Interestingly, no. I don’t see 404 specifically. However, disabling “Secure Access” resolves the issue immediately.
I don’t want to leave it like that, but I will until I figure this out.
I just rebooted the server and grabbed the log after a few minutes. Here is every line containing the word “CERT”:
Oct 02, 2020 18:26:00.722 [0x7fe157fb0180] DEBUG - CERT: Installed certificate with fingerprint d0:77:bb:3a:6f:75:74:7e:ea:d8:26:21:45:aa:3b:d9:1a:e1:18:08.
Oct 02, 2020 18:26:00.723 [0x7fe157fb0180] DEBUG - CERT: Installed new private key.
Oct 02, 2020 18:26:00.723 [0x7fe157fb0180] DEBUG - CERT: Subject name is /C=US/ST=California/L=Los Gatos/O=Plex, Inc./CN=*.4df42e245dc944ab9fad0f389c72edcf.plex.direct
Oct 02, 2020 18:26:00.723 [0x7fe157fb0180] DEBUG - CERT: OCSP requests for stapling will be made to 'http://ocsp.digicert.com/'.
Oct 02, 2020 18:26:00.724 [0x7fe157fb0180] DEBUG - CERT: Installed intermediate certificate.
Oct 02, 2020 18:26:00.728 [0x7fe14fcb2700] DEBUG - HTTP requesting GET http://ocsp.digicert.com/MFEwTzBNMEswSTAJBgUrDgMCGgUABBRa0O%2BtN66dcUoU8s4f6J4%2Bqp5hQgQUlIuJ90hyifJRStmIe%2BVhtaqc1QECEA4E6UvvMwzpVm9BWzZfHgM%3D
Oct 02, 2020 18:26:01.330 [0x7fe14fcb2700] DEBUG - HTTP 200 response from GET http://ocsp.digicert.com/MFEwTzBNMEswSTAJBgUrDgMCGgUABBRa0O%2BtN66dcUoU8s4f6J4%2Bqp5hQgQUlIuJ90hyifJRStmIe%2BVhtaqc1QECEA4E6UvvMwzpVm9BWzZfHgM%3D
Oct 02, 2020 18:26:03.734 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:10.588 [0x7fe136fed700] DEBUG - CERT: Certificate will not expire soon.
Oct 02, 2020 18:26:15.592 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.605 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.618 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.631 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.659 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.671 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.683 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.692 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:15.721 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:26:18.017 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:27:15.748 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:27:15.756 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:27:15.765 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:27:15.774 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:27:15.787 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:28:15.805 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:28:15.814 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:28:15.823 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:28:15.832 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:28:15.846 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:15.863 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:15.873 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:15.883 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:15.892 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:15.906 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:29:25.242 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:30:05.608 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:30:15.998 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:30:16.023 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:30:16.035 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:30:16.045 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:30:16.058 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:31:16.075 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:31:16.084 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:31:16.092 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:31:16.101 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:31:16.114 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:32:16.132 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:32:16.141 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:32:16.149 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:32:16.157 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:32:16.171 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:16.188 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:16.197 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:16.206 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:16.214 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:16.227 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:33:33.410 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:38.229 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:38.229 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:40.455 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.049 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.066 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.067 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.072 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.080 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.080 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.084 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.085 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.240 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.248 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:33:42.260 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:34:16.244 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:16.253 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:16.261 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:16.270 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:16.283 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:16.625 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:34:16.638 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:34:16.640 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:34:16.645 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: sslv3 alert certificate unknown
Oct 02, 2020 18:34:17.873 [0x7fe14ecb0700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
Oct 02, 2020 18:34:36.629 [0x7fe14f4b1700] DEBUG - CERT: incomplete TLS handshake: tlsv1 alert unknown ca
I can upload the whole log if needed.