Outlook 2013 & red x HTTPS images not displaying in HTML emails

I spent better part of an hour working on why Outlook 2013 would not properly display inline, linked email images.  I got the dreaded red “x”.


Backstory: I am working with a team to roll out an improved daily newsletter.  After trying Constant Contacts and Mailchimp, I was thoroughly impressed with Mailchimp.  For example, Constant Contacts did not have “smart tags” or “merge tags” as Mailchimp calls them.  In other words, with Mailchimp I can insert a PHP date code in the heading bar of my email template:

*|DATE:l \t\h\e jS \of F, Y|*

which every day generates a clean date that looks like:

Tuesday the 16th of June, 2015

Back on point: After setting up SPF and DKIM authentication with Mailchimp everything seemed smooth with one major catch: all the images were broken.  Mobile devices were fine.  Viewing the email in a browsers (IE & Chrome) were fine.  It was Outlook.

After searching and searching, I actually misread this post from Slipstick under “Encrypted page setting”.  A few minutes later I stumbled across this Microsoft KB article 30333864.  This immediately solved the issue after restarting Outlook.

Uncheck “Do not save encrypted pages to disk” and hit “Apply” and “OK”.


Ironically the MSDN blog has some caution on why NOT to enable this option.  We had enabled this option long ago via GPO due to HIPAA compliant web-based applications.  Now with Bitlocker and other supporting security, this is a risk-reward compromise.