Let's Encrypt Failing DVSNI Challenge

Question

I'm trying to configure Let's Encrypt certificates on a server that is publically accessible. Originally, the server was hiding behind a router, but I have since forwarded ports 80 and 443.

The certificate seems to have completed a majority of the install process, but fails with the message: Failed to connect to host for DVSNI challenge.

Full stack trace:

Updating letsencrypt and virtual environment dependencies......
    Requesting root privileges to run with virtualenv: sudo /bin/letsencrypt certonly --standalone -d example.net -d www.example.net
    Failed authorization procedure. example.net (tls-sni-01): urn:acme:error:connection :: The server could not connect to the client to verify the domain :: Failed to connect to host for DVSNI challenge

IMPORTANT NOTES:
 - The following 'urn:acme:error:connection' errors were reported by
   the server:

   Domains: example.net
   Error: The server could not connect to the client to verify the
   domain

Any support would be greatly appreciated!

I looked around elsewhere for a solution and haven't had much luck. Most other similar situations were resolved by forwarding port 443, but I am certain this port is already forwarded and open, albeit no service is currently running on it.

It shouldn't make a difference, but I'm trying to configure this certificate for use with Node JS on a Raspberry Pi.

Answer 1

I finally figured out what was going on. I discovered that the --manual flag steps through the authentication process interactively.

Each phase in the process will display a prompt similar to the following:

Make sure your web server displays the following content at
http://www.example.net/.well-known/acme-challenge/twJCKQm9SbPEapgHpyU5TdAR1ErRaiCyxEB5zhhw0w8 before continuing:

twJCKQm9SbPEapgHpyU5TdAR1ErRaiCyxEB5zhhw0w8.t7J7DDTbktMGCCu2KREoIHv1zwkvwGfJTAkJrnELb4U

If you don't have HTTP server configured, you can run the following
command on the target server (as root):

mkdir -p /tmp/letsencrypt/public_html/.well-known/acme-challenge
cd /tmp/letsencrypt/public_html
printf "%s" twJCKQm9SbPEapgHpyU5TdAR1ErRaiCyxEB5zhhw0w8.t7J7DDTbktMGCCu2KREoIHv1zwkvwGfJTAkJrnELb4U > .well-known/acme-challenge/twJCKQm9SbPEapgHpyU5TdAR1ErRaiCyxEB5zhhw0w8
# run only once per server:
$(command -v python2 || command -v python2.7 || command -v python2.6) -c \
"import BaseHTTPServer, SimpleHTTPServer; \
s = BaseHTTPServer.HTTPServer(('', 80), SimpleHTTPServer.SimpleHTTPRequestHandler); \
s.serve_forever()"

Press ENTER to continue

As I discovered, the process, despite being run as root itself, did not have the privileges to start the challenge server itself. Surely, this might be a bug in the API.

Running the script in the prompt directly produces the following error:

$(command -v python2 || command -v python2.7 || command -v python2.6) -c \
> "import BaseHTTPServer, SimpleHTTPServer; \
> s = BaseHTTPServer.HTTPServer(('', 80), SimpleHTTPServer.SimpleHTTPRequestHandler); \
> s.serve_forever()"

Traceback (most recent call last):
  File "<string>", line 1, in <module>
  File "/usr/lib/python2.7/SocketServer.py", line 419, in __init__
    self.server_bind()
  File "/usr/lib/python2.7/BaseHTTPServer.py", line 108, in server_bind
    SocketServer.TCPServer.server_bind(self)
  File "/usr/lib/python2.7/SocketServer.py", line 430, in server_bind
    self.socket.bind(self.server_address)
  File "/usr/lib/python2.7/socket.py", line 224, in meth
    return getattr(self._sock,name)(*args)
socket.error: [Errno 13] Permission denied

But running it as root (as the prompt itself stated) started the server correctly and could be monitored as the external server queried it to complete the challenge:

sudo $(command -v python2 || command -v python2.7 || command -v python2.6) -c "import BaseHTTPServer, SimpleHTTPServer; \
s = BaseHTTPServer.HTTPServer(('', 80), SimpleHTTPServer.SimpleHTTPRequestHandler); \
s.serve_forever()"

66.133.109.36 - - [08/Jan/2016 21:25:10] "GET /.well-known/acme-challenge/SZ88SorxBGXBtSZCTn4FX2g7u5XjnPFOOV3f5S5DuXB HTTP/1.1" 200 -
66.133.109.36 - - [08/Jan/2016 21:25:10] "GET /.well-known/acme-challenge/twJCKQm9SbPEapgHpyU5TdAR1ErRaiCyxEB5zhhw0w8 HTTP/1.1" 200 -

This error took awhile to diagnose as many things could have prevented the challenges from failing and the servers spawned were failing silently in the background.