The death of IP based reputation

Back in the dark ages of email delivery the only thing that really mattered to get your email into the inbox was having a good IP reputation. If your IP sent good mail most of the time, then that mail got into the inbox and all was well with the world. All that mattered was that good IP reputation. Even better for the people who wanted to game the system and get their spam into the inbox, there were many ways to get around IP reputation.
Every time the ISPs and spam filtering companies would work out a way to block spam using IP addresses, spammers would figure out a way around the problem. ISPs started blocking IPs so spammers moved to open relays. Filters started blocking open relays, so spammers moved to open proxies. Filters started blocking mail open proxies so spammers created botnets. Filters started blocking botnets, so spammers started stealing IP reputation by compromising ESP and ISP user accounts.  Filters were constantly playing catchup with the next new method of getting a good IP reputation, while still sending spam.
While spammers were adapting and subverting IP based filtering a number of other things were happening. Many smart people in the email space were looking at improving authentication technology. SPF was the beginning, but problems with SPF led to Domains Keys and DKIM. Now we’re even seeing protocols (DMARC) layered on top of DKIM. Additionally, the price of data storage and processing got cheaper and data mining software got better.
The improvement in processing power, data mining and data storage made it actually feasible for ISPs and filtering companies to analyze content at standard email delivery speeds. Since all IPv4 addresses are now allocated, most companies are planning for mail services to migrate to IPv6. There are too many IPv6 IPss to rely on IP reputation for delivery decisions.
What this means is that in the modern email filtering system, IPs are only a portion of the information filters look at when making delivery decisions. Now, filters look at the overall content of the email, including images and URLs. Many filters are even following URLs to confirm the landing pages aren’t hosting malicious software, or isn’t content that’s been blocked before. Some filters are looking at DNS entries like nameservers and seeing if those nameservers are associated with bad mail. That’s even before we get to the user feedback, in the form of “this is spam” or “this is not spam” clicks, which now seem to affect both content, domain and IP reputation.
I don’t expect IP reputation to become a complete non-issue. I think it’s still valuable data for ISPs and filters to evaluate as part of the delivery decision process. That being said, IP reputation is so much less a guiding factor in good email delivery than it was 3 or 4 years ago. Just having an IP with a great reputation is not sufficient for inbox delivery. You have to have a good IP reputation and good content and good URLs.
Anyone who wants good email delivery should consider their IP reputation, but only as one piece of the delivery strategy. Focusing on a great IP reputation will not guarantee good inbox delivery. Look at the whole program, not just a small part of it.

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DNS, SERVFAIL, firewalls and Microsoft

