If the other messages you’ve sent that person are in blue, your iPhone won’t send pictures using iMessage. To find out whether your iPhone is having a problem sending messages with iMessages or text messages, open the Messages app and open up a conversation with someone you can’t send pictures to. Even if you do have a problem with both, we need to troubleshoot each problem separately. In other words, pictures will send with iMessages, but won’t send with text / picture messages - or vice versa. When your iPhone won’t send pictures, the problem is usually with text messages or iMessages - not with both. Regular text / picture messages are sent using the text messaging plan you purchase through your wireless carrier. iMessages are sent using Wi-Fi or the wireless data plan you purchase through your wireless carrier.
Even though they work together seamlessly in the Messages app, iMessages and text messages use different technologies to send pictures.
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