Thursday, December 25, 2025

macos – Troubleshoot network routing problem which disappears on safe boot

  • MacMini running latest MacOS
  • MacBook Pro running latest MacOS
  • Raspberry Pi running Ubuntu 22.04
  • Eero Wifi Network
  • MacBook Pro is able to both ping and ssh to Pi
  • MacMini fails with errors:
~ ping 192.168.5.77
PING 192.168.5.77 (192.168.5.77): 56 data bytes
ping: sendto: No route to host
ping: sendto: No route to host
Request timeout for icmp_seq 0

~ ssh -vvv [email protected]
OpenSSH_9.8p1, LibreSSL 3.3.6
debug1: Reading configuration data /Users/pitosalas/.ssh/config
debug1: /Users/pitosalas/.ssh/config line 2: Applying options for *
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 21: include /etc/ssh/ssh_config.d/* matched no files
debug1: /etc/ssh/ssh_config line 54: Applying options for *
debug2: resolve_canonicalize: hostname 192.168.5.77 is address
debug3: expanded UserKnownHostsFile '~/.ssh/known_hosts' -> '/Users/pitosalas/.ssh/known_hosts'
debug3: expanded UserKnownHostsFile '~/.ssh/known_hosts2' -> '/Users/pitosalas/.ssh/known_hosts2'
debug1: Authenticator provider $SSH_SK_PROVIDER did not resolve; disabling
debug3: channel_clear_timeouts: clearing
debug3: ssh_connect_direct: entering
debug1: Connecting to 192.168.5.77 [192.168.5.77] port 22.
debug3: set_sock_tos: set socket 3 IP_TOS 0x48
debug1: connect to address 192.168.5.77 port 22: No route to host
ssh: connect to host 192.168.5.77 port 22: No route to host
  • LanScan on Mac mini sees the IP address
  • tracers on Mac mini sees the IP address:
~ traceroute 192.168.5.77
traceroute to 192.168.5.77 (192.168.5.77), 64 hops max, 40 byte packets
 1  192.168.5.77 (192.168.5.77)  2.777 ms  2.407 ms  2.058 ms
~
  • Booting MacMini in safe mode solves the problem
  • Turning off every startup item and then booting normal: the problem reapears

enter image description here

  • NOTE: During the first few seconds after boot up I can successfully ping and ssh and then it starts failing. Which implies that something at that point in the boot sequence causes the problem

Next Steps?

  • Any suggestion on how to identify what is causing the problem

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