When you look up a host name, a mailserver or anything else there are three types of reply you can get. The way they’re described varies from tool to tool, but they’re most commonly referred to using the messages dig returns – NXDOMAIN, NOERROR and SERVFAIL.
NXDOMAIN is the simplest – it means that there’s no DNS record that matches your query (or any other query for the same host name).
NOERROR is usually what you’re hoping for – it means that there is a DNS record with the host name you asked about. There might be an exact match for your query, or there might not, you’ll need to look at the answer section of the response to see. For example, if you do “dig www.google.com MX” you’ll get a NOERROR response – because there is an A record for that hostname, but no answers because there’s no MX record for it.
SERVFAIL is the all purpose “something went wrong” response. By far the most common cause for it is that there’s something broken or misconfigured with the authoritative DNS for the domain you’re querying so that your local DNS server sends out questions and never gets any answers back. After a few seconds of no responses it’ll give up and return this error.
Microsoft
Over the past few weeks we’ve heard from a few people about significant amounts of delivery failures to domains hosted by Microsoft’s live.com / outlook.com, due to SERVFAIL DNS errors. But other people saw no issues – and even the senders whose mail was bouncing could resolve the domains when they queried Microsofts nameservers directly rather than via their local DNS resolvers. What’s going on?
A common cause for DNS failures is inconsistent data in the DNS resolution tree for the target domain. There are tools that can mechanically check for that, though, and they showed no issues with the problematic domains. So it’s not that.
Source ports and destination ports
If you’re even slightly familiar with the Internet you’ve heard of ports – they’re the numbered slots that servers listen on to provide services. Webservers listen on port 80, mailservers on port 25, DNS servers on port 53 and so on. But those are just the destination ports – each connection comes from a source port too (it’s the combination of source port and destination port that lets two communicating computers keep track of what data should go where).
Source ports are usually assigned to each connection pretty much randomly, and you don’t need to worry about them. But DNS has a history of the source port being relevant (it used to always use source port 53, but most servers have switched to using random source ports for security reasons). And there’s been an increasing amount of publicity about using DNS servers as packet amplifiers recently, with people being encouraged to lock them down. Did somebody tweak a firewall and break something?
Both source and destination ports range between 1 and 65535. There’s no technical distinction between them, just a common understanding that certain ports are expected to be used for particular services. Historically they’ve been divided into three ranges – 1 to 1023 are the “low ports” or “well known ports”, 1024-49151 are “registered ports” and 49152 and up are “ephemeral ports”. On some operating systems normal users are prevented from using ports less than 1024, so they’re sometimes treated differently by firewall configurations.
While source ports are usually generated randomly, some tools let you assign them by hand, including dig. Adding the flag -b "0.0.0.0#1337" to dig will make it send queries from  source port 1337. For ports below 1024 you need to run dig as root, but that’s easy enough to do.
A (slightly) broken firewall
“sudo dig -b "0.0.0.0#1024" live.com @ns2.msft.net” queries one of Microsofts nameservers for their live.com domain, and returns a good answer.
“sudo dig -b "0.0.0.0#1023" live.com @ns2.msft.net” times out. Trying other ports above and below 1024 at random gives similar results. So there’s a firewall or other packet filter somewhere that’s discarding either the queries coming from low ports or the replies going back to those low ports.
Older DNS servers always use port 53 as their source port – blocking that would have caused a lot of complaints.
But “sudo dig -b "0.0.0.0#53" live.com @ns2.msft.net” works perfectly. So the firewall, wherever it is, seems to block DNS queries from all low ports, except port 53. It’s definitely a DNS aware configuration.
DNS packets go through a lot of servers and routers and firewalls between me and Microsoft, though, so it’s possible it could be some sort of problem with my packet filters or firewall. Better to check.
“sudo dig -b "0.0.0.0#1000" google.com @ns1.google.com” works perfectly.
So does “sudo dig -b "0.0.0.0#1000" amazon.com @pdns1.ultradns.net“.
And “sudo dig -b "0.0.0.0#1000" yahoo.com @ns1.yahoo.com“.
The problem isn’t at my end of the connection, it’s near Microsoft.
Is this a firewall misconfiguration at Microsoft? Or should DNS queries not be coming from low ports (other than 53)? My take on it is that it’s the former – DNS servers are well within spec to use randomly assigned source ports, including ports below 1024, and discarding those queries is broken behaviour.
But using low source ports (other than 53) isn’t something most DNS servers will tend to do, as they’re hosted on unix and using those low ports on unix requires jumping through many more programming hoops and involves more security concerns than just limiting yourself to ports above 1023. There’s no real standard for DNS source port randomization, which is something that was added to many servers in a bit of a hurry in response to a vulnerability that was heavily publicized in 2008. Bind running on Windows seems to use low ports in some configurations. And even unix hosted nameservers behind a NAT might have their queries rewritten to use low source ports. So discarding DNS queries from low ports is one of the more annoying sorts of network bugs – one that won’t affect most people at all, but those it does affect will see it much of the time.
If you’re seeing DNS issues resolving Microsoft hosted domains, or you’re seeing patterns of unexpected SERVFAILs from other nameservers, check to see if they’re blocking queries from low ports. If they are, take a look and see what ranges of source ports your recursive DNS resolvers are configured to use.
(There’s been some discussion of this recently on the [mailop] mailing list.)

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Weird mail problems today? Clear your DNS cache!

A number of sources are reporting this morning that there was a problem with some domains in the .com zone yesterday. These problems caused the DNS records of these domains to become corrupted. The records are now fixed. Some of the domains, however, had long TTLs. If a recursive resolver pulled the corrupted records, it could take up to 2 days for the new records to naturally age out.
Folks can fix this by flushing their DNS cache, thus forcing the recursive resolver to pull the uncorrupted records.
EDIT: Cisco has published some more information about the problem. ‘Hijacking’ of DNS Records from Network Solutions

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Mail that looks good on desktop and mobile

Over the weekend I noticed a new CSS framework aimed at email rather than web development, “Antwort“.
This isn’t the first or only framework for email content, but this one looks simple and robust, and it allows for content that doesn’t just adapt for different sized displays but looks good on all of them. The idea behind it is to divide your content into columns, magazine style, then display the columns side-by-side on desktop clients and top to bottom on mobile clients. That opens up much more interesting designs than the more common single fluid column approach.

It looks nice, it supports pretty much every interesting email client, but it also comes with some directions based on real world experience.

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