How to get images in Jira's HTML emails to work in Outlook?

After upgrading to Jira 5, my company is loving the shiny new HTML emails with their various embedded imagery.

The problem is that the images sometimes work & sometimes don't. We all use Outlook in this office, mostly 2010.

In my case, I use 2 computers: a desktop PC and a laptop. The laptop will always display the images in emails yet the desktop has never worked. Both computers can reach Jira fine & I know Outlook uses IE for credential management, so I've tested that the image URLs (obtained via "view source") work if I load the in IE, both before & after logging in.

For some other users, the images had previously worked on their computer but have now stopped loading completely. It's not that we're not logged in, as Jira will happily serve up some content without a session. The images are rendered as the "red x on a white page" icon:

jira html emails not rendering in outlook

Usually when Outlook blocks the download of external images, it allows me to "download pictures from this sender" but in this case Outlook is not presenting that option.

We have no VPN or Proxy required between our workstations and our Jira instance, so it *should* be reachable.

This issue seems to be exclusive to Jira - no other system email, or external marketing email, or any email is having the same problem.

Has anyone else experienced this issue? Do you know how to resolve it? I'm not sure if it's just an internal configuration issue somewhere or if it's more widespread. If you are finding this issue too, could you leave a comment or vote up this question so I can be sure I'm not going crazy?!

8 answers

1 accepted

1 vote
Accepted answer

I'm not sure if it was just coincidence, but since upgrading to Outlook 2013 the images have started loading as expected. I'll leave this here as an answer for people to up/down vote or comment on if it has worked for them.

There seems to be a discussion here regarding the same and it looks like it is related to avatars being used. Jamie has a workaround too there.

Thanks for the suggestion. This doesn't seem to be the problem though, I can see the difference between authenticated & non-authenticated content. When not logged into Jira on a *working* PC, the sillouhette is displayed and so is the issue type icon. On the broken PCs, nothing displays at all.

I found the following answer at Microsoft about Outlook hanging; sure enough, I went to Tools -> Trust Center -> Automatic Download and unchecked the option with "Permit downloads in e-mail... used by the Junk E-mail filter" (since the top option "Don't download pictures..." was already checked).

Sorry, some details about my situation:

I'm on Outlook 2007 using Jira 5.0. Outlook hangs for a minute or so but finally shows the message (unless I do my fix above).

I'm only getting it for my filter subscription emails; all the other emails work, even though they have the same types of image references.

We do use a VPN, but I'm having this problem even when I'm connected to it.

Obviously this is a sucky workaround since everyone with Outlook needs to do it.

I gave this a shot and it's helped in that I now get the "pictures are blocked, click here to download" bar but downloading the pictures still fails. Outlook 2010 for me.

Oh, you're right: same for me. This fix is only for when Outlook hangs for a while on the pictures... I found this thread while searching for my problem, but I guess it doesn't totally solve yours.

We recently ugraded to Jira 5 and are experiencing the same thing with Outlook 2010.

Same issues for me, i have installed the JIRA trial on one of my dev servers and compared it to my production version and it happens for both.

This is an issue with how Outlook handles cookies. It uses IE cookies for authentication, but seems to have an issue with it. If you are logged into JIRA through IE and have the "Remember Me" box checked, you should have a JIRA authentication cookie.
Outlook "should" use that cookie to be able to display the images. It works sporadically for me when its all set up properly. If outlooks fails to get the image the first time, it will not try again until you clear the IE cache and restart Outlook. It must be cached in memory or something.

When outlook attempts to view an image, it issues a GET request to JIRA. If outlooks fails to use the cookie, it sends an "anonymous" login request, which JIRA replies with a 302 redirect to the login page. At that point outlooks gives up and displays the red X image placeholder.

Theoretically, if you are authenticated with a valid cookie and session on JIRA, outlook should have no problem getting the image. Other email clients (gmail, OWA, thunderbird) all get the image fine once you are authenticated through a browser. Outlook works sometimes.

At least that's all I can figure out

Thanks for the response. I don't think this is the issue, as most of the images don't require authentication and those that do (e.g. profile pics) have un-authenticated fallbacks (i.e. you get a sillouhette instead of the avatar). Even the Jira logo & other images the work directly when unauthenticated are failing.

If you happen to be using JEMH, there is an option in current releases to inline Avatar images. This means they are not then subject to authentication, and will be rendered on all mail clients.

We have same issue and the web server address in "<img src=..." is different than in other links. So, can it be a JIRA setup issue?

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