Heritage Cirqa SMTP mail through Office 365

[Wcallender]

Hi all

 

Has anyone who uses Cirqa and office 365 had any luck getting cirqa to send mail?

 

I've followed MS's guide to setting up application SMTP to the letter and Cirqa can not send. After a few calls with iso oxford we've run through a few different options and are now discovering that MS themselves are kicking back authentication as per the cirqa mail log:

 

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 [HE1PR0402CA0015.eurprd04.prod.outlook.com]

 

I've got a feeling that the words "anonymous" and "Mail From" are Microsoft's way of telling us that the mail headers are not being populated with a mail from address.

 

Before i go through the MS support process just wanted to ask if anyone else has run into this issue?