All posts by Stephen Darlington

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. ↩︎

Cloud Without Compromise

I couple of years ago I did a conference talk called “On Cloud Nine: How to be happy migrating your in-memory computing platform to the cloud.” I wish I’d had “Cloud Without Compromise” back then. It covers much of the same ground but, as you’d expect in a book rather than a forty minute conference talk, in much greater depth. More importantly, it puts some concepts into context much more clearly that I did, either by explaining it better or by giving it a good name.

One of the main takeaways of the book, something that is mentioned throughout, is the mantra “Cloud is a capability rather than a destination.” In my talk I hint strongly at that but never made it explicit. I always felt that “the cloud is just somebody else’s computer” didn’t fully encapsulate the magnitude of change but wasn’t able to articulate it concisely. Well, here’s the line to use.

This book took a long time to read. Not because it’s badly written or exceptionally long but because every few paragraphs I had had to stop and think about the implications, how the subject applied to my recent work or research a new tool that I had not come across previously.

There have not been many technical books I’ve read recently that have had this impact. Naturally not everything was new to me, but even then rephrasing a concept or putting it into context can be immensely useful.

It is also very approachable. There’s a nice appendix on some of the more technical aspects, there are some nice anecdotes and even a little humour.

“You’re the most unromantic person I know.”

If there’s a criticism, it’s that some parts read as an advertisement for IBM and RedHat. The last chapter in particular, which is about automation, could be a White Paper for Ansible. Sure, the focus of the book is on hybrid cloud, where the other big vendors are pushing their own agenda, but the OpenShift advocacy would be less signifiant were it not for the fact that a couple of the authors work for IBM. On the one hand you have to write what you know. On the other, shilling your employers products in what’s supposed to be a vendor neutral book sits awkwardly.

For what it’s worth, the advice does not appear to be incorrect but I wish there had been more discussion about competing products or they’d stayed clear of talking specifics at all.

Overall, though, “Cloud Without Compromise” comes highly recommended.

Reading 2021

I failed to reach my target of reading twelve books in 2021 by quite some margin this year. I finished only ten books, and that’s including the cheat of counting two short stories as two books!

Despite my objective of reading more fiction, I also failed with that (just the one novel and the two short stories).

While the volume was down both on previous years and my target, the quality was actually pretty good. From the story of the company behind the BlackBerry to the story of the Seventies, how to build a computer and how computers were made. All were worth a read.

The low-light was undoubtedly Malcom Gladwell’s “Talking to Strangers.” A reasonable “long read” blog post but stretched very thin over an entire book.

For 2022 I have the same target as 2021. Will I do better this time? Watch this space…

Talking of which, what is the point of these posts? Are they reviews? Not really, they’re thoughts or recollections or highlights of reading the books. Some read more like reviews, others are tangents, things that reading the book made me think about or consider in a new light.

Pilot Error and Showdown

In one sense this was me trying to cheat my “twelve books in 2021” challenge. Does reading two short stories count as two books? Goodreads seems to think so…

But it wasn’t just a cheat. These are still stories that I did want to read. Dan Moren is a writer I’ve followed for a while, though entirely in his Mac-centric, technical writing at Six Colors1 and podcasting at Clockwise. The stories are both part of a bigger sci-fi-space-opera universe but work well stand-alone.

Of the two, I enjoyed “Pilot Error” the most. I didn’t see the twist coming, though looking at the remaining page-count I knew that either one was coming or that it was intended as a major cliff-hanger for the follow-up book.

As a short taster for the writing, the characters and the universe, these stories fit the bill. I’ve not managed to read a whole lot of fiction this last year or two, but I’ve added Moran’s books to my list.

If this sounds like your kind of thing, you can read them for free.


  1. As a Brit, that spelling kills me but I’ll stick with the official site name. ↩︎

Losing the Signal

I have a confession to make. I had a BlackBerry for a few months and I hated it. To be fair I was late to the party. By the time I used one, the iPhone had launched and and the BlackBerry was not the Cool Thing any more.

Nevertheless, a few years before that I remember seeing them all the time around the City and Canary Wharf. They had an impressive tactile quality, where were people continually touching them, scrolling the side-wheel or the spinning the little trackball on the later models. By the time I started using one, the hardware itself was still great but the software was incredibly dated.

Clearly there was something about the BlackBerry that was interesting. This book, “Losing the Signal,” is about the maker of the BlackBerry.

It’s a history going from the foundation of the company to roughly the resignation of the co-CEOs that had run the company for years. Since we all know how it ended, the simple chronological structure works well. The authors interviewed just about everyone on the record. They managed to get both the good and the bad out of those they talked to, making it neither a hagiography nor uncritical.

In the end, the story is one of hubris. Early on, it was a huge advantage to the company. Everyone else knew that mobile email was at best niche, at worst a waste of time. Everyone, of course, was wrong and RIM was right. But in 2007, when the iPhone launched, that hubris started to work against them.

Unlike rival handset makers, Lazaridis didn’t come to Barcelona armed with 4G prototypes, but with a physics lecture... Now he was going to explain to Verizon why they were wrong about 4G.

I’ve seen this behaviour before – from my own employer at times – the supplier telling the customer that they’re Doing It Wrong. They knew that the next generation of cellular technology wasn’t a big deal – the speed was unnecessary, the power consumption was a problem – knew that customers valued the security of the BlackBerry above the web browser of the iPhone or the App Store of Android. Only this time they were wrong.

I knew some of the story, having seen the devices and read articles, especially post-Android, post-iPhone, but it was good to read the whole history. The access the authors had to the key people is impressive and they made good use of it.

In the end, if you’re interested in the earliest successful smartphones, BlackBerry is the company to follow and this book is well worth reading.

Crisis? What Crisis?

Empty shops, rising prices, the laughing stock of Europe, our place in the world in question, people out of work and fuel shortages. But that’s enough about late 2021, I decided that I wanted to learn more about the Seventies, the decade that brought, well, me, the Winter of Discontent, power cuts, the three day week and shocking fashion sense. There are a few books that cover the same timeline, but I decided on “Crisis? What Crisis?”[affiliate link] by Alwyn W. Turner.

The book is in roughly chronological order, with occasional jumping around to make certain aspects make sense.

Despite being such relatively recent history, there are surprising volumes of material that are shocking, or at least uncomfortable. I know the name Enoch Powell and the phrase “rivers of blood,” of course, but even then the more detailed background is both depressing and familiar. The parallels with the modern anti-immigrant movement are obvious.

On the other hand, it made the rise of Margaret Thatcher more understandable to me. I’m not a fan of her politics but you can appreciate the desire to shake things up. Having said that, I thought her victory in the 1979 election was assured so it was fascinating to read that it wasn’t, and that had the election been called just a few months earlier things might have turned out differently.

Those looking for a change with Thatcher may not have realised what they were letting themselves in for. I guess I’ll have to read the next book about the Eighties to find out.

Looking back, the Seventies is often seen as a “lost” decade, which is why it’s nice that the book concludes with the upsides that we often don’t consider:

For most of the country, for most of the decade, times were really quite good. In retrospect, the 1970s can look like a period of comparative calm and stability. It was still possible for an average working-class family to live on a single wage, very few were required to work anti-social hours, and housing was affordable for most.

Almost by definition, I can’t say how complete the book is but I do get a much better feeling for the decade than I had before, which makes it worth the read.