We have a user who is experiencing an issue with Outlook Web. She has some emails that display the images and other messages that do not. It doesn't seem to be consistent as it sometimes happens with her signature image as well as images from senders.
I've attached a screenshot of what is happening. The images display with an icon and then image.jpeg. 
Eugene, the images are coming from a sender, it is not our user who is sending but receiving.
Outlook automatically blocks external URLs for images in the message body. You need to unblock them in Outlook.
Below are some common configurational changes that can help users access restricted emails in Outlook. It includes:
Unblock Images for Single and Multiple Email
Clear Temporary File Folder
Allow Blocked Web Contents for Trusted Senders
Sometimes images or emails can be inaccessible because of PST file corruption. In that case, you need to repair the PST file by using any alternative tool.
For more information, check this reffrence: https://techcommunity.microsoft.com/t5/outlook/outlook-live-com-not-showing-external-images-in-messages/m-p/2763629
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Hi @JoeLalonde-5890 ,
Welcome to our forum!
Does the issue occur when you receive messages from other senders who uses signature with image?
If the issue only occurs with the specific sender, it's suggested that you could contact the sender to check if the message format is HTML. On the other hand, it's also suggested that you could change the browser to check if there're any differences.
If the issue occurs with all senders, would you like to provide more information about your case?
1.What's your account?(Outlook.com/Exchange on-premises/Exchange online)
2.When other user received the same message, do they get the same result?
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Hi @JoeLalonde-5890 ,
Just checking in to see if above information was helpful. If you have any further updates on this issue, please feel free to post back. If you think my reply is helpful to you, please remember to mark it as an answer. Warm thanks.
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