Update: I almost forgot about my most recent healthcheck-related discovery. By adding the healthcheck (as described here) I was able to get a debug log off of the test system that contains the errors.
I am not sure if this is the same bug. The behaviour looks the same, though.
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Configuration loaded from flags."
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Traefik version 2.8.8 built on 2022-09-30T12:20:13Z"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Static configuration loaded {\"global\":{\"checkNewVersion\":true},\"serversTransport\":{\"maxIdleConnsPerHost\":200},\"entryPoints\":{\"websecure\":{\"address\":\":443\",\"transport\":{\"lifeCycle\":{\"graceTimeOut\":\"10s\"},\"respondingTimeouts\":{\"idleTimeout\":\"3m0s\"}},\"forwardedHeaders\":{},\"http\":{},\"http2\":{\"maxConcurrentStreams\":250},\"udp\":{\"timeout\":\"3s\"}}},\"providers\":{\"providersThrottleDuration\":\"2s\",\"docker\":{\"watch\":true,\"endpoint\":\"unix:///var/run/docker.sock\",\"defaultRule\":\"Host(`{{ normalize .Name }}`)\",\"swarmModeRefreshSeconds\":\"15s\"}},\"api\":{\"dashboard\":true},\"log\":{\"level\":\"DEBUG\",\"format\":\"common\"},\"pilot\":{\"dashboard\":true}}"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="\nStats collection is disabled.\nHelp us improve Traefik by turning this feature on :)\nMore details on: https://doc.traefik.io/traefik/contributing/data-collection/\n"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=warning msg="Traefik Pilot is deprecated and will be removed soon. Please check our Blog for migration instructions later this year."
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Starting provider aggregator aggregator.ProviderAggregator"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Starting TCP Server" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Starting provider *traefik.Provider"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="*traefik.Provider provider configuration: {}"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Configuration received: {\"http\":{\"services\":{\"api\":{},\"dashboard\":{},\"noop\":{}},\"serversTransports\":{\"default\":{\"maxIdleConnsPerHost\":200}}},\"tcp\":{},\"udp\":{},\"tls\":{}}" providerName=internal
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="No default certificate, generating one" tlsStoreName=default
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Starting provider *docker.Provider"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="*docker.Provider provider configuration: {\"watch\":true,\"endpoint\":\"unix:///var/run/docker.sock\",\"defaultRule\":\"Host(`{{ normalize .Name }}`)\",\"swarmModeRefreshSeconds\":\"15s\"}"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=info msg="Starting provider *acme.ChallengeTLSALPN"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="*acme.ChallengeTLSALPN provider configuration: {}"
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Provider connection established with docker 20.10.18 (API 1.41)" providerName=docker
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Filtering unhealthy or starting container" container=traefik-example-5655860f14af23736df5596882d2562b344013594f3aa7c0e75ca5a8fb09fd88 providerName=docker
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="Configuration received: {\"http\":{\"routers\":{\"whoamiA\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiA-example\",\"rule\":\"Host(`whoamiA.example`)\",\"tls\":{}},\"whoamiB\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiB-example\",\"rule\":\"Host(`whoamiB.example`)\",\"tls\":{}},\"whoamiC\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiC-example\",\"rule\":\"Host(`whoamiC.example`)\",\"tls\":{}},\"whoamiD\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiD-example\",\"rule\":\"Host(`whoamiD.example`)\",\"tls\":{}},\"whoamiE\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiE-example\",\"rule\":\"Host(`whoamiE.example`)\",\"tls\":{}},\"whoamiF\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiF-example\",\"rule\":\"Host(`whoamiF.example`)\",\"tls\":{}},\"whoamiG\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiG-example\",\"rule\":\"Host(`whoamiG.example`)\",\"tls\":{}},\"whoamiH\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiH-example\",\"rule\":\"Host(`whoamiH.example`)\",\"tls\":{}},\"whoamiI\":{\"entryPoints\":[\"websecure\"],\"middlewares\":[\"default_ssl\"],\"service\":\"whoamiI-example\",\"rule\":\"Host(`whoamiI.example`)\",\"tls\":{}}},\"services\":{\"whoamiA-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.11:80\"}],\"passHostHeader\":true}},\"whoamiB-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.6:80\"}],\"passHostHeader\":true}},\"whoamiC-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.4:80\"}],\"passHostHeader\":true}},\"whoamiD-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.9:80\"}],\"passHostHeader\":true}},\"whoamiE-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.7:80\"}],\"passHostHeader\":true}},\"whoamiF-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.3:80\"}],\"passHostHeader\":true}},\"whoamiG-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.2:80\"}],\"passHostHeader\":true}},\"whoamiH-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.5:80\"}],\"passHostHeader\":true}},\"whoamiI-example\":{\"loadBalancer\":{\"servers\":[{\"url\":\"http://172.24.0.10:80\"}],\"passHostHeader\":true}}}},\"tcp\":{},\"udp\":{}}" providerName=docker
example-traefik-1 | time="2022-10-06T15:05:39Z" level=debug msg="No default certificate, generating one" tlsStoreName=default
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" middlewareName=pipelining middlewareType=Pipelining routerName=whoamiA@docker serviceName=whoamiA-example entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" routerName=whoamiA@docker serviceName=whoamiA-example entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.11:80" serverName=0 serviceName=whoamiA-example entryPointName=websecure routerName=whoamiA@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.11:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiA-example" entryPointName=websecure routerName=whoamiA@docker middlewareName=tracing middlewareType=TracingForwarder
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiA@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" middlewareType=Pipelining entryPointName=websecure routerName=whoamiH@docker serviceName=whoamiH-example middlewareName=pipelining
