Force all images to load over HTTPS using an image proxy
Outlook.com currently loads HTTP images sent to you in emails. This causes mixed content warnings in Google Chrome and causes the page to no longer be 'secure'.
It also exposes your IP address to the sender of the email.
Please load images through an image proxy like Gmail does. See here:
https://gmail.googleblog.com/2013/12/images-now-showing.html
This is long overdue. Gmail did this 5 years ago.

Again, thank you for the great feedback. This change is now rolling out and you all should be seeing it over the coming days.
Please keep the feedback coming.
David Los
2 comments
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kai commented
I don't think the feature is working reliably. Looking at my network requests, they are still just being loaded directly from the senders' servers even when I have the option enabled.
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Matthew Thompson commented
This is really good to hear David and the change has now hit my mailbox. I now consistently receive a HTTPS connection without mixed content.
This places Outlook.com on par with Gmail.
Thank you for the follow up, and please send my regards to the Microsoft Exchange / Office365 developers who implemented this feature. Keep up the good, privacy and security focused work!