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The issue I am trying to solve is to do with users getting a Cannot Send Item error in Outlook 2007 connecting to Exchange 2007. Basically if there is an image in the email (either one they have pasted in or one from another email in the chain) they get a "Cannot Send Item" error. Initially thought it was a citrix issue but users get it when they RDP to a server as well. Changing the message to Rich Text works 80% of the time but I do not think this is a solution but more of a temporary workaround.

After some troubleshooting we found that the error can be fixed by adding the user as a member of the local power users group. of course this is not really a fix. My thoughts were that the ability of a power user to add/remove software may give them more access to the registry which might allow them to get round a restriction that is in place for a normal user. I have tried going through a procmon but the wealth of information is confusing. It initially looked like it may be an Outlook 2007 email security setting but this does not change between power user and normal user (set to 1 in the registry, "Use the security setting from Outlook Security Settings Public Folders").

I am struggling to fine tune my troubleshooting to work out exactly what is blocking it. Has anyone had an experience with an error similar to this? Or are there any tips for trying to track down issues via procmon as I must admit my approach seems somewhat lacking :)

EDIT: So I have trawled through the two logs we have from process monitor (one as a power user and one a normal user). annoyingly I can find no obvious difference where something is denied access. There are more access denied events in the normal user log but these are quickly followed by sucessful entries to the same path fractions of a second later. The only thing that does stand out is an access denied to HKCR.html. This does not even appear in the power user version of the log. From what I understand this helps determine the default browser which ties in nicely with the fact that 9 out of 10 times you can send the message as Rich Text.

EDIT: Looks like KB2509470 was causing the issue. Not really sure why but when I can work out what it does and why it causes the problem will post here unless anyone beats me to it!

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Well this seems like it may be incorrect but finally twigged what was causing this. Turns out it was WinZip and not the Outlook updates as previously suspected. Something in the WinZip release we are using (version 12) was causing this. Disabling the Oulook Companion that it installs allows all messages to be sent. We have since upgraded to the latest release and all is fine and dandy.

Very strange issue but resolved all the same.

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