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  • Which SMTP engine is your relay using?

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  • I'm running it through IIS 6.0.

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  • I'm admittedly weak with IIS and SMTP. check the SMTP log to see what you can find. It looks like your relay's accepting messages. It's a matter of seeing why it isn't sending them. 

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  • I am using the same setup with no issues. Here is a blog post that helped me verify all my settings: http://www.configureoffice365.com/configure-office-365-smtp-relay

     

    That should clarify things.

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  • Also, verify the credentials that you are using are correct.

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  • Credentials were one of the first things I checked. I'll go back over everything that is in that blog post and see if anything doesn't look good.

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  • Have you checked to make sure that the SMTP service is running? We had ours crash inexplicably and without any notification anywhere. Once we restarted it after looking in the services and seeing it listed as Stopped, everything went back to running happily.

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  • Okay, I was starting to work through the blog post and hadn't made any changes yet, and all of the application generated emails that had been queuing up were delivered to my inbox. Not sure what was wrong, but as it's working again I can remove this from my to-do list. Thanks everybody for the suggestions.

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  • Some sort of temporary service degradation?

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  • I'm not sure. I still don't know what caused it, but I have verified that new messages are successfully being relayed.

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  • Good to hear and good luck finding the cause.

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  • I would make sure the SMTP service starts on a reboot.  I don't think it does by default in Microsoft Server.  Maybe I'm wrong, but it seems like the relay only worked when using an admin credential and not a standard user.

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