1. The problem I’m having:
Summary - Trying to start Caddy in Windows 11, but it shows a “timeout during connect” error and then hangs on “trying to solve challenge.”
Background info - I was successfully using Caddy as a reverse proxy to host my family home videos Emby server for years. When I tried upgrading the NVMe drive, I had issues and ended up reinstalling Windows, which undid a lot of the Caddy config. It didn’t erase the CaddyFile, dynamic DNS (provided by No-ip), or any of my router’s network settings. I downloaded Caddy again from the website, cleared out the cache folders, and added the firewall rules back. But it’s still failing with the errors described above and I can’t figure out what’s wrong.
Happy to provide more info, I’m just stumped and would appreciate some help looking. I’m not a networking pro, apologies if I’m missing basic things (and don’t be afraid to suggest them). Thank you!
2. Error messages and/or full log output:
No logs actually get created in the “logs” folder, but this is the error message in Command Prompt. I cut a lot out because I was way over character limit. Please let me know if you need a more specific line and I’ll get it:
2025/01/11 18:16:23.275 ERROR challenge failed {"identifier": "dingdonghonk.gotdns.ch", "challenge_type": "http-01", "problem": {"type": "urn:ietf:params:acme:error:connection", "title": "", "detail": "71.181.79.164: Fetching http://dingdonghonk.gotdns.ch/.well-known/acme-challenge/ehI7K6HmgcEoWzw12B4b_wLz6RRG1jF5qQXeTQwo6JI: Timeout during connect (likely firewall problem)", "instance": "", "subproblems": null}}
github.com/mholt/acmez/v3.(*Client).pollAuthorization
github.com/mholt/acmez/v3@v3.0.0/client.go:557
github.com/mholt/acmez/v3.(*Client).solveChallenges
github.com/mholt/acmez/v3@v3.0.0/client.go:378
github.com/mholt/acmez/v3.(*Client).ObtainCertificate
github.com/mholt/acmez/v3@v3.0.0/client.go:136
github.com/caddyserver/certmagic.(*ACMEIssuer).doIssue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:477
github.com/caddyserver/certmagic.(*ACMEIssuer).Issue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:371
github.com/caddyserver/caddy/v2/modules/caddytls.(*ACMEIssuer).Issue
github.com/caddyserver/caddy/v2@v2.9.1/modules/caddytls/acmeissuer.go:249
github.com/caddyserver/certmagic.(*Config).obtainCert.func2
github.com/caddyserver/certmagic@v0.21.6/config.go:626
github.com/caddyserver/certmagic.doWithRetry
github.com/caddyserver/certmagic@v0.21.6/async.go:104
github.com/caddyserver/certmagic.(*Config).obtainCert
github.com/caddyserver/certmagic@v0.21.6/config.go:700
github.com/caddyserver/certmagic.(*Config).ObtainCertAsync
github.com/caddyserver/certmagic@v0.21.6/config.go:505
github.com/caddyserver/certmagic.(*Config).manageOne.func1
github.com/caddyserver/certmagic@v0.21.6/config.go:415
github.com/caddyserver/certmagic.(*jobManager).worker
github.com/caddyserver/certmagic@v0.21.6/async.go:73
2025/01/11 18:16:23.275 ERROR validating authorization {"identifier": "dingdonghonk.gotdns.ch", "problem": {"type": "urn:ietf:params:acme:error:connection", "title": "", "detail": "71.181.79.164: Fetching http://dingdonghonk.gotdns.ch/.well-known/acme-challenge/ehI7K6HmgcEoWzw12B4b_wLz6RRG1jF5qQXeTQwo6JI: Timeout during connect (likely firewall problem)", "instance": "", "subproblems": null}, "order": "https://acme-v02.api.letsencrypt.org/acme/order/2163030015/343319742995", "attempt": 1, "max_attempts": 3}
github.com/mholt/acmez/v3.(*Client).ObtainCertificate
github.com/mholt/acmez/v3@v3.0.0/client.go:152
github.com/caddyserver/certmagic.(*ACMEIssuer).doIssue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:477
github.com/caddyserver/certmagic.(*ACMEIssuer).Issue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:371
github.com/caddyserver/caddy/v2/modules/caddytls.(*ACMEIssuer).Issue
github.com/caddyserver/caddy/v2@v2.9.1/modules/caddytls/acmeissuer.go:249
github.com/caddyserver/certmagic.(*Config).obtainCert.func2
github.com/caddyserver/certmagic@v0.21.6/config.go:626
github.com/caddyserver/certmagic.doWithRetry
github.com/caddyserver/certmagic@v0.21.6/async.go:104
github.com/caddyserver/certmagic.(*Config).obtainCert
github.com/caddyserver/certmagic@v0.21.6/config.go:700
github.com/caddyserver/certmagic.(*Config).ObtainCertAsync
github.com/caddyserver/certmagic@v0.21.6/config.go:505
github.com/caddyserver/certmagic.(*Config).manageOne.func1
github.com/caddyserver/certmagic@v0.21.6/config.go:415
github.com/caddyserver/certmagic.(*jobManager).worker
github.com/caddyserver/certmagic@v0.21.6/async.go:73
