Reputation and "the cloud"

As Reddit recently learned it’s not a great idea to use the Amazon EC2 cloud to host mailservers. There are a number of reasons for this, most of them related to the reputation of mail coming from EC2 servers.
When you’re using machines in the cloud, changing IP addresses is as simple as initializing a new server. Spammers discovered this almost as soon as the EC2 cloud became public. They would set up a mailserver and send spam through that server until it was blocked. Then they’d just start another instance to avoid the block and keep spamming. They had an almost unlimited number of IP addresses to abuse and moving around was easy to do. Amazon did little to stop the spam coming from the cloud so many ISPs and spam filtering companies blocked email from the entire range of IP addresses allocated to the EC2 cloud.
Blocking large swathes of network space that are consistent sources of abuse is well accepted as a method of dealing with spam. Yes, this form of blocking has inconvenienced legitimate companies who aren’t actually doing anything wrong. But when a service provider doesn’t take sufficient action to stop customers from spamming through their networks, then ISPs will implement countermeasures.

Reddit and email
ISPs may face blocking challenges

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Reddit and email

Ben over at Mailchimp writes about Reddit discovering a lot of their mail was being blocked because they were sending from the Amazon EC2 cloud.

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Reputation

It used to be that every potential client that called me up to ask me to help them with their delivery issues would tell me they weren’t a spammer. Over the last year or so that’s changed to telling me that they have a good reputation and don’t understand why they’re having delivery problems.
This leads me to believe that there is some confusion about what reputation is and what reputation is not.
Reputation is a shorthand term for a complex formula measuring the history of email from an IP address. Some reputation schemes measure the history of email containing a particular URL or domain.
Recipient domains measure a lot of things and use them at various points during the email transaction. Some measurements are integrated into a single value that is queried during the SMTP transaction. If the measurement is too bad, the email is rejected or rate limited. Other measurements are queried after the email is accepted by the ISP, and those values determine if an email is delivered to the inbox or the bulk folder.
There are a couple important things to remember about reputation.

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How reputation and content interact

Recently, one of my clients had a new employee make a mistake and ended up sending newsletters to people in their database that had not subscribed to those particular newsletters. This resulted in their recipients getting 3 extra emails from them. These things happen, people fat-finger database queries or aren’t as careful with segmentation as they should be.
My clients were predictably unhappy about sending mail their users hadn’t signed up for and asked me what to do to fix their reputation. I advised they not do anything other than make sure they don’t do that again. The first send after their screw-up had their standard 100% inbox delivery. The second send had a significant problem with bulk foldering at Hotmail and Yahoo. The third send had their standard 100% inbox delivery.
So what happened on the second send? It appears that on that send they had a link or other content that “filled the bucket.” Generally, their IP reputation is high enough that content isn’t sufficient to send their mail into the bulk folder. However, their reputation dipped based on the mistake last week, and thus the marginal content caused the bulk foldering.
Overall, these are senders with a good reputation. Their screw up wasn’t enough to damage their delivery itself, but may have contributed to all their mail going into the bulk folder the other day. I expect that their reputation will rebound quickly and they will be able to send the same content they did and see it in the inbox.

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