21am

I gave you the exact command; all you have to do is copy it into a cmd prompt and press ENTER.

Harpalus · November 28, 2020, 1:23am

Ok, I entered your command. No change in result

rg305 · November 28, 2020, 1:25am

Well the file is not found (404).
So the directory in use is not the one where you think it should be.
First, let's be sure the file was put there correctly:
[from a cmd prompt - please show]
dir C:\inetpub\wwwroot\.well-known\acme-challenge\

Harpalus · November 28, 2020, 1:26am

Directory of C:\inetpub\wwwroot.well-known\acme-challenge

11/27/2020 05:22 PM .
11/27/2020 05:22 PM ..
11/27/2020 05:22 PM 10 test-1234
1 File(s) 10 bytes
2 Dir(s) 982,906,478,592 bytes free

rg305 · November 28, 2020, 1:27am

Ok so the file is there but IIS is not serving it.
That can only mean that c:\inetpub\wwwroot\ is not the root of http://www.fileit.org/

Harpalus · November 28, 2020, 1:29am

When I put the txt file in there, with the extension, IIS serves up the txt file

rg305 · November 28, 2020, 1:29am

Go ahead and rename test-1234 to test-1234.txt
Let me see that in action.

Harpalus · November 28, 2020, 1:30am

OK, https://www.fileit.org/.well-known/acme-challenge/test-1234.txt

rg305 · November 28, 2020, 1:32am

Yes, both HTTP and HTTPS show the text file when it has the .txt extension.
IIS is not liking files without an extension.
You have to set a MIME TYPE for such files to "text/html"

Not sure right now where that is in Windows.
We can consult with the Google Gods for that - LOL

Harpalus · November 28, 2020, 1:32am

Ok, ,I'll try that. Thanks for your help.

rg305 · November 28, 2020, 1:33am

If you run into any other problems, you know where we are

Harpalus · November 28, 2020, 1:34am

Done, I created a new mime type based on nothing for an extension and the server is serving up the file without the extension

rg305 · November 28, 2020, 1:35am

Ok
Much better.

Now try the command again:

Harpalus · November 28, 2020, 1:36am

c:\inetpub\wwwroot>certbot certonly --webroot
Saving debug log to C:\Certbot\log\letsencrypt.log
Plugins selected: Authenticator webroot, Installer None
Please enter in your domain name(s) (comma and/or space separated) (Enter 'c'
to cancel): FileIT.org
Obtaining a new certificate
Performing the following challenges:
http-01 challenge for fileit.org
Input the webroot for fileit.org: (Enter 'c' to cancel): C:\inetpub\wwwroot
Waiting for verification...
←[31mChallenge failed for domain fileit.org←[0m
http-01 challenge for fileit.org
Cleaning up challenges
←[31mSome challenges have failed.←[0m
←[1m
IMPORTANT NOTES:
←[0m - The following errors were reported by the server:

Domain: fileit.org
Type: unauthorized
Detail: Invalid response from
http://fileit.org/.well-known/acme-challenge/MzEbMjiJdoPnKZGJKBcB2yrJtjHiGWTp
OK1BJgEGOPo
[184.71.17.182]: "\r\nNo
t
Found\r"

rg305 · November 28, 2020, 1:41am

Is that an administrative cmd prompt?

If not, open cmd prompt as admin, then try it again.
If so, then maybe the folder permissions are blocking certbot from putting the file there and we may need to run it with more verbosity -vvv to see why this fails [and add --dry-run so you don't start hitting limits].