SMTP Relay in IIS not delivering e-mail most of the time

G

Gary OConnor

Hello all,

I have recently started a new role and am learning the many systems in place. All users use O365 for e-mail, we previously had an on-prem Exchange.

All multi function printers are on their own subnet and VLAN so it's not possible to configure each device to scan directly to smtp.office365.com so it has been setup by the previous IT Manager that they relay to the old on prem exchange server where IIS Manager has been configured to act as an SMTP Relay. This was working perfectly well.

A strange problem has just occurred where most (but not all users) can no longer scan to e-mail. From the printer, the job is processed without error but the e-mail is not received.

It's so bizarre because if I do a scan to e-mail to my email, it doesn't work and the same for many others yet my colleagues comes through instantly. Our e-mail addresses are in the same format, same domain, etc

I have looked at the event logs and there is an error about the mail server certificate being expired, this probably needs addressing but having checked, the certificate has been expired for

nearly 2 years. I don't really want to change this at the moment as don't think this is linked and don't want to make things worse. I have tried restarting the server which made no difference. I have also checked that the credentials used for SMTP are correct and that I can log on to an Office 365 mailbox with them.

I have attached an image of the setup in IIS and a typical printer config. I have not done much at all in IIS unfortunately so going in a bit blind here so any help would be much appreciated.

1540317.jpg1540318.jpg

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