I’m struggling with Let’s Encrypt SSL renewals failing for a domain in Virtualmin 7.20. The error says “Challenge validation failed” despite working previously. Manual renewal also fails.
Details:
Platform: Virtualmin 7.20 Pro, Webmin 2.105 (checked via System Information).
OS: Ubuntu 22.04 LTS, fully updated.
Server: VPS, 4GB RAM, Apache 2.4.52, single domain.
Setup: Let’s Encrypt SSL enabled via Virtualmin > Server Configuration > SSL Certificate.
Logs: /var/log/letsencrypt/letsencrypt.log shows “HTTP 404” for .well-known/acme-challenge.
Steps Taken:
Requested new certificate via Virtualmin > SSL Certificate > Let’s Encrypt tab; got “Challenge validation failed.”
Checked .well-known/acme-challenge directory permissions (755); created test file, accessible via browser.
Ran virtualmin check-config; no issues reported.
Disabled/re-enabled Let’s Encrypt in Virtualmin; same error.
Verified DNS (A record correct, no CAA issues).
Searched forum; found a 2024 Let’s Encrypt thread but no fix for 404 errors.
Expected: SSL certificate renews automatically or manually via Virtualmin. Actual: Renewal fails with “Challenge condition failed” due to timeout.
Has anyone hit this Let’s Encrypt 404 issue on Virtualmin 7.20? Is it a config, firewall, or Let’s Encrypt bug? Any debug tips or workarounds? Thanks for any help!
I don’t think the behavior you described is possible. If you can reach files in .well-known you can’t be getting a 404 if you’re requesting a certificate for the same domain you’ve tested in your browser.
I suspect this is a ChatGPT generated post to get karma to begin posting spam.
But, on the off-chance you genuinely have this question I’m not banning you, yet. You’ll need to look at the web server log to see what’s happening with the request, as what you describe sounds literally impossible unless you went out of your way to break only Let’s Encrypt requests.
especially when negative reference to some other thread implying not resolved in 2024 (a long time ago and probably as out of date) - I cannot believe someone goes to the slight expense of upgrading to Pro version and then seems to ignore updating!
Thanks for the replies and for not banning me! The Let’s Encrypt 404 issue is fixed now. I checked the web server logs as Joe suggested and found incorrect permissions on the .well-known directory. After fixing them (set to 755), the certificate request worked. I’ve also upgraded to Virtualmin 7.20 Pro, as my 7.10 version was outdated. Sorry for the confusion—definitely not a bot, just missed the 2024 thread’s resolution. Appreciate the guidance!