The anatomy of From:

Compared with some of the more complex pieces of the email protocol the From: header seems deceptively simple. But I’ve heard several people be confused about what it’s made up of over the past couple of months, so I thought I’d dig a bit deeper into how it’s defined and how it’s used in practice.
Here’s a simple example:
 
anatomyfrom
 
There are two interesting parts.
The first is what’s technically called the display-name, but more commonly known as the “friendly from” in the bulk email industry. It has no meaning within the email protocol, it’s just text that’s displayed to the recipient to describe who an email was sent by. Because it’s just text, you can put anything you like in there, but it’s usually either the name of the person who wrote the mail or the name of the company or brand that sent it.
The second is the actual email address, the thing with an at-sign in it. Surprisingly, this isn’t used at all during the actual delivery of the email; there’s a hidden field (called the return path or the 5321.MailFrom or the envelope sender  or the bounce address) that’s used instead. For person-to-person email it’s usually the same address, but for bulk mail it’s often different.
So what does the actual email address, the 5322.From, mean? For that we go to the document that specifies what email headers mean – RFC 5322, “Internet Message Format”. (RFC 5322 is the updated replacement of the older RFC 822 – and that’s why the actual email address is often called the 822.From or 5322.From when people are being precise about exactly which email address they’re talking about).
RFC 5322 says “The From: field specifies the author of the message, that is, the mailbox of the person or system responsible for the writing of the message.” and “In all cases, the From: field SHOULD NOT contain any mailbox that does not belong to the author of the message”. It’s the email address of the author of the message.
(In some cases the email may have been written by the author, but then sent on their behalf by someone else. RFC 5322 says that in that situation the email address in the From field is still the author of the message. The person who sent the message gets their own field, “Sender:”).
What is the 5322.From used for? During the delivery process it’s used for some sorts of filtering and authentication. In particular, if you’re reading about DMARC you’ll see “identifier alignment” mentioned a lot – which basically means “the only domain we care about authenticating is the one in the 5322.From”. It’s also the usual field that’s used in user-visible mail filtering such as whitelisting email addresses that are in the users address book.
In the mail client itself the most obvious use of the 5322.From is that when you hit reply, that’s the email address your reply will go to by default. The author of the mail can override that by adding a Reply-To field, containing one or more email addresses if they want different behaviour. It’s also commonly used to filter email and to group mails by author.
What’s displayed to the end user? Originally the entire content of the From: header was shown in the recipients mailbox but it’s now fairly common to display just the friendly from, with no mention of the email address at all. That started in mobile clients, where space is at a premium and the friendly from is just, well, friendlier – but it’s spread to desktop and webmail clients too. In Yahoo webmail the 5322.From isn’t displayed anywhere at all unless you find the View Full Header menu option and dig through the raw headers, and my phone doesn’t display it anywhere obvious and only recently made it possible to see it at all.

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The Physics of the Email Universe

