MacOS & iOS - Unable to access home network over WiFi

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Rogério Domingos

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Feb 3, 2021, 5:08:52 PM2/3/21
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I have setup a home OpenVPN server on a Raspberry Pi according to the instructions on https://pimylifeup.com/raspberry-pi-vpn-server/ so that I can access my home network when I am away from home.

I can connect and access my home network devices as if I was physically there when I connect on Android tablet (Samsung Galaxy S6 Lite) over WiFi or on my iPhone Xr if using mobile data. However, if I am using a WiFi connection on the iPhone or on a Mac computer (Mac Air on OSX Catalina), the OpenVPN Connect client or Tunnelblick shows as connected but I cannot access any of the devices on the home network.

If I go online and use an "what is my ip address" website, it displays the IP address of my home network. It seems therefore that the VPN connected correctly. So why can I not access my home devices? Why does it work over WiFi on a Android tablet but not on iOS or Mac OSX?

I've searched online but could not find any explanation or help on how to fix this issue. Looking at the logs I cannot see any errors. Surely I am not the first person to encounter this issue. Albeit I am fairly technical, I'm a total zero when it comes to network setups. Any help would be greatly appreciated!

Diagnostic info:

*Tunnelblick: macOS 10.15.7 (19H512); Tunnelblick 3.8.4a (build 5601); prior version 3.8.1 (build 5400); Admin user
git commit 73f5ce7b5ccd45d0286a1c9fc30064a914046d3f
The Tunnelblick.app process is not being translated
System Integrity Protection is enabled

Configuration rogerio

"Sanitized" condensed configuration file for /Users/rogerio/Library/Application Support/Tunnelblick/Configurations/rogerio.tblk:

client
dev tun
proto udp
remote r-------------.org 1966
resolv-retry infinite
nobind
persist-key
persist-tun
key-direction 1
remote-cert-tls server
tls-version-min 1.2
verify-x509-name server_VyzrtRJeVKbFXYCr name
cipher AES-256-CBC
auth SHA256
auth-nocache
verb 3
<ca>
[Security-related line(s) omitted]
</ca>
<cert>
[Security-related line(s) omitted]
</cert>
<key>
[Security-related line(s) omitted]
</key>
<tls-auth>
[Security-related line(s) omitted]
</tls-auth>


================================================================================

Files in rogerio.tblk:
      Contents/Resources/config.ovpn

================================================================================

Tunnelblick Kext Policy Data:


================================================================================

Configuration preferences:

-routeAllTrafficThroughVpn = 1
-keychainHasPrivateKey = 1
-openvpnVersion = -
-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0
-loggingLevel = 3
-consecutiveSuccessfulIPAddressChanges = 2
-lastConnectionSucceeded = 1

================================================================================

Wildcard preferences:

-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0

================================================================================

Program preferences:

launchAtNextLogin = 1
tunnelblickVersionHistory = (
    "3.8.4a (build 5601)",
    "3.8.1 (build 5400)"
)
lastLaunchTime = 634079289.720709
showConnectedDurations = 0
lastLanguageAtLaunchWasRTL = 0
connectionWindowDisplayCriteria = showWhenConnectingAndConnected
maxLogDisplaySize = 102400
lastConnectedDisplayName = rogerio
keyboardShortcutIndex = 1
updateCheckAutomatically = 1
NSWindow Frame ConnectingWindow = 488 418 389 187 0 0 1366 745
detailsWindowFrameVersion = 5601
detailsWindowFrame = {{223, 207}, {920, 468}}
detailsWindowLeftFrame = {{0, 0}, {167, 350}}
detailsWindowViewIndex = 0
detailsWindowConfigurationsTabIdentifier = log
leftNavSelectedDisplayName = rogerio
AdvancedWindowTabIdentifier = connectingAndDisconnecting
haveDealtWithOldTunTapPreferences = 1
haveDealtWithOldLoginItem = 1
haveDealtWithAfterDisconnect = 1
SUEnableAutomaticChecks = 1
SUScheduledCheckInterval = 86400
SULastCheckTime = 2021-02-03 21:08:10 +0000
SUHasLaunchedBefore = 1
WebKitDefaultFontSize = 16
WebKitStandardFont = Times

================================================================================

Forced preferences:

(None)

================================================================================

Deployed forced preferences:

(None)

================================================================================

Tunnelblick Log:

