Here is the readout when I use "--verbose"
C:\Windows\system32>osqueryd.exe --verbose --flagfile="C:\Program Files\osquery\osquery.flags"
I0225 14
5655.412991 492 init.cpp:340] osquery initialized [version=4.2.0]
I0225 14
5655.450927 492 system.cpp:330] Found stale process for osqueryd (2676)
I0225 14
5655.450927 492 system.cpp:362] Writing osqueryd pid (1544) to \Program Files\osquery\osqueryd.pidfile
I0225 14
5655.473908 492 extensions.cpp:349] Could not autoload extensions: Failed reading: \Program Files\osquery\extensions.load
I0225 14
5655.473908 5492 watcher.cpp:583] osqueryd watcher (1544) executing worker (5436)
I0225 14
5655.521196 4764 init.cpp:337] osquery worker initialized [watcher=1544]
I0225 14
5655.521196 4764 rocksdb.cpp:131] Opening RocksDB handle: \Program Files\osquery\osquery.db
I0225 14
5655.599743 4764 tls_enroll.cpp:69] TLSEnrollPlugin requesting a node enroll key from:
https://192.168.1.10:8080/api/v1/osquery/enroll
I0225 14
5655.599743 5672 interface.cpp:268] Extension manager service starting: \\.\pipe\osquery.em
I0225 14
5655.599743 4764 system.cpp:289] Using host identifier: D8F242BE-9FA7-4402-9736-6E4A3169205D
Thrift: Tue Feb 25 14
5655 2020 Client connected.
Thrift: Tue Feb 25 14
5655 2020 Client connected.
Thrift: Tue Feb 25 14
5655 2020 TPipe ::GetOverlappedResult errored GLE=errno = 109
Thrift: Tue Feb 25 14
5655 2020 TPipe ::GetOverlappedResult errored GLE=errno = 109
Thrift: Tue Feb 25 14
5655 2020 TConnectedClient died: TPipe: GetOverlappedResult failed
Thrift: Tue Feb 25 14
5655 2020 TConnectedClient died: TPipe: GetOverlappedResult failed
I0225 14
5656.693370 4764 tls.cpp:253] TLS/HTTPS POST request to URI:
https://192.168.1.10:8080/api/v1/osquery/enroll
W0225 14
5656.693370 4764 tls.cpp:100] Cannot read TLS server certificate(s): "c:\Program Files\osquery\kolide.pem"
W0225 14
5657.052332 4764 tls_enroll.cpp:76] Failed enrollment request to
https://192.168.1.10:8080/api/v1/osquery/enroll (Request error: certificate verify failed) retrying...