Recent Posts

Spam is about invading other people's space

At the recent Sendgrid Emailmatter’s conference Sally Lehman advised attendees to “Treat someone’s inbox like it was their home.” This is advice I’ve been giving clients for a long time. I think it’s even more relevant now as so many people have data enabled phones and are checking email so frequently. It’s not just their home, it’s their personal space they can take with them.
Seanan McGuire, a friend and NY Times bestselling author, wrote a blog post today about how she views promotion and marketing as an artist and someone who is expected to promote her work. She also talks about what it feels like to be a target of promotion and offers some advice about how to promote your products online.  She talks about how she, as an author and creative type, is expected to do some level of self promotion and how that promotion is done in her space – whether that space be on twitter or her blog.

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November 2014 – the month in email

Over the years, we get many of the same questions again and again. This isn’t a complaint; it’s a useful opportunity for us to check in and see if the technologies, policies and best practices have evolved over time, or if our previous recommendations still stand. One example this month of something that has changed (the situation has improved a bit): Using URL shorteners and one that has not: The Best Time to Send Email.

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Congestion at Verizon

Yahoo! finally found their broken cable (I had no idea Yahoo had fiber) and fixed it. Now, I’m seeing a lot of reports that Verizon is accepting mail very, very slowly. Some folks are reporting no more than 20 messages a minute. This could be due to congestion, and just an underpowered system, or it could be some purposeful throttling on Verizon’s end.
In any case, this is affecting a lot of senders and not just the marketing end of things.
Updates as I get them.

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Friendly email addresses

Most of the time when we’re talking about email addresses, we’re talking about the actual user@domain format that’s used to send mail over the wire, but that’s not how we most often see them. When they’re used in a To: or From: header they’re usually associated with a display name – the “real name” of the user with the associated email address. In the From: field that’s often called the “friendly from”, but the syntax used in the To:, Cc: and Bcc: fields is identical.
The display name is important, as it’s shown more in mail clients than the actual email address is. Some mobile clients don’t display the email address at all, just the display name.
There are three ways you can put an email address in a header field.
The best way is to wrap the email address itself in angle brackets, and put the display name in front of it.

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My holiday email prediction

I was on IRC with a group of ESP delivery specialists last week and one of them was looking for something to blog about. I suggested a list of holiday predictions. Not that I have a huge number of holiday predictions, but I did come up with one.
During the holiday season at least one retailer will decide that they have information so important that they will ignore my opt-0ut request and add me to their holiday blast list.
So what’s your holiday email prediction?
 

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Yahoo problems

I’m seeing scattered reports today that a lot of places are seeing backed up queues to Yahoo. They’ve had some problems over the last few days and seem to be still recovering. It’s looking like it’s something internal to Yahoo. One set of error messages I’ve seen reported by numerous people is: “451
4.3.2 Internal error reading data.”
It’s not you, and it’s not spam related. But it is putting a crimp in a lot of companies attempts to send lots of email ahead of black friday and cyber monday.

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Changing the email client

We’re in the thick of hiring and next week is Thanksgiving, so blogging is going to be very light for the next two weeks.
One thing I have noticed is that lately there are attempts to “change how people interact with email.” Google released their Inbox product. And today I saw a post about an IBM attempt to change email and how people use it as a tool.
I find as I juggle more and more incoming email that most email clients just don’t cope with the whole process well. For a long time I could use my inbox as a todo list and manage what needed to be done. With the company growing and changing, an inbox todo list is just not as workable as it used to be. Maybe the Verse client from IBM is one solution.
I’m glad people are looking at how to improve the email client. Fundamentally, the client I’m using now is not that much different than the GUI client I was using at MAPS back in 2000 and 2001. Sure, it’s visually different, but the functionality isn’t much different.
A few years ago I blogged that people should look at building new email interfaces. I’m glad that some companies are actually looking at the interface and rethinking how people interact with email. Who knows, maybe we’ll end up with some specialized clients that are featured around getting work done by email and other clients focused around a more casual use of email, like shopping and networking.
 
 

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Cloud sending with Momentum from MessageSystems

Earlier this week MessageSystems announced a new cloud platform, SparkPost, letting smaller companies have access to the power of the MessageSystems’s Momentum platform.
MessageSystems announced this at their user conference in San Diego. There was a lot of great information from ISPs and Momentum customers presented at the conference. If you get a chance check out the conference tweet stream (#msusercon) and the tweets by their director of Industry Relations Len Schneyder.
Now everyone can use the Momentum engine to send mail and take advantage of the features designed for large companies to communication with their millions of customers.

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STARTTLS and misplaced outrage

About a month ago someone posted a heavily elided screenshot that they claimed was evidence of their ISP, AT&T, sabotaging SMTP connections being sent over their network, meaning that anyone could sniff their passwords and traffic.
This is it:
STARTTLS-tampering
 
 
Most email people looking at that saw the asterisks in the banner and went “Oh. That’s not the ISP tampering with the traffic, the person running the mailserver doesn’t know how to configure their PIX firewall.”
It’s a very, very, very, well known issue.
But some groups who should know better, such as Ars Technica and the EFF, don’t seem to understand – even when they know about PIX fixup – that this isn’t tampering by intermediate ISPs, it’s just the operator of the mailserver in question not knowing how to configure his firewall. And it’s not a general attempt by consumer ISPs to “tamper with email encryption”, it’s just the operator of one mailserver not knowing how to configure his firewall.
PIX is a simple NAT/firewall appliance from Cisco. It’s a reasonable firewall, but it has some quirks. One of them is it’s “MailGuard” or “SMTP fixup” feature. When that’s turned on, it intercepts SMTP traffic and “sanitizes” it, to protect the mailserver from hostile traffic. To do this, it does a couple of things. One is that it blocks any attempt at sending a command that’s not one of the bare basic SMTP commands, by intercepting them and rejecting them with the error “502 5.5.2 Error: command not recognized”. The other is that it hides the software that’s running on the mailserver, removing any mention of it from the banner string sent when you connect. In fact, it replaces any character other than “2” or “0” with an asterisk.
I had an old PIX that I’ve not used in years, so I thought I’d set it up to show you. Here it is, being guarded by Freddy Chimpenheimer.
pix
I set it up as though it was protecting our mailserver.
Here’s what happens when I connect to the mailserver with the PIX configured correctly:
7__steve_infrastructure_____ssh_
And here’s what happens when I configure the PIX to use “fixup protocol smtp 25” and try and connect to the mailserver again:
7__steve_infrastructure_____ssh_
Looks pretty similar to the “ISP tampering with the traffic” screenshot this all started with. I’m using an older PIX firmware image (I really didn’t want to spend the time and money to upgrade my PIX) so it errors out on EHLO, rather than just on STARTTLS. And because this old firmware doesn’t support EHLO, you also don’t see it using “XXX” to block out the string “STARTTLS” in the response to EHLO – the line in the original that says “250-XXXXXXXXA” said “250-STARTTLSA” before the PIX censored it.
Now I have those screenshots I’m going to disconnect my PIX and put it back in the pile of spare networking gear.
So the whole issue is just a mailserver operator who has a badly misconfigured firewall in front of his mailserver, nothing more.

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Email problems are costly

Last week Zulily released their quarterly earnings. Their earnings’ report was disappointing, resulting in a drop in their stock prices. The chairman of the company told reporters on a conference call that part of the reason for the drop in earnings were due to deliverability problems “at a large ISP.”

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