I confirm you the issue, I'm on an 8.6.1 stack.
After the reboot, my service seems to be running (on systemctl):
root@SRV-ElasticSearchAgent:~# systemctl status elastic-agent
● elastic-agent.service - Elastic Agent is a unified agent to observe, monitor and protect your system.
     Loaded: loaded (/etc/systemd/system/elastic-agent.service; enabled; vendor preset: enabled)
     Active: active (running) since Tue 2023-02-14 16:51:33 CET; 5min ago
   Main PID: 526 (elastic-agent)
      Tasks: 63 (limit: 9460)
     Memory: 618.7M
        CPU: 12.576s
     CGroup: /system.slice/elastic-agent.service
             ├─526 /opt/Elastic/Agent/elastic-agent
             ├─600 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/filebeat -E setup.ilm.enabled=false -E setup.template.enabled=false -E manageme>
             ├─602 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/metricbeat -E setup.ilm.enabled=false -E setup.template.enabled=false -E manage>
             ├─605 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/fleet-server --agent-mode -E logging.level=debug -E logging.to_stderr=true -E h>
             ├─606 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/filebeat -E setup.ilm.enabled=false -E setup.template.enabled=false -E manageme>
             ├─613 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/metricbeat -E setup.ilm.enabled=false -E setup.template.enabled=false -E manage>
             └─617 /opt/Elastic/Agent/data/elastic-agent-b8553c/components/metricbeat -E setup.ilm.enabled=false -E setup.template.enabled=false -E manage>
févr. 14 16:51:33 SRV-ElasticSearchAgent systemd[1]: Started Elastic Agent is a unified agent to observe, monitor and protect your system..
And on my fleet integration, I don't see my two agents online and healthy after reboot.
I have installed the server agent with the quick install integration, last command to install it is:
./elastic-agent install   --fleet-server-es=https://<elastic-ip>:9200   --fleet-server-service-token=<token-provided>   --fleet-server-policy=fleet-server-policy   --fleet-server-es-ca-trusted-fingerprint=8fc9cf3da149e5b4d2b6aea8e9e2143cb3d279a0bf9391e50f1b1274db793b07 --insecure
I don't understand if there is a config file to edit. I don't have any TLS implemented on the stack for the moment. I receive agents data without issue before the server reboot.
To complete my message, I receive well logs from the agents, I think that it is only about agent and the fleet server that there is an issue:
here is the fleet server log:
And here the windows agent logs
15:53:09.605
elastic_agent
[elastic_agent][info] Unit state changed system/metrics-default (STARTING->HEALTHY): Healthy
16:51:01.939
elastic_agent
[elastic_agent][warn] Possible transient error during checkin with fleet-server, retrying
16:52:12.802
elastic_agent
[elastic_agent][warn] Unit state changed endpoint-default-e50a5103-f72f-453e-9b84-ab19e42b9462 (HEALTHY->DEGRADED): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
16:52:12.803
elastic_agent
[elastic_agent][warn] Unit state changed endpoint-default (HEALTHY->DEGRADED): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
16:52:39.331
elastic_agent
[elastic_agent][warn] Possible transient error during checkin with fleet-server, retrying
16:52:52.815
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default-e50a5103-f72f-453e-9b84-ab19e42b9462 (DEGRADED->HEALTHY): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
16:52:52.815
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default (DEGRADED->HEALTHY): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
16:55:28.698
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:03:10.587
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:15:10.081
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:23:42.070
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:30:41.501
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:42:38.325
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:49:08.067
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
17:57:51.593
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
18:07:32.657
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
18:16:03.454
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
18:28:48.687
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
18:41:41.563
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
18:51:47.884
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:03:58.562
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:18:48.143
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:24:57.999
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:30:46.553
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:42:26.619
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:50:05.698
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
19:58:55.743
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:11:37.533
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:19:04.464
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:29:08.276
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:42:10.242
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:51:19.503
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default-e50a5103-f72f-453e-9b84-ab19e42b9462 (HEALTHY->CONFIGURING): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
20:51:19.503
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default (HEALTHY->CONFIGURING): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
20:51:39.515
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default-e50a5103-f72f-453e-9b84-ab19e42b9462 (CONFIGURING->HEALTHY): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
20:51:39.515
elastic_agent
[elastic_agent][info] Unit state changed endpoint-default (CONFIGURING->HEALTHY): Applied policy {e50a5103-f72f-453e-9b84-ab19e42b9462}
20:52:26.651
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
20:59:34.003
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
21:13:54.020
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
21:21:18.748
elastic_agent
[elastic_agent][error] Cannot checkin in with fleet-server, retrying
Later, there is a connection for a short period of time (I did nothing which can explain that)
I hope this could help 