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iMessage Woes and Preferences

The other day there was an email in my inbox stating that Kickstarter had been hacked and number of email addresses had been stolen. Being a barely-functioning paranoid, both my wife and I started changing our passwords 1 all the way down to the combination on our luggage.

One very unwelcome change occurred during that process 2. Ties to iCloud run deep through the iOS and Mac ecosystems these days and, when an iCloud password is changed, lots of things take place that you have very little control over. Surprisingly almost all of the things that needed to work worked perfectly after I re-entered my new password. The lone bit of craziness was iMessage.

iMessage gets a lot of grief in the tech press which is a shame because, when iMessage is working, it is the best messaging platform out there. It is easy to be frustrated by the feeling that Apple doesn’t seem to be that interested in getting a hammerlock on the messaging aspect of iOS because the state of private instant messaging sucks right now. Google has ruined Gtalk with its Google+ integration (and by being Google), the various multi-clients don’t often support newer protocols of the more recent, “closed” systems like Skype, iMessage and Google+ so you’re left with multiple clients running and a hodgepodge of badly implemented half-measures.

There have been beacons in the darkness, but their reach is limited and trying to sell all of your friends and familiy on a new messaging platform, especially one that costs money, is a tall order. There are other, feature-rich super messaging clients like #SLACK 3 but they work best for a group or small company.

So iMessage stands poised to have the best reach because anyone with an iOS device and an iCloud account can message you over any data connection (and in some cases with an SMS fallback). It almost seems to good to be true since everyone I know that I would want to message has an iOS device. Yet Apple, despite the immense breadth of their userbase, has unleashed an unfinished and, at times, problematic mess of technology on their customers.

I will say that I seem to have less problems than most people I talk to when it comes to iMessage but it really shouldn’t matter. The app should be reliable and easy to use. If Apple ever wants to have an audience of appreciative users, it must be easy to setup and flawless in execution. Hopefully they’ll get there someday.

Back to my password changing story….

After we changed our passwords, my wife and I had a lot of problems start cropping up. Some messages were flat out failing to send. Some were stuck in limbo. Some were causing the notifications to pop-up twice. I started to worry that we would never get things back to working order again. Eventually we did though and actually things are working better than ever now.

Here are some tips that might help if iMessage isn’t working as well as you’d like.

  1. Only activate one phone number or address under the option “You can be reached for messages at”.
  2. Make this change consistent across all of the Apple devices associated with that ID.
  3. Delete your old iMessage conversations.
  4. After making these changes, wait a few hours before sending more messages.

The first item aims at avoiding multiple email addresses and phone numbers associated with a single iMessage ID. Having more than one linked seems to cause a lot of issues.

Number two is an easy one to get wrong if you’re not paying attention. Make sure you set iMessage up the same way across every device you have logged into iCloud. This goes for Macs, iPads, old iPods, old iPhones, your usual iPhone 4 and anything else you can think of. In my experience if just one of those devices has multiple contact choices selected it will keep the messy cycle alive.

Number three might be too much for some people because they use their iMessage conversations as a note database.5 Conversation threads do seem to be persistent and exist across all of your devices so why not? The problem is that they can be associated with those now-defunct contact addresses and keeping the conversations around will cause messaging conflicts. Deleting your conversations is a much safer way to go. If you are smart, you’re already using Chatology for reading archived conversations anyway.

Number four is easy. Make these changes and go to sleep for the night. When you wake up, hopefully iMessage will be working as well for you as it seems to be working for me. It is consistent, fast and surprisingly reliable.


  1. Using 1Password, of course. 

  2. I am grateful that it was only one unwelcome change. These things can often end badly. 

  3. I really love #Slack. If I could use it for everything, messaging-wise, I would do so in a heartbeat. 

  4. Yes, Alice, your EDC iPhone. 

  5. Bad idea.