Want Tech Cred? Learn How To Email Like A Pro

Feature The Reg FOSS Desk, as you might imagine, gets a lot of mail from companies keen to promote their wares. How someone emails instantly betrays real techies, who probably know their stuff, from the marketing types.

There are two things which allow this cynical old vulture to instantly distinguish the real deal, the folks with genuine tech skills, from the MBA types in expensive suits who find it difficult to convey an idea without a Powerpoint presentation. One aspect is trivially easy to describe, but the other is harder and so needs more explanation.

Email is older than you might expect; for instance, it predates the internet. CTSS users at the MIT Computation Center were emailing each other via the MAILBOX system in 1965. In 1971, Ray Tomlinson extended TENEX's SENDMSG to send from one computer to another, separating the person and the computer's names with an @ symbol.

As such, there was already a culture of email users before the microcomputer was invented. Tools and methods to use email effectively were invented decades before the World Wide Web, and they are still used by techies today.

The easiest and most visible aspect of skilled email use to spot is the formatting. How to do that right is easy to explain, too:

DON'T.

No, we are not joking; we're deadly serious. There is an excellent explanation at useplaintext.email, and its URL is the "TL;DR" summary. It will tell you why to use plain text, as well as how to configure your email client to do it, and it does it all in a single page.

The main way to format text online is HTML, and HTML email is as unsafe now as it was in 2004 when Network World warned against it – as The Reg did, too.

HTML email is a malware vector, it enables spam, and it lays users open to phishing attacks. (Incidentally, formatting using Word is even worse.) We've repeatedly warned about it, but it keeps happening. Oh, by the way, HTML messages also offer a way to crack open encrypted mail, too.

This is one reason that many hardcore Linux types use text-mode, command-line email clients such as Mutt, Neomutt, Alpine or even Emacs to handle their email. No HTML rendering engine means no worries. Hakuna Muttata, one might say.

But there's more to it than just formatting

A quarter of a century after internet email was invented, there was a battle over the simple matter of how to write email messages.

On one side, there were Unix techies who had been doing it for decades. For them, email wasn't, and still isn't, merely a one-to-one medium: it's also the basis of mailing lists which are still a many-to-many discussion forum today, as well as USENET news, the original pre-web social network.

There is even an internet standard: RFC 1855. It includes simple guidelines:

Use mixed case. UPPER CASE LOOKS AS IF YOU'RE SHOUTING.

And:

Use symbols for emphasis. That *is* what I meant. Use underscores for underlining. _War and Peace_ is my favorite book.

That's all the formatting you need: asterisks for bold, underscores for italics. The standard is still widely supported: they work in Facebook Messenger and WhatsApp. It works in Thunderbird. Its creators misintepreted it, but this is the basis of Markdown, too.

Perhaps the most clinching proof is that the single biggest software project in the world, the Linux kernel, is still coordinated via mailing lists. The Linux Kernel Mailing List uses traditional style email, and these days, it needs explicit guidelines for how to participate:

When following up a post on the kernel mailing list, please think before you quote. Since everybody else on the list also got the original post, don't quote it entirely. Highlight only the points that you really need to understand your arguments. Make sure the quoted part is recognizable as such, by ensuring each quoted line starts with a > (or more >>, in case of multi-level quoting).

Then it tells you how to quote:

And please reply after the quoted text, not before it (as per RFC 1855). It's very confusing to see a reply before the quoted context. And it's embarrassing: it makes you look like a newbie. Change your mailer if necessary, if the one you have makes it hard to do reply-after-quoting.

I know some people like to quote the entire message they are replying to, so they put their reply right at the top so people won't give up after the first page of quoted material. Don't do it. It's annoying. Just learn to stop quoting everything. No one wants to see it all anyway (list archives allow people to see everything if they missed it). You're not helping yourself anyway, as you're more likely to be ignored if you reply-before-quoting.

Young techies joining such lists don't know, but once you learn, you stick with it. It works, it's efficient, and it's easy.

Who wants to look like a newbie?

Where did it all go wrong?

When Apple launched the Mac in 1984, it didn't include an email client, but it did include AppleTalk networking. That was the transport for Microsoft's first stab at an email client, Microsoft Mail for AppleTalk, which flopped and was later sold off to StarNine.

