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I am trying to use Office 365 Exchange as the mail transport for CiviCRM, but 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 have looked at enter link description here, and links therein which seemed to indicate that a STARTTLS issue was fixed.

Office 365 Exchange has these instructions for SMTP connections: enter link description here

I am running a development system under Windows so don't have a mail server on board, and in any case don't want to overcomplicate things - performance isn't an issue.

Any suggestions?

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Which version of civi are you using? https://issues.civicrm.org/jira/browse/CRM-14814 it's fixed on a fairly recent version of civicrm only

Another reason can be the confirguration of your network or your server: can you start a connection on port 587 to smtp.office365.com ?

However, before you spend too much time on it, last time I checked: - smtp on office365 was limited in volume, ie find at low volume, but won't work for production - 365 doesn't handle "+" notation, so and email to bounce+something@yourdomain.org won't end up in your bounce mailbox. This is needed to handle bounces in civicrm

so I would recommend you: if it's for testing purpose, use a gmail account if it's for production purpose, use an external provider to do the bulk mailing and integrate it with your civi, for instance sendgrid and this extension: https://civicrm.org/extensions/sendgrid-event-notification-processor

  • CiviCRM 4.7.16+, i.e. a pull from the latest master branch. I saw CRM-14814 that it was supposed to have been fixed, which is why I asked the question. It is not a production environment and the failure occurs at the Save and Test stage of setting up outbound emails. In other words, it is not even making the first connection. I can make a connection on that port using a putty terminal. What am I doing wrong?I have also tested out and concur that VERP doesn't appear to be supported - adding a redirection rule doesn't catch the bounce+ email before it is rejected. – Stephen Palmstrom Mar 2 '17 at 17:06

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