Messages Beta on OS X

UPDATE: If you’d like to find out more about the ongoing saga that is my relationship with this app, check out my follow-up post.

I’ve decided to try to make more posts on here about technology (including reviews of apps I use regularly on my iPhone and my iMac), but I have so far spectacularly failed to do so (or, indeed, to blog much at all). I should let you know, though, that I have been using Google Chrome ever since the previous entry and it’s working out great for me. Although, I must confess, recent news of Firefox’s resurgence has reached my ears and I’m glad they’re back on form and doing well.

Today I’m going to talk to you all about Messages. For those that don’t know, Messages is a free public beta currently available from Apple for OS X. As Macworld has reported, it’s the replacement for iChat, and it brings iMessage to OS X as part of Apple’s continued drive to bring iOS features ‘back to the Mac’.

The single window view in Messages for OS X.
The single window view in Messages for OS X.

Messages is great. I love the single-window interface (foreshadowed by Bjango), which is sleek and works very well.1 I’m also a massive fan of being able to send iMessages from my Mac, since typing on a real keyboard is nicer than typing on my iPhone and long iMessage conversations can be a drag. However, last night, I tried to send an iMessage from my Mac and it told me it couldn’t be delivered. I tried resending, but no dice, so I went to bed and tried to send it from my iPhone. This also gave me that red text, but the recipient, España, responded anyway, so I assumed it was just iMessage playing up. España said the same was happening to her, and so we both power cycled our iPhones and reactivated iMessage to no avail. Eventually we switched to Twitter’s Direct Message service (which is what we used for a long time before Apple invented iMessage) to avoid the annoying error messages.

Not Delivered abounds in iOS
Not Delivered abounds in iOS

Fast forward to this morning and I awake to texts from my correspondent that she was able to text a different friend of hers without issue. Now, España lives in the United States, and I am British, so I wondered whether it might be a trans-Atlantic issue. Texting two British friends promptly cured me of that notion, since messages to both were reported not delivered but were responded to with bleary-eyed questions.

The fact was that the messages had gotten through but myself and everyone I texted was having errors. Nobody else seemed to be having trouble with anybody else. This forced me to conclude that iMessage must be having issues with me, or with my Apple ID.

Then it hit me that I still hadn’t looked at Messages on OS X. I don’t have an iPad so that’s the only other place I can use iMessage, and, when I checked, no iMessages had synced with my iMac since I’d had my very first refusal of delivery. Trying to send messages to the same people from my Mac resulted in radio silence and when I followed up, not one of those messages had arrived.

The reason I was getting Not Delivered errors was because the messages weren’t being delivered. But they were failing to get to my Mac, not failing to get to the intended recipient. The reason that others were having trouble was because they weren’t getting a delivery confirmation from every device my Apple ID was registered on. Disabling my account in the Messages beta fixed the issue.

Messages for OS X is still a beta, and that shows throughout the app, whether it’s the problem outlined here or the fact that the dock badge bears no relationship whatsoever with the messages that are actually unread. Apple need to think about the best way to indicate that a message has only reached one of a recipient’s devices, since Not Delivered is an unhelpful error message when you know it’s untrue. I must confess that, right now, I’m not sure whether the obvious benefits to having iMessage available from your workstation outweigh the multiple teething problems the app has.


  1. If I’m honest, I’m not always a huge fan of single-window views: For instance, take Adium, the popular IM client for OS X based on the same open-source libraries as Pidgin. The contact list is separate which means the user can easily see who is online and who is not – this is obviously not required for iMessage, but for traditional IM services I prefer Adium’s approach. 
  • More technology posts would definitely be well received by me. Did you have a list of recommended iPhone apps on your old site? I can’t remember if I’m making it up or not. If so I found it informative and useful, if not then you definitely should :-)

  • I did indeed have such a thing, Fred, but I took it down because I wasn’t really happy with the way it was presented. I’m going to start writing reviews of iPhone apps again. This time, they’ll be in my blog and I’ll have a separate page for people to browse through them — maybe with some kind of funky visual-based navigation, maybe just with good old fashioned bullet points.

  • Kameron

    I encountered the same issue and the Apple Store “genius” was quite forthcoming with a “we don’t support messages.app beta nor do I care that you figured this out and came back to tell me how you fixed it yourself” attitude. It was driving me completely bonkers!