Hello @Rahoeft , Thank you for checking in on the issue. I am sorry your images not displaying as you expect. Unfortunately there has been no update or change in the situation. At this time the same workarounds are being suggested:
Here is a workaround for a setting change that can be done in Outlook 2010, 2013, 2016, and 2019.
Here is a different workaround that can be used in the above versions of Outlook and Outlook 365.
As previously mentioned, you can also change the image URL's used in an email to start with HTTP instead of HTTPS. I'll paste the steps Kara previously listed below:
For each image that is not showing:
Click to open the image as if you were going to change it
Right click on the image
Copy image address
Go to the Image URL tab
Paste the URL
Remove the "s" from the https, leaving the image as http
Preview the image and insert it.
Repeat for all images
Test to outlook client
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