Outgoing Mail Connections
SINCE 7.1.1.17
In contrast with Jira, Email This Issue supports multiple Outgoing Mail Connections which brings the following important improvements:
Emails may be sent via various Outgoing Mail Connections if needed, even depending on issue fields.
The email subject prefix is optional, and not a mandatory value as it is in Jira.
It gives a better insight into outgoing emails with the help of the Outgoing Mail Queue. Read more about it here.
Search
The mail connection list is searchable with the Search button on the top left part of the list. The filter search in the Name, Description, Host, and Username fields.
Adding connections
Connections can be added in the Outgoing Mail Connections menu. Go to OUTGOING EMAILS ADMINISTRATION --> Outgoing Mail Connections.
Outgoing Mail Connections dialog - generic settings
Name - enter the preferred name to identify the connection
Description (optional) - short description to help identify the connection
From Address - email address that will show as the "From address" when using this connection. This can be the same as the Username, but it can also be a shared address that the user you authorize the connection with has access to. To use an email address as the From address, you need to have the proper permissions on the mail server side.
Reply-to Address (optional) - specify a different email address where replies are sent when someone responds to an email sent from this connection.
Subject Prefix (optional) - a prefix to appear in front of the Subject in the receiving mail clients.
Timeout - Timeout for connection attempts to the mail server in milliseconds, valid values: 1-60000 msec.
Message Size Limit - The Maximum size of the email in bytes that the configured mail server accepts for delivery. Set 0 for unlimited.
Debug - add additional logs for troubleshooting the connection.
Retry failed emails automatically - If this option is enabled, sending out failed emails from the error queue will be retried by this email connection at 15-minute intervals and a maximum of 3 times. If the email is still in the error queue after the third attempt, manual retry is still possible (as described here).
Fall back to Jira - If this option is enabled and there are delivery problems via this connection, Email This Issue attempts to deliver the email via Jira's Outgoing Mail connection.
Connection Mode - specific settings
Email This Issue supports login and OAuth authentication mechanisms for Outgoing Mail Connections. You can select it by selecting the correct protocol.
SMTP: log in with username and password; this can be used for custom mail server connections. For detailed steps, go to Custom Mail Server: Basic Authentication.
Google OAuth2: OAuth for Gmail/Gsuite
Microsoft 365 SMTP (w/ OAuth2): OAuth for Microsoft account using SMTP protocol
Microsoft 365 Graph API (w/ OAuth2): OAuth for Microsoft account using Graph API
Google OAuth2 connection
Create the OAuth2 credentials: Gmail with OAuth2
Select the Client Credentials you created on the credentials page.
Enter the user name of the Outgoing Mail Connection you want to use.
Click on the "Authorize" button to grant access to Email This Issue to send emails from your account.
In the dialog, select the account that belongs to the email address you use for login:
Note: If you have multiple Google accounts, select the one with the email that matches the username in the Outgoing Mail Connection dialog. Emails will be sent from that account.If you get the below warning, do the following:
Click Advanced.
Click the "Go to meta-inf.hu (unsafe)" link.
Confirm your choice by clicking Allow.
Result: You can send emails in Email This Issue from Gsuite with OAuth Authentication.
If you want to revoke the access from Email This Issue to your Gmail account, you can do it by visiting Account Settings.
Microsoft Connections
Microsoft SMTP with OAuth 2.0
Set up the OAuth2 credentials: Microsoft IMAP and SMTP with OAuth2
Enter the Username you would like to authenticate with.
Click Authorize
You will be redirected to the Microsoft login page, where you will be logged in automatically if you have SSO enabled. If the Username is not the same as the one you have an active session with, you will need to log in to Microsoft with the username before Authorizing - this way you should be able to choose the correct account to complete the Authorization process with.
Microsoft Graph with OAuth2
Set up the OAuth2 credentials: Microsoft Graph API with OAuth2, you will be able to choose between application access or delegated access.
Delegated access (OAuth2 credentials were created with Auth Code Grant type)
Enter the Username you would like to authenticate with.
Click Authorize
You will be redirected to the Microsoft login page, where you will be logged in automatically if you have SSO enabled. If the Username is not the same as the one you have an active session with, you will need to log in to Microsoft with the username before Authorizing - this way you should be able to choose the correct account to complete the Authorization process with.
Application access (OAuth2 credentials were created with Client Credentials Grant type)
Fill out the Username field, as it is a requirement for the connection health check.
The Authorization will be checked automatically after you select the credentials; no login is necessary.
Microsoft OAuth 2.0 host settings
For OAuth2-based Microsoft 365 SMTP connections, the hostname "smtp.office365.com" is used by default when connecting to the mail server. However, in certain scenarios, the use of a custom hostname might be required. In such cases, there is a possibility to override the default value by enabling the respective "Override default host setting" toggle and selecting the desired host from the "Host" dropdown appearing below.
Shared mailbox settings
A shared mailbox is a mailbox that multiple users can use to read and send e-mail messages. You can read more about them here: https://docs.microsoft.com/en-us/exchange/collaboration/shared-mailboxes/shared-mailboxes
To use a shared mailbox you just have to enter the email address of the shared mailbox into the From Address field then proceed with the settings as if it was a normal mail account. For the username and password fields (or for the OAuth authorization) use the credentials of the account you want to log in with.
Test connections
There are two ways to test configured connections:
Testing connections on the Edit Outgoing Mail Connection screen
It is possible to test the connections before saving it. Immediate results are received as popup flags.
Sending test emails
It is possible (and recommended) to test the connections by sending test emails. Click the three dots next to a connection and choose Send Test Email.
Click Send Email to get a detailed output.
Use Outgoing Mail Connections to Deliver Emails
Connections need to be set in the Contexts in order to activate them and to start sending emails through them. This means it is possible to use different connections depending on the issue fields because Contexts may be configured with an arbitrary JQL scope.
Once emails are dispatched via the connections configured in Email This Issue, you can use the Outgoing Mail Queue to monitor the status of the delivery and resolve problems.
Message size limit
This attribute is used with manual emails. If the total size of attachments added to the email exceeds this value, a warning message pops up before the email is dispatched.
Default outgoing mail connections
An outgoing connection may be marked as Default. Contexts can be configured to send emails via the Default connection instead of directly binding them to one dedicated connection.
It is possible to mark another connection as Default without having to change any of the Contexts configured to use the Default connection.
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