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network – Why can’t my laptop see a certain LAN device by IP?

news_fiverr
By news_fiverr
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In my home I have a Synology device at 192.168.1.180. My iPhone, on WiFi, can connect to the device by IP without issue. My laptop on the same WiFi cannot:

  • Using a Synology app on the phone to connect to the IP, it works. If I use the equivalent app on the laptop, it fails to connect.

  • If I put the IP into Safari on the phone, I get a login screen. If I put the IP into Safari on the laptop, it eventually times out. If I put the IP into Chrome on the laptop, I quickly get an ERR_ADDRESS_INVALID screen.

Some hopefully-relevant Terminal investigation from the laptop:

phrogz@PhrogzBook ~ % ping 192.168.1.180    
PING 192.168.1.180 (192.168.1.180): 56 data bytes
Request timeout for icmp_seq 0
Request timeout for icmp_seq 1
^C
--- 192.168.1.180 ping statistics ---
3 packets transmitted, 0 packets received, 100.0% packet loss

phrogz@PhrogzBook ~ % traceroute 192.168.1.180
traceroute: bind: Can't assign requested address

phrogz@PhrogzBook ~ % sudo /usr/libexec/ApplicationFirewall/socketfilterfw --getglobalstate
Firewall is disabled. (State = 0)

phrogz@PhrogzBook ~ % ifconfig
lo0: flags=8049<UP,LOOPBACK,RUNNING,MULTICAST> mtu 16384
    options=1203<RXCSUM,TXCSUM,TXSTATUS,SW_TIMESTAMP>
    inet 127.0.0.1 netmask 0xff000000
    inet6 ::1 prefixlen 128 
    inet6 fe80::1%lo0 prefixlen 64 scopeid 0x1 
    nd6 options=201<PERFORMNUD,DAD>
gif0: flags=8010<POINTOPOINT,MULTICAST> mtu 1280
stf0: flags=0<> mtu 1280
anpi0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:40
    media: none
    status: inactive
anpi2: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:42
    media: none
    status: inactive
anpi1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:41
    media: none
    status: inactive
en4: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:20
    nd6 options=201<PERFORMNUD,DAD>
    media: none
    status: inactive
en5: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:21
    nd6 options=201<PERFORMNUD,DAD>
    media: none
    status: inactive
en6: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether c6:83:5f:2c:6e:22
    nd6 options=201<PERFORMNUD,DAD>
    media: none
    status: inactive
en1: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
    options=460<TSO4,TSO6,CHANNEL_IO>
    ether 36:f3:65:f4:1f:80
    media: autoselect <full-duplex>
    status: inactive
en2: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
    options=460<TSO4,TSO6,CHANNEL_IO>
    ether 36:f3:65:f4:1f:84
    media: autoselect <full-duplex>
    status: inactive
en3: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
    options=460<TSO4,TSO6,CHANNEL_IO>
    ether 36:f3:65:f4:1f:88
    media: autoselect <full-duplex>
    status: inactive
bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=63<RXCSUM,TXCSUM,TSO4,TSO6>
    ether 36:f3:65:f4:1f:80
    Configuration:
        id 0:0:0:0:0:0 priority 0 hellotime 0 fwddelay 0
        maxage 0 holdcnt 0 proto stp maxaddr 100 timeout 1200
        root id 0:0:0:0:0:0 priority 0 ifcost 0 port 0
        ipfilter disabled flags 0x0
    member: en1 flags=3<LEARNING,DISCOVER>
            ifmaxaddr 0 port 10 priority 0 path cost 0
    member: en2 flags=3<LEARNING,DISCOVER>
            ifmaxaddr 0 port 11 priority 0 path cost 0
    member: en3 flags=3<LEARNING,DISCOVER>
            ifmaxaddr 0 port 12 priority 0 path cost 0
    nd6 options=201<PERFORMNUD,DAD>
    media: <unknown type>
    status: inactive
ap1: flags=8802<BROADCAST,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether 7e:e9:1e:89:0f:cf
    media: autoselect
en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=6460<TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>
    ether 5c:e9:1e:89:0f:cf
    inet6 fe80::a8:c850:c9ad:8dbc%en0 prefixlen 64 secured scopeid 0xf 
    inet 192.168.1.13 netmask 0xffffff00 broadcast 192.168.1.255
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect
    status: active
awdl0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=6460<TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>
    ether 36:37:dd:14:37:1b
    inet6 fe80::3437:ddff:fe14:371b%awdl0 prefixlen 64 scopeid 0x10 
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect
    status: active
llw0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether 36:37:dd:14:37:1b
    inet6 fe80::3437:ddff:fe14:371b%llw0 prefixlen 64 scopeid 0x11 
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect
    status: inactive
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500
    inet6 fe80::9ea:f549:1e53:80ef%utun0 prefixlen 64 scopeid 0x12 
    nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::acdc:d2ca:9927:72da%utun1 prefixlen 64 scopeid 0x13 
    nd6 options=201<PERFORMNUD,DAD>
utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
    inet6 fe80::b851:13d6:ae77:3168%utun2 prefixlen 64 scopeid 0x14 
    nd6 options=201<PERFORMNUD,DAD>
utun3: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1000
    inet6 fe80::ce81:b1c:bd2c:69e%utun3 prefixlen 64 scopeid 0x15 
    nd6 options=201<PERFORMNUD,DAD>
utun4: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::5346:3701:5013:df6f%utun4 prefixlen 64 scopeid 0x16 
    nd6 options=201<PERFORMNUD,DAD>
utun5: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::bd02:a0ec:bc51:9adc%utun5 prefixlen 64 scopeid 0x17 
    nd6 options=201<PERFORMNUD,DAD>
en7: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=6464<VLAN_MTU,TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>
    ether b0:4f:13:25:b8:ad
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect (none)
    status: inactive

phrogz@PhrogzBook ~ % route -n get default

   route to: default
destination: default
       mask: default
    gateway: 192.168.1.1
  interface: en0
      flags: <UP,GATEWAY,DONE,STATIC,PRCLONING,GLOBAL>
 recvpipe  sendpipe  ssthresh  rtt,msec    rttvar  hopcount      mtu     expire
       0         0         0         0         0         0      1500         0

I do have VPN software installed on the laptop (and phone), but no VPN is actively connected. I’m not sure what to look for here to see how VPN may be messing things up.

Laptop is currently running Sonoma 14.6.1

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