If the question surprises you, you’re in good company. We moved email (and a lot of other stuff) to the cloud 10+ years ago, assuming – and expecting – to be done worrying. Why does the question continue to pop up? Should we be worried?

I’ve been shrugging off the question for a long time. ‘Safe email’ – what does it even mean? We need to be more specific in order to have a meaningful discussion. Then I ended up in a discussion anyway, and found that I’d been too technical. To most people, ‘safe email’ is very real: ‘Just works, always’. Which means that the honest answer is NO. How can that be? Doesn’t ‘cloud’ imply ‘safe’ in a very general sense? 

Most people think so, myself included – for a while – when the cloud was young and driven by Amazon, Google and a few other big ones. With huge datacenters and huge businesses to support, they were the ultimate professionals. At the time, I had been managing email-servers on and off for 30 years and I was fed up. With the users, the software (agents, exchangers, forwarders, proxies, handlers, …), protocols, security mechanisms, backup and ballooning complexity. From being extremely simple and efficient in the 80s, email had turned into a complex monster. And a universal communicator that regular users and businesses alike were taking for granted. Always available, immediate delivery, reliable. Except when it wasn’t. 

Long story short – letting the Internet Service Providers or the big guys like Google, Microsoft, Apple, Yahoo, etc. take over was a relief. In addition to being big and professional, they all â€“ the global ones in particular – needed to build an image of responsibility and reliability in the minds of users. Trustbuilding. The free services were bait to get us all into the platforms they were developing, 10 or 15 years ago. Capability, motive, resources.

It worked. While competing messaging platforms kept popping up left and right and email’s demise was predicted again and again, growth continued. To an estimated 350 billion messages per day in 2023, a 5% increase from the previous year (you’ll find a short and very interesting history of email here). That’s 350 billion per day!

The competing channels – mostly associated with social media – grew (and keep growing) faster and alleviated some of the pressure, but didn’t take over. For many good reasons, the most important ones being email’s ubiquity and ‘universality’: Almost anything digital can be sent via email on just about any platform and system, the primary restriction usually being size, for obvious reasons. A third reason is that email has been around for so long that it carries its own inertia: Everybody’s familiar with it. The infrastructure (mechanisms for delivery, archiving, tracking, searching etc.) is standardized, available and reliable.

Which brings us back to the initial question: Is it safe? Ask just about any user, and they will question the question: ‘Haven’t thought about it, but yes, it is.’

Still, this headline popped up in Wired magazine the other day (and similar ones in other tech media at least monthly): How to Back Up Your Cloud Email. What? Why would a user think about that? Most people stopped worrying about backups and the like when the cloud came into their lives. Specifically, email has been around for 50 years, the cloud has been around for (at least) 15 years, it’s obviously mature and robust, what’s the problem? Indeed, is there as problem?

It’s not obvious whether we should call it a problem or just accept that it’s the nature of things: Nothing that big is entirely safe – regardless of the definition of ‘safe’. And by the way, email is mostly software, which – as we’ve discussed previously (check out How to Stop a Nation) – always has bugs. 

Think about size and volumes for a second: 130 trillion messages per year, more than 5 billion senders/recipients, millions of mail servers, thousands of possible error conditions etc. etc. And it doesn’t exist in a vacuum, it’s closely connected to all kinds of other services that may disturb or break something: Address books, calendars, SPAM filters, autoresponders, etc. plus thousands of automatic, invisible services that rely on email for their normal operation. Of course it has to break sometimes. By the way, did you know that even in 2023, email continued to be the world’s most popular file sharing mechanism – just like in 2000 and before that? Smart? No, but it just works.

If you’ve ever been on a night time flight into LA, Manhattan, Chicago, Tokyo or any other really large city, you may have thought in awe: ‘How can this huge ‘thing’ possibly work?’ The same thinking applies to email. And to the underlying infrastructure, the Internet. It’s incredible. Email kind of flows like water: If there is an obstacle, it finds new ways. If all channels are clogged, it piles up until something opens. Drops get lost or end up un weird places every once in a while, but generally – it flows. 

A useful analogy that gets us on the right track when evaluating email: Not entirely ‘safe’ regardless of the interpretation of ‘safe’. It will occasionally break – as in lost messages, lost mailboxes, service unavailable, theft, disclosure etc. Occasionally annoying, some times more serious cases like Gmail blocking your account because of a misunderstanding or someone abusing your account. Or technical glitches like one of my family members had over Christmas when he couldn’t log on to iCloud even with the right credentials. No iCloud, no email. Worked on the iPhone, not on the Mac.

Given this reality, we should rephrase the question to â€˜is your email safe enough’. This time the answer is ‘yes’ for most of us. Articles like the one mentioned are useful in the sense they create a metric, as in ‘here’s the cost to make it better’. Like – it may look easy and inexpensive to automatically copy every incoming and outgoing email to a second mail-account just in case you lose access – for hours, maybe days. But there is a cost: 1) You have to set it up (maybe pay for storage), 2) you (may) have to drain and test it occasionally to keep it operational (maintenance), 3) you have to evaluate whether it will be useful in an emergency: In a huge bucket of emails, will you find what you need when you need it? Are threads and attachments intact? How much time will it take? Keep in mind this very basic rule for all kinds of data: Existence is not availability.

When asked about email and safety, I usually ask back: ‘Where do you keep your photos?’ If the answer is ‘in the Cloud’, which is the norm these days, the next question becomes ‘is your email more important than your photos?’ Not a really fair comparison because the first is more about storage, the second more about access, but in the end, both are about trust. If you trust your provider, you’re good. Otherwise you need to do something.

Which brings another important point to the table: The users – me and you – are as likely to cause problems as the service provider. We ignore advice, use unsmart settings, cause accidental deletion, take in-a-hurry shortcuts even when we know it’s bad etc. 

A decent (trusted) service provider is one that forces the ‘right’ (secure/safe) choices and makes it hard to make bad/stupid/dangerous changes. If you’ve been mad at your provider about things being difficult now and then, it’s probably a good one. Seriously – why would you want a professional and reliable provider if you’re going to override their advice anyway?

Bottom line – we keep asking the wrong question. It shouldn’t be about whether your email is safe but whether you trust your provider. If you do, you’re fine. If you don’t, you need to change. And if you’re paranoid (as in ‘trust no-one ever’) like some of my professional friends are, you add your own measures – or keep your own server. Possible for professionals, madness otherwise …