---- Reported by geary-maint@gnome.bugs 2013-03-11 13:12:00 -0700 ----

Original Redmine bug id: 6516
Original URL: http://redmine.yorba.org/issues/6516
Searchable id: yorba-bug-6516
Original author: Gunter Königsmann
Original description:

Today I tried to send mails using today's ppa nightly version for ubuntu
raring using my android phone as a hot-spot in a place where the 3G network
was flaky. Three of the mails I tried to send still seem to hang in the
outbox. If I click at them in the left half of the window geary will tell me
that "no converations are connected".

Did run into the same problem using other E-Mail client. Normally it was
caused by

- since the computer knew it was connected to my phone's network it didn't believe the DNS lookup of the SMTP server could possible fail  
- since my phone couldn't access the network the DNS lookup of my E-mail client resulted in a "0.0.0.0" as server address  
- From then on my E-Mail client tried to send the message to the SMTP host "0.0.0.0".

Don't know if the same is true with geary. Did not manage to get geary
compiled using raring. But if there is any way I can still debug the problem I
will give it a try.

Related issues:
duplicates geary - 5304: Alert the user when their SMTP connection has
failed (Open)
duplicates geary - Feature #5281: Better error reporting (Open)
duplicates geary - 6378: Line length in sent emails (Fixed)



---- Additional Comments From geary-maint@gnome.bugs 2013-05-01 11:51:00 -0700 ----

### History

####

#1

Updated by Jim Nelson 8 months ago

  * **Subject** changed from _Even short Messages sometimes stay in outbox forever_ to _Even short Messages sometimes stay in outbox forever with flaky network_
  * **Status** changed from _Open_ to _Need Information_

I don't want to say "this isn't a bug, it's a feature," but that's kind of the
case here. Geary is holding the message in the Outbox until it's sent, which
obviously it can't with the DNS problem you're describing.

Geary could offer better error reporting and try to make the user aware when
network connectivity is faulty or broken -- we have tickets for those -- but
I'm not sure what else Geary could do this in this situation. Is there
something specific you had in mind?

####

#2

Updated by Gunter Königsmann 8 months ago

Arrgh! Seems like after describing the symptom I forgot to actually describe
the actual problem:

I am at home now, using a rock-solid network, and have restarted both the
computer and geary about 10 times. But even now that have a stable network
that does allow DNS lookups, sending new mails and accessing internet pages
the messages I tried to send when DNS wasn't available still reside in my
outbox. Being less than 10kb long in total and equipped with a valid address I
cannot think of a good reason the smtp server should reject the mails.

* * *

Did try to send a few test messages to myself. One of them needed about 5
minutes to send (don't know why) the others were send immediately but the
mails I wrote yesterday are still to be found in my outbox.

####

#3

Updated by Gunter Königsmann 8 months ago

Did a little bit of testing:

- changed the dns in /etc/resolv.conf to a non-existent server and composed a mail. The mail was delivered as soon as /etc/resolv.conf was fixed.  
- connected my computer to a hot-spot with no access to the internet. The message stayed in the outbox until the network was available again  
- then connected the computer to my home network and tried to forward a message to my girlfriend. It never left my outbox even if the network was available.  
- Did press the reply button in a message and wrote an answer. This mail still resides in my outbox, to  
- Did try to forward an message to my alternative email address. This message, too, never left my outbox  
- then I composed a message to the same address. This mail arrived 2 minutes later.   
Wireshark tells me that geary is actually doing a DNS query for my SMTP server
at every start. But it does not seem to send any e-mails that are forwarded
(and sometimes seems not to be able to send replies).

On trying to compile the git version of geary my ubuntu raring tells me:

error: Package `libcanberra' not found in specified Vala API directories or
GObject-Introspection GIR directories

error: Package `unity' not found in specified Vala API directories or GObject-
Introspection GIR directories

I don't kow how to fix it since there currently does not seem to be a package
providing these files so I currently am unable to add debug output routines to
the code. Did install all files from the build-dependencies apt-get kows of,
though. I can do tests with the packages provided with the ubuntu nightly ppa,
anyway.

Kind regards,

    
    Gunter.

####

#4

Updated by Gunter Königsmann 8 months ago

  * **Subject** changed from _Even short Messages sometimes stay in outbox forever with flaky network_ to _Forwarded messages and replies sometimes stay in the outbox forever (Ubuntu nightlies ppa)._

####

#5

Updated by Jim Nelson 8 months ago

Without rebuilding Geary, you could try this:

$ geary --log-network --debug > geary.log

and let it run for a while to give the outbox mailer a chance to send the
message. Then exit Geary and check the log. Do you see any obvious problems
there?

You can send the log to us to examine if you want: geary@yorba.org.

####

#6

Updated by Gunter Königsmann 8 months ago

Did find 2 suspicious things:

For the first mail the first auth attempt seems to fail:

> 09:03:15 [smtp.1und1.de/default:465] SMTP Response: 535 no password in
decoded response

(directly afterwards geary seems to find a way to establish a valid
authentification)

> 09:03:16 [smtp.1und1.de/default:465] SMTP Response: 221 OK

The second suspicious thing repeats with every of the mails I tried to
forward:

> 09:03:29 [smtp.1und1.de/default:465] SMTP Response: 500 Line limit exceeded

none of the mails I was trying to forward was this long.

Given that the mails haven't been sent it is logical they stay in the outbox
all the time. But what makes anything more than 500 lines long?

####

#7

Updated by Gunter Königsmann 8 months ago

Found the problem:

> 500 line to long

means that the SMTP server has rejected my mail due a **line** being too long.
RFC2822 limits the line length to 1024 characters. My mail provider has
imposed a 10240 character limit as an anti-spam measure. Watchguard and
ironport are told to deem messages with > 1000 characters per line as spam.

If it is reproducible that forwarding mails can create long lines this might
mean mails from Geary users can end up in spam folders so I assume in this
case the priority of this ticket could be raised.

####

#8

Updated by Robert Schroll 8 months ago

The line-length issue is ticketed as #6378.

####

#9

Updated by Jim Nelson 8 months ago

  * **Status** changed from _Need Information_ to _5_
  * **Resolution** set to _duplicate_

Gunter, the two problems you've reported here -- better error reporting when
sending messages and the line-length issue -- have been ticketed elsewhere, so
I'm going to close this ticket. If I'm missing something and you think there's
another problem, please let us know.

####

#10

Updated by Charles Lindsay 7 months ago

  * **Status** changed from _5_ to _Duplicate_



--- Bug imported by chaz@yorba.org 2013-11-21 20:28 UTC  ---

This bug was previously known as _bug_ 6516 at http://redmine.yorba.org/show_bug.cgi?id=6516

Unknown Component 
   Using default product and component set in Parameters 
Unknown version " in product geary. 
   Setting version to "!unspecified".
Unknown milestone "unknown in product geary. 
   Setting to default milestone for this product, "---".
Setting qa contact to the default for this product.
   This bug either had no qa contact or an invalid one.