Problem configuring WSUS e-mail notifications using SMTP relay

Videik 71

Hi.

We are having problems configuring e-mail notifications from our WSUS server to an office365 recipient.
Our WSUS server along with other servers are on a private domain. The domain is not published to the internet.
We are looking for a way to configure sending of notifications from our wsus server using a virtual SMTP server
to relay to office 365 as described for example in this guide:
https://social.technet.microsoft.com/Forums/ie/en-US/f0c29236-fb3c-4e87-aac7-8a9a8a1f1c45/wsus-email-notifications-smtp-relay-office-365?forum=winserverwsus

We have configured the server the way this guide describes. If we press test to test sending email from e-mail server configuration under e-mail notifications the sending is apparantly OK. Nothing in the event log indicates what can be the problem.
Is there another location for specific SMTP logs?
The e-mail isn't recieved at the other end. And in the mailbox for the user we are using nothing appears in sent items or inbox.

The other question is have we configured the advanced delivery settings under properties - delivery - advanced correct?

The settings for now are:
Fully qualified domain name : as the complete domain name to our wsus server.
Smart host: as standard office 365 smtp server.
We have not written anything at masquerade domain.

On the e-mail server configuration at our wsus server we have used local ip-adress for server as outgoing server adress as described in the guide. Should we be using localhost (127.0.0.1) ip-adress instead?

We have also tried to add a sertificate for server authentification. The system log under windows logs in event viewer indicated that it could be a problem with TLS sertificate and that TLS was disabled for that reason. After we added a ceritifcate this problem was solved.

is there anyone with tips on to how to configure this properly and that maybe can point us to a working guide how to do this?

Rita Hu -MSFT 9,626 Reputation points

2021-10-21T08:11:57.227+00:00

Thanks for your posting on Q&A.

According to this Official Document, we could review the software distribution log to get more informations if the e-mail notification is not working properly. And I will leave the office tomorrow. I will come back next Tuesday and I'm sorry for the delay response.

Thanks for your understanding and cooperation. Have a nice day.

Regards,
Rita
Videik 71 Reputation points

2021-10-22T08:37:54.413+00:00

Thanks for imput on log files.

It seems after reading the log that the virtual smtp server get the message but is unable to resend it to our office 365 recipient.

Maybe this is a problem with the fully qualified domain name or smart host settings so we will have a look at those.

Regards,
Vidar
Videik 71 Reputation points

2021-10-22T13:37:05.193+00:00

If we look in SMTP-root at c:\ and files in the queue folder, the message appears here. So it is recieved by the virtual smtp server.
Rita Hu -MSFT 9,626 Reputation points

2021-10-26T07:55:51.787+00:00

@Videik
Sorry for the delay. I was out of the office last week. we're very sorry for any inconvenience that may caused.

As you mentioned above that the test email worked successfully. In fact, I'm not a expert in office 365. In order to resolve this issue as fast as possible, It is suggested to submit a service request to MS Professional tech support service so that a dedicated Support Professional can further assist with this request.

Here is a link for your reference:
https://support.microsoft.com/en-us/help/13948/global-customer-service-phone-numbers

Thanks for your understanding and cooperation.

Regards,
Rita
Videik 71 Reputation points

2021-10-29T12:33:48.657+00:00

Thanks for the input and a number to call.
We will contact global customer service, and ask.