2021-02-03 21:10:21.963796 *Tunnelblick: macOS 10.15.7 (19H512); Tunnelblick 3.8.4a (build 5601); prior version 3.8.1 (build 5400)
2021-02-03 21:10:22.264892 *Tunnelblick: Attempting connection with rogerio using shadow copy; Set nameserver = 769; monitoring connection
2021-02-03 21:10:22.265827 *Tunnelblick: openvpnstart start rogerio.tblk 59283 769 0 1 0 1098544 -ptADGNWradsgnw 2.5.0-openssl-1.1.1i
2021-02-03 21:10:22.286877 *Tunnelblick: openvpnstart starting OpenVPN
2021-02-03 21:10:22.425484 DEPRECATED OPTION: --cipher set to 'AES-256-CBC' but missing in --data-ciphers (AES-256-GCM:AES-128-GCM). Future OpenVPN version will ignore --cipher for cipher negotiations. Add 'AES-256-CBC' to --data-ciphers or change --cipher 'AES-256-CBC' to --data-ciphers-fallback 'AES-256-CBC' to silence this warning.
2021-02-03 21:10:22.426266 OpenVPN 2.5.0 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Dec 14 2020
2021-02-03 21:10:22.426290 library versions: OpenSSL 1.1.1i  8 Dec 2020, LZO 2.10
2021-02-03 21:10:22.427843 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:59283
2021-02-03 21:10:22.427899 Need hold release from management interface, waiting...
2021-02-03 21:10:22.890444 *Tunnelblick: openvpnstart log:
     OpenVPN started successfully.
     Command used to start OpenVPN (one argument per displayed line):
          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.5.0-openssl-1.1.1i/openvpn
          --daemon
          --log /Library/Application Support/Tunnelblick/Logs/-SUsers-Srogerio-SLibrary-SApplication Support-STunnelblick-SConfigurations-Srogerio.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_1098544.59283.openvpn.log
          --cd /Library/Application Support/Tunnelblick/Users/rogerio/rogerio.tblk/Contents/Resources
          --machine-readable-output
          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 5601 3.8.4a (build 5601)"
          --verb 3
          --config /Library/Application Support/Tunnelblick/Users/rogerio/rogerio.tblk/Contents/Resources/config.ovpn
          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/rogerio/rogerio.tblk/Contents/Resources
          --verb 3
          --cd /Library/Application Support/Tunnelblick/Users/rogerio/rogerio.tblk/Contents/Resources
          --management 127.0.0.1 59283 /Library/Application Support/Tunnelblick/moogpeimgcelgjbajdcnfnmgbfeajbeokindagdm.mip
          --management-query-passwords
          --management-hold
          --redirect-gateway def1
          --script-security 2
          --route-up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw
          --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw
2021-02-03 21:10:22.903557 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:59283
2021-02-03 21:10:22.932490 MANAGEMENT: CMD 'pid'
2021-02-03 21:10:22.932598 MANAGEMENT: CMD 'auth-retry interact'
2021-02-03 21:10:22.932637 MANAGEMENT: CMD 'state on'
2021-02-03 21:10:22.932685 MANAGEMENT: CMD 'state'
2021-02-03 21:10:22.932724 MANAGEMENT: CMD 'bytecount 1'
2021-02-03 21:10:22.933293 *Tunnelblick: Established communication with OpenVPN
2021-02-03 21:10:22.934686 *Tunnelblick: >INFO:OpenVPN Management Interface Version 3 -- type 'help' for more info
2021-02-03 21:10:22.936647 MANAGEMENT: CMD 'hold release'
2021-02-03 21:10:22.938069 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2021-02-03 21:10:22.992591 *Tunnelblick: Obtained passphrase from the Keychain
2021-02-03 21:10:22.993827 MANAGEMENT: CMD 'password [...]'
2021-02-03 21:10:22.998880 Outgoing Control Channel Authentication: Using 256 bit message hash 'SHA256' for HMAC authentication
2021-02-03 21:10:22.998917 Incoming Control Channel Authentication: Using 256 bit message hash 'SHA256' for HMAC authentication
2021-02-03 21:10:22.999253 MANAGEMENT: >STATE:1612386622,RESOLVE,,,,,,
2021-02-03 21:10:23.128606 TCP/UDP: Preserving recently used remote address: [AF_INET]148.63.86.191:1966
2021-02-03 21:10:23.128781 Socket Buffers: R=[786896->786896] S=[9216->9216]
2021-02-03 21:10:23.128829 UDP link local: (not bound)
2021-02-03 21:10:23.128870 UDP link remote: [AF_INET]148.63.86.191:1966
2021-02-03 21:10:23.129106 MANAGEMENT: >STATE:1612386623,WAIT,,,,,,
2021-02-03 21:10:23.305274 MANAGEMENT: >STATE:1612386623,AUTH,,,,,,
2021-02-03 21:10:23.305355 TLS: Initial packet from [AF_INET]148.63.86.191:1966, sid=0d415dd0 70b78b20
2021-02-03 21:10:23.420716 VERIFY OK: depth=1, CN=ChangeMe
2021-02-03 21:10:23.421968 VERIFY KU OK
