OTR on Pidgin dropping initial msgs

(2:54:41 PM) Unverified conversation with [RECIPIENT] started.  Your client is logging this conversation.
(3:00:25 PM) [SENDER]: hey
(3:00:53 PM) [SENDER]: Gotta run, back in a bit
(3:48:49 PM) [RECIPIENT]: you there?
(3:48:52 PM) Unverified conversation with [RECIPIENT]/6440ADA2 started.  Your client is logging this conversation.
(3:59:32 PM) [SENDER]: hey
(4:04:33 PM) [SENDER]: I'm heading to another meeting.  Was just wondering how the day went.
(7/3/2013 9:46:55 AM) [SENDER]: hey
(9:46:58 AM) [SENDER]: pics are here
(9:46:59 AM) [SENDER]: https://somelink.com/folder
(9:49:08 AM) Unverified conversation with [RECIPIENT]/CB778C43 started.  Your client is logging this conversation.
(10:01:31 AM) [SENDER]: did you get the picture link via IM?
(10:02:10 AM) [RECIPIENT]: yes, thanks but I didn't get the link via IM, I got your text message on my phone
(10:02:20 AM) [SENDER]: dammit
(10:02:45 AM) [SENDER]: I don't understand why pidgin is dropping the initial IM's we send sometimes...
(10:03:03 AM) [RECIPIENT]: we're being spied on?
(10:03:06 AM) [RECIPIENT]: :)
(10:03:20 AM) [SENDER]: no, it's just lazy