ntpd -s doesn't work with constraints when the date is too far off. At least that's my current hypothesis.
Example from latest octeon snap: octeon:~$ doas date 201409112020 Thu Sep 11 20:20:00 CEST 2014 octeon:~$ doas ntpd -v -d -s ntp engine ready constraint request to 2a00:1450:4013:c00::69 constraint request to 216.58.211.100 tls failed: 2a00:1450:4013:c00::69: connect no constraint reply from 2a00:1450:4013:c00::69 received in time, next query 900s tls failed: 216.58.211.100: connect failed: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed no constraint reply from 216.58.211.100 received in time, next query 900s no reply received in time, skipping initial time setting ^Cntp engine exiting Terminating octeon:~$ doas vi /etc/ntpd.conf # <------ comment constraints line. octeon:~$ doas ntpd -v -d -s ntp engine ready reply from 46.165.212.205: offset 31536038.233497 delay 0.033760, next query 8s set local clock to Fri Sep 11 20:22:23 CEST 2015 (offset 31536038.233497s) reply from 78.47.254.155: offset 15768019.117504 delay 31536038.275234, next query 8s reply from 81.88.24.155: offset 15768019.106225 delay 31536038.277960, next query 7s reply from 85.10.246.234: offset 15768019.118702 delay 31536038.277447, next query 6s reply from 85.10.246.234: offset 0.002484 delay 0.039208, next query 6s reply from 81.88.24.155: offset -0.010518 delay 0.041345, next query 6s reply from 46.165.212.205: offset -0.000368 delay 0.032194, next query 8s reply from 78.47.254.155: offset 0.002271 delay 0.039435, next query 8s reply from 85.10.246.234: offset 0.002595 delay 0.039722, next query 9s reply from 81.88.24.155: offset -0.009674 delay 0.041825, next query 9s ^Cntp engine exiting octeon:~$ doas vi /etc/ntpd.conf # <- enable constraints, works like magic octeon:~$ doas ntpd -v -d -s ntp engine ready constraint request to 2a00:1450:4007:806::1012 constraint request to 216.58.211.100 tls failed: 2a00:1450:4007:806::1012: connect no constraint reply from 2a00:1450:4007:806::1012 received in time, next query 900s constraint reply from 216.58.211.100: offset -1.009538 reply from 87.230.95.114: offset -0.000038 delay 0.033070, next query 8s set local clock to Fri Sep 11 20:30:23 CEST 2015 (offset -0.000038s) reply from 129.70.132.34: offset 0.002208 delay 0.041274, next query 7s reply from 129.250.35.250: offset -0.003325 delay 0.040867, next query 6s reply from 5.100.133.221: offset 0.021947 delay 0.046111, next query 7s reply from 129.250.35.250: offset -0.002102 delay 0.035490, next query 6s reply from 129.70.132.34: offset 0.003127 delay 0.040334, next query 5s reply from 5.100.133.221: offset 0.022393 delay 0.046518, next query 5s reply from 87.230.95.114: offset -0.001053 delay 0.031630, next query 8s reply from 129.250.35.250: offset -0.000493 delay 0.035583, next query 6s reply from 129.70.132.34: offset 0.003118 delay 0.040750, next query 9s reply from 5.100.133.221: offset 0.022552 delay 0.045970, next query 9s ^Cntp engine exiting Terminating I'm not singling out octeon, it's just very noticeable there.