Outgoing mail test fail to O365

[Joe]

Hi,

Just realised that our outgoing mail to O365 from Service Manager is not going, and the test button confirms it. Outgoing via Hornbill was ok but that's not what we need. The config looks ok to me.

Example errors attached, extract below:

Unable to login to the SMTP server

HornbillMailLog VerifySmtpLogin: DllDate: Mar 18 2019 ....

........ --sendCmdToSmtp readSmtpResponse: Failed to read beginning of SSL/TLS record. b: 0 dbSize: 0 nReadNBytes: 0 idleTimeoutMs: 30000 Failed to receive more TLS application data. tlsApp: Socket operation timeout. elapsedMs: Elapsed time: 30919 millisec idleTimeoutMs: 30000 --readSmtpResponse --auth_login Failed to login using LOGIN method --smtpAuthenticate --smtpAuthenticate --smtpConnectAndAuthenticate initSmtp: Socket operation timeout. Failed. --VerifySmtpLogin --ChilkatLog

 

[Keith Stevenson]

Joe,

Thanks for the post.  I have edited your post to remove the TXT files you added which contained your  account details for the O365 accounts. As for the error. This suggests as office 365 problem. Can you confirm that you can log via Office365 and that says no error in status

Kind Regards

 

 

 

[Joe]

Oops. Thanks for removing the attachments, and prompt response Keith.

I confirmed that I can log on to O365 with the accounts associated with the Shared Mailboxes. I noticed that the test error has a Hornbill from address that may explain the failure. "sendMailFrom: mailFrom: do-not-reply@live.hornbill.com sendCmdToSmtp: SmtpCmdSent: MAIL FROM:<do-not-reply@live.hornbill.com><CRLF> --sendCmdToSmtp --sendMailFrom"

So I tried manually sending using the action button: Only when the send account that matches the account for configued outgoing mail  in Admin does it work. It does not work with a different account specified in Admin and when using the Acion button. So there's 2 things:

Should the test button work with O365?

How can I use different outgoing mailboxes if there's only a single O365 logon specified in Outgoing Mail? Perhaps creating the mailboxes first messed it up, and the "automatically create" option didn't work?

 

[Joe]

Hi, sorry to chase but I urgently need a resolution based on the question above/below 

How can I use different outgoing mailboxes if there's only a single O365 logon specified in Outgoing Mail? Perhaps creating the mailboxes first messed it up, and the "automatically create" option didn't work?

[Martyn Houghton]

@Joe

We have multiple shared mailboxes setup which use a common outgoing mail server.

The account that you are putting in the outgoing mail server, must have SendAs permission on the other mailboxes you want to send from. 

Then under each Hornbill shared mailbox you specify the emails addresses you want to be able SendAs from the shared mailbox, you can have more than one but you need to specify one as default.

Then when you send an email from the shared mailbox it will come from the email address you linked to the shared mailbox not the one that is associated with the outgoing mail server.

Cheers

Martyn

 

[Joe]

Thanks Martyn, that seems to work.