Hi,
Thank you for your detailed sharing, and I'm truly sorry for the difficulties you have experienced.
Based on your description, Microsoft does have a support article for an earlier issue with the identical error message Images are not displayed in emails, newsletters, or signatures in classic Outlook | Microsoft Support, but that incident was attributed to the May 12, 2026 updates and is marked as fixed. The Current Channel release notes for Version 2608 only state “Various fixes to functionality and performance”, and there is no official article or documentation confirming that Builds 20228.20190 and 20326.20100 introduced this specific signature-image regression, as well as a published ETA for a corrective update.
Therefore, this could be a new regression or an environment-specific recurrence. Since rolling back to older channels helps resolve the situation, I highly recommend staying in the older channel and reporting this issue to Microsoft through Outlook > Help > Feedback so the engineering team can acknowledge and investigate it.
For your second concern, turning off Disable Updates is not necessarily authoritative in a managed business environment, as Microsoft 365 Apps updates can be controlled by several mechanisms like Group Policy, Microsoft Intune, Microsoft 365 Apps admin center Cloud Update, Office Deployment Tool configuration, etc.
Therefore, if Office updates again after you disable Auto Updates, the best next step I would suggest is to reach out to your company's IT department and ask for their help. They can help you check whether there is a Cloud Update configuration, Group Policy, or Intune that forces Office updates on your device.
Also, you can request your Global Administrator to open a support case with Microsoft regarding the image display issue in classic Outlook. A technical support engineer can initiate a remote session, assess backend configurations, and perform diagnostics. If necessary, they can escalate the matter to a specialized team for further investigation.
Please note that, as an independent advisor, I do not have access to Microsoft's internal systems, diagnostic tools, or backend resources that would be required to investigate or resolve account-specific issues. However, I sincerely hope the information provided helps point you in the right direction and assists you in finding a resolution.
I hope you find this information useful. If you have any questions or need further support, please don’t hesitate to reach out at any time.
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