Using classic Outlook for Windows in business environments
Hello @Kieran Stafford
Could you please let me know which version of Outlook you are using? To check this, please open Outlook and navigate to File > Office Account (or File > Account) and share the complete version and build number shown under About Outlook.
Based on your description, this behavior could be related to how the images are referenced in the HTML signature. In some cases, Microsoft 365 security policies, email security gateways, or the recipient's mail server may block or prevent the download of externally linked images, which can result in blank image placeholders or red X icons appearing in the message.
If the signature appears blank or some images are missing, could you please confirm whether the same behavior occurs across all Outlook platforms, such as Outlook on the web, Outlook classic and new Outlook?
Additionally, using CID-embedded images (Content-ID embedded images) can often be more reliable than externally linked images because the images are included within the email itself rather than being downloaded from an external location. However, while this approach may reduce issues caused by image blocking, it does not guarantee that images will display correctly in every email client or environment.
You should manually remove and reinsert each image in the signature one by one, save the changes, and then have a test email. Please let me know whether the issue still occurs after re-adding the images.
I look forward to your update.