Renewal problem; macOS Server 5.5

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My domain is:

I ran this command: sudo certbot renew

It produced this output:
Saving debug log to /var/log/letsencrypt/letsencrypt.log

Processing /etc/letsencrypt/renewal/

Cert not yet due for renewal

Processing /etc/letsencrypt/renewal/

Cert is due for renewal, auto-renewing…
Plugins selected: Authenticator webroot, Installer None
Renewing an existing certificate
Performing the following challenges:
http-01 challenge for
Waiting for verification…
Cleaning up challenges
Attempting to renew cert ( from /etc/letsencrypt/renewal/ produced an unexpected error: Failed authorization procedure. (http-01): urn:acme:error:unauthorized :: The client lacks sufficient authorization :: Invalid response from "

404 Not Found

Not Found

<p". Skipping. All renewal attempts failed. The following certs could not be renewed: /etc/letsencrypt/live/ (failure)

The following certs are not due for renewal yet:
/etc/letsencrypt/live/ (skipped)
All renewal attempts failed. The following certs could not be renewed:
/etc/letsencrypt/live/ (failure)

1 renew failure(s), 0 parse failure(s)


My web server is (include version):
Server version: Apache/2.4.28 (Unix)
Server built: Oct 9 2017 19:54:20

The operating system my web server runs on is (include version):
macOS High Sierra 10.13.3

My hosting provider, if applicable, is: N/A

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

I set up certs for two domains on this server: and I am able to renew, but began failing with the above after the first round of renewals. I have tried placing a readable file in $WEBROOT/.well-known/acme-challenge and am able to view the file from a browser.

The machine where these domains are hosted crashed a few days ago—but after the first failed renewal attempt—and $WEBROOT has changed as a result. This change did not affect’s renewal. (I restored the machine from a backup from the day before I had renewed the certificate.) I have checked and verified permissions for the domain, verified the IP address, and am currently able to call up with the current certificate.

I’m at a loss for what to try next. The certificate for expires on 6 March 2018.

Please place a test file in the directory $WEBROOT/.well-known/acme-challenge/ (for which we can try to access.

I added “foo.txt” to that directory and can access it at:

Is the webroot directory in /etc/letsencrypt/renewal/ still the one you expect? (Remember that the webroot path itself should not contain the /.well-known/acme-challenge.)

Ah! That was it. Many thanks for your help. Changing the path fixed the renewal. (Why it still successfully renewed the other site, which also had a bad path, I have no idea… but am less concerned about that now.)

If you originally got the other certificate with -a apache or --apache, the CA would still allow a validation by the deprecated HTTPS-01 technology on port 443, which is unaffected by redirects. That's one possibility.

I obtained both original certs at the same time from letsencrypt.

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