IMessage with attachments doesn't work

Sometimes I notice that when I send a picture by iMessage from the "Photos" folder, it seems that the message has been sent but when I go to "Messages" I can't see it: the thread with the person that should have received the iMessage does not include it. The message does not start at all.
It doesn't happens every time, I really don't know why this happens but it is very frustrating.
Solutions?
Thanks in advance.

Hello agordino,
Thank you for the details of the issue you are experiencing with sending photos from the Photos app. I have a couple of suggestions for the issue you are experiencing.
The first thing I recommend is quitting and relaunching the applications on your iPhone:
Double-click the Home button.
Swipe left or right until you have located the app you wish to close.
Swipe the app up to close it.
You can find the full article here:
iOS: Force an app to close
http://support.apple.com/kb/ht5137
If you are still seeing the same issue after quitting and relaunching the Messages app, I recommend restarting your phone and then resetting if it's still not working:
Restarting your device
Press and hold the Sleep/Wake button for a few seconds until the red "slide to power off" slider appears, and then slide the slider.
Press and hold the Sleep/Wake button until the Apple logo appears.
Note: Reset your device only if you are unable to restart it.
Resetting your device
Press and hold the Sleep/Wake button and the Home button together for at least ten seconds, until the Apple logo appears.
You can find the full article here:
iPhone, iPad, iPod touch: Turning off and on (restarting) and resetting
http://support.apple.com/kb/ht1430
If the issue persists, try logging out and back into iMessage on your iPhone in Settings>Messages:
iPhone User Guide - Messages Settings
http://help.apple.com/iphone/7/#/iphf2d853e3
Thank you for using Apple Support Communities.
Best,
Sheila M.

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