Office 365 & PHP mail

Our client recently switched to Office 365. Previously his email was hosted with his domain. He runs a web store and each time people order something or ask for info he receives an email about it. We had to adjust the PHP code of course in order to make it work with the smtp settings of Office 365.

Ever since the switch we noticed not everything is received by email when using the website forms or placing orders. We tested all email addresses with  testconnectivity.microsoft.com and found no problems. We checked the Mail flow in Exchange and the missing emails are nowhere to be found. We double checked the SPF records to be sure, everything is ok.

Is Microsoft forbidding you to use PHP mail with Office 365?
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IT MeetjeslandAsked:
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Julian HansenCommented:
Is Microsoft forbidding you to use PHP mail with Office 365?

How would MS know? Sending an email is a process of connecting to an SMTP server and passing the message on - the application that actually does that is mostly obscured from the process.

When you made the change - what else changed?
Are you sending through a different server?
Is it possible the mails are being blocked as spam?
On the Web server are there logs you can examine to see the status of the delivery to the SMTP server - that is where you should start. Start from where the email is generated - check what that connects to and check the logs - if nothing found then check what the next step in the process is - usually the receiving SMTP server - check the logs there and so on.
Ray PaseurCommented:
Short answer, No.  Microsoft does not care.  

Longer answer, Email is the wrong tool (and always has been the wrong tool) for eCommerce.  It seemed to make sense a dozen years ago, but that is ancient history now.  When you buy something from Amazon or eBay, do you think there are people sitting around waiting to receive email messages?  Of course not!  You might want to encourage your client to refactor the application into a traditional eCommerce platform.

There are many things that can go wrong with email including spam filters.  And there is no accountability for the messages - everything in the message can be spoofed.  If you have a dependency on email, you might want to consider working with one of the professional email firms like ConstantContact.  They have it figured out; most of the rest of us do not.
Dave BaldwinFixer of ProblemsCommented:
Actually Microsoft does care and they can detect whether the emails came from the web page or from a regular email client.  I have done the tests.  An email sent from a PHP web form and from a desktop email client thru the mail server for the same site will be treated differently.  The one from the web form was ignored and the one from the desktop was received.

It may also depend on the 'reputation' of your mail server, at least that's what the Microsoft page on the subject says.  http://mail.live.com/mail/troubleshooting.aspx
Mark GalvinManaging Director / Principal ConsultantCommented:

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IT MeetjeslandAuthor Commented:
We moved the website to another hosting, everything is working fine now. The current hosting was blocking the use of secure SMTP for office 365.
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