Problems RDP'ing to PC while on VPN

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Chris Mueller

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Jan 10, 2026, 10:54:13 AM (2 days ago) Jan 10
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Using Windows App to connect to my work laptop while traveling.  Successfully connected to VPN via Tunnelblick.  No issues while within my home network (VPN or not).

But when I'm outside my home network, connected to VPN I can ping my local PC.  But simply cannot connect to RDP.   Tried opening all the settings I can for Remote Desktop on the Windows side and still no luck.

Untitled.png

*Tunnelblick: macOS 26.2 (25C56); Tunnelblick 8.1beta03 (build 6340); prior version 8.0 (build 6300); Admin user

git commit b3311c3c6e4caf2598029ce6e1647fd66ac81fbf

The Tunnelblick.app process is not being translated (arm64)

System Integrity Protection is enabled

Model: Mac16,8


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


Configuration client2


"Sanitized" condensed configuration file for /Library/Application Support/Tunnelblick/Shared/client2.tblk:


client

dev tap

proto tcp

sndbuf 0

rcvbuf 0

push "sndbuf 393216"

push "rcvbuf 393216"

remote cjmueller08.mynetgear.com 12974

resolv-retry infinite

nobind

persist-key

persist-tun

ca ca.crt

cert client.crt

key client.key

cipher AES-128-CBC

comp-lzo

verb 0


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


Files in client2.tblk:

      Contents/Resources/cli….crt

      Contents/Resources/ca.crt

      Contents/Resources/config.ovpn

      Contents/Resources/cli….key


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


Configuration preferences:


useDNS = 1

-authenticateOnConnect = 1 (forced)

-routeAllTrafficThroughVpn = 1

-loadTap = 

-loadTun = 

-openvpnVersion = -

-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0

-enableIpv6OnTap = 0

-allowChangesToManuallySetNetworkSettings = 1

-lastConnectionSucceeded = 1

-prependDomainNameToSearchDomains = 1


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


Wildcard preferences:


-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0


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


Program preferences:


launchAtNextLogin = 1

tunnelblickVersionHistory = (

    "8.1beta03 (build 6340)",

    "8.0 (build 6300)"

)

statusDisplayNumber = 0

lastLaunchTime = 789750138.574756

lastLanguageAtLaunchWasRTL = 0

connectionWindowDisplayCriteria = showWhenConnecting

maxLogDisplaySize = 102400

lastConnectedDisplayName = client2

keyboardShortcutIndex = 1

namedCredentialsThatAllConfigurationsUse = Common

updateCheckAutomatically = 1

updateCheckBetas = 1

NSWindow Frame SettingsSheetWindow = 425 192 829 548 0 0 1663 1044 

NSWindow Frame ConnectingWindow = 637 635 389 217 0 0 1663 1044 

NSWindow Frame ListingWindow = 2733 165 500 428 2560 0 2560 1410 

detailsWindowFrameVersion = 6340

detailsWindowFrame = {{356, 495}, {920, 522}}

detailsWindowLeftFrame = {{0, 0}, {167, 402}}

detailsWindowViewIndex = 0

detailsWindowConfigurationsTabIdentifier = settings

leftNavSelectedDisplayName = client2

AdvancedWindowTabIdentifier = whileConnected

haveDealtWithOldTunTapPreferences = 1

haveDealtWithAlwaysShowLoginWindow = 1

haveDealtWithOldLoginItem = 1

haveDealtWithAfterDisconnect = 1

SULastCheckTime = 2026-01-10 15:02:18 +0000


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


Forced preferences:


{

    "client2-authenticateOnConnect" = 1;

}


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


Deployed forced preferences:


(None)


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


Tunnelblick Kext Policy Data:


net.tunnelblick.tap|Z2SG5H3HC8|Jonathan Bullard|1|5

net.tunnelblick.tun|Z2SG5H3HC8|Jonathan Bullard|1|5


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


Tunnelblick Log:



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


Installer log:


2026-01-10 08:04:31.047858: Tunnelblick installer (build 6340) getuid() = 501; geteuid() = 0; getgid() = 20; getegid() = 20

currentDirectoryPath = '/'; 3 arguments:

     0x0001 (ClearLog CopyConfig)

     /Library/Application Support/Tunnelblick/Shared/client2.tblk

     /private/var/folders/fv/13fy3b0j3qb5spttgbtmjgkr0000gn/T/net.tunnelblick.tunnelblick-zqWrL5/client2.tblk

