Outlook refuses to show embedded images on Citrix Windows 2008 R2

[Neko-]

Receiving e-mail with embedded images shows the mail with a red X instead of the images.

Works on my workstation (Windows XP SP3) with Outlook 2003, doesn't work on the server (Windows 2008 R2 64bit running Citrix XenApp 6.5) with Outlook 2003. So it's not a restriction on internet access based on user. I'm using the same account for both. If I access Outlook directly on the server (foregoing Citrix) it also does not work. On our old Citrix environment (Windows 2003 32bit running Citrix Presentation Server 4.5) we can view the mail normally. So it might be a quirk of Windows 2008 R2 somewhere. Windows and Office have been patched to the fixes released in December 2012.

Tried on a server that has Outlook 2010 installed, and it failed on there too. So the version of Outlook can't be a cause.

On the user that reported the problem, we cleaned out the profile (i.e. trashed it). The profile is roaming, so it was recreated upon the next logon of the user. Made no difference. So I'm excluding the profile as the cause.

We had a go with the download settings in Outlook: Outlook: Download pictures automatically without right-click | a Tech-Recipes Tutorial - No change. Besides, if the profile was recreated this is set to the default. It's set to the top three ticks enabled. Any changes to this don't result in changes in the display of the e-mail itself.

Forwarding the e-mail might show the pictures in some cases. Not in ours. Pictures remain undownloaded.

Checked the Internet format settings (Cannot view embedded images in an HTML message using Outlook 2003) - No change, no matter what we alter here.

Next there's a pointer that IE doesn't connect to the Internet properly. Not the case. I start IE8 on the server, and connect to the outside world just fine, through the locally installed TMG client. Even when I physically fill in the proxy data it does not make a difference. We tried a reset for IE too. No difference. IE isn't set to work offline.

Checked the proxy for any errors being reported from the client and user trying to open the e-mail. Proxy reports anything requested comes in properly.

Found Description of the Outlook 2003 hotfix package: April 22, 2008 - a possible hotfix. Tested it. No change. Tried Detect and Repair, which in some cases solved the issue. Also no change.

The OutlookSecureTemp fix was next. I don't see anything saved in there, unless I open attachments which do get saved in here. The folder is local to the server, and is deleted on logoff. The folder is empty by default. Using Process Manager seems to hint at the fact that there can't be anything written to the folder, but then why do attachments get stored there with no trouble? We verified the ACL's on the folder, found them to be okay.

Last thing I found was Outlook 2003 not showing Embedded Images - which hints at a copy-test, and deleting files from a folder. When I copy the red X from the mail and paste it to Word on the server in the same session, the picture is shown properly. Going back to Outlook and changing the preview to a different e-mail and going back makes it even less clear: The picture is now shown! The rest of the pictures isn't tho. When looking in the C:\Windows\Downloaded Program Files folder, the only thing in there is an expected desktop.ini. So while this hints at a solution, it isn't one in itself.

About the only thing I can imagine being the cause would be the links to the files. For instance http://www.computable.nl/pcit/img.db?2223468 instead of a real .jpg file.

Me and my colleague have somewhat exhausted our direct ideas to solve this issue. Anyone want to chip with something we can still try?

[Diane Poremsky]

the link could be the problem - but i'm not convinced.

Are you using a proxy server? Outlook sometimes has problems authenticating to proxy servers as it can't pass credentials.

[Neko-]

the link could be the problem - but i'm not convinced.

Are you using a proxy server? Outlook sometimes has problems authenticating to proxy servers as it can't pass credentials.

As my original mail shows, the link used works on my Windows XP SP3 machine, and doesn't on Citrix. The link itself (while looking a bit odd) seems to work fine for Outlook.
If you read my statement about IE connecting to the Internet properly, then yes, we use a proxy server. It can authenticate, for I can access the internet just fine. Even worse, saving the e-mail that doesn't show the pictures to an HTML file somewhere, and opening that in IE shows everything just fine. The proxy doesn't report any blockages on downloads, and when opening the HTML with the same references in it, it works like it's supposed to.

If Outlook downloads stuff differently from IE, then it could be that Outlook just doesn't request the pictures for whatever reason. But if that's the case, I'm wondering about my last test, in which a copy of the non-displaying image pasted to Word shows up, and then also shows up in Outlook, without any further intervention on my behalf.

Same proxy is used on the workstation and the server. So the proxy doesn't seem to be the cause.

[Neko-]

Nobody willing or able to hazard any guesses as to why this behavior occurs???

[larry]

Is external content saved to secure temp or to TIF? (I don't know.) If Word saves to TIF and Outlook looks there first, it would explain why Outlook can find the images after word gets them.

If Outlook is started using Run as Admin, does it get the images?

[Neko-]

I can't find any saving of the content done locally. The Temporary Internet Folders remain empty.

I know I'm looking in the right place, since if I open an attachment, it's temporarily saved to that folder. This folder however does not contain any image files. I'm unable to determine if Outlook saves these images anywhere, and if it does, where specifically it does. Normally the red X would indicate the folder to have 100 images stored, and running into problems because of that. But I can't find any images being saved.

Changing the OutlookSecureTemp registry key to a folder I know exists, changes the location of the attachments being stored, so I know that key is working. Just that embedded HTML pictures do not get stored there.

Starting Outlook as an administrative user on the 2008 R2 machine makes no difference. Pictures remain elusive.

When I save a mail that does not display the images to an HTML file, and open that file in Internet Explorer, pictures are shown as if nothing is wrong. So it seems that Outlook has issues displaying the pictures, depite it (apparently) using IE to render/download the pictures, and IE having no issues whatsoever.

[Diane Poremsky]

Yes, Outlook 2003 uses IE for rendering HTML. Embedded images should go into the TIF folder, not secure temp. Go to tools, options, security tab. What zone are you in? It should be Restricted - see if changing it fixes the problem.

[Neko-]

We've restricted access to the IE options pretty much on the Citrix environment under Windows 2008 R2, so the security tab is done through Group Policy, and unaccessable for the user. Since I'm not sure where that TIF folder should be, I can't verify what zone that folder is in (if that's what you mean), or where specifically you want me to check...

[Diane Poremsky]

Using the restricted zone won't normally cause problems like this, but if you can't change it, then you can't test it. With group policy, security should be the same for all. It's perplexing because you've tried all the typical causes and it only fails for this one person, correct?

[Neko-]

Oh, I can alter Group Policies if need be... But they're set for every user that logs on to the Citrix environment in the same way.

I've had the problem reported from two users, tested it under my own user account, and tested it when logging in locally on the server with an administrative account (in which case I can review the zone-settings for IE). In all 4 cases the pictures did not show up embedded in the mails. So I'm at present seeing a problem with atleast 4 accounts, and am willing to assume it's a problem that spans all my users. Just that some users either don't care about embedded images, don't receive those kinds of mails, or just neglect to mention it.

Like I said, copying a red-crossed item in an Outlook, starting Word, pasting the picture shows it properly. When I then return to Outlook the picture is also shown in the embedded e-mail. Also (again): Saving the e-mail as an HTML file and then opening it from IE shows all pictures as expected. So it's just Outlook having issues.

As said, as the administrative user on the server I can access my e-mail box (given the administrative useraccount rights to my mailbox), and I have access to the IE settings, so if I know what you want me to look for I can have a go to see if I can change the behavior.