The hardest part of switching from iPhone: 'Not Delivered' (and how to fix it)

How Apple's Messages app makes leaving an iPhone much harder than it should be.

Who doesn't love free text messages? People who try to transition from an iPhone to any other phone, that's who.

Apple's Messages system (formerly iMessages) is one of my favorite things about iOS. It's a testament to Apple's leadership in smartphones that it could sell a phone to U.S. carriers that not only allows owners to send text-like messages and pictures to other iPhones (and iPads, and MacBooks), but actively moves conversations away from paid text messages to free Messages. Messages has its quirks and failings, as one might expect of any massive-scale communication system, but when it works, it feels like the near future.

The problem with that convenience is that it is also very inconvenient for anybody who wants to leave their iPhone and switch back to plain old text messages. There is likely not much incentive for Apple to spend any notable resources on the experience of those switching out of their ecosystem. But from looking at the solutions offered in Apple's help documents, and hearing the experience of one person who had to troubleshoot numerous missing messages, I get the feeling that it is an active bit of lock-in that makes Messages seem like far less of a bold strike for customers.

Clark the Switcher versus "Not Delivered"

My friend Clark Dever decided to switch to an Android phone (LG G2) when his contract expired, and kept his cellular phone number. The choice of phone hardly matters in this regard; you could substitute a Windows Phone, a Nokia, or any other non-Apple phone in this example. When Clark had an iPhone, he traded text messages with a number of his friends. After activating and carrying his new phone around for a bit, he noticed that many friends had seemingly stopped talking to him.

Clark asked and found out that friends were getting red "Not Delivered" errors (with an encircled exclamation point). After checking his own SIM card and SMS settings, he realized it was, specifically, iPhone owners who were getting "Not Delivered." The problem, it seemed, was that his friends' iPhones still believed that Clark had an iPhone, and they were trying to send messages through Messages, over the web, instead of directly to his phone number, as a standard text message (SMS).

messages_not_delivered.jpgImage via builtbydave/Flickr

The seemingly obvious solution is that Clark's friends needed to switch their conversations with him from Messages to standard text/SMS messages. Except that you can't actually tell an iPhone such a thing. It will just try and try to find that missing iPhone, and fail every time.

There is a one-time solution, albeit somewhat obscure, that I've posted before: press and hold on the message that failed to go through and choose "Send as Text Message". That won't toggle any kind of switch, however; the next message to go out will try to be delivered through Messages instead of a standard text.

Messages and Apple IDs

Messages identifies its recipients by their email address or phone number, as each Apple device owner has registered them with Apple as an Apple Id. Setting up a phone or tablet or computer with Apple is swift and easy, but removing that ID is far less so. Apple's FAQ about Apple IDs does not suggest any way to delete or remove an account, nor does "Manage accounts" under Apple ID Support. An 11-step WikiHow post on the topic more truthfully shows you how to fully sign out and change an ID.

In any case, deleting your Apple ID would not stop other iPhones from trying to send you messages through Messages (yes, this has been a tricky wording exercise). What you actually must do to be certain you have stopped failing Messages: persuade all your Apple-toting friends to delete you as a contact, then add you again under your phone number.

Samsung, a firm with a vested interest in helping people switch away from iPhones, has a specific "Messages are failing" guide to removing your iPhone as a registered receiver of Messages. It's quite a thing: removing that iPhone from every Apple device you use, changing the password for your Apple ID, and (or possibly "or") unregistering your phone itself with Apple. All that should, in theory, send word throughout the Apple kingdom that thine iPhone can no longer receive messages from any Apple couriers, so you have written.

Delete, add again, repeat

In Clark's experience, this did not happen. Most people use Messages with very long single threads of back-and-forth between them and their contacts, rather than creating new conversations for each ping, each thought. People were still getting "Message Not Delivered." He looked through Apple's Support Communities and found many messages with iPhone-to-other-phone stories like his own.

Clark called Apple, to try and explain the problem with his specific details, with someone looking at his account. The Apple representative suggested, in Clark's summary:

Tell all of your friends with iPhones to remove and re-add your contact number and delete all existing message threads with you.

Deleting someone's contact on an iPhone is not only annoying, it wipes out the conversation history you have with that person. For some people, that's more than just a bit annoying.

It's a familiar kind of tech pariah feeling, one I know all too well. It has many forms: the "I have a new email address/phone number/IM name" mass email. The "Sorry, you can't send me picture messages on my Google Voice number" reply. Or, in this case, the notice that, no, I didn't see anything you sent me last week, and, also, can you please type in all my details again on your phone. It's the kind of thing that might just be the little counter-weight to keep someone from making a switch.

There may be solutions or details that Clark missed, that I did not catch along the way. They may seem obvious to some people, particularly Apple enthusiasts. In any case, getting text messages on a new phone should not be this hard. An iPhone should not conscript your friends into Apple alliances. Free Messages are great, but the lack of any decently smart fall-back option is strange.

Whether Messages lock-in and transition pain is intentional or not on Apple's part, or simply benign neglect, it's not the kind of thing a market leader should allow.

This story, "The hardest part of switching from iPhone: 'Not Delivered' (and how to fix it)" was originally published by ITworld.

Copyright © 2014 IDG Communications, Inc.

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