2025/01/11 18:16:23.298 DEBUG http request {"method": "POST", "url": "https://acme-v02.api.letsencrypt.org/acme/authz/2163030015/459162479545", "headers": {"Content-Type":["application/jose+json"],"User-Agent":["Caddy/2.9.1 CertMagic acmez (windows; amd64)"]}, "response_headers": {"Boulder-Requester":["2163030015"],"Cache-Control":["public, max-age=0, no-cache"],"Content-Length":["1090"],"Content-Type":["application/json"],"Date":["Sat, 11 Jan 2025 18:16:24 GMT"],"Link":["<https://acme-v02.api.letsencrypt.org/directory>;rel=\"index\""],"Replay-Nonce":["2NJzUBzXd0_Iv2aMLwJa9VFz8YpOTDrk0nhdxitI51mdq6uKwI4"],"Server":["nginx"],"Strict-Transport-Security":["max-age=604800"],"X-Frame-Options":["DENY"]}, "status_code": 200}
2025/01/11 18:16:23.300 ERROR challenge failed {"identifier": "dingdonghonk.ddns.net", "challenge_type": "http-01", "problem": {"type": "urn:ietf:params:acme:error:connection", "title": "", "detail": "71.181.79.164: Fetching http://dingdonghonk.ddns.net/.well-known/acme-challenge/8NeCg2jdH47V7MfFLjbMPTyt7Zlr1kv3yJGN77u1Io0: Timeout during connect (likely firewall problem)", "instance": "", "subproblems": null}}
github.com/mholt/acmez/v3.(*Client).pollAuthorization
github.com/mholt/acmez/v3@v3.0.0/client.go:557
github.com/mholt/acmez/v3.(*Client).solveChallenges
github.com/mholt/acmez/v3@v3.0.0/client.go:378
github.com/mholt/acmez/v3.(*Client).ObtainCertificate
github.com/mholt/acmez/v3@v3.0.0/client.go:136
github.com/caddyserver/certmagic.(*ACMEIssuer).doIssue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:477
github.com/caddyserver/certmagic.(*ACMEIssuer).Issue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:371
github.com/caddyserver/caddy/v2/modules/caddytls.(*ACMEIssuer).Issue
github.com/caddyserver/caddy/v2@v2.9.1/modules/caddytls/acmeissuer.go:249
github.com/caddyserver/certmagic.(*Config).obtainCert.func2
github.com/caddyserver/certmagic@v0.21.6/config.go:626
github.com/caddyserver/certmagic.doWithRetry
github.com/caddyserver/certmagic@v0.21.6/async.go:104
github.com/caddyserver/certmagic.(*Config).obtainCert
github.com/caddyserver/certmagic@v0.21.6/config.go:700
github.com/caddyserver/certmagic.(*Config).ObtainCertAsync
github.com/caddyserver/certmagic@v0.21.6/config.go:505
github.com/caddyserver/certmagic.(*Config).manageOne.func1
github.com/caddyserver/certmagic@v0.21.6/config.go:415
github.com/caddyserver/certmagic.(*jobManager).worker
github.com/caddyserver/certmagic@v0.21.6/async.go:73
2025/01/11 18:16:23.301 ERROR validating authorization {"identifier": "dingdonghonk.ddns.net", "problem": {"type": "urn:ietf:params:acme:error:connection", "title": "", "detail": "71.181.79.164: Fetching http://dingdonghonk.ddns.net/.well-known/acme-challenge/8NeCg2jdH47V7MfFLjbMPTyt7Zlr1kv3yJGN77u1Io0: Timeout during connect (likely firewall problem)", "instance": "", "subproblems": null}, "order": "https://acme-v02.api.letsencrypt.org/acme/order/2163030015/343319743075", "attempt": 1, "max_attempts": 3}
github.com/mholt/acmez/v3.(*Client).ObtainCertificate
github.com/mholt/acmez/v3@v3.0.0/client.go:152
github.com/caddyserver/certmagic.(*ACMEIssuer).doIssue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:477
github.com/caddyserver/certmagic.(*ACMEIssuer).Issue
github.com/caddyserver/certmagic@v0.21.6/acmeissuer.go:371
github.com/caddyserver/caddy/v2/modules/caddytls.(*ACMEIssuer).Issue
github.com/caddyserver/caddy/v2@v2.9.1/modules/caddytls/acmeissuer.go:249
github.com/caddyserver/certmagic.(*Config).obtainCert.func2
github.com/caddyserver/certmagic@v0.21.6/config.go:626
github.com/caddyserver/certmagic.doWithRetry
github.com/caddyserver/certmagic@v0.21.6/async.go:104
github.com/caddyserver/certmagic.(*Config).obtainCert
github.com/caddyserver/certmagic@v0.21.6/config.go:700
github.com/caddyserver/certmagic.(*Config).ObtainCertAsync
github.com/caddyserver/certmagic@v0.21.6/config.go:505
github.com/caddyserver/certmagic.(*Config).manageOne.func1
github.com/caddyserver/certmagic@v0.21.6/config.go:415
github.com/caddyserver/certmagic.(*jobManager).worker
github.com/caddyserver/certmagic@v0.21.6/async.go:73
3. Caddy version:
v2.9.1 h1:OEYiZ7DbCzAWVb6TNEkjRcSCRGHVoZsJinoDR/n9oaY=
4. How I installed and ran Caddy:
I downloaded the .exe with no addons from caddyserver.com yesterday.
I’m using the same CaddyFile that had been working before.
a. System environment:
Windows 11 Home (OS Build 26100.2605)
b. Command:
caddy start
c. Service/unit/compose file:
d. My complete Caddy config:
{
debug
email soulsaturn@yahoo.com
}
# import *.CaddyFile
### Photoprism ###
dingdonghonk.gotdns.ch {
reverse_proxy http://127.0.0.1:2342
basicauth * {
R****** [****************************80-char-password-hash*****************************]
}
#basicauth /library/index/files/Mom* {
# M****** [****************************80-char-password-hash*****************************]
#}
#
}
### Emby ###
dingdonghonk.ddns.net {
reverse_proxy http://127.0.0.1:8096
}
#basicauth * {
# R****** [****************************80-char-password-hash*****************************]
#}