Outlook on the web (outlook.com) no longer displaying images. How can I restore that functionality?

Context

All was fine until recently and Microsoft did something, probably for "security" reasons, namely every time I click on an email, none of the images show.

To replicate, I use Google Chrome on Windows 10. I open up my outlook account and click on an email in my inbox, though could be anywhere else.

Here is an example using a Disney Movie Insiders email:

Outlook.live.com not showing images

What I've tried

Here are troubleshooting steps taken:

  • Under Settings (gear top right area) → View all outlook settings → Junk email → Filters
    • I unchecked the box for "Block attachments, pictures...".
  • The checkbox for "Only trust email from addresses in Safe senders..." is unchecked.
  • In Mail → Layout → Sender image"
    • I see the "Show sender images" radio button has the check.

I am not interested in adding every email address/domain to safe senders, nor did I check if that resolves the issue. I have the two checkboxes unchecked, so that should take care of junk email reasons.

Question

How can I show images again in my e-mails on outlook.com without adding every email address/domain to the safe senders list?


This seems to be a recent outlook.com issue, according to this thread (found by doing a websearch for "outlook.com does not show images"):

outlook.live.com not showing external images in messages

I can't get outlook.live.com to show images.
...

Up to a few weeks ago, things were fine. But now mailing lists that I subscribe to (like Harbor Freight Tools advertisements, or The Wall Street Journal, or Redfin search matches, or ...) aren't showing images. This makes email pretty much unusable, since there's no UI to explicitly allow images for that email message.

I've added the email sender to my contacts and to safe senders. The mailing list is known to Outlook in the options -- seems like that's allowed, too.

...

How can I get images to load? Why did they break?

In that same thread a workaround is given (bolding mine):

same problem here.
...
enable conversations and the images will show
...

This article explains how you can enable conversation view:

  1. At the top of the page, select Settings Settings to open Quick settings.
  2. Under Conversation view, choose one of the following:
    • To sort messages by conversation, select Newest messages on top or Newest messages on bottom.
    • To show email as individual messages, select Off.

Or if you're using classing Outlook on the web:

  1. At the top of the message list, select Filter.
  2. Select Show as > Messages or Conversations.