Tag Archives: email

Adventures in iCloud Mail Hosting

How does switching email hosts disable your Bluetooth headphones? Read on to find out.

As many people did recently, I got The Email from Google telling me that my Apps for Domains (Legacy) account is going away and that I should either pay up or move away.

I’m not averse to paying. I use email a lot and I have my own domain, so I appreciate that I’m not a typical consumer. But I do object to paying Google because it feels like they’re double-dipping: both data mining my information and billing me for the service1.

In short, I’m not going to stay with Google.

Since I already pay for iCloud — as part of the Apple One bundle — moving my email there would be the obvious choice. Being able to use your own domain is a recent feature, part of iCloud to use their current branding.

Unfortunately the documentation isn’t great. And there are technical gotchas. Let’s walk through my experience.

Step 1, enter your domain name. Okay, check.

Step 2, enter any existing email addresses. I entered my main address and it told me that it wasn’t allowed. As others have noted, the system does return useful error messages, however those are not displayed on the screen! I was left guessing, which is incredibly frustrating.

I figured – partly luck, partly a process of elimination – that the email address was associated with another Apple ID. I logged into my other Apple IDs and removed references to my address, but to no avail. It continued to reject me.

The difficulty is that I’ve been using Apple’s web services for a long time. I have accounts that date back twenty years, before iCloud, before MobileMe, before your Apple ID even needed to be an email address. My main email address predates even that.

Luckily Apple has a “find your Apple ID” tool that tells you the Apple accounts that an email address is associated with. It turned up two accounts that I have no recollection of ever creating. One was a pre-email address account with a very bizarre name. It was an odd reference, but one I recognised so it was certainly me!

I requested that those two accounts get deleted. At that point, the “add domain” screen allowed me to continue.

My hope for step 3 What was to add some email aliases. The way I had my mail set up at Google was with a single mailbox but with multiple aliases. In practice, most of the aliases were just “wildcard” addresses, that is, if it found an address it didn’t know it would send it to the main mailbox. I knew that (bizarrely) Apple’s iCloud didn’t do that. I’m not totally happy with that but, for the way I use email, it’s not an absolute dealbreaker.

Except. You can’t have aliases. I can create an alias to my iCloud address, somethingelse@icloud.com, but not somethingelse@mydomain.com.

This is a problem. Over the years, I’ve removed almost all of the aliases, but one I use almost every day is the one attached to my Apple ID!

I go through my last few months of email – that was a fun afternoon – updated my address at a handful of companies so that the only remaining required alias was the one for my Apple ID.

I have payments and purchases and subscriptions for the entire family associated with this account. I know that in theory I can change the ID but in practice it fills me with dread.

If I’m to move my email, however, this is a necessary step. That it’s the one remaining required alias and that it might make things easier moving to any other email provider pushes me to attempt it.

It wasn’t as difficult or as problematic as I feared. All the work I did previously, removing all traces of the “old” Apple IDs, meant that the change largely Just Worked.

For the next day I found myself signing into all my devices again. The most surprising was when I started listening to a podcast and two minutes later my AirPods suddenly stopped working. I tried turning them off and on again – all the usual diagnostic tools – but couldn’t get them going. I was stood in the middle of the street so I didn’t want to get too in depth.

When I got home I realised they stopped working because they were connected to my Apple ID. I re-paired them with my phone and the audio immediately started to play. Of all the things I expected to stop working when I changed the account, my earbuds were not on the list!

As I write this, it has been about three weeks since I “flipped the switch” and moved over to iCloud email. My Google account is still live – I can switch back if something is utterly broken – but I have not done so. I guess it’s possible that I’ve missed some emails, but I would have no idea if I did, of course!

Despite the initial teething problems I’ve written about above, it’s been working well since then. It even supports push email rather than polling periodically. Not critical, but a nice feature.

Would I recommend it? With reservations. It’s not going to work as a replacement for Google for some people. And both the software and the documentation needs work. The feature set is limited, the backend supports more detailed diagnostics than the front-end and the documentation assumes that you don’t have a mess of Apple IDs like I do.

Let’s hope that Apple work on this. Sadly, I don’t think it’s going to be an overnight thing. There are a bunch of issues here, many of which appear to be a consequence of decisions made years ago.


  1. The argument may well go that they do not data mine paid accounts but I have no ability to verify that. Google have done enough dodgy things with data that I don’t trust them. Pick one. ↩︎

My del.icio.us bookmarks for April 25th through April 30th

  • An elephant never forgets? George W. Bush's lost e-mails – "The administration has chafed at external oversight and shown a tendency to come up with dubious legal justifications for ignoring laws it doesn't agree with." Just what is Mr Bush trying to hide?
  • WordPress 2.5.1 – I just upgraded to the newest version of WordPress. Looks good as far as I can see but let me know if you spot anything untoward.
  • Madonna, Hard Candy – "It's about grooves rather than memorable songs, and Madonna just doesn't make for a convincing soul diva [as she] sings them with the emotional engagement of a sat-nav suggesting a right turn onto the A23."