2021-02-03 21:10:23.422040 Validating certificate extended key usage
2021-02-03 21:10:23.422099 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
2021-02-03 21:10:23.422131 VERIFY EKU OK
2021-02-03 21:10:23.422156 VERIFY X509NAME OK: CN=server_VyzrtRJeVKbFXYCr
2021-02-03 21:10:23.422181 VERIFY OK: depth=0, CN=server_VyzrtRJeVKbFXYCr
2021-02-03 21:10:23.524707 Control Channel: TLSv1.3, cipher TLSv1.3 TLS_AES_256_GCM_SHA384, 2048 bit RSA
2021-02-03 21:10:23.524791 [server_VyzrtRJeVKbFXYCr] Peer Connection Initiated with [AF_INET]148.63.86.191:1966
2021-02-03 21:10:24.630310 MANAGEMENT: >STATE:1612386624,GET_CONFIG,,,,,,
2021-02-03 21:10:24.630584 SENT CONTROL [server_VyzrtRJeVKbFXYCr]: 'PUSH_REQUEST' (status=1)
2021-02-03 21:10:24.678439 PUSH: Received control message: 'PUSH_REPLY,dhcp-option DNS 8.8.8.8,dhcp-option DNS 8.8.4.4,block-outside-dns,redirect-gateway def1,route-gateway 10.8.0.1,topology subnet,ping 1800,ping-restart 3600,ifconfig 10.8.0.2 255.255.255.0,peer-id 0,cipher AES-256-GCM'
2021-02-03 21:10:24.678597 Options error: Unrecognized option or missing or extra parameter(s) in [PUSH-OPTIONS]:3: block-outside-dns (2.5.0)
2021-02-03 21:10:24.678625 WARNING: You have specified redirect-gateway and redirect-private at the same time (or the same option multiple times). This is not well supported and may lead to unexpected results
2021-02-03 21:10:24.678675 OPTIONS IMPORT: timers and/or timeouts modified
2021-02-03 21:10:24.678692 OPTIONS IMPORT: --ifconfig/up options modified
2021-02-03 21:10:24.678706 OPTIONS IMPORT: route options modified
2021-02-03 21:10:24.678719 OPTIONS IMPORT: route-related options modified
2021-02-03 21:10:24.678760 OPTIONS IMPORT: --ip-win32 and/or --dhcp-option options modified
2021-02-03 21:10:24.678799 OPTIONS IMPORT: peer-id set
2021-02-03 21:10:24.678824 OPTIONS IMPORT: adjusting link_mtu to 1624
2021-02-03 21:10:24.678887 OPTIONS IMPORT: data channel crypto options modified
2021-02-03 21:10:24.678909 Data Channel: using negotiated cipher 'AES-256-GCM'
2021-02-03 21:10:24.680211 Outgoing Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
2021-02-03 21:10:24.680276 Incoming Data Channel: Cipher 'AES-256-GCM' initialized with 256 bit key
2021-02-03 21:10:24.683532 Opened utun device utun4
2021-02-03 21:10:24.683707 MANAGEMENT: >STATE:1612386624,ASSIGN_IP,,10.8.0.2,,,,
2021-02-03 21:10:24.683769 /sbin/ifconfig utun4 delete
                           ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2021-02-03 21:10:24.697055 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2021-02-03 21:10:24.697097 /sbin/ifconfig utun4 10.8.0.2 10.8.0.2 netmask 255.255.255.0 mtu 1500 up
2021-02-03 21:10:24.700463 /sbin/route add -net 10.8.0.0 10.8.0.2 255.255.255.0
                           add net 10.8.0.0: gateway 10.8.0.2
2021-02-03 21:10:24.707794 /sbin/route add -net 148.63.86.191 192.168.1.254 255.255.255.255
                           add net 148.63.86.191: gateway 192.168.1.254
2021-02-03 21:10:24.710766 /sbin/route add -net 0.0.0.0 10.8.0.1 128.0.0.0
                           add net 0.0.0.0: gateway 10.8.0.1
2021-02-03 21:10:24.715810 /sbin/route add -net 128.0.0.0 10.8.0.1 128.0.0.0
                           add net 128.0.0.0: gateway 10.8.0.1
                           21:10:24 *Tunnelblick:  **********************************************
                           21:10:24 *Tunnelblick:  Start of output from client.up.tunnelblick.sh
                           21:10:27 *Tunnelblick:  Disabled IPv6 for 'Wi-Fi'
                           21:10:27 *Tunnelblick:  Disabled IPv6 for 'iPhone USB'
                           21:10:27 *Tunnelblick:  Disabled IPv6 for 'Bluetooth PAN'
                           21:10:27 *Tunnelblick:  Disabled IPv6 for 'Thunderbolt Bridge'
                           21:10:27 *Tunnelblick:  Retrieved from OpenVPN: name server(s) [ 8.8.8.8 8.8.4.4 ], search domain(s) [ ] and SMB server(s) [ ] and using default domain name [ openvpn ]
                           21:10:27 *Tunnelblick:  Not aggregating ServerAddresses because running on macOS 10.6 or higher
                           21:10:27 *Tunnelblick:  Setting search domains to 'openvpn' because the search domains were not set manually (or are allowed to be changed) and 'Prepend domain name to search domains' was not selected
                           21:10:28 *Tunnelblick:  Saved the DNS and SMB configurations so they can be restored
                           21:10:28 *Tunnelblick:  Changed DNS ServerAddresses setting from '192.168.1.254' to '8.8.8.8 8.8.4.4'
