Adventures with Outlook 2010 Problems

Adventures with Outlook 2010 Problems

Summary: I've written recently about Exchange problems and how Outlook problems have been overwhelming the Help Desk. Another issue popped up that tops the cake.

TOPICS: Open Source

I've written recently about Exchange problems and how Outlook problems have been overwhelming the Help Desk. Another issue popped up that tops the cake. It was brought to my attention that some users, receiving some emails, cannot see PDF attachments. But, not only does Outlook refuse to show the attachments, it gives no indication to the user that there is something wrong. So, the user has no idea that there are attachments, other than relying on the sender to notify them in some way. We verified that the attachments are in the message, because Outlook reports the message size correctly which takes into account the extra size that the attachments take up. And, when having the user log in to Outlook Web App, the attachments show up. Seriously, this is idiotic. This is just unexcusable when you are dealing with customers and need to have reliable email correspondence. Already this has caused issues, since the customer needs to ask our staff if they got the attachment and why they have not responded regarding it. Our staff explains that they never got the attachment and back and forth fun begins.

Anyway, we go to research the issue. Thread after thread in various groups, we find posts on this same issue. A majority of the posts mention Outlook and the attachments probably being "inline", yet there is no fix for Outlook. And, I actually laugh at the responses which portray the Microsoft mentality perfectly. Things like: "Please restart exchange Mailbox server to resolve any potential issues.", or "try to create a new Outlook profile.", or even "Test the problem in another computer. If you can see the attachment by Outlook 2010, the problem should be in the corrupted windows profile or Outlook client.".

Oh sure, let's just reboot the server whenever we need. Give me a break, this is a production system, we should not have to reboot the server to fix silly issues like this. And we have seen Outlook and Windows profiles become corrupted which re-creating these seems to be a common IT solution for Windows problems. In our case, it didn't fix it.

Other replies include : "Try having the sender attach the files in Zip or Rar format". Oh sure, we are going to ask clients to attach and re-send attachments to drag them into the troubleshooting procedures. I don't think so.

Then, in forums that are run on the Microsoft TechNet websites, moderators that work at Microsoft are marking the issues as having answers, even when the original poster has not confirmed that things are working. So those of us crawling think it's a solution but end up in the same boat when the answer that is flagged doesn't work. For example, these posts show a couple of replies that are marked as answers. Very misleading.

It gets even better. There's a Microsoft article on this issue, which can be found here for Office 2007 (there is no post at Microsoft on this issue with Office 2010 yet):;en-us;961940. And the posted resolution? To quote:

"To work around this issue, you will have to view the e-mail message in Outlook Web Access to see the inline attachments. Note Even when you use this workaround, there is no paperclip icon to indicate that an attachment exists within the message."

Brilliant. So users are supposed to automatically know that there should be an attachment, and gee, I guess instinctively know that they should go over to OWA and open the message there which magically finds the attachment. Hooray, all is well with the world again... We wish.

While I can understand this issue may not be solely a Microsoft one, as the sender's email software could have malformed the mime type and/or attachment data, it doesn't explain why Outlook Web Access does work. And with the number of complaints about this issue, it is a common and widespread one. Why can't Microsoft use the same algorithm used by Outlook Web Access to look for attachments, in Outlook? Especially knowing that Microsoft has acknowledged that OWA works and Outlook doesn't.

In summary, the issue is still there, and unfortunately we are left without a fix. However, in our tests, messages sent with different PDF attachments from the exact same sender all of a sudden starting working fine and everything magically showed up in Outlook but only for new messages. In all of the years in IT work, this issue makes it in the top 10 of idiotic issues. This issue was around in Office 2007, and 4 years later, still unresolved. And it's a serious malfunction in my opinion. I have never seen this happen with any other product other than Outlook. What I have seen frequently in other email client software are attachments for "winmail.dat", which are proprietary attachments that only Outlook puts on messages and can parse; this was just another Microsoft move that totally ignored existing email standards. But in non-Outlook software I have also seen miscellaneous attachment types which show up but depending on the operating system used, may or may not easily be opened or viewed. But they show up, which is the main thing. I just hope Microsoft steps up to the plate, and improves Outlook so that it can better detect attachments like Outlook Web Access does. This is embarrassing for the users of Outlook.

Topic: Open Source

Chris Clay

About Chris Clay

After administering Linux and Windows for over 17 years in multiple environments, my focus of this blog is to document my adventures in both operating systems to compare the two against each other. Past and present experiences have shown me that Linux can replace Windows and succeed in a vast variety of environments. Linux has proven itself many times over in the datacentre and is more than capable for the desktop.

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  • I wonder if forwarding such malfunctioning Outlook emails to your standard live/gmail type webmail would reveal the missing attachments? Hardly a solution on a large scale, but maybe ok for an emergency.
    roger andre
  • roger andre :

    We did try that, and it works. Even forwarding from Outlook 2010 itself (which cannot see the attachments) to a GMail account, GMail can see the attachments just fine! It seems to be that everything sees them fine, except for poor old Outlook 2010 (and probably any earlier versions of Outlook as well, which we haven't tested). In our case, we can open the messages just fine with Outlook Web Access internally, and get to the attachments that way, so they really don't need to be forwarded to an outside email service.

    Thanks for the feedback.
  • I have have had this problem - randomly - with jpg files on Outlook for years (i.e. on jpgs within the e mail, not as attachments.) The outline frame is present so I know that something should be there. It's just bloody irritating and the solutions offered by MS are gobbledy-gook to me.
    However, if I Forward the e mail the jpgs appear.
  • robertcglewis :
    You are probably talking about the issue where images show up in outlook as a "red x". That is an old Outlook problem that has been around for years, just as you said. In fact, we still get that too, and have never been able to get it completely resolved. It varies from message to message, and sometimes it happens and sometimes not. I suspect that Outlook doesn't like the way that the images are embedded in the message and just blocks them. We've also had the same issue you describe with fonts, where fonts do not show correctly in the original message, but when you click Forward, everything shows up like magic and can be read. I guess Microsoft is more concerned with changing the frontend and making Outlook look shinier with each version, rather than fixing underlying bugs.
  • UPDATE: Just this morning I saw yet another mysterious Outlook issue. This time, users started reporting that meeting reminders were re-appearing in Outlook 2010 repeatedly even after they were dismissed, and some emails were not showing up that were for sure sent to them (messages would show up in Outlook Web Access but not Outlook). After further investigating, we found that Outlook had been randomly skipping over emails and seems to be failing to completely sync the entire user's mailbox. About 1 in every 20 would never show up in Outlook. When clicking on the "Send and Receive All" button, nothing would happen... nothing! Outlook is supposed to attempt to sync and show a progress bar but nope, not this time. The users also moved messages around in their mailboxes, and after looking in OWA their changes were not there. No errors were showing up in Sync Errors in Outlook. After turning off Cached Mode, everything appeared instantly and was working fine, even though this is not the recommended way to use Outlook by mass amounts of users. There has been a level of frustration among users because now they are needing to go back and look for missing emails that they may not have followed up for. And before any Microsoft apologists can say "it's our fault", we have not updated the PC, server, nor the user accounts; this issue came up out of nowhere. Great job, Microsoft, way to go on this great messaging platform. It looks like we'll be researching these issues (among the list of others).