How do you make sure email you send programmatical

Question

This is a tricky one and I've always relied on techniques, such as permission-based emails (i.e. only sending to people you have permission to send to) and not using blatantly spamish terminology.

Of late, some of the emails I send out programmatically have started being shuffled into people's spam folder automatically and I'm wondering what I can do about it.

This is despite the fact that these particular emails are not ones that humans would mark as spam, specifically, they are emails that contain license keys that people have paid good money for, so I don't think they're going to consider them spam

I figure this is a big topic in which I am essentially an ignorant simpleton.

Answer 1

You can tell your users to add your From address to their contacts when they complete their order, which, if they do so, will help a lot.

Otherwise, I would try to get a log from some of your users. Sometimes they have details about why it was flagged as spam in the headers of the message, which you could use to tweak the text.

Other things you can try:

• Put your site name or address in the subject
• Keep all links in the message pointing to your domain (and not email.com)
• Put an address or other contact information in the email

Answer 2

Delivering email can be like black magic sometimes. The reverse DNS is really important.

I have found it to be very helpful to carefully track NDRs. I direct all of my NDRs to a single address and I have a windows service parsing them out (Google ListNanny). I put as much information from the NDR as I can into a database, and then I run reports on it to see if I have suddenly started getting blocked by a certain domain. Also, you should avoid sending emails to addresses that were previously marked as NDR, because that's generally a good indication of spam.

If you need to send out a bunch of customer service emails at once, it's best to put a delay in between each one, because if you send too many nearly identical emails to one domain at a time, you are sure to wind up on their blacklist.

Some domains are just impossible to deliver to sometimes. Comcast.net is the worst.

Make sure your IPs aren't listed on sites like http://www.mxtoolbox.com/blacklists.aspx.

Answer 3

You need a reverse DNS entry. You need to not send the same content to the same user twice. You need to test it with some common webmail and email clients. Personally I ran mine through a freshly installed spam assassin, a trained spam assassin, and multiple hotmail, gmail, and aol accounts.

But have you seen that spam that doesn't seem to link to or advertise anything? That's a spammer trying to affect your Bayesian filter. If he can get a high rating and then include some words that would be in his future emails it might be automatically learned as good. So you can't really guess what a user's filter is going to be set as at the time of your mailing.

Lastly, I did not sort my list by the domains, but randomized it.

Answer 4

In addition to all of the other answers, if you are sending HTML emails that contain URLs as linking text, make sure that the URL matches the linking text. I know that Thunderbird automatically flags them as being a scam if not.

The wrong way:

Go to your account now: <a href="http://www.paypal.com.phishers-anonymous.org/">http://www.paypal.com</a>

The right way:

Go to your account now: <a href="http://www.yourdomain.org/">http://www.yourdomain.org</a>

Or use an unrelated linking text instead of a URL:

<a href="http://www.yourdomain.org/">Click here to go to your account</a>

Answer 5

Sign up for an account on as many major email providers as possible (gmail/yahoo/hotmail/aol/etc). If you make changes to your emails, either major rewording, changes to the code that sends the emails, changes to your email servers, etc, make sure to send test messages to all your accounts and verify that they are not being marked as spam.

Answer 6

I always use: https://www.mail-tester.com/

It gives me feedback on the technical part of sending an e-mail. Like SPF-records, DKIM, Spamassassin score and so on. Even though I know what is required, I continuously make errors and mail-tester.com makes it easy to figure out what could be wrong.