Outlook 2016 Not Loading Images on Windows 8

A user today ran into an issue with Outlook 2016 where it would display HTML emails correctly, but almost all images in those emails were broken links, with the red X in the top-left corner in typical Internet Explorer style. We directed her to instructions on how to set Outlook not to block images in messages, but she sent us a screenshot showing that these were not set, which I confirmed when I visited her.

On Google, I found and attempted some solutions, including clearing the Outlook secure temp folder and confirming that Internet Explorer was not set not to save encrypted pages to disk, but these had no effect.

On a hunch, I copied the link to a broken image out of Outlook into Chrome, and found that it loaded the image without issue. Then, I copied the link into Internet Explorer, and lo and behold, received an error message that IE could not connect to the webpage.

This computer was imaged at a time when TLS 1.2 (and, in this user's case, 1.1) were not enabled by default on Windows 8 in Internet Explorer. Chrome loaded the images without issue because it supports these newer versions by default, but Internet Explorer (and therefore, by extension, Outlook) were not so set, so the hosting servers were refusing their connections, and so not serving the images. Once I set IE to enable TLS 1.1 and 1.2, Outlook began loading images immediately.

Ultimately, we will resolve this issue more thoroughly by refreshing the user's computer with one that runs Windows 10, but as a stopgap until that time, this works.