1

Hi All ,

I am using office 365 cloud service as mail server but i am not able to send email notification in Wsus and Symantec end protection manger , I tired to configure smtp relay agent in sever 2008 but i am not able to resolve this .If any one have knowledge how to resolve this please help me out .

Thanks every one in advance

Regards

Sachin Verma

5 Spice ups
2

Give us some errors to work with, without errors it is likely your AV could be blocking these or perhaps firewall ports not being allowed

3

Hi Rod ,

Thanks for your reply . I checked av and firewall ports there is no issue in yhis side . Please find the error detail what i am getting .

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

at Microsoft.UpdateServices.Internal.BaseApi.SoapExceptionProcessor.DeserializeAndThrow(SoapException soapException)

at Microsoft.UpdateServices.Internal.DatabaseAccess.AdminDataAccessProxy.SendTestEmail(String emailLanguage, String smtpUserName, String senderEmailAddress, String smtpHostName, Int32 smtpPort, String recipients)

at Microsoft.UpdateServices.Internal.BaseApi.EmailNotificationConfiguration.SendTestEmail()

at Microsoft.UpdateServices.UI.SnapIn.Dialogs.EmailNotificationSettingsDialog.backgroundWorker_DoWork(Object sender, DoWorkEventArgs e)

I tried these links to resolve the issue but did not get any solution

http://www.configureoffice365.com/configure-office-365-smtp-relay/

Please look into this and help me out .

Thanks you in advance

Regards

Sachin verma

4

The error is simple, you are not authenticating or your system is not using or able to use TLS as per this guide.

Office 365 required an SMTP connection that supports TLS encryption and many legacy devices or applications don’t support this.

Either setup an internal IIS box to rely or use a system that supports TLS

1 Spice up
5

We moved a lot of our stuff to

Makes life easier and for alerting the $5 a month model does us

Or your ISP might have a relay open to their clients and source IPs

6

Hi Rod ,

I tried to set up smtp relay on server 2008 but this is not working can you please share any link i will follow and try to resolve this .

Thanks you in advance

7

what isn’t working - IIS relay is really simple - is this where you get the above error?

8

I tired to configure through this link .

http://www.configureoffice365.com/configure-office-365-smtp-relay/

But when i try to check to send test mail in wsus e mail notification same here i am getting what i already shared with you .

9

Your error is clearly marked in what you posted

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

Are you providing authentication details to be allowed to relay?

10

http://www.configureoffice365.com/wp-content/uploads/2012/01/2008-server-smtp-relay-office365-outbound-security.png

This as well as this, is key

The important information is:

11

Yup i am providing authentication details in relay

12

Your error above says you are not or the connection is not secure.

13

Rod ,

Can you please share any link to resolve this issue . I will highly indebted for you .

14

The first link you provided should be enough. please make sure you are using port 587 and TLS.

In the authentication box linked make sure you are using your O365 email address and password, NOT your domain credentials (in case you was)

http://www.configureoffice365.com/wp-content/uploads/2012/01/2008-server-smtp-relay-office365-outbound-security.png

your WSUS box MUST be pointing to your internal relay and NOT Office365 servers, the relay box will talk to O365 for you, which is why it is configured using TLS

15

Rod is correct based on the error you posted WSUS is not configured to use your relay, but is trying to contact Office 365 directly or you have configured the relay to require authentication/TLS for internal resources to communicate with it.

16

Hi Rod & Nathonsweetman

I have configured relay to require authentication/TLS for internal resources to communicate with it in local windows server 2008 . But this is not working

Regards

Sachin Verma

17

Sachin

I think you misunderstood me you should not force authentication/TLS for internal resources to the relay. You should configure the relay to allow internal resources to access it anonymously and restrict access by IP.

18

Another option would be to setup a relay on your O365 server, which will only allow connection via the IP you specify, and not use an account or encryption. I did this for some older equipment I have that doesn’t support TLS.

Here’s a how-to on getting it all setup:

http://community.spiceworks.com/how_to/98692-create-an-smtp-relay-in-o365-to-allow-a-unitrends-appliance-or-other-device-to-send-email-without-tls

1 Spice up