Using classic Outlook for Windows in business environments
Dear Caroline,
Good day, and thank you for the detailed description of your issue.
I'm truly sorry to hear that encrypted emails stopped opening in the Classic Outlook after the latest update. I can only imagine how disruptive this must be when encrypted messages are essential for your daily work, especially after you and your IT team have already tried restarting, updating, and rebooting without success. As a forum moderator, I genuinely wish I could directly investigate the update and resolve this for you. Unfortunately, my role here is limited to providing general guidance and pointing you to the right support channel.
Since multiple users are reporting the same problem and your IT team has been unable to identify the cause, this looks like it may be a build-specific issue introduced by the recent Outlook update, which needs to be investigated by Microsoft's engineering side. I would strongly recommend that the Global Admin in your organization open a service request with Microsoft Support. A technical support engineer can review your exact Outlook build and update channel, collect diagnostic logs from an affected machine, and confirm whether this is a known regression in the current release. If it is, they can escalate the case to the product team, which is genuinely the fastest path to getting a fix rolled out for everyone affected. For detailed instructions on how to get support, please refer to Get support - Microsoft 365 admin.
For additional assistance, use this link to find the appropriate contact number from your region: Global Customer Service phone numbers - Microsoft Support
In the meantime, I understand that you do not prefer the web version. However, if Outlook on the web is able to open and read your encrypted messages without issue, I would recommend using it temporarily while the support case is being investigated. It is not ideal, but it should keep your work moving until a fix is available.
I truly hope this gets resolved swiftly. Please know that even though I cannot directly intervene, pointing you toward the correct, specialized support is genuinely the most effective help I can offer from my position. Thank you for your patience and understanding. Please let me know if you need anything else.
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