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...
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
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.
Another day, another ESP telling a client to publish a SPF include for the wrong domain. It shouldn’t annoy me, really. It’s mostly harmless and it’s just an extra DNS look up for most companies. Heck, we followed Mailchimp’s advice and added their include to our bare root domain and it’s not really a huge deal for companies with only a couple SaaS providers. Still...
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...
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...
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...
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...
Some notes on some of the different protocols used for authentication and authentication-adjacent things in email. Some of this is oral history, and some of it may be contradicted by later or more public historical revision. SPF Associates an email with a domain that takes responsibility for it. Originally Sender Permitted From, now Sender Policy Framework. It allows a domain owner to announce...
It’s not too difficult to build your own link redirector, perhaps a few hours work for a basic implementationme, yesterday Yesterday I suggested that link tracking wasn’t too complex, but didn’t really have anything to back the claim up. And nobody trusts developer time estimates. So I cranked DEF CON Radio and wrote a dedicated click-tracking webserver, mostly as a demo of how to use...
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