                           21:10:28 *Tunnelblick:  Changed DNS SearchDomains setting from '' to 'openvpn'
                           21:10:28 *Tunnelblick:  Changed DNS DomainName setting from 'lan' to 'openvpn'
                           21:10:28 *Tunnelblick:  Did not change SMB NetBIOSName setting of ''
                           21:10:28 *Tunnelblick:  Did not change SMB Workgroup setting of ''
                           21:10:28 *Tunnelblick:  Did not change SMB WINSAddresses setting of ''
                           21:10:28 *Tunnelblick:  DNS servers '8.8.8.8 8.8.4.4' will be used for DNS queries when the VPN is active
                           21:10:28 *Tunnelblick:  The DNS servers include only free public DNS servers known to Tunnelblick.
                           21:10:28 *Tunnelblick:  Flushed the DNS cache via dscacheutil
                           21:10:28 *Tunnelblick:  /usr/sbin/discoveryutil not present. Not flushing the DNS cache via discoveryutil
                           21:10:28 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed
                           21:10:28 *Tunnelblick:  Not notifying mDNSResponderHelper that the DNS cache was flushed because it is not running
                           21:10:28 *Tunnelblick:  Setting up to monitor system configuration with process-network-changes
                           21:10:28 *Tunnelblick:  End of output from client.up.tunnelblick.sh
                           21:10:28 *Tunnelblick:  **********************************************
2021-02-03 21:10:28.677314 Initialization Sequence Completed
2021-02-03 21:10:28.677425 MANAGEMENT: >STATE:1612386628,CONNECTED,SUCCESS,10.8.0.2,148.63.86.191,1966,,
2021-02-03 21:10:29.894255 *Tunnelblick: DNS address 8.8.4.4 is being routed through the VPN
2021-02-03 21:10:30.002708 *Tunnelblick: DNS address 8.8.8.8 is being routed through the VPN
2021-02-03 21:10:37.408872 *Tunnelblick: This computer's apparent public IP address changed from 82.154.77.129 before connection to 148.63.86.191 after connection
2021-02-03 21:12:43.327697 *Tunnelblick: Disconnecting; VPN Details… window disconnect button pressed
2021-02-03 21:12:43.473303 *Tunnelblick: Disconnecting using 'kill'
2021-02-03 21:12:43.642407 event_wait : Interrupted system call (code=4)
2021-02-03 21:12:43.644326 /sbin/route delete -net 148.63.86.191 192.168.1.254 255.255.255.255
                           delete net 148.63.86.191: gateway 192.168.1.254
2021-02-03 21:12:43.648683 /sbin/route delete -net 0.0.0.0 10.8.0.1 128.0.0.0
                           delete net 0.0.0.0: gateway 10.8.0.1
2021-02-03 21:12:43.655588 /sbin/route delete -net 128.0.0.0 10.8.0.1 128.0.0.0
                           delete net 128.0.0.0: gateway 10.8.0.1
2021-02-03 21:12:43.659081 Closing TUN/TAP interface
2021-02-03 21:12:43.659883 /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -9 -d -f -m -w -ptADGNWradsgnw utun4 1500 1552 10.8.0.2 255.255.255.0 init
                           21:12:43 *Tunnelblick:  **********************************************
                           21:12:43 *Tunnelblick:  Start of output from client.down.tunnelblick.sh
                           21:12:43 *Tunnelblick:  Cancelled monitoring system configuration changes
                           21:12:43 *Tunnelblick:  Restored State:DNS
                           21:12:43 *Tunnelblick:  Removed Setup:DNS
                           21:12:43 *Tunnelblick:  Restored DNS and SMB settings
                           21:12:43 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Wi-Fi"
                           21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "iPhone USB"
                           21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Bluetooth PAN"
                           21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Thunderbolt Bridge"
                           21:12:44 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache
                           21:12:44 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed
                           21:12:44 *Tunnelblick:  End of output from client.down.tunnelblick.sh
                           21:12:44 *Tunnelblick:  **********************************************
2021-02-03 21:12:44.197740 SIGTERM[hard,] received, process exiting
2021-02-03 21:12:44.197792 MANAGEMENT: >STATE:1612386764,EXITING,SIGTERM,,,,,
2021-02-03 21:12:44.463550 *Tunnelblick: Expected disconnection occurred.

