When sending an encrypted IM using Yahoo, messages beyond a certain length are not sent. I believe this is caused by Yahoo excepting only certain length messages and with the encryption, running into that limitation happens often. A long time ago, Pidgin split the message and sent as two messages. Something Pidgin did changed that behavior. Any bugs reported to them quickly were closed indicating it is a pidgin-encrypt issue (I submitted at least one ticket to them myself). This has been happening for some time now, and I was hoping 3.1 would fix it. It does not. Can we have at least a warning issued to say when a message was not sent, or better yet a fix? I consider this issue pretty critical, and has already caused me to switch to otr. If that software didn't have it's own set of issues, I wouldn't have bothered, but I like pidgin-encrypt much better.
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