Could not connect to smtp.gmail.com: No route to host

[Andreas E.]

When starting Geary for the first time, it prompts to add account details. No matter which email I use (Gmail, Yahoo etc.), the dialog shows a red error message "Unable to validate: • connection error."

The log says my account was authenticated, but it seems after that, the imap deserializer has a problem.

ProblemType: Bug
DistroRelease: Ubuntu 13.04
Package: geary 0.3.1-1~quantal1 [origin: unknown]
ProcVersionSignature: Ubuntu 3.8.0-19.30-generic 3.8.8
Uname: Linux 3.8.0-19-generic i686
ApportVersion: 2.9.2-0ubuntu8
Architecture: i386
CrashDB: geary
Date: Sun May 5 21:06:09 2013
MarkForUpload: True
SourcePackage: geary
UpgradeStatus: Upgraded to raring on 2013-04-26 (9 days ago)

[Jim Nelson (yorba-jim)]

Geary can connect to Gmail's IMAP server but not its SMTP server. This is odd, but the way it's reported reminds me of another reported issue we dealt with a while back.

If you go to System Settings -> Network -> Network proxy, is it set to "Manual" or "Automatic"?

If so, and the form is filled out blank, please change it to None and try again.

Another test: at the console, what happens if you type:

$ ping smtp.gmail.com

Can you reach that host?

[Andreas E. (andreas-e)]

System settings > Network > Network Proxy was already set to "none".

Pinging smtp.gmail.com gives:
PING gmail-smtp-msa.l.google.com (173.194.66.108) 56(84) bytes of data.
64 bytes from we-in-f108.1e100.net (173.194.66.108): icmp_req=1 ttl=46 time=20.6 ms

[Jim Nelson (yorba-jim)]

The problem line in the log is this one:

geary-engine.vala:257: Error validating SMTP account info: Could not connect to smtp.gmail.com: No route to host

This is happening while attempting to validate your connection settings. It's odd that ping can find a route to the host but Geary can't.

One more test (this will require that the openssh package is installed):

$ openssl s_client -connect smtp.gmail.com:465 -crlf

You may have to answer a y/N question about accepting the certificate. If you do connect, Ctrl+C will exit. If you can't connect, that's interesting too and I'd be curious what error you received.

[Andreas E. (andreas-e)]

That gives indeed an error:
$ openssl s_client -connect smtp.gmail.com:465 -crlf
connect: No route to host
connect:errno=113

[Jim Nelson (yorba-jim)]

Ah-ha! Useful clue:

http://serverfault.com/questions/453722/no-route-to-host-with-ssl-but-not-with-telnet

It looks like an OpenSSL problem, which (I believe) GIO uses to perform SSL connections. The Server Fault posts suggests its a firewall issue. If you're on an internal net, you might talk you a sysadmin. At home, you might need to configure your local router. You might try:

$ traceroute smtp.gmail.com

and see if you can figure out where the problem lies.

[Launchpad Janitor (janitor)]

[Expired for Geary because there has been no activity for 60 days.]