================================================================================

Down log:

21:12:43 *Tunnelblick:  **********************************************
21:12:43 *Tunnelblick:  Start of output from client.down.tunnelblick.sh
21:12:43 *Tunnelblick:  Cancelled monitoring system configuration changes
21:12:43 *Tunnelblick:  Restored State:DNS
21:12:43 *Tunnelblick:  Removed Setup:DNS
21:12:43 *Tunnelblick:  Removed State:SMB
21:12:43 *Tunnelblick:  Restored DNS and SMB settings
21:12:43 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Wi-Fi"
21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "iPhone USB"
21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Bluetooth PAN"
21:12:44 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Thunderbolt Bridge"
21:12:44 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache
21:12:44 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed
21:12:44 *Tunnelblick:  End of output from client.down.tunnelblick.sh
21:12:44 *Tunnelblick:  **********************************************

================================================================================

Previous down log:

18:37:26 *Tunnelblick:  **********************************************
18:37:26 *Tunnelblick:  Start of output from client.down.tunnelblick.sh
18:37:26 *Tunnelblick:  Cancelled monitoring system configuration changes
18:37:26 *Tunnelblick:  Restored State:DNS
18:37:26 *Tunnelblick:  Removed Setup:DNS
18:37:26 *Tunnelblick:  Removed State:SMB
18:37:26 *Tunnelblick:  Restored DNS and SMB settings
18:37:26 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Wi-Fi"
18:37:26 *Tunnelblick:  Re-enabled IPv6 (automatic) for "iPhone USB"
18:37:26 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Bluetooth PAN"
18:37:26 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Thunderbolt Bridge"
18:37:26 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache
18:37:26 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed
18:37:26 *Tunnelblick:  End of output from client.down.tunnelblick.sh
18:37:26 *Tunnelblick:  **********************************************

================================================================================

Network services:

An asterisk (*) denotes that a network service is disabled.
Wi-Fi
iPhone USB
Bluetooth PAN
Thunderbolt Bridge

Wi-Fi Power (en0): On

================================================================================

ifconfig output:

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
en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=400<CHANNEL_IO>
    ether 5c:f9:38:95:ce:52
    inet 192.168.1.140 netmask 0xffffff00 broadcast 192.168.1.255
    inet6 fe80::43c:477:aea2:6717%en0 prefixlen 64 secured scopeid 0x4
    inet6 2001:8a0:77d5:5d01:483:558a:8868:8dd7 prefixlen 64 autoconf secured
    inet6 2001:8a0:77d5:5d01:b0c8:2e76:3b55:b458 prefixlen 64 autoconf temporary
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect
    status: active
en1: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
    options=460<TSO4,TSO6,CHANNEL_IO>
    ether 82:0d:78:ec:80:00
    media: autoselect <full-duplex>
    status: inactive
bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=63<RXCSUM,TXCSUM,TSO4,TSO6>
    ether 82:0d:78:ec:80:00
    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 5 priority 0 path cost 0
    nd6 options=201<PERFORMNUD,DAD>
    media: <unknown type>
    status: inactive
p2p0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 2304
    options=400<CHANNEL_IO>
    ether 0e:f9:38:95:ce:52
    media: autoselect
    status: inactive
awdl0: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1484
    options=400<CHANNEL_IO>
    ether 06:df:b6:18:7e:a0
    inet6 fe80::4df:b6ff:fe18:7ea0%awdl0 prefixlen 64 scopeid 0x8
    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 06:df:b6:18:7e:a0
    inet6 fe80::4df:b6ff:fe18:7ea0%llw0 prefixlen 64 scopeid 0x9
    nd6 options=201<PERFORMNUD,DAD>
    media: autoselect
    status: active
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::1ced:4173:7e8d:9ad8%utun0 prefixlen 64 scopeid 0xa
    nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
    inet6 fe80::b714:235d:3f41:3c28%utun1 prefixlen 64 scopeid 0xb
    nd6 options=201<PERFORMNUD,DAD>
utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::5a86:82ba:4fdb:6781%utun2 prefixlen 64 scopeid 0xc
    nd6 options=201<PERFORMNUD,DAD>
utun3: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
    inet6 fe80::92a0:dd03:813e:8a47%utun3 prefixlen 64 scopeid 0xd
    nd6 options=201<PERFORMNUD,DAD>

================================================================================

Non-Apple kexts that are loaded:

Index Refs Address            Size       Wired      Name (Version) UUID <Linked Against>
  165    3 0xffffff7f83c1c000 0xf2000    0xf2000    org.virtualbox.kext.VBoxDrv (6.1.16) DAF044F0-5043-3B8E-8758-5A462567BDAA <8 6 5 3 1>
  168    0 0xffffff7f83d0e000 0x8000     0x8000     org.virtualbox.kext.VBoxUSB (6.1.16) CA33FA52-5933-3F0E-9B40-8B1ECF4D6A36 <167 165 64 8 6 5 3 1>
  170    0 0xffffff7f83d16000 0x5000     0x5000     org.virtualbox.kext.VBoxNetFlt (6.1.16) C93EAF6A-676F-3370-BAE2-BDFD2BF16582 <165 8 6 5 3 1>
  171    0 0xffffff7f83d1b000 0x6000     0x6000     org.virtualbox.kext.VBoxNetAdp (6.1.16) 76200407-D2F0-3D84-BCCF-7EEA18F16654 <165 6 5 1>

================================================================================

Quit Log:

2021-02-03 18:38:17.580303 applicationShouldTerminate: termination because of Quit; delayed until 'shutdownTunnelblick' finishes)
2021-02-03 18:38:17.583974 shutDownTunnelblick: started.
2021-02-03 18:38:17.584976 shutDownTunnelblick: Starting cleanup.
2021-02-03 18:38:17.585414 cleanup: Entering cleanup
2021-02-03 18:38:17.585765 synchronized user defaults
2021-02-03 18:38:18.289463 shutDownTunnelblick: Cleanup finished.
2021-02-03 18:38:18.290174 Finished shutting down Tunnelblick; allowing termination

================================================================================

Console Log:

