Outgoing Mail Connections

SINCE 7.1.1.17

In contrast with Jira, Email This Issue supports multiple Outgoing Mail Connections that 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 to 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, Username fields.

Outgoing Mail Connections

Adding connections

Connections can be added in the Outgoing Mail Connections menu. Go to OUTGOING EMAILS ADMINSTRATION --> Outgoing Mail Connections.

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

• 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

Adding an outgoing mail connection with password authentication

Adding an outgoing mail connection with OAuth2 authorization

When using OAuth2 connection protocol, a reduced set of fields are shown because attributes like host, port, password are not required.

Microsoft OAuth 2.0 host settings

For OAuth2-based Microsoft365 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.

The dropdown contains a pre-defined set of hostnames, which are globally available. If you have even more specific needs, please contact our support team.

Microsoft OAuth 2.0 host settings

.

OAuth2 Authorization

If you want to connect to an Outgoing Mail Connection service using OAuth2 after specifying the OAuth Credential and Username you must start the authorization process by clicking the Authorization button.

The authorization is specific to the service provider. The procedure is detailed here:

Authorize Email This Issue to access Gmail accounts

Authorize Email This Issue to Access Microsoft 365 Accounts

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.

Outgoing Mail Connection Attributes

Attribute	Description	Applicable to Connect protocols	Mandatory
Name	Unique name of the Outgoing Mail connection	SMTP OAUTH2
Description	Longer description what's the purpose of this connection	SMTP OAUTH2
From Address	The email address set as the sender of the emails sent via this connection, unless overridden in the Contexts	SMTP OAUTH2
Prefix	Optional value that is added to each email's subject if specified.	SMTP OAUTH2
Connect Mode	This is a new attribute with values: Smtp or OAuth. It indicates how we connect to the service. Either with direct password authentication (Smtp) or via OAuth2. SINCE 8.1.0	SMTP OAUTH2
OAuth2 Credentials	This is a new attribute is used when OAuth2 authorization is activated. It selects the OAuth2 Client Credential to be used when connecting this this service. SINCE 8.1.0	OAUTH2
Encryption	Supported encryptions: No encryption SSL/TLS STARTTLS	SMTP
Host	Host of the mail server	SMTP
Port	Optional, if not specified, we use the default ports. Leave blank or 0 for default (plain SMTP: 25, SSL/TLS: 465, STARTTLS: 587).	SMTP
Timeout	Connection timeout.	SMTP OAUTH2
Message Size Limit	Maximum size of the email in bytes this SMTP service accepts for delivery. Set 0 for unlimited.	SMTP OAUTH2
Username	Connection credentials.	SMTP OAUTH2
Password	Connection credentials.	SMTP
Debug	If enabled, Outgoing Mail Connection details are written to the log files	SMTP OAUTH2
Fall back to Jira	If this option is enabled and there are delivery problems via this connections, Email This Issue attempts to deliver the email via Jira's Outgoing Mail connection.	SMTP OAUTH2
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 minutes intervals and maximum 3 times. If the email is still in the error queue after the third trial, retrying manually is still possible (as described here).	SMTP OAUTH2

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.

Filtering the connections

The Outgoing Mail Connection list can be filtered by clicking on the Search button. After clicking, a free text field will be opened, in which the search term can be entered. The filter searches in the Name, Description, Host, and Username fields.