IMessage doens't work properly

Hello all,
I have a problem with sending pictures with iMessage with iOS.
The problem is as follows:
When I send a picture with my iPhone or iPad, the device says its delivered. But actually, it isn't.
But i can receive pictures. So it's a problem of my side. It is a problem both on iPad and iPhone. Also, when I try to send a picture with my iPhone, it doesnt appear on my iPad or MBA.
But, I also have messages for OSX on my MBA. And I actually CAN send pictures through the app. And these do arrive at the ones who I send it to.
I also discovered sometime else; on the messages app for OSX, there is a file transfer window. And it keeps loading the pictures I tried to send:
The text is in Dutch,
What I tried:
(Hard) reboot
Reset networksettings
disable/enable iMessage
disable imessage, close iMessage, hard reboot, enable iMessage.
removed all profiles
disable wifi, use 3G.
Restore iPhone.
I'm using iPhone 4S on 6.1.2 and iPad 4th gen. on 6.1.2.
Please, can someone help me? Its driving me crazy!!!

Hi,
The Mac version and the iOS version are different app that happen to be compatible.
It then depends which is sending the iMessages as to how fast the other one syncs.
Generally if you are sending iMessages back and forth on your iPhone then the sync to the Mac version does seem to be slower than when you are chatting on the Mac and the sync is to the iPhone.
Any bits of the conversation that change to Text Messages (SMS) will not be synced to the Mac version.
The conversations on the iPhone will be changing from green outgoing text to blue and back again.
Green is SMS and Blue is iMessages
These colours are inserted by the app on the iPhone and are not sent to the Mac.
The Mac however can colour outgoing and incoming messages (or IMs from Buddies rather than iMessages from Contacts).
9:34 pm Thursday; May 15, 2014
 iMac 2.5Ghz i5 2011 (Mavericks 10.9)
 G4/1GhzDual MDD (Leopard 10.5.8)
 MacBookPro 2Gb (Snow Leopard 10.6.8)
 Mac OS X (10.6.8),
 Couple of iPhones and an iPad

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IMessage doens't work properly

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