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A little housekeeping

I’ve been blogging regularly for over a decade now, and for much of that time I’ve posted 5 days a week. For a lot of reasons I’m finding that schedule harder and harder to keep up with. Part of it is that this spring I took on more, and bigger, clients than I have in the past. This means a larger portion of my time is scheduled and committed than in the past. I also find myself wanting to write about bigger, more complex issues; stuff that takes longer than the 45 minutes – 2 hours I regularly spend on blog posts.
The last few months, I’ve been considering what to do about blogging. I could simply cut back the amount I write here. Except that regularly blogging forces me to think about what’s going on in the broader industry, and that’s important to me and I think makes me a better consultant. I could write a few short posts a week, and a bigger meatier post once or twice a month, but I’ve been me long enough to know that’s not the best solution. I could just keep going as I have been most of this year and just post when I have something to say and not worry about frequency.
I still don’t have the answer. Of course, there’s not a right answer, there’s just a move forward and do what works. I have a lot of travel coming up next month (including speaking at Activate: The ActiveCampaign Conference) so things might get wonky for a while. But, I’m not planning on giving up blogging.
One of the consequences of my time constraints is that I have handed comment moderation off to other folks. Comments might sit for longer than they used to before approval. They’re being processed, just a little more slowly than they have in the past. I don’t think it’s a big deal, it’s not like there’s a significant horde of commenters here. When I was moderating comments basically anything that contributed to the discussion and didn’t come from a forged email address was approved. The current policy is similar.
I am around on the email geeks slack channel, and am often talking about stuff on the deliverability channel.
Thus ends the housekeeping.
 

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Want some history?

I was doing some research today for an article I’m working on. The research led me to a San Francisco Law Review article from 2001 written by David E. Sorkin. Technical and Legal Approaches to Unsolicited Electronic Mail (.pdf link). The text itself is a little outdated, although not as much as I expected. There’s quite a good discussion of various ways to control spam, most of which are still true and even relevant.

From a historical perspective, the footnotes are the real meat of the document. Professor Sorkin discusses many different cases that together establish the rights of ISPs to filter mail, some of which I wasn’t aware of. He also includes links to then-current news articles about filtering and spam. He also mentions different websites and articles written by colleagues and friends from ‘back in the day’ discussing spam on a more theoretical level.
CNET articles on spam and filtering was heavily referenced by Professor Sorkin. One describes the first Yahoo spam folder. Some things never change, such as Yahoo representatives refusing to discuss how their system works. There were other articles discussing Hotmail deploying the MAPS RBL (now a part of Trend Micro) and then adding additional filters into the mix a few weeks later.
We were all a little naive back then. We thought the volumes of email and spam were out of control. One article investigated the effectiveness of filters at Yahoo and Hotmail, and quoted a user who said the filters were working well.

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EFAIL PGP / S/MIME "flaw" ?

There’s going to be a lot of hype today about something the security researchers who found it are calling “EFAIL”. Interviews, commemorative T-Shirts, press tours, hype.
The technical details are interesting, but the un-hyped end-user advice would probably be “If you’re using a mail client that’s got bugs in it’s MIME handling, and you’ve configured it to load remote content automatically, and you’re using a less secure encryption tool or protocol, and you’ve configured it to decrypt things automatically, and security of your email is so important to you that you’re defending against skilled attackers who have already acquired the encrypted emails you’re concerned about (by compromising your ISP? Sniffing non-TLS traffic?) then you may have a problem.”
I can’t imagine anyone for whom email security is a critical issue would make all those mistakes, so this mostly merits a heads-up to the MUA developers (which has happened) and maybe a “Do people rely on S/MIME? Why?” retrospective. But as someone on twitter described it “The Vulnerability Hype Train has begin, choo choo.”
 

 
There are several different issues all mixed together by the efail folks. All of them require an attacker to already have access to (encrypted) sensitive emails, and to send copies of those to you wrapped up in another message and to have you decrypt that incoming mail.

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Dodgy PDF handling at Gmail

We sent out some W-9s this week. For non-Americans and those lucky enough not to have to deal with IRS paperwork those are tax forms.
They’re simple single page forms with the company name, address and tax ID numbers on them. Because this is the 21st Century we don’t fill them in with typewriters and snail mail them out, we fill in a form online at the IRS website which gives us PDFs to download that we then send out via email.

