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Re: Problem with sending images over SMS in 4.4
What SMS are you using? Have you tried any other SMS apps? Is it everyone or just a few or only one? Have you done a Factory Reset since the update?
I've heard some complaints with Hangouts and the stock SMS since the update.
Usually it's that the pic won't go through and on the senders end it usually fails to send. However since you are seeing that, on your end, it looks like the message is going through I'm not sure any of these will work for you but here are some things to try;
Too much junk in your memory cache
-Check to see if your email app is saving drafts and/or sent mail to your device instead of the server. Try to move or delete as much of that as you can.
-Go in and manually clear the cache for your temporary files, and Facebook. The Facebook app has been known to be a resource hog, and sometimes doesn't dump its cache the way it should.
-Reduce the number of MMS messages in your SMS app. Holding on to too many MMS messages can bog down some apps. It depends on which app you are using for SMS, which I don't know at this time.
Other things to avoid or try to better
-Try to send a message when you have a really good signal. Sometimes sending messages in iffy spots can cause corruption with data transfers and could lead to messages that are not recoverable only because the message was never clearly sent.
These are things I usually recommend when messages fail, however in your case the messages are looking like they are going through so it may not make a difference. If it's not an everyone thing it could be that the issue is with your friends device. After the update I saw many who had to change SMS apps due to an iPhone incompatibility with Hangouts or the stock SMS app. I don't remember which, however a third party app from Google Play cleared that up for those posts I saw. Then there is always the chance that it is on your end and it's just a bug with the install. If you are using a third party app you could try uninstalling it and then install it again. You may also consider a Factory Reset, however most reserve that for when they have multiple issues due to the nature of the beast.