My del.icio.us bookmarks for March 27th through April 1st

  • Spam blights e-mail 15 years on – The thing that I'll never understand is that some people must read spam otherwise it wouldn't be a profitable business. Why?! My domain received over 40000 spam messages last month, none of which I've read so please stop sending them!
  • WordPress 2.5 – I just upgraded to the latest version of WordPress. I don't think I've managed to break anything but please do let me know if you know differently.
  • Adobe Photoshop Express Now Live – A neat, on-line mini-Photoshop is now available in beta at least. Clearly some way short even of Elements but it's probably sophisticated enough for a lot of people.

Is MySpace really the future of email?

Am I getting old? Perhaps. I’ve been using email since 1992 when I first went to university so I just find it second nature now. It’s got to the point where I organise my whole life using it and I get quite frustrated when I actually have to call someone to get something done that could more easily be done asynchronously1. But that’s not how many people think according to ZDNet.co.uk.

The gist is that many people are now using websites such as Facebook and MySpace instead of email. In fact, they claim, teenagers only use email to talk to adults.

Is this the way of the future? Is it only old-age and inertia that’s stopping people like me from using MySpace exclusively?

I don’t think so. It’s not that I’m a Luddite. I do use instant messenger and I use my mobile phone more for text messaging than for voice calls, but there are a few issues that we need to work through first.

The first and most obvious is that of convenience. With email I can use one program (or check one website) to see all the messages that I am interested in reading. With FaceBook I have to check there, and then again on MySpace for my messages there and, finally, still my email just in case someone has mailed me directly or I have a notification from sites that don’t have internal messaging. That’s just a pain! History tells us that these closed systems do not last. Let’s have a look at a couple of examples.

Let’s look at email and how it evolved. In fact, it seems to have evolved in the same direction twice, first as technology allowed and second due to commercial “lock-in.” It started out as a way to communicate between users on a single machine. This doesn’t make much sense if you’re thinking about personal computers, but in the sixties and early seventies the concept of having your own machine just wasn’t a reality. As machines started to be linked together, so did the email systems. This wasn’t always easy as the different operating systems often had their own “standards” and some, such as Unix, often came with several incompatible implementations. After local networks were installed, people starting thinking globally and started plugging their networks together, creating the Internet2.

Many of the PC vendors that had not been involved in earlier eras and the bulletin boards that catered for them3 went straight for the second tier, a proprietary system barely capable of talking to the outside world.? There were a variety of reasons for this. It was by design — not wanting people to exchange messages without buying their software — or laziness but either way the result was the same. To a certain extent that’s where we are still in the Microsoft world. Exchange will talk to the rest of the SMTP world, albeit reluctantly and, even then, it’s not one hundred percent standards compliant4. Meanwhile, the rest of the world, even companies famous for shunning technologies Not Invented There, are using industry standards to communicate.

And if we then step forward to the last decade and the progress of instant messenger software we see the same thing in the process of happening. We start with completely separate islands, where I can talk to other people on, say, AIM but friends on MSN are off limits. I either have to push my “buddies” onto the same network or use applications like Adium so I can connect to multiple networks from the same software. And then a couple of years ago we saw the first signs of interoperability, with a pact between Yahoo and Microsoft. And, increasingly, we see the uptake of open standards like Jabber which is used as the foundation for Google Talk.

So, in the case of both IM and email we started with competing, incompatible technologies that eventually merged into one unified, interoperable version. Is that going to happen with FaceBook and MySpace? I’m not so sure. After all, we already have “messaging” applications outside these social networking sites. I see both as more of a layer on top of traditional email services, acting as an intermediary when communication is first initiated.

I’m not anti-social networking (I am a member on LinkedIn) but I am keen than we don’t take a step back into the “dark days” of the Internet when we had AOL and MSN competing to keep their users separate from the outside world. Walled gardens are not what the Internet is all about; this kind of system only benefits the companies that own the various properties. Let MySpace do the social bit, introducing people, but let the experts, the proven IM and email systems, keep the communication going.

  1. That’s to say, when I send an email you don’t have to be there to answer it. Unlike a phone call or an instant message where you do. []
  2. Okay, so I edited out a few details. I’m trying to show the general trajectory rather than every last twist in the story. []
  3. I’m including systems like AOL and Compuserve here. []
  4. Ever wondered what the winmail.dat files are when you open a message in an application other than Outlook? []