This article provides the steps on how to resolve problems when FogBugz On-Premise environments are unable to deliver outbound emails through Office 365 Exchange's mailing services.
FogBugz/Manuscript On-Premise, On-Site and For Your Server, in NAT/ internal networks with dynamic outbound IP
Office 365 Email Exchange
Administrative access to the Office 365 account
For On-premise environments (including FogBugz For-Your-Server, FogBugz On-Site, and Manuscript On-Premise), sending emails can be a challenge. On-Premise environments depend on external mailing services such as Gmail or Office 365 Exchange. Once configured, it is seldom modified throughout the usage of the application.
All outbound emails can stop being delivered at some point. You may get an alert in the Administration area like this:
Some mail recipients do not exist - Hide Notification
<date> <time>: Some of the recipients of this message do not exist, so the message could not be delivered to them. The other recipients will receive the message.
Insufficient system storage.
The error message can sometimes be misleading and point to a generic error that's unrelated to the real root cause.
If you are unable to send emails from FogBugz and you are using Office365 Exchange, make sure that the settings are correct and unchanged. Microsoft is constantly evolving its products. A previously working setting could stop functioning because of a change in their policies. The Office 365 administrator is notified in advance when these changes happen. Unfortunately, these notifications are often misinterpreted or misunderstood.
Office 365 Exchange allows email relay, which comes quite handy since you can define the settings for the Exchange Server to relay email to your FogBugz installation. You can access these settings on the FogBugz UI under Site Configuration > Mail:
When the FogBugz application stops delivering emails while you are connected to an Intranet connection or a LAN environment, there might be changes in your outbound IP from your internal network, causing the relay settings to reject all outbound mail.
To resolve this issue, make sure that Office 365 has the IP information updated:
Determine the public IP for your FogBugz server. You can do this easily by using Google to run a search for "my IP" from the FogBugz server:
It should give you the IP address that's visible outside your network.
Update your Exchange settings:
Go to your Office 365 account, click Admin, and then click Exchange to go to the Exchange admin center.
In the Exchange admin center, go to Mail flow > Connectors.
Check the list of connectors set up for your organization.
Once you find the inbound connector, verify that the IP address of the sending server matches one of the IP addresses that belong to your organization on the next screen. Update the IP address to your public IP address, accordingly.
Leave all the other fields with their default values, and select Save:
You should be able to send emails again on your FogBugz environment using Office 365 Exchange.
Configuring Your SMTP Settings to Work with Office 365 in Relay Mode
For extended details on how to configure your SMTP settings to work with Office 365 in relay mode, please refer to the following Microsoft KB articles: