Using classic Outlook for Windows in educational settings
From what you’ve described, this appears to be a known issue affecting classic Outlook for Windows. Specifically, it has been observed that images in emails, newsletters, and signatures may display correctly while composing. However, after the message is sent, the images can disappear. As a result, recipients, as well as your own Sent Items, may show the message "The linked image cannot be displayed".
According to Microsoft, this issue began after the May 12, 2026 updates and is related to how certain images are formatted within the message. You may find more details in Microsoft’s documentation under: Images are not displayed in emails, newsletters, or signatures in classic Outlook
To begin with, I recommend checking your current Outlook version and ensuring that all Office updates are installed. You can do this by going to File > Office Account > About Outlook (to view your version/build), and then File > Office Account > Update Options > Update Now (to install updates).
Microsoft has already released a fix in newer builds. Additionally, for update channels that had not yet received it, the fix was expected to be included in the public updates released on June 9, 2026.
Furthermore, Microsoft notes that this issue is often linked to images using the "Top and Bottom" text wrapping option. Therefore, as a temporary workaround, you can try recreating your email signature and ensuring that any images are set to "In Line with Text" instead of "Top and Bottom" or other floating wrap styles. This setting can also be controlled through the Insert/paste pictures as option in the Outlook/Office editor.
In summary, I would recommend the following steps:
Update your Outlook/Office installation to the latest version.
Check your signature image formatting and switch it to “In Line with Text.”
Recreate your signature after updating, and test it by sending a new message.
I hope this information helps improve the situation. Please feel free to reach out if you have any questions or need further assistance.
Wishing you all the best.
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