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" serviceName=whoamiH-example entryPointName=websecure routerName=whoamiH@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.5:80" serviceName=whoamiH-example entryPointName=websecure serverName=0 routerName=whoamiH@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.5:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiH-example" middlewareType=TracingForwarder entryPointName=websecure routerName=whoamiH@docker middlewareName=tracing
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiH@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" entryPointName=websecure routerName=whoamiG@docker serviceName=whoamiG-example middlewareType=Pipelining middlewareName=pipelining
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" entryPointName=websecure routerName=whoamiG@docker serviceName=whoamiG-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.2:80" serviceName=whoamiG-example serverName=0 entryPointName=websecure routerName=whoamiG@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.2:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiG-example" routerName=whoamiG@docker entryPointName=websecure middlewareName=tracing middlewareType=TracingForwarder
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" routerName=whoamiG@docker entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" entryPointName=websecure middlewareName=pipelining middlewareType=Pipelining routerName=whoamiI@docker serviceName=whoamiI-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" serviceName=whoamiI-example entryPointName=websecure routerName=whoamiI@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.10:80" serverName=0 entryPointName=websecure routerName=whoamiI@docker serviceName=whoamiI-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.10:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiI-example" routerName=whoamiI@docker middlewareName=tracing middlewareType=TracingForwarder entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiI@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" middlewareName=pipelining middlewareType=Pipelining entryPointName=websecure routerName=whoamiB@docker serviceName=whoamiB-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" entryPointName=websecure routerName=whoamiB@docker serviceName=whoamiB-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.6:80" routerName=whoamiB@docker serviceName=whoamiB-example entryPointName=websecure serverName=0
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.6:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiB-example" routerName=whoamiB@docker middlewareName=tracing middlewareType=TracingForwarder entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" routerName=whoamiB@docker entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" entryPointName=websecure routerName=whoamiD@docker serviceName=whoamiD-example middlewareName=pipelining middlewareType=Pipelining
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" serviceName=whoamiD-example entryPointName=websecure routerName=whoamiD@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.9:80" entryPointName=websecure routerName=whoamiD@docker serviceName=whoamiD-example serverName=0
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.9:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiD-example" middlewareName=tracing middlewareType=TracingForwarder entryPointName=websecure routerName=whoamiD@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiD@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" routerName=whoamiE@docker serviceName=whoamiE-example middlewareName=pipelining middlewareType=Pipelining entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" serviceName=whoamiE-example entryPointName=websecure routerName=whoamiE@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.7:80" routerName=whoamiE@docker serviceName=whoamiE-example serverName=0 entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.7:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiE-example" entryPointName=websecure routerName=whoamiE@docker middlewareName=tracing middlewareType=TracingForwarder
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiE@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" middlewareType=Pipelining routerName=whoamiF@docker entryPointName=websecure serviceName=whoamiF-example middlewareName=pipelining
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" entryPointName=websecure serviceName=whoamiF-example routerName=whoamiF@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.3:80" serverName=0 serviceName=whoamiF-example routerName=whoamiF@docker entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.3:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiF-example" entryPointName=websecure middlewareName=tracing middlewareType=TracingForwarder routerName=whoamiF@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiF@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" middlewareName=pipelining entryPointName=websecure routerName=whoamiC@docker serviceName=whoamiC-example middlewareType=Pipelining
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating load-balancer" entryPointName=websecure routerName=whoamiC@docker serviceName=whoamiC-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating server 0 http://172.24.0.4:80" serverName=0 entryPointName=websecure routerName=whoamiC@docker serviceName=whoamiC-example
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="child http://172.24.0.4:80 now UP"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Propagating new UP status"
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Added outgoing tracing middleware whoamiC-example" entryPointName=websecure middlewareName=tracing middlewareType=TracingForwarder routerName=whoamiC@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=error msg="middleware \"default_ssl@docker\" does not exist" entryPointName=websecure routerName=whoamiC@docker
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Creating middleware" entryPointName=websecure middlewareName=traefik-internal-recovery middlewareType=Recovery
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamib.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamii.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamie.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamig.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamic.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamia.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamih.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamid.example with TLS options default" entryPointName=websecure
example-traefik-1 | time="2022-10-06T15:05:40Z" level=debug msg="Adding route for whoamif.example with TLS options default" entryPointName=websecure