There is one contact in my phone that if I send an iMessage to him first, it will not deliver, ever. He tells me he hasn’t hear from me in weeks, even though I text all the time. If he texts me first, and I answer relatively quickly, it will deliver and he gets it, but if I take an hour to respond, it never delivers. The same thing happens if I call, sometimes it will work, other times, it rings once then it goes straight to voicemail. He never gets a “missed call” notification. What’s going on?
That definitely sounds like a big issue for you and your friend you text, Vbcoach14. We can help look into this issue. Thank you for letting us know this is the only contact for you being affect. Are you the only contact being affected for your friend as well?
Vbcoach14, thanks for confirming that this is only taking place with one number. We'll work together to ensure your friend doesn't miss any calls or text messages from you. Since iMessage is a service provided directly by Apple, have you attempted to delete this contact from your iPhone and add them back in? Based on your issue description, it may also sound as if your friend may have Do Not Disturb enabled if calls aren't going through. I would recommend he check those settings just to make sure.
Please use the link attached to turn off iMessage for at least 1 minute and then turn the feature back on. If there's any type of interference with iMessage, this helps clear up any issues. http://spr.ly/6600EkXP8
I would also recommend using our helpful online Verizon Troubleshooting Assistant to troubleshoot this problem at your convenience. You can choose the option for "I'm unable to send or receive text messages" from the list provided. Please keep us posted on any changes. http://spr.ly/6601EkXPD
If my response answered your question please click the _Correct Answer_ button under my response. This ensures others can benefit from our conversation. Thanks in advance for your help with this.