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Based on the details you shared, I understand that inline images in the body of emails sent by internal users are failing to display in Outlook on the Web (OWA), even though they render perfectly fine in the Outlook Desktop client. This issue affects multiple recipients across different web browsers, regardless of whether they are accessing OWA from inside or outside the corporate network. Interestingly, the missing images suddenly become visible as soon as the user clicks "Reply" or "Forward."
After researching this behavior, this specific symptom is heavily linked to a known issue introduced by a recent security mitigation on Exchange Server backend environments. To narrow this down, could you please let me know which version of Exchange Server your organization is currently running? (e.g., Exchange Server 2016, Exchange Server 2019, or Exchange Server Subscription Edition).
Depending on your specific Exchange Server environment, here are the steps to address this rendering bug:
- If you are running Exchange Server 2016 or Exchange Server 2019: Only customers who enrolled in the Period 2 Extended Security Update (ESU) program are eligible to receive Exchange Server 2016 and 2019 security updates released between May and October 2026.
- If you are running Exchange Server Subscription Edition (SE): If your organization has already transitioned to Exchange Server SE, the recommended path to fix this behavior is to safely remove the temporary mitigation script and immediately apply the June 2026 Security Update (SU).
For full, step-by-step instructions on how to safely manage the mitigation or apply these updates on your session hosts, please refer to the official Microsoft Tech Community and Exchange Server update documentation regarding recent Security Updates.
Please pass this information along to your Exchange IT Administrator so they can check the patch level of your mail servers. Let me know if you need help finding the specific download links for the updates!
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