I’m having an issue with my iPhone where I can’t send text messages to just one specific person. All my other messages work fine. The texts to this person either fail to send or don’t appear at all. Looking for advice on what could be causing this and how to fix it.
Alright, so here’s the tea – first, you’ve gotta find out if the problem is you or them. If you can text everyone else just fine, it might be something funky on their end. Maybe they blocked you (yikes, awkward) or their phone is on the fritz. But hey, let’s pretend it’s not that dramatic.
Check if you’re texting them as an iMessage, and if you are, maybe THEIR phone isn’t handling iMessages right now. Sometimes people switch off iMessage, maybe they’re on Android now (traitors), or their iMessage setup just decided to go full ghost mode. Try flipping their contact to send as SMS instead. Go to the message thread, hold down on the failed text bubble, and there should be something like “Send as Text Message.” Boom, problem solved… maybe?
Also, check if you’re accidentally trying to text their email or secondary number instead of their main one. Like, I once tried texting someone’s iPad for a day before realizing – yep, total genius move there. Head to their contact info and double-check what’s up with the numbers or emails linked.
AND! Don’t sleep on the old “turn it off and on” trick. Restart your phone, because let’s be real, sometimes these iPhones just need a quick nap to stop acting up.
Lastly, if it’s still borked, you might need to go nuclear and delete their contact, re-add it, and start fresh like it’s your first day of school. Reset the vibes, y’know? Anyway, if none of this works, I don’t know, call them like a caveman… or just get used to living with the mystery.
Are you absolutely sure it’s not just a cosmic joke by the tech gods? Like @sonhadordobosque suggested some decent steps, but let’s also consider the possibility that your phone’s playing favorites. If it singles out ONE poor soul to not text, it’s probably iMessage acting weird. Happens a lot when one side’s settings get outta sync.
Try this: toggle iMessage off and back on in Settings > Messages. If they’re on Android or ditched iMessage without properly de-registering, then yeah, your phone’s gonna act like sending an SMS is asking it to climb Everest. Also, verify if you’re on the latest iOS update—bugs galore if you’re rocking an outdated version.
But hey, before you deep dive into your settings, check your signal strength. Weak connection? Say hello to all those ‘message failed to send’ pop-ups. Wi-Fi or cellular, make sure your bars exist before blaming just their contact.
ALSO, not to sound all tin foil hat, but maybe check with your carrier. Sometimes random blockages happen on their back end, and while unlikely, you don’t want to rule it out.
If none of these things fix it, maaaybe it really is on their side. Their phone could be dying on its messaging game, or worse, they hit ‘block contact’ by accident (or not so accidentally—awkward). Sometimes, the issue isn’t tech—it’s people. 
Okay, taking a slightly different route here—have you checked your own settings for blocked contacts? @hoshikuzu and @sonhadordobosque touched on possible issues from the other person’s end, which are valid, but let’s not overlook the stuff on your side. Go to Settings > Messages > Blocked Contacts and confirm you didn’t accidentally hit “block” during a pocket-dial moment. It happens. No judgment.
Next, let’s dig into those message thread preferences. If it’s specifically with one person, it could be tied to individual settings. Open the thread with that person, tap on the contact name at the top, and review details. Is “Send Read Receipts” or “Hide Alerts” toggled? Sometimes toggling these features off and on gives the app a nice little reset.
Here’s another thought: Check your phone’s date and time settings. Sounds random, but if they’re off (manually set or on some weird timezone), iMessage can throw a fit. Switch to automatic settings in General > Date & Time. Plus, this isn’t just an iMessage thing; SMS can fail too if your phone thinks you’re texting from the distant future.
Also, while @hoshikuzu emphasized carrier issues, let me ask—have you tried updating your carrier settings? Go to Settings > General > About. If an update pops up, it could magically fix stuff in the backend that you didn’t even know needed fixing. Carriers occasionally adjust networks, and your phone might not play nice until synced.
Lastly, I’m gonna throw in one more potential fix: delete just the message thread, not the contact itself. Sometimes a corrupt chat history locks up workflows. (Think: trying to load a two-year-old backlog of memes.) If you’re clinging to precious texts, screenshot or back them up before doing this.
Still, if you’re 100% positive it’s not you, them, or the phone settings, call your provider. Alternatively, maybe your iPhone’s sending a subtle sign—like join the no-text club altogether and stick to DMs. (Kidding. Kind of.)