Cannot let problems lie around for too long so I dug into it a few inches deeper and compared it to the output of one of our linux clients, which btw. work flawlessly.
The Windows request seems to die when trying the Certificate Request. Here is the debug output of both clients:
Linux:
[root@ClientHostNameHere ~]# cmk-agent-ctl register -H ClientHostNameHere -s CMKHostNameHere -i CMKInstance -U AdminAcc -P AdminPW -vv --trust-cert
INFO [cmk_agent_ctl] starting
INFO [cmk_agent_ctl] Loaded config from '"/var/lib/cmk-agent/cmk-agent-ctl.toml"', legacy pull 'LegacyPullMarker("/var/lib/cmk-agent/allow-legacy-pull")' absent
DEBUG [reqwest::connect] starting new connection: https://CMKHostNameHere/
DEBUG [reqwest::async_impl::client] response '200 OK' for https://CMKHostNameHere/CMKInstance/check_mk/api/1.0/domain-types/internal/actions/discover-receiver/invoke
DEBUG [reqwest::connect] starting new connection: https://CMKHostNameHere:8000/
DEBUG [reqwest::async_impl::client] response '200 OK' for https://CMKHostNameHere:8000/CMKInstance/agent-receiver/pairing
!!! => Somewhere here the windows agent dies !!!
DEBUG [reqwest::connect] starting new connection: https://CMKHostNameHere:8000/
DEBUG [rustls::client::hs] No cached session for DnsName(DnsName(DnsName("CMKHostNameHere")))
DEBUG [rustls::client::hs] Not resuming any session
DEBUG [rustls::client::hs] Using ciphersuite TLS13_AES_256_GCM_SHA384
DEBUG [rustls::client::tls13] Not resuming
DEBUG [rustls::client::tls13] TLS1.3 encrypted extensions: []
DEBUG [rustls::client::hs] ALPN protocol is None
DEBUG [rustls::client::tls13] Got CertificateRequest CertificateRequestPayloadTLS13 { context: , extensions: [SignatureAlgorithms([ECDSA_NISTP256_SHA256, ECDSA_NISTP384_SHA384, ECDSA_NISTP521_SHA512, ED25519, ED448, Unknown(2057), Unknown(2058), Unknown(2059), RSA_PSS_SHA256, RSA_PSS_SHA384, RSA_PSS_SHA512, RSA_PKCS1_SHA256, RSA_PKCS1_SHA384, RSA_PKCS1_SHA512, Unknown(771), ECDSA_SHA1_Legacy, Unknown(769), RSA_PKCS1_SHA1])] }
DEBUG [rustls::client::common] Client auth requested but no cert/sigscheme available
DEBUG [rustls::client::tls13] Ticket saved
DEBUG [rustls::client::tls13] Ticket saved
DEBUG [reqwest::async_impl::client] response '204 No Content' for https://CMKHostNameHere:8000/CMKInstance/agent-receiver/register_with_hostname
DEBUG [reqwest::connect] starting new connection: https://CMKHostNameHere:8000/
DEBUG [rustls::client::hs] No cached session for DnsName(DnsName(DnsName("CMKHostNameHere")))
DEBUG [rustls::client::hs] Not resuming any session
DEBUG [rustls::client::hs] Using ciphersuite TLS13_AES_256_GCM_SHA384
DEBUG [rustls::client::tls13] Not resuming
DEBUG [rustls::client::tls13] TLS1.3 encrypted extensions: []
DEBUG [rustls::client::hs] ALPN protocol is None
DEBUG [rustls::client::tls13] Got CertificateRequest CertificateRequestPayloadTLS13 { context: , extensions: [SignatureAlgorithms([ECDSA_NISTP256_SHA256, ECDSA_NISTP384_SHA384, ECDSA_NISTP521_SHA512, ED25519, ED448, Unknown(2057), Unknown(2058), Unknown(2059), RSA_PSS_SHA256, RSA_PSS_SHA384, RSA_PSS_SHA512, RSA_PKCS1_SHA256, RSA_PKCS1_SHA384, RSA_PKCS1_SHA512, Unknown(771), ECDSA_SHA1_Legacy, Unknown(769), RSA_PKCS1_SHA1])] }
DEBUG [rustls::client::common] Attempting client auth
DEBUG [rustls::client::tls13] Ticket saved
DEBUG [rustls::client::tls13] Ticket saved
DEBUG [reqwest::async_impl::client] response '200 OK' for https://CMKHostNameHere:8000/CMKInstance/agent-receiver/registration_status/SomeNiceIDHere
Windows:
PS C:\ProgramData\checkmk\agent\bin> .\cmk-agent-ctl.exe register --trust-cert -H ClientHostNameHere -s CMKHostNameHere -i CMKInstance -U AdminAcc -P AdminPW -vv
[2022-11-04 13:20:49.407595 +01:00] INFO [cmk_agent_ctl] src\main.rs:14: starting
[2022-11-04 13:20:49.408645 +01:00] INFO [cmk_agent_ctl] src\lib.rs:41: Loaded config from '"C:\\ProgramData\\checkmk\\agent\\cmk-agent-ctl.toml"', legacy pull 'LegacyPullMarker("C:\\ProgramData\\checkmk\\agent\\allow-legacy-pull")' exists
[2022-11-04 13:20:49.417123 +01:00] DEBUG [reqwest::connect] C:\Users\sk\.cargo\registry\src\github.com-1ecc6299db9ec823\reqwest-0.11.11\src\connect.rs:560: starting new connection: https://CMKHostNameHere/
[2022-11-04 13:20:49.471035 +01:00] DEBUG [reqwest::async_impl::client] C:\Users\sk\.cargo\registry\src\github.com-1ecc6299db9ec823\reqwest-0.11.11\src\async_impl\client.rs:2017: response '200 OK' for https://CMKHostNameHere/CMKInstance/check_mk/api/1.0/domain-types/internal/actions/discover-receiver/invoke
[2022-11-04 13:20:50.009310 +01:00] DEBUG [reqwest::connect] C:\Users\sk\.cargo\registry\src\github.com-1ecc6299db9ec823\reqwest-0.11.11\src\connect.rs:560: starting new connection: https://CMKHostNameHere:8000/
thread 'reqwest-internal-sync-runtime' panicked at 'capacity overflow', library\alloc\src\raw_vec.rs:518:5
note: run with `RUST_BACKTRACE=1` environment variable to display a backtrace
thread 'main' panicked at 'event loop thread panicked', C:\Users\sk\.cargo\registry\src\github.com-1ecc6299db9ec823\reqwest-0.11.11\src\blocking\client.rs:1118:5