We started to get replies from people we’d sent them to that we hadn’t included the tax ID number. Which was odd, because it was definitely there in the PDFs we’d sent.
The reports of missing numbers came from Google Apps users, so we sent a copy to one of our Gmail addresses to see. Sure enough, when you click on the attachment it’s mostly there, but some of the digits of the tax ID number are missing.

And all the spaces have been stripped from our address.

The rest of the form looked fine, but the information we’d entered was scrambled. Downloading the PDF from Gmail and displaying it – everything is there, and in the right place.
Weird. After a brief “Are gmail hiding things that look like social security numbers?” detour I realized that the IRS website was probably generating the customized forms using PDF annotations.
PDF is a very powerful, but very complex, file format. It’s not just an image, it’s a combination of different elements – images, lines, vector artwork, text, interactive forms, all sorts of things – bundled together into a single file. And you can add elements to an existing PDF file to, for example, overlay text on to it. These “annotations” are a common way to fill in a PDF form, by adding text in the right place over the top of an existing template PDF.
I cracked the PDF open with some forensics tools and sure enough, the IRS had generated the PDF form using annotations.
 

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Is purging always effective?

 

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Data never dies

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Anyone know why…

Countless questions about email troubleshooting start with “does anyone know why.” Unfortunately, most of these questions don’t contain enough detail to get a useful answer.

In the case of email, even the smallest redactions, like the IP address and the domain in question, can make it difficult for anyone to provide help. Details matter.
Every detail matters, sending IP and domain are just the beginning. Who’s doing the sending? What is their authentication setup? What IP are they using? How were the addresses collected? What is their frequency? What MTA is used? Are they linking to outside sites? Are they linking to outside services? Where are images hosted?  Is the mail going to the bulk folder or being rejected? What ISPs or filters are involved?
The relevant questions go on and on and on.
We send fairly detailed question lists to clients. I regularly look at them to try and make them shorter. But the reality is these are questions that are relevant. Without enough information we simply cannot troubleshoot delivery problems.
 

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How to hire an affiliate

Yesterday I talked about all the reasons that using affiliate email can hurt overall delivery. In some cases, though, marketing departments and the savvy email marketer don’t have a choice in the matter. Someone in management makes a decision and employees are expected to implement it.
If you’re stuck in a place where you have to hire an affiliate, how can you protect the opt-in marketing program you’ve so painstakingly built? Nothing is foolproof, but there are some ways you can screen affiliates.

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Affiliate marketing overview

Most retailers have realized that sending unsolicited email is bad for their overall deliverability. Still, the idea they can send mail to people who never heard of them is seductive.
Enter affiliate email. That magical place where companies hire an agency, or a contractor, or some other third party to send email advertising their new product. Their mail and company reputation is protected because they aren’t sending the messages. Even better, affiliates assure their customers that the mail is opt-in. I’m sure some of them even believe it.
The reality is a little different from what affiliates and their customers want to believe.

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SNDS issues and new Gmail

A bunch of folks reported problems with Microsoft’s SNDS page earlier today. This afternoon, our friendly Microsoft rep told the mailop mailing list that it should be fixed. If you see problems again, you can report it to mailop or your ESP and the message will get shared to the folks who can fix it.
The other big thing that happened today was Gmail rolled out their new inbox layout.
It’s… nice. I’ll be honest, I am not a big gmail user and have never been a huge fan. I got my first account way-back-during-the-beta. I used it to handle some of my mailing list mail. I could never work out how to get it to stop breaking threads by deciding to put some mail into the junk folder. I just gave up and went back to my shell with procmail (now sieve) scripts. I still have a couple lists routed to my gmail account, and the filtering is much improved – I can at least tell it to never bulk folder certain email.
The feature I’m really interested in is the confidential, expiring email. I’m interested in how that’s going to work with non-Gmail accounts. Within Gmail makes perfect sense, but I don’t think Gmail can control mail once it’s off their system.

My best guess is that Gmail will end up sending some type of secure link to recipients using non-Gmail mail servers. The message itself will stay inside Google and recipients will only be able to view mail through the web. That’s how the vast majority of secure mail systems work.
If anyone has the secure message already, feel free to send me a secure message. I’ll report back as to how it works.

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