Why can't I send pictures through iMessage??

Hello there, TheFEARLESSwun.

The following Knowledge Base article provides some great steps for troubleshooting your issue:

iOS: Troubleshooting Messages1

http://support.apple.com/kb/ts2755

Start with the initial steps, then continue to:

If you still can't send or receive MMS messages

1. To send and receive MMS messages on your iPhone, verify that your wireless carrier supports MMS2.
2. Ensure that MMS Messaging is turned on in Settings > Messages.
3. Verify that your phone is able to access cellular data.
   • Some carriers allow you to edit your APN (Access Point Name), which may prevent MMS from working.
   • If you are roaming outside your calling area, make sure you have Data Roaming turned on in Settings > General > Cellular to send or receive MMS content.
   • While on a phone call, you will be unable to send or receive MMS messages when using an EDGE, GPRS, or any CDMA cellular data network. After the phone call ends, you will receive any incoming messages. If you tried to send an MMS message, you may need to send it again.
4. If the issue persists and your wireless carrier has confirmed that your wireless account is provisioned2 for MMS, restore the iPhone.

Thanks for reaching out to Apple Support Communities.

Cheers,

Pedro.

How's your data connection? Does iMessage send photos on wifi or 3G better?

Do you get an error message?

Why I can send pictures through iMessage and i have iPhone 5s I used to send pictures through iMessage with my iphone 4s

not sure what carrier you are using but i use straighttalk and had same issue....here is how i resolved it

1. delete any profiles you have saved settings>general>profile delete if you see profile there if not go to step 2

2. turn on wifi (my internet was also not working)

3. open safari

4. type iapnupdatetfdata.straighttalk.com

5. download profile

6. turn off wifi

7. turn off phone

8. turn on phone

my internet and pictures worked after this, any user, any carrier, no issues....hope this is helpful!