ActiveX bypass in Outlook 2010 & 2013 for specially crafted html file

Whilst testing an IE exploit to see if a Windows system was patched or vulnerable, I noticed a difference in the way Outlook behaves compared to Internet Explorer when opening a .html file containing ActiveX code.
POC system is Windows 7 Version 6.1.7601 Service Pack 1 Build 7601 using either Outlook 2010 or Outlook 2013.
Use case 1. If I open the .html file in the OS, the default program is IE and I am prompted that ActiveX is restricted in the lovely yellow pop up banner, before I click "Allow Blocked Content" and pwn the machine and crash the browser and DEP
kicks in to save the day.
Use case 2. If I email the .html file to myself and open the email attachment from Outlook 2010 or 2013. I get the prompt from Outlook warning about "opening the attachment" which is pretty standard, but no warning in IE about ActiveX code
and pwn the machine straight away as it would appear that the browser ActiveX controls are bypassed or just not there? DEP then kicks in to save the day again.
Use case 3. Same as use case 2 except this time using Outlook.com as the email client. This email client provides little warning, the file download prompt asks "do I want to open or download the file", I click open and the file download
runs the file by opening up another browser tab without prompting any ActiveX warnings and bang! IE has to recover from a crash.
Does anyone know why use case 2 and 3 prevent the browser from prompting for ActiveX or bypass the browser from prompting for ActiveX and seemingly the user accepting the opening of an attachment in Outlook or the downloading of the file from Outlook.com
is then a gateway to having the exploit run in the browser?
Finally, I appreciate that all the above controls are pretty weak and so probably no need for a big essay like this and we're all weary of users opening mysterious attachments, but I was intrigued by the disparity in the user experience and ActiveX.
Any takers?

Hi,
In case 3, what does it mean by "using Outlook.com as the email client"? Did you configure an Outlook.com account in Outlook client, or use Outlook.com account on web?
Please open Outlook, go to FILE -> Options -> Trust Center -> Trust Center Settings -> Automatic Download -> Uncheck "Permit downloads from Web sites in this security zone: Trusted Zone" -> OK. I'm not sure if this helps but you can have
a try.
Regards,
Melon Chen
TechNet Community Support

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