Brandon,
Success…? Both my VirtualBox VM and physical server show the wrong date/time on the SYN/ACK using the updated testing script you sent. This was just a confirmation for what you had already confirmed as a reproducible issue though. I don’t have any next steps suggestions, sorry.
$ tshark -t ud -r lo-port-80.pcap
1 2018-04-10 22:07:21 ::1 → ::1 TCP 94 60782 > http [SYN] Seq=0 Win=43690 Len=0 MSS=65476 SACK_PERM=1 TSval=4294828850 TSecr=0 WS=128
2 2018-04-10 22:07:21 ::1 → ::1 TCP 74 http > 60782 [RST, ACK] Seq=1 Ack=1 Win=0 Len=0
3 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 74 39762 > http [SYN] Seq=0 Win=43690 Len=0 MSS=65495 SACK_PERM=1 TSval=4294828850 TSecr=0 WS=128
4 2106-01-31 09:17:55 127.0.0.1 → 127.0.0.1 TCP 74 http > 39762 [SYN, ACK] Seq=0 Ack=1 Win=43690 Len=0 MSS=65495 SACK_PERM=1 TSval=4294828850 TSecr=4294828850 WS=128
5 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=1 Ack=1 Win=43776 Len=0 TSval=4294828850 TSecr=4294828850
6 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 HTTP 139 GET / HTTP/1.1
7 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 http > 39762 [ACK] Seq=1 Ack=74 Win=43776 Len=0 TSval=4294828851 TSecr=4294828851
8 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 83 [TCP segment of a reassembled PDU]
9 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=74 Ack=18 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
10 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 103 [TCP segment of a reassembled PDU]
11 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=74 Ack=55 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
12 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 103 [TCP segment of a reassembled PDU]
13 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=74 Ack=92 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
14 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 129 [TCP segment of a reassembled PDU]
15 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=74 Ack=155 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
16 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 HTTP 838 HTTP/1.0 200 OK (text/html)
17 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [ACK] Seq=74 Ack=927 Win=45312 Len=0 TSval=4294828856 TSecr=4294828856
18 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 http > 39762 [FIN, ACK] Seq=927 Ack=74 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
19 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 39762 > http [FIN, ACK] Seq=74 Ack=928 Win=45312 Len=0 TSval=4294828856 TSecr=4294828856
20 2018-04-10 22:07:21 127.0.0.1 → 127.0.0.1 TCP 66 http > 39762 [ACK] Seq=928 Ack=75 Win=43776 Len=0 TSval=4294828856 TSecr=4294828856
$
$ tcpdump -ttttnnr lo-port-80.pcap
reading from file lo-port-80.pcap, link-type EN10MB (Ethernet)
2018-04-10 15:28:49.065635 IP6 ::1.49766 > ::1.80: Flags [S], seq 2880441537, win 43690, options [mss 65476,sackOK,TS val 1116497470 ecr 0,nop,wscale 7], length 0
2018-04-10 15:28:49.065668 IP6 ::1.80 > ::1.49766: Flags [R.], seq 0, ack 2880441538, win 0, length 0
2018-04-10 15:28:49.065840 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [S], seq 3964604917, win 43690, options [mss 65495,sackOK,TS val 1116497470 ecr 0,nop,wscale 7], length 0
1985-11-08 19:53:43.822714 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [S.], seq 3727387360, ack 3964604918, win 43690, options [mss 65495,sackOK,TS val 1116497470 ecr 1116497470,nop,wscale 7], length 0
2018-04-10 15:28:49.065886 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 1, win 342, options [nop,nop,TS val 1116497470 ecr 1116497470], length 0
2018-04-10 15:28:49.065973 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [P.], seq 1:74, ack 1, win 342, options [nop,nop,TS val 1116497471 ecr 1116497470], length 73: HTTP: GET / HTTP/1.1
2018-04-10 15:28:49.065987 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [.], ack 74, win 342, options [nop,nop,TS val 1116497471 ecr 1116497471], length 0
2018-04-10 15:28:49.176734 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 1:18, ack 74, win 342, options [nop,nop,TS val 1116497581 ecr 1116497471], length 17: HTTP: HTTP/1.0 200 OK
2018-04-10 15:28:49.176760 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 18, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 0
2018-04-10 15:28:49.176813 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 18:55, ack 74, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 37: HTTP
2018-04-10 15:28:49.176831 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 55, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 0
2018-04-10 15:28:49.176886 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 55:92, ack 74, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 37: HTTP
2018-04-10 15:28:49.176900 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 92, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 0
2018-04-10 15:28:49.176951 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 92:132, ack 74, win 342, options [nop,nop,TS val 1116497581 ecr 1116497581], length 40: HTTP
2018-04-10 15:28:49.176966 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 132, win 342, options [nop,nop,TS val 1116497582 ecr 1116497581], length 0
2018-04-10 15:28:49.177003 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 132:154, ack 74, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 22: HTTP
2018-04-10 15:28:49.177016 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 154, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 0
2018-04-10 15:28:49.177051 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 154:156, ack 74, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 2: HTTP
2018-04-10 15:28:49.177064 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 156, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 0
2018-04-10 15:28:49.177124 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [P.], seq 156:5992, ack 74, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 5836: HTTP
2018-04-10 15:28:49.177142 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [.], ack 5992, win 1365, options [nop,nop,TS val 1116497582 ecr 1116497582], length 0
2018-04-10 15:28:49.177212 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [F.], seq 5992, ack 74, win 342, options [nop,nop,TS val 1116497582 ecr 1116497582], length 0
2018-04-10 15:28:49.178159 IP 127.0.0.1.44468 > 127.0.0.1.80: Flags [F.], seq 74, ack 5993, win 1365, options [nop,nop,TS val 1116497583 ecr 1116497582], length 0
2018-04-10 15:28:49.178176 IP 127.0.0.1.80 > 127.0.0.1.44468: Flags [.], ack 75, win 342, options [nop,nop,TS val 1116497583 ecr 1116497583], length 0
$