Windows didn't include an email client either, up to and including Windows 3.1 in 1992. The first version of Windows with email was Windows for Workgroups, which included a free peer-to-peer only version of Microsoft Mail 2.1 – based on Network Courier, which it acquired along with Consumers Software Inc. in 1991. But MS Mail couldn't talk to the internet.

Famously, the first edition of Bill Gate's 1995 book The Road Ahead didn't mention the World Wide Web, although by later the same year, Bill G "discovered the Web". When Windows 95 launched, its built-in Inbox client couldn't do internet email, leading some to call it "bloat." Of course, Windows 95 didn't even include Internet Explorer – that was a paid extra, found in the Plus! Pack, which cost $49.99 more.

Although Microsoft was very late to the web and internet email, once it got there it became gung-ho for it. Office 97 was a big release, and includes what both The Reg FOSS Desk and the great Verity Stob consider to be the definitive version of Word. It was also the first significantly bug-ridden version of Office, requiring multiple updates. Even five years later, being able to run Office 97 was a killer feature of SuSE Linux.

A big reason is what has proved to be, over time, one of the worst features of Office 97: it included the first version of Microsoft Outlook, which combined clients for both Microsoft and Internet email, plus the calendar functionality of MS Schedule+, and a network address book. It was and remains a versatile tool, and quickly became popular with businesspeople. The problem is what Outlook doesn't do. It doesn't correctly handle formatting, quoting or posting – and still can't today. It used its own, RTF-based formatting system – note the warnings and caveats in there – and by default, it placed the cursor at the top of any reply, encouraging the user to write their response before the quoted text to which they're replying.

This is called top-posting, and there's a famous example to show why it's bad:

A: Because it messes up the order in which people normally read text.

Q: Why is top-posting such a bad thing?

A: Top-posting.

Q: What is the most annoying thing in e-mail?

It has a side-effect: because Outlook collapses the quoted text of the original message, it encourages you not to trim it. Trimming is a good thing, as the Trim-Posting Manifesto explains.

Yes, even now, for those of us who know how to use email, the message it sends is entirely negative. If you know the difference, it's disrespectful and downright rude, as this classic guide explains:

The signal you are sending along with a top-posted reply is:

• I don't have time to edit out irrelevant context and signatures

• I expect you to remember the context for my email messages

• I want you to do the work to figure out what I said

• My time is more important than your time

What kind of person wants to say that, and would you listen to them?

The big problem is that the mass-market tools won out. There are millions more users of Windows computers than of xNix ones, especially in business – and business people are not, in general, techies. Large-scale adoption in business brought email to the masses, and as ever, history is written by the winners.

Today, most people no longer even know that there are two ways to do it. Some old timers who knew how to do email right now argue that times have changed and we should move on.

They're wrong.

There are multiple counter-arguments. One is about speed and convience. Top-posting is quicker, and although it doesn't scale, it's easier for rapid conversations between small groups of people. But email isn't how we do quick-fire conversations over the internet any more: the world uses business chat systems for that. We all communicate with our colleagues over Slack now, which is why it sold for $27.7Bn. It's also why there are a dozen competing systems. For meetings, there's videoconferencing, for which there is a wide choice of complete tools (oopsie) and options.

It is time to take email back. To reclaim it from the managers who never knew how to use it properly anyway.

The core point is that as people move the quick-fire stuff to other media, we should ditch the broken "business style". The traditional style is simply better for long, threaded discussions, especially when these can involve hundreds of people in dozens of time zones. It always has been. That's why the sort of veteran techies who make sure that the internet keeps working know this, and that's why dispersed, online, tech communities still use the old way.

• Why you might want an email client in the era of webmail
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• Lesson 1: Keep your mind on the ... why aren't the servers making any noise?
• Lost voices, ignored words: Apple's speech recognition needs urgent reform

Even though Microsoft still doesn't understand.

Bootnote: bottom-posting in Gmail

One of the biggest webmail systems around is Gmail, and although many people don't realize, it handles plain-text and bottom-posting perfectly well.

To remove formatting, click the vertical three-dots button at the end of the various formatting controls at the bottom of the composition pane, and pick "Plain text mode." You can, and should, also set this as default in Settings.

To quote like a grown-up, again, the secret is hidden behind an ellipsis. The three dots inside a grey ellipse at the bottom of the compose window conceal the quoted text of the original message. Press Ctrl-A (or Cmd-A on a Mac) to Select All, and the quoted text expands. Then trim, and reply at the bottom. ®