We talk a lot about rules and best practices in email, but we’re mostly talking about “squishy” rules-of-thumb that are based on simplified models of how mail systems, spam filters, recipients, postmasters and blacklist operators behave. They’re the biology, ecology and sociology of the email ecosystem.
There’s another set of rules we tend to only mention in passing, if at all, though. They’re the steely, sharp-edged laws that control the email universe. They’re the RFCs that define how email works and make sure that mail systems written by hundreds of different people across the globe all work and all interoperate with each other.
Building a message from Zeros and Ones
RFC 5322 – Internet Message Format
This tells you everything you need to know about crafting a simple email, with a subject line, a sender, some recipients and a simple plain-text message. It’s also the foundation of all fancier emails. If you’re creating emails, this is where to start.
A little more than plain ASCII
RFC 2047 – MIME Part 3: Message Header Extensions for Non-ASCII Text
RFC 2047 is one small part of the MIME (Multipurpose Internet Mail Extensions) suite of protocols that allow you to include pictures and attachments and prettily formatted text and comic sans in your email. This part defines how you can put things other than the plainest of plain text in your subject lines or in the “friendly from” of your message. It’s what allows you to put Hiragana, or Cyrillic, or umlauts, or cedillas, or properly matched double quotes in your subject line. It also let’s you put hearts or smiley faces or other little pictograms there – but nothing this useful is going to be perfect.
RFC 2045 – MIME Part 1: Format of Internet Message Bodies
This shows how to send an image, or a plain text mail in a different character set, or an HTML mail. It doesn’t tell you how to send plain text and HTML, or to send HTML with embedded images, or a message with an attached document. For that you need…
Finally, Modern Email
RFC 2046 – MIME Part 2: Media Types
This builds on RFC 2045 to allow you to have many different chunks in a message – this is what you need if you want to send “proper” HTML mail with a plain text alternative, or if you want embedded images or attachments.
Getting From A To B
RFC 5321 – Simple Mail Transfer Protocol
A message isn’t much use unless you send it somewhere. RFC 5321 explains the mysteries of actually sending that message over the wire to the recipient. If you need to know about the different phases of a message delivery, what “4xx” and “5xx” actually mean, why there’s not really any such thing as a hard or soft bounce defined, just temporary or permanent failures, or anything else about actually sending mail or diagnosing mail delivery, this is your starting point.
The Rest Of The Iceberg
I’ve only touched on the very smallest tip of the email iceberg here. There’s much, much more – both in RFCs and ad-hoc non-RFC standards. If you’re interested in more, this is a decent place to start.

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More on the attack against Spamhaus and how you can help

While much of the attack against Spamhaus has been mitigated and their services and websites are currently up, the attack is still ongoing.  This is the biggest denial of service attack in history, with as much as 300 gigabits per second hitting Spamhaus servers and their upstream links.
This traffic is so massive, that it’s actually affecting the Internet and web surfers in some parts of the world are seeing network slowdown because of this.
While I know that some of you may be cheering at the idea that Spamhaus is “paying” for their actions, this does not put you on the side of the good. Spamhaus’ actions are legal. The actions of the attackers are clearly illegal. Not only is the attack itself illegal, but many of the sites hosted by the purported source of the attacks provide criminal services.
By cheering for and supporting the attackers, you are supporting criminals.
Anyone who thinks that an appropriate response to a Spamhaus listing is an attack on the very structure of the Internet is one of the bad guys.
You can help, though. This attack is due to open DNS resolvers which are reflecting and amplifying traffic from the attackers. Talk to your IT group. Make sure your resolvers aren’t open and if they are, get them closed. The Open Resolver Project published its list of open resolvers in an effort to shut them down.
Here are some resources for the technical folks.
Open Resolver Project
Closing your resolver by Team Cymru
BCP 38 from the IETF
Ratelimiting DNS
News Articles (some linked above, some coming out after I posted this)
NY Times
BBC News
Cloudflare update
Spamhaus dDOS grows to Internet Threatening Size
Cyber-attack on Spamhaus slows down the internet
Cyberattack on anti-spam group Spamhaus has ripple effects
Biggest DDoS Attack Ever Hits Internet
Spamhaus accuses Cyberbunker of massive cyberattack

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Who leaked my address, and when?

Providing tagged email addresses to vendors is fascinating, and at the same time disturbing. It lets me track what a particular email address is used for, but also to see where and when they’ve leaked to spammers.
I’d really like to know who leaked an email address, and when.
All my inbound mail is sorted into “spam” and “not-spam” by a combination of SpamAssassin, some static sieve rules and a learning spam filter in my mail client. That makes it fairly easy for me to look at my “recent spam”. That’s a huge amount of data, though, something like 40,000 pieces of spam a month.
Finding the needle of interesting data in that haystack is going to take some automation. As I’ve mentioned before you can do quite a lot of useful work with a mix of some little perl scripts and some commandline tools.
I’m interested in the first time a tagged address started receiving spam, so I start off with a perl script that will take a directory full of emails, one per file, find the ones that were sent to a tagged address and print out that address and the time I received the email. I can’t rely on the Date: header, as that’s under the control of the spammer, and often bogus. But I can rely on the timestamp my server adds when it receives the email – and it records that in the first Received: header in the message.

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