Using JIRA with multiple SMTP servers or SMTP Relay

Andreas Gounaris
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November 14, 2012

Hi,

My requirement is to be able to send notifications using different email accounts and domains. This is mandatory for our processes and we can't do that directly from JIRA, since it supports only one SMTP server.

What we currently do is using an local hosted SMTP relay server which receives and redirects messages directly to the target. This solution was adequate for sending local emails within our domain, avoiding the extra network overhead plus restrictions posed by Google mail (our email hosting provider).

Now, we have a new situation where we're forced to send emails using different FROM addresses and domains (2 domains, multiple addresses per domain). The issue here is that we have to upgrade to a more stable, robust - enterprise kind solution for our SMTP relay and the effort for doing that (plus monitoring, maintenance and support for the new system) is not justified well enough for the required resources we don't have.

If JIRA could only let you configure multiple SMTP servers and multiple accounts per SMTP server, this could be effective enough for our needs. Unfortunately it doesn't.

Before I start investigating external SMTP relay services, I'd like to have some feedback from Atlassian support and the JIRA community.

* Have you ever faced problems like this and how did you deal with it?

* What are the most important things an external SMTP service should provide?

* Should you direct me with a list of suggested companies or at least what's out there?

* A new idea or approach that might be considered?

Thank you in advance,

Andreas

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Andreas Gounaris
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November 16, 2012

Sent a query to Google team and here is what they said:

Sending mail from a different address

I'll give it a shot and hope that it works for me.

Andy Brook [Plugin People]
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November 16, 2012

Yes, google will allow you to 'associate' alternate 'from' addresses that it will allow you to define. So, if you have a bunch of gmail addresses, and do the association to another account within the domain, then the single smtp server would permit those different from's to be used, but you'd probably have to associate them one by one. How many do you anticpate needing to support?

Andreas Gounaris
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November 16, 2012

will be 3 addresses, correction: 4 addresses, 1 from a different domain.

And that's my concern, although both domains are hosted by Google, could I use a single account to connect to SMTP and be authorized to send mails from behalf of the other domain's account?

Andy Brook [Plugin People]
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November 17, 2012

Not sure, I have one domain only. Let me knowhow it works out :)

Andreas Gounaris
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November 18, 2012

Well, good news. It works with alternate domains too. The configuration permits entering an SMTP server and port of your choice. I used smtp.gmail.com since both domains are hosted by Google.

The only drawback is that someone can see the original address when viewing the raw message headers in the Return-Path field. However, it doesn't mean that a reply will go to the original address, unless it's specified otherwise.

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Andy Brook [Plugin People]
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November 14, 2012

Mulitple SMTP servers is a current open issue in JIRA JRA-1739, potentially, but the current JIRA notifications are quite hard wired into the exisitng single SMTP server (eg rendering, queue management). Its not trivial to 'add' this in plugins such as JEMH.

Enabling relaying within a domain is what I've done in the past, enabling @jira.mydom.net">*@jira.mydom.net, specificially this was done using a Postfix and Dovecot combination providing a Virtual Mailbox (all mail goes to one domain), with 'jira.mydom.net' effectivly owned by my server, the integration of exchange to forward all mail to my local mail server worked a treat. I was able to support projectKey@ addresses, supporting n projects with n addresses from a single mailbox/inbound mail handler. For reference, my Ubuntu mailserver integrated seamlessly with Exchange 200x of the day.

Andreas Gounaris
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November 16, 2012

This is great, but as I said, no resources to setup a hosted solution. I don't worry about incoming, I care about sending from a different domain or email address. No mail server, we use google mail services.

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