Send Email using Outlook through PHP Pear - php

Question

I'm trying to send an email using PHP Pear. It works when I send email using Gmail with this settings:
$smtp = Mail::factory('smtp', array(
'host' => 'ssl://smtp.gmail.com',
'port' => '465',
'auth' => true,
'username' => 'username#gmail.com',
'password' => 'password!2016'
));
But before I make this work, I have to "allow less secure apps" to access my account, which you can read here on how to do it.
I tried to use an Outlook account with this settings:
$smtp = Mail::factory('smtp', array(
'host' => 'tls://smtp.office365.com',
'port' => '587',
'auth' => true,
'username' => 'email#domain.org',
'password' => 'greatPasswordComesWithGreatResponsibilities'
));
but I get this error:
Failed to connect to ssl://smtp.office365.com:587 [SMTP: Failed to connect socket: fsockopen(): unable to connect to ssl://smtp.office365.com:587 (Unknown error) (code: -1, response: )]
I checked the official article by Microsoft regarding their SMTP settings. So I thought I have the right settings, but it's not working.
Am I missing something? Why do I get this error? Is there a setting I have to configure in my outlook account, like with the Gmail, before a third party app be allowed to send email?

Answer 1

This may not help but the title of your post just said Outlook account but the link and smtp settings refer to Office365 for Business accounts. I can't shed any light on the business account but if you actually have a personal Outlook.com account the settings are different. And, there is an option on the account you must change to enable pop/smtp access as you did with gmail.
The official Microsoft article is:
https://support.office.com/en-us/article/Add-your-Outlook-com-account-to-another-mail-app-73f3b178-0009-41ae-aab1-87b80fa94970?ui=en-US&rs=en-US&ad=US&fromAR=1
But, the summary is the smtp server is smtp-mail.outlook.com and to enable pop/smtp in your Outlook account look for Options > Managing your account > Connect devices and apps with POP.
Update:
If you are actually using business account, you should check this post which claims to have it working: https://stackoverflow.com/a/26004690/2891120
The key item in his code is he doesn't have "tls://" in front of the host name. I have a consumer outlook account and get a similar socket failure to you with tls:// prefix. If I remove that prefix I get much farther (set debug=true in factory) but fail later with an auth failure. Using 5.2.16 PHPMailer instead I successfully send mail but the headers leave me worried about spam rejection rates (no DKIM, SPF was softfail for my AWS entity, warning about -f, and others). And, the email did end up in the junk folder of my other test recipient #outlook.com. But I digress.