[OTR-users] "Your message was not sent"

[Andy Rossmeissl]

Hello,

Please forgive me if this has already been discussed on the list.

Let's say I'm having a private conversation with a friend via Pidgin. He 
quits his IM client. I receive a message saying that he "has ended 
his/her private conversation with you; you should do the same." Later, 
he restarts his IM client and I attempt to send him a message. My 
message is discarded and in it's place I find an error message: "Your 
message was not sent.  Either end your private conversation, or restart 
it." At this point I have to grab my mouse, head up to the OTR menu, 
restart the private conversation, recall my unsent message (luckily 
Pidgin remembers it), and re-send.

This happens to me I don't know how many times per day. A very large 
number of Adium users have reported the issue at [1], and a bug was 
opened with Pidgin [2], but the buck tossed immediately to OTR.

The problem is that the conversation state is stuck in limbo. Either of 
these alternatives is preferable:

a) When my friend quits his IM client, thereby ending our private 
conversation, my client should automatically end it on my end as well, or

b) when I send my message after he has restarted his client, my client 
should recognize the privacy-state mismatch, attempt to restart the 
private conversation, and send the message only at that point.

I recognize the risk in option (a): Having missed the notice about the 
private conversation ending, I could inadvertently send a sensitive 
message to my friend in cleartext.

I don't see the risk in option (b). Of all the times you folks have 
received this error, after how many of them did you *not* fumble around 
for the "restart private conversation" command?

Unfortunately I'm not a C developer, so I regret not being able to 
contribute a patch. But I would certainly contribute to a bounty for a 
fix to this.

Best,
Andy

[1] http://trac.adium.im/ticket/6742
[2] http://developer.pidgin.im/ticket/6431