2021-02-03 18:30:06.070726 Tunnelblick[3958] Tunnelblick: macOS 10.15.7; Tunnelblick 3.8.4a (build 5601)
2021-02-03 18:30:06.571080 Tunnelblick[3958] Tunnelblick cannot run when it is on /private because the volume has the MNT_NOSUID statfs flag set.
2021-02-03 18:30:10.771815 Tunnelblick[3958] Tunnelblick needs to:
                                         • Be installed in /Applications as Tunnelblick
                                         • Change ownership and permissions of the program to secure it
                                         • Secure configurations
2021-02-03 18:30:10.771892 Tunnelblick[3958] Beginning installation or repair
2021-02-03 18:30:12.461440 Tunnelblick[3958] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2021-02-03 18:30:10.823240. 1 arguments: 0x0017
                                       getuid() = 501; getgid() = 20; geteuid() = 0; getegid() = 20
                                       Changed permissions from 744 to 755 on /var/log/Tunnelblick
                                       Created or checked '/Users/rogerio/Library/Application Support/Tunnelblick'; owner = 501:80; permissions = 488
                                       Created or checked '/Users/rogerio/Library/Application Support/Tunnelblick/Configurations'; owner = 501:80; permissions = 488
                                       Copied /private/var/folders/q3/90qc2tz92r3413wv_ch9dxsr0000gn/T/AppTranslocation/5DF8CCF0-76F7-4CA0-A832-C64A80C8E8C2/d/Tunnelblick.app to /Applications/Tunnelblick.app
                                       Removed any 'com.apple.quarantine' extended attributes
                                       Changed ownership of /Applications/Tunnelblick.app and its contents from 501:80 to 0:0
                                       Changed ownership of the contents of /Users/rogerio/Library/Application Support/Tunnelblick/Configurations from 501:80 to 501:80
                                       Changed permissions from 700 to 740 on /Users/rogerio/Library/Application Support/Tunnelblick/Configurations/rogerio.tblk/Contents/Resources/config.ovpn
                                       Changed ownership of the contents of /Library/Application Support/Tunnelblick/Users/rogerio from 0:0 to 0:0
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/rogerio/rogerio.tblk/Contents/Resources/config.ovpn
                                       Need to replace and/or reload 'tunnelblickd':
                                           daemonHashesMatch  = NO
                                           plistHashesMatch   = YES
                                           activePlistMatches = YES
                                       Replaced /Library/LaunchDaemons/net.tunnelblick.tunnelblick.tunnelblickd.plist
                                       Used launchctl to load tunnelblickd
                                       Tunnelblick installer finished without error
2021-02-03 18:30:12.706116 Tunnelblick[3977] Tunnelblick: macOS 10.15.7; Tunnelblick 3.8.4a (build 5601)
2021-02-03 18:30:12.728805 Tunnelblick[3958] cleanup: Entering cleanup
2021-02-03 18:30:12.729407 Tunnelblick[3958] cleanup aborted because Tunnelblick did not finish launching
2021-02-03 18:30:12.730082 Tunnelblick[3958] Finished shutting down Tunnelblick; allowing termination
2021-02-03 18:30:24.308115 Tunnelblick[3977] Warning: program has not finished after 10 seconds: /usr/sbin/diskutil
2021-02-03 18:30:26.213423 Tunnelblick[3977] Sparkle: ===== Tunnelblick =====
2021-02-03 18:30:26.213997 Tunnelblick[3977] Sparkle: Verified appcast signature
2021-02-03 18:31:28.216318 Tunnelblick[3977] Can't retrieve Keychain item: service = 'Tunnelblick-Auth-rogerio'; account = 'privateKey'; status was -25300: 'The specified item could not be found in the keychain.'
2021-02-03 18:31:40.508316 Tunnelblick[3977] Can't find Keychain item to delete: service = 'Tunnelblick-Auth-rogerio'; account = 'privateKey'; status was -25300: 'The specified item could not be found in the keychain.'
2021-02-03 18:32:00.923440 Tunnelblick[3977] The OpenVPN log contains the following message:
                                       
                                       "Unrecognized option or missing or extra parameter(s)".
                                       
                                       This error means that an option that is contained in the OpenVPN configuration file or was "pushed" by the OpenVPN server:
                                       
                                            • has been misspelled,
                                       
                                            • has missing or extra arguments, or
                                       
                                            • is not implemented by the version of OpenVPN which is being used for this configuration. It may be a new option that is not implemented in an old version of OpenVPN, or an old option that has been removed in a new version of OpenVPN. You can choose what version of OpenVPN to use with this configuration in the "Settings" tab of the "Configurations" panel of Tunnelblick's "VPN Details" window.
                                       
                                       See the VPN log in the "Log" tab of the "Configurations" panel of Tunnelblick's "VPN Details" window for details.
2021-02-03 18:37:26.064756 Tunnelblick[3977] Set 'expect disconnect 1 -SLibrary-SApplication Support-STunnelblick-SUsers-Srogerio-Srogerio-Dtblk-SContents-SResources'
2021-02-03 18:38:17.585334 Tunnelblick[3977] cleanup: Entering cleanup
2021-02-03 18:38:17.585706 Tunnelblick[3977] synchronized user defaults
2021-02-03 18:38:18.036830 Tunnelblick[3977] Set 'expect disconnect 0 ALL'
2021-02-03 18:38:18.290073 Tunnelblick[3977] Finished shutting down Tunnelblick; allowing termination
2021-02-03 21:08:08.295686 Tunnelblick[4959] Tunnelblick: macOS 10.15.7; Tunnelblick 3.8.4a (build 5601)
2021-02-03 21:08:10.862213 Tunnelblick[4959] Sparkle: ===== Tunnelblick =====
2021-02-03 21:08:10.862702 Tunnelblick[4959] Sparkle: Verified appcast signature
2021-02-03 21:08:40.938955 Tunnelblick[4959] Removing *-skipWarningAboutDownroot
2021-02-03 21:08:40.939107 Tunnelblick[4959] Removing *-skipWarningAboutNoTunOrTap
2021-02-03 21:08:40.939219 Tunnelblick[4959] Removing *-skipWarningUnableToToEstablishOpenVPNLink
2021-02-03 21:08:40.939320 Tunnelblick[4959] Removing *-skipWarningThatCannotConnectBecauseOfOpenVPNOptions
2021-02-03 21:08:40.939420 Tunnelblick[4959] Removing *-skipWarningThatNotUsingSpecifiedOpenVPN
2021-02-03 21:08:40.939514 Tunnelblick[4959] Removing *-skipWarningThatCannotConnectBecauseOfOpenVPNOptionConflicts
2021-02-03 21:08:40.939616 Tunnelblick[4959] Removing *-skipWarningThatMayNotConnectInFutureBecauseOfOpenVPNOptions
2021-02-03 21:08:59.955478 Tunnelblick[4959] Removing *-skipWarningAboutDownroot
2021-02-03 21:08:59.955628 Tunnelblick[4959] Removing *-skipWarningAboutNoTunOrTap
2021-02-03 21:08:59.955737 Tunnelblick[4959] Removing *-skipWarningUnableToToEstablishOpenVPNLink
2021-02-03 21:08:59.955835 Tunnelblick[4959] Removing *-skipWarningThatCannotConnectBecauseOfOpenVPNOptions
2021-02-03 21:08:59.955931 Tunnelblick[4959] Removing *-skipWarningThatNotUsingSpecifiedOpenVPN
2021-02-03 21:08:59.956025 Tunnelblick[4959] Removing *-skipWarningThatCannotConnectBecauseOfOpenVPNOptionConflicts
2021-02-03 21:08:59.956126 Tunnelblick[4959] Removing *-skipWarningThatMayNotConnectInFutureBecauseOfOpenVPNOptions
2021-02-03 21:10:24.681721 Tunnelblick[4959] The OpenVPN log contains the following message:
                                       
