Handling External Disclaimer Exceptions for Trusted Application Relays in Exchange Hybrid

Handling External Disclaimer Exceptions for Trusted Application Relays in Exchange Hybrid

Exchange, Exchange Online, Exchange Server SE / 2019 / 2016, Hybrid, Security & Hardening
In Exchange Hybrid environments, it is common to use mail flow rules to add an external disclaimer or warning banner to messages received from outside the organization. A typical warning may look like this: WARNING: This email originated from outside the organization. Do not click links or open attachments unless you recognize the sender. This is a good security control. It helps users identify messages that came from external sources. However, there are some scenarios where messages generated by internal application servers may also receive this external disclaimer. This usually happens when an internal application server submits email anonymously to Exchange Server on-premises, and Exchange then routes the message to Exchange Online. In this article, we will look at how to handle this scenario safely by using a custom header…
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Force OWA Light Users to Premium OWA After Exchange Server May 2026 CVE Mitigation

Force OWA Light Users to Premium OWA After Exchange Server May 2026 CVE Mitigation

Exchange, Exchange Server SE / 2019 / 2016, Migration & Upgrade, Security & Hardening
Microsoft recently published guidance for Exchange Server addressing the May 2026 vulnerability. One important note in the article is related to OWA Light. Microsoft states that OWA Light — accessed by using an OWA URL ending with /?layout=light — does not work properly after the mitigation is applied. Microsoft also notes that this feature was deprecated several years ago and is not intended for regular production use. For a deeper look at the OWA request path and frontend/backend authentication design, see Exchange OWA Authentication Deep Dive – Part 1. This can become a practical issue if some users previously selected the following option in Outlook on the web: "Use the light version of Outlook" When this option is selected, the user may continue to be redirected to the Light version…
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