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SharePoint 2013 which has been sending emails with no issues since 2014.

This past October, staff noticed that emails being sent to addresses outside of their domain weren't not being sent. This included emails sent to SharePoint users which have email addresses outside the domain and to email addresses not associated with SharePoint users.

The issue is with all external emails, both as part of workflows and not.

We've tried all the commonly recommended troubleshooting. There is a receive connector configured correctly in Exchange. Outgoing email configuration settings are configured correctly in Central Admin and for specific SP applications.

All of the workflows are 2010 workflows.

There are no known changes to the SharePoint configuration that happened between the last time external emails were sent successfully and when they stopped being sent.

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  • I would continue troubleshooting on Exchange-side. They have a log there, which shows every connection and why it gets blocked. This information normally does not get written to SharePoint's ULS-Log, so troubleshooting on SharePoint-side is very hard.
    – MHeld
    Jan 11, 2018 at 14:35
  • @MHeld, good idea. I'm having them send over Exchange logs.
    – virtuesplea
    Jan 11, 2018 at 15:03

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I'm not really well up on this and I don't work on that side of things however I remember experiencing something similar within our company but these were still working for those using a VPN when working from home. As I said I don't work on that side of things so I don't know the exact details but in this case it turned out to be a problem within outlook so it might be something similar?

Sorry if this is no use at all

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    It's all external emails, so I don't think this is it. We might have a couple of VPN users, but most are in-office. Thank you for the input though.
    – virtuesplea
    Jan 11, 2018 at 15:02
  • No problem :) I thought it was worth mentioning even if not useful in case it did point you in the right direction
    – Kirito
    Jan 11, 2018 at 15:15
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couple of things to check:

  • Make sure all your SharePoint server register with exchange rely(this configuration allow to send the email to external address).
  • Do you have multiple IP address configured on the Servers, if yes then make sure they are also added into the exchange relay.
  • Enable the verbose logging, check the logs when the alerts timer job ran and see where the email is stuck.
  • Also try to command line tool on sharepoint server to send the test email to external email address this will also tell u if you exchange configuration is good for sharepoint.
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