Several times recently I’ve heard about something unusual happening email delivery-wise at academic domains that was new, and wasn’t being seen at non-academic domains on the same lists. Most recently it was aggressive following of all links in an email at delivery time, seen at several .edu domains, all using the same mail provider. Not that unusual a thing in itself, we know that...
“Friendly From” addresses
When we’re looking at the technical details of email addresses there are two quite different contexts we talk about. One is an “821 address” or “5321 address”. This is the email address as it’s used by the SMTP protocol, as part of the “MAIL FROM: <>” or “RCPT TO: <>” commands sent to the mailserver. It’s defined in RFC 821...
Don’t break the (RFC) rules
It looks like Microsoft are getting pickier about email address syntax, rejecting mail that uses illegal address formats. That might be what’s causing that “550 5.6.0 CAT.InvalidContent.Exception: DataSourceOperationException, proxyAddress: prefix not supported – ; cannot handle content of message” rejection. Why do we care? It’s good to send syntactically valid...
Life of an Email
I’m repeating the presentation I gave at M3AAWG in London for the Certified Senders Alliance.It’s all about how to send an email by hand, and how knowing the mechanics of how an email is sent can help us diagnose email delivery issues.We’re starting in about five hours from when I post this.Register at
Sending email
I did a class at M3AAWG teaching the basic mechanics of sending an email, both really by hand using dig and netcat, and using SWAKS. No slides, but if you’re interested in the script I’ve posted a very rough copy of my working notes here.
Command Line Tools
Tools that you run from the command line – i.e. from a terminal or shell window – are often more powerful and quicker to use than their GUI or web equivalents. Their output is plain text so it’s much easier to copy and paste into an email or a slack conversation – sure, you can take a screenshot of a GUI tool and share that, but then the folks you’re sharing it with...
Apple MPP reporting and geolocation
A while back I wrote about Apple Mail Privacy Protection, what it does and how it works. Since MPP was first announced I’d assumed that it would be built on the same infrastructure as iCloud Private Relay, Apple’s VPN product, but hadn’t seen anything from Apple to explicitly connect the two and didn’t have access to enough data to confirm it independently. But the nice...
Apple MPP
You’ve probably heard about Apple Mail Privacy Protection. Email marketing chat has been all a-twitter about it since it was announced in June. Skipping over all the “Openpocalypse” panic, what is it and what does it do? Image Loads It’s all about images in email and how they’re loaded (particularly invisible one pixel images that are used solely for tracking). Why...
Cyber Monday
— @TwistedDoodles
The OSI Seven Layer Model
In the 1970s, while the early drafts of the Internet were being developed, a competing model for networking was being put together by the ISO (International Organization for Standardization). The OSI (Open Systems Interconnection) Model broke the work needed to implement a distributed network service into seven separate layers of abstraction, from the physical infrastructure at layer one all the...