                                       "Unrecognized option or missing or extra parameter(s)".
                                       
                                       This error means that an option that is contained in the OpenVPN configuration file or was "pushed" by the OpenVPN server:
                                       
                                            • has been misspelled,
                                       
                                            • has missing or extra arguments, or
                                       
                                            • is not implemented by the version of OpenVPN which is being used for this configuration. It may be a new option that is not implemented in an old version of OpenVPN, or an old option that has been removed in a new version of OpenVPN. You can choose what version of OpenVPN to use with this configuration in the "Settings" tab of the "Configurations" panel of Tunnelblick's "VPN Details" window.
                                       
                                       See the VPN log in the "Log" tab of the "Configurations" panel of Tunnelblick's "VPN Details" window for details.
2021-02-03 21:12:43.617514 Tunnelblick[4959] Set 'expect disconnect 1 -SLibrary-SApplication Support-STunnelblick-SUsers-Srogerio-Srogerio-Dtblk-SContents-SResources'

******
The "Unrecognized option or missing or extra parameter(s)" from the VPN Log is:

2021-02-03 21:10:24.678439 PUSH: Received control message: 'PUSH_REPLY,dhcp-option DNS 8.8.8.8,dhcp-option DNS 8.8.4.4,block-outside-dns,redirect-gateway def1,route-gateway 10.8.0.1,topology subnet,ping 1800,ping-restart 3600,ifconfig 10.8.0.2 255.255.255.0,peer-id 0,cipher AES-256-GCM'
2021-02-03 21:10:24.678597 Options error: Unrecognized option or missing or extra parameter(s) in [PUSH-OPTIONS]:3: block-outside-dns (2.5.0)
2021-02-03 21:10:24.678625 WARNING: You have specified redirect-gateway and redirect-private at the same time (or the same option multiple times). This is not well supported and may lead to unexpected results




Tunnelblick developer

unread,
Feb 3, 2021, 6:10:57 PM2/3/21
to tunnelblick-discuss
These two log entries caught my eye:

  • 2021-02-03 21:10:24.678597 Options error: Unrecognized option or missing or extra parameter(s) in [PUSH-OPTIONS]:3: block-outside-dns (2.5.0)

  • 2021-02-03 21:10:24.678625 WARNING: You have specified redirect-gateway and redirect-private at the same time (or the same option multiple times). This is not well supported and may lead to unexpected results
The first one is not causing the problem you mention. It's a Windows-only option and you should check that it is OK for OpenVPN to ignore it.

The second one is probably the cause of the problem you're having. You don't have a --redirect-private appearing anywhere (it isn't in your configuration file and isn't being pushed, and Tunnelblick doesn't add it as an option when starting OpenVPN, so I don't understand why this message is appearing.

Both are messages from OpenVPN, you should consult OpenVPN experts for more help. See Tunnelblick Support page for OpenVPN support links.

Note: Tunnelblick is adding --redirect-gateway as an option because you checked Tunnelblick's "Send all IPv4 traffic through the VPN". Un-checking that might get rid of the warning, but I still don't see where "redirect-private" is coming from.
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