sending mail with php & escaping hotmails junk folder

Question

I have been trying to get PEAR::mail to successfully deliver emails to hotmail users without being flagged as SPAM and ending up in the junk folder, i have no problems with

Answer 1

Email Deliverability is closer to an art than a science. I can pretty much guarantee that it has nothing to do with your headers. Trying to spoof headers is likely the worst thing you can do. The received: header is added by the mail servers as they receive the messages: spoofing this will cause your email to get flagged as spam: one of the spam filters commonly used is to count then number of relays (ie received: headers). If there's too many you get a higher spam score.

Reverse DNS and SPF are the minimum entry barriers. For hotmail in particular, there are three other very important factors AFTER you get your SPF and DNS records in line:

• IP/Domain Reputation
• Volume
• Being in the Address Book

Reputation isn't the same as being blacklisted. You need to build trust with hotmail. Hotmail uses Sender Score Certified as their main reputation broker -- you can check your reputation with them if you want, but it may cost you.

If you're on a shared host or an IP address that has a checkered past, you won't have much luck with hotmail.

You build reputation by having a consistent volume with low spam complaints. You can send 1M messages an hour all day long, as long as you do it every day. If you're sending less than 10,000 messages a day, you likely won't be able to build up a decent reputation. You can get a report on your volume at Sender Base.

Finally, the best way to make sure you end up in the inbox is to get your users to add the sending email address to their address book. Hotmail uses this as a safe sender list. In fact, I think there's an additional trusted sender option in Hotmail now too (it's been awhile since I've been in the delivery game and I don't use hotmail).

Here are some other best practices for sending email:

• ALWAYS use the same IP address
• ALWAYS use the same FROM address
• if you have a large list that you send newsletters to, make sure you retire old addresses (ie, check open rates)
• if you have a large list, try segmenting it and sending from different IP addresses based on risk (ie, newer addresses may mark the message as spam)