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:

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?!