SMTP Connections

In contrast with Jira, Email This Issue supports multiple SMTP Server Connections that brings three important improvements.

  • Emails may be sent via various SMTP connections if needed, even depending on issue fields
  • Email subject prefix is only optional, not a mandatory value as in Jira
  • Better insight into the outgoing emails via the Outgoing Mail Delivery Queue

Add Connections

SMTP Server Connetions may be added via the SMTP Connections menu

SMTP Connections have a set of mandatory and optional attributes. The new Protocol Attribute is used to specify if connection to the provider is based on password authentication or on OAuth2.

Add SMTP Connection with Password authentication

Add SMTP 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.

OAuth2 Authorization

If you want to connect to an SMTP service using OAuth2, then 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 and takes a couple of steps as detailed here for Gmail and o365.

Authorize Email This Issue to access Gmail accounts

Authorize Email This Issue to Access Microsoft 365 Accounts

SMTP Connection Attributes

AttributeDescriptionApplicable to Connect protocolsMandatory
NameUnique name of the SMTP connection (tick)
DescriptionLonger description what's the purpose of this connection 
From AddressThe email address set as the sender of the emails sent via this connection, unless overridden in the Contexts (tick)
PrefixOptional value that is added to each email's subject if specified. 
Connect Mode

This is a new attribute with values: Smtp or OAuth. It indicates how we connect to the SMTP service. Either with direct password authentication (Smtp) or via OAuth2.

 (tick)
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.

(tick)
Encryption

Supported encryptions:

  • No encryption
  • SSL/TLS
  • STARTTLS
(tick)
HostHost of the SMTP server(tick)
PortOptional, if not specified, we use the default ports. Leave blank or 0 for default (plain SMTP: 25, SSL/TLS: 465, STARTTLS: 587).
TimeoutSMTP connection timeout.  
Message Size LimitMaximum size of the email in bytes this SMTP server accepts for delivery. Set 0 for unlimited. 
UsernameConnection credentials. 
PasswordConnection credentials.
DebugIf enabled, SMTP connections details are written to the log files 
Fall back to JiraIf 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. 

Test Connections

There are two ways to test a configured connections.

Test Connection in the Edit SMTP Connection screen

It is possible to test the connections before saving it. Immediate results are received as popup flags.

Send Test Emails

It is possible (and recommended) to test the connections by sending test emails.

The popup dialog allows you to send the email and get detailed output.

Use SMTP Connections to Deliver Emails

SMTP 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 SMTP connections depending on the issue fields because Contexts may be configured with an arbitrary JQL scope.

Once emails are dispatched via the SMTP Connections configured in Email This Issue, you can use the Outgoing Mail Delivery Queue to monitor the status of the delivery and resolve problems.

Message Size Limit

This attribute is used in sending Emails Manually. If the total size of attachments added to the email exceeds this value, a warning message pops up before the email is dispatched