Hi @Andrew Talbot
I understand that you have 20 users on Classic Outlook for Microsoft 365 using an email signature that includes a banner image linked directly from your server. When you replace the image file on your server to reflect a new banner, Outlook continues to display the previously cached image instead of downloading the new one. You are looking for a solution to force the updated image to display without needing to manually change the URL in every user's signature.
This step helps us understand the server-side environment. Could you please describe in more detail exactly where this image is stored? Furthermore, what is your exact process for updating the image (for example, overwriting the file via FTP, updating it through a web portal, etc.)?
To isolate the behavior, I conducted a test in my own environment. I hosted an image on OneDrive, inserted it into an Outlook signature (adding both the image and the link), and then edited and cropped the image directly within OneDrive. Upon checking Outlook, it did not automatically sync the newly cropped image. I found that I needed to manually navigate into the signature settings and save it again to force the client to fetch the latest version.
This step checks for environmental variables. Because I do not have full visibility into your specific network or hosting setup, comparing my test results with your exact workflow will help us determine the best path forward. It will help us identify if we need to adjust something on the server side or if we need to look at a client-side deployment script.
Please reply with the additional details regarding where the image is stored and how it is updated. Thank you for your understanding.
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