Moodle Email and TLS/Live@Edu

[Mr.Ben]

I'm in the process of moving our VLE offering to Moodle 2.2-

I'm stuck on setting up the Email messaging options. We use the SFGfL and using our old easymail settings for the SMTP server work correctly, moodle can send notifications.

However I moved away from using Easymail some time ago, and wish to use my live@edu settings instead.

Live@edu settings are as follows:

SMTP server: podxxxxxd.outlook.com:587 (where xxxxx is our detail)
username: xxx@xxx.org.uk (where xxx is the username/domain)

There is no option for TLS, so I added TLS:// to the SMTP server as instructed here: Messaging settings - MoodleDocs - No Joy (SMTP cannot authenticate)

I have also tried the workaround given here: [#MDL-30960] No option in email settings to speccify SSL or TLS (SMTPSecure property of PHPMailer) - Moodle Tracker - No joy again, although all I get is a blank screen.

Anyone have any suggestions. I suspect a firewall issue myself.

Regards, Ben

[jamesbmarshall]

How to configure an SMTP relay for Office 365 - Have you tried following the steps outlined here? (I can't guarantee this is true for Live@edu too, without testing).

[nadeem]

It would be interesting to know, as we use live@edu as well

[PiqueABoo]

I don't love the steps outlined in the KB (IIRC some is recycled from old documentation, the *.com bit is guaranteed to trip some folk up), but I'm 100% certain you can use the IIS SMTP service to relay mail out through Live@Edu in that manner. Know it works on server 2008 R2, and see no reason whatsoever why it wouldn't on 2008 and 2003. If you use that KB then you do it with the IIS 6.0 Manager and it's simplest to do all the configuration it mentions (Basic Authentication, credentials, TLS, port 587, smarthost, Relay restrictions) on the SMTP virtual server properties i.e. do not make a Domains->*.com entry.

Possible gotchas: Your LAN or RBC/LA/ISP don't let port 587 traffic out to the MS Live@Edu servers. AV software has been known to block all outbound SMTP related connections as potential spambots. You must configure anything sending mail this way to send mail with a From address which matches the mail address for the Live@Edu account used by the SMTP service. It gets used too much for diverse recipients and the Live@Edu account hits the Live@Edu recipient limits.