A client would like to send emails from their mojoPortal site using Office365 SMTP.

This is documented here: https://support.office.com/en-us/article/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-office-365-69f58e99-c550-4274-ad18-c805d654b4c4 

This is not working for us, trying settings like the following:

<add key="SMTPServer" value="smtp.office365.com" />
<add key="SMTPRequiresAuthentication" value="true" />
<add key="SMTPUseSsl" value="true" />
<add key="SMTPPort" value="587" />
 <add key="SMTPUser" value="a@b.com" />
<add key="SMTPPassword" value="xxxxxxxx" />

or

<add key="SMTPServer" value="smtp.office365.com" />
<add key="SMTPRequiresAuthentication" value="true" />
<add key="SMTPUseSsl" value="true" />
<add key="SMTPPort" value="25" />
<add key="SMTPUser" value="a@b.com" />
<add key="SMTPPassword" value="xxxxxxxx" />

We get this in the error log:

2018-03-23 10:29:56,567 ERROR xx.xx.xx.xx - en-GB - /contact-us - mojoPortal.Net.Email - all retries failed sending email to a@b.org.uk from a@b.com, message was: Crispin<br />xxxxxx@esdm.co.uk<br /><br /><p>test</p>
<br /><br />HTTP_USER_AGENT: Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/58.0.3029.110 Safari/537.36 Edge/16.16299<br />REMOTE_HOST: xx.xx.xx.xx<br />REMOTE_ADDR: xx.xx.xx.xx<br />LOCAL_ADDR: xx.xx.xx.xx<br />
System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [DB6PR0501CA0047.eurprd05.prod.outlook.com]
   at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCode, String response)
   at System.Net.Mail.MailCommand.Send(SmtpConnection conn, Byte[] command, MailAddress from, Boolean allowUnicode)
   at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
   at System.Net.Mail.SmtpClient.Send(MailMessage message)
   at mojoPortal.Net.Email.Send(SmtpSettings smtpSettings, MailMessage message)

I'm suspecting the mojoPortal code possibly doesn't support TLS1.0 or above? Is that it, or could it be something else?

thanks!

I have also successfully sent from a mojoPortal 2.4.1.0 installation. This is running on the same server as the 2.5.0.0 site where it succeeded.

So, it's either some difference between the two servers, or something wrong with the client's Office365 account or configuration.

Next test - try the client site using one of our Office365 accounts that worked above...

Already done!

I have now found that the client site CAN send email using my own Office365 account, so the issue is clearly not in mojoPortal or our server, it must be something to do with the Office365 config or the particular account.

So for the record, mojoPortal 2.4.1.0 and later can definitely send email using Office365 SMTP, which is nice to know.