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I have a web app which needs to send emails to clients 'From' staff email addresses. What's the best way to prevent my messages from being flagged as spam?

For instance, if I own charles@gmail.com, I'd like to be able to send mail "From" that address with PHP in my App, without getting the "This message may not have been sent by...." message.

Right now I'm just using the mail() function within PHP, with Headers for the From, Return Path, and X-Mailer variables.

I'm generally pretty confused by everything I've read so far about SPF and DKIM, so I appreciate any advice. Thanks.

Charles
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  • Some spamfilters use reverse DNS to check that the sender's domain really belongs to the sender (preventing spoofing of mailaddresses). You won't be able to do that for the gmail.com domain :) – PeeHaa Jun 29 '11 at 19:40

4 Answers4

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This is a very lengthy subject with lots of things to consider.

The most important rule is to not use HTML and to send only correct mails that people want, and that the recipients do not flag as spam theirselves.

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cweiske
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  • Google themselves state that "If the email wasn't sent with Gmail, but the sender includes authentication data in the message, we'll show you the sender's name and the service that authenticated the message." https://support.google.com/mail/troubleshooter/2411000?p=sent_warning&rd=1 This is likely the best solution - anyone know how to actually do this? – Nathan Hornby Mar 07 '14 at 11:49
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For instance, if I own charles@gmail.com, I'd like to be able to send mail "From" that address with PHP in my App, without getting the "This message may not have been sent by...." message.

If you own a gmail address you could just sent the messages via gmail's SMTP service, but keep in mind that gmail has a 500 email sent limit. Below is a topic describing how to use gmail's SMTP server with the popular PHPMailer.

Right now I'm just using the mail() function within PHP, with Headers for the From, Return Path, and X-Mailer variables.

Outsourcing this is probably the way to go using for example:

We also offer a Free Plan with 200 Email Credits per day.

To read pricing visit http://sendgrid.com/pricing.html

No monthly committments, no minimums, no limits. Just pay for what you use at $0.001 / email or less.

Email messages are charged at $0.10 per thousand.

http://aws.amazon.com/ses/pricing/

Just to name a few which are very cheap to use without any hassle/setup.

Alfred
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If instead of using the mail() function, you use an SMTP mailer such as the PEAR mailer package then you can send the mail using google's own SMTP servers. This will require you to provide the correct credentials to the google account you wish to send from. This should avoid the issue you are having.

hughes
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One of the first things you need to ensure is that the email "From:..." really is from your server e.g your_mailings@yourcompany.com and it must exist and be a valid email on the server where the script works. You should try setting the sendmail user at the top of your script (assumes Linux server):

ini_set('sendmail_from', 'your_email@your_server.com');

Then you add a "Reply-To:" header and use your staff addresses perhaps and recipients will at least seem to have got an email that can be replied to. Without that you probably won't even get as far as being spam, you will get blocked on the way there.

This thread shows some of that and note the comments on PHPMailer - it is a good way to handle mailing and I have found it more successful than simple mail(); PHP mail form isn't working

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Steve
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