DLP fails to perform detection when Microsoft Information Protection files are sent via email.
And, you notice these entries in the FileReader logs from your detection server,
File: Email_Prevent_4\logs\debug\ContentExtractionHost_FileReader.log.5
Date: 7/7/2022 5:09:24 PM
Level: ERROR
Source: MicrosoftInformationProtectionPlugin @ ..\..\..\..\MIPUtil\MIPUtil\RequestHandler.cpp (188)
PID: 7732
Thread: 5796
Message: curl_easy_perform() failed: SSL connect error (35) - attempt: 4 retries left: 0
File: Email_Prevent_4\logs\debug\ContentExtractionHost_FileReader.log.5
Date: 7/7/2022 5:09:24 PM
Level: TRACE
Source: MicrosoftInformationProtectionPlugin @ ..\..\..\..\MIPUtil\MIPUtil\RequestHandler.cpp (319)
PID: 7732
Thread: 5796
Message: Curl: == Info: OpenSSL SSL_connect: SSL_ERROR_SYSCALL in connection to api.aadrm.com:443
Release : 15.8
You are forwarding email from the DLP Network Prevent for Email detection server onto a Proxy server. The TLS negotiation is failing when the plugin is using (industry-standard communication library) libcurl to get a token from api.aadrm.com. The proxy is interfering with the connection during TLS negotiation.
The issue is outside of DLP and must be corrected by your Proxy server admin.