Issues displaying linked image pasted into email sent via Outlook to distribution list

Occasional Visitor

This is my first time posting here, so please let me know if it belongs elsewhere.

 

I've got an issue that has me a bit stumped. As mentioned in the title, a specific user sends a daily email via Outlook to the entire company and typically uses Snip and Sketch app to grab a small screenshot then copy it into the body of the email. When recipients view the email the place holder for the copied image has a small white box in the top-left corner and the following error: "The linked image cannot be displayed. The file may have been moved, renamed, or deleted. Verify that the link points to the correct file and location."

 

 
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Typically resending the email a second time allows the image to display as expected. Strangely sending a similar email to individual recipients with an image snipped and copied works without issue, so it seems isolated to sending to this large group of recipients via the distribution list.

The problem seems somewhat intermittent and has persisted through Office repair, use of different apps (snipping tool, snip & sketch, and screen clipping via Outlook)), as well as attempts to troubleshoot based on research online (moving temporary internet files folder, some registry edits, and modifying internet options ('Do not save encrypted pages to disk' based on MSFT documentation) all to no avail.

Any ideas out there why this may be occurring or resources to learn more about this behavior? Please let me know if including any additional information would be helpful.

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