2026-01-10 08:04:31.053695: Determined username 'cjmueller08' from getuid(): 501

2026-01-10 08:04:31.075997: renamex_np() succeeded renaming /Library/Application Support/Tunnelblick/installer-temp to /Library/Application Support/Tunnelblick/Shared/client2.tblk

2026-01-10 08:04:31.076599: Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Shared/client2.tblk

2026-01-10 08:04:31.076788: Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents

2026-01-10 08:04:31.076918: Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources

2026-01-10 08:04:31.077012: Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources/client.crt

2026-01-10 08:04:31.077113: Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources/ca.crt

2026-01-10 08:04:31.077206: Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources/config.ovpn

2026-01-10 08:04:31.077298: Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources/client.key

2026-01-10 08:04:31.081183: Kext is up-to-date: tunnelblick-tun.kext

2026-01-10 08:04:31.082614: Kext is up-to-date: tunnelblick-tap.kext

2026-01-10 08:04:31.082673: Tunnelblick installer succeeded


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


Down log:


08:25:42 *Tunnelblick:  **********************************************

08:25:42 *Tunnelblick:  Start of output from client.down.tunnelblick.sh

08:25:43 *Tunnelblick:  Cancelled monitoring system configuration changes

08:25:43 *Tunnelblick:  Restored State:DNS

08:25:43 *Tunnelblick:  Removed Setup:DNS

08:25:43 *Tunnelblick:  Removed State:SMB

08:25:43 *Tunnelblick:  Restored DNS and SMB settings

08:25:43 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache

08:25:43 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed

08:25:43 *Tunnelblick:  Up to six 'No such key' messages may appear next and may be ignored.

08:25:43 *Tunnelblick:  End of output from client.down.tunnelblick.sh

08:25:43 *Tunnelblick:  **********************************************


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


Previous down log:


08:06:19 *Tunnelblick:  **********************************************

08:06:19 *Tunnelblick:  Start of output from client.down.tunnelblick.sh

08:06:19 *Tunnelblick:  Ignoring change of Network Primary Service from 2DDC4127-C1AA-4125-98EE-0581BCF1354F to 

08:06:19 *Tunnelblick:  Cancelled monitoring system configuration changes

08:06:19 *Tunnelblick:  Restored State:DNS

08:06:19 *Tunnelblick:  Removed Setup:DNS

08:06:19 *Tunnelblick:  Removed State:SMB

08:06:19 *Tunnelblick:  Restored DNS and SMB settings

08:06:19 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache

08:06:19 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed

08:06:19 *Tunnelblick:  Notified mDNSResponderHelper that the DNS cache was flushed

08:06:19 *Tunnelblick:  Up to six 'No such key' messages may appear next and may be ignored.

08:06:19 *Tunnelblick:  End of output from client.down.tunnelblick.sh

08:06:19 *Tunnelblick:  **********************************************


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


Network services:


An asterisk (*) denotes that a network service is disabled.

USB 10/100/1000 LAN

Paper Pro

Wi-Fi

iPhone USB


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

anpi0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=400<CHANNEL_IO>

ether e6:8c:15:af:f9:b8

media: none

status: inactive

anpi1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=400<CHANNEL_IO>

ether e6:8c:15:af:f9:b9

media: none

status: inactive

anpi2: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=400<CHANNEL_IO>

ether e6:8c:15:af:f9:ba

media: none

status: inactive

en4: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=400<CHANNEL_IO>

ether e6:8c:15:af:f9:98

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 e6:8c:15:af:f9:99

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 e6:8c:15:af:f9:9a

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 36:32:c1:0e:5b:40

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 36:32:c1:0e:5b:44

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 36:32:c1:0e:5b:48

media: autoselect <full-duplex>

status: inactive

bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=63<RXCSUM,TXCSUM,TSO4,TSO6>

ether 36:32:c1:0e:5b:40

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

media: <unknown type>

status: inactive

utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500

inet6 fe80::6b05:7abe:3f4:33f7%utun0 prefixlen 64 scopeid 0x10 

nd6 options=201<PERFORMNUD,DAD>

ap1: flags=8822<BROADCAST,SMART,SIMPLEX,MULTICAST> mtu 1500

options=400<CHANNEL_IO>

ether 92:30:b6:46:47:2d

nd6 options=201<PERFORMNUD,DAD>

media: autoselect (none)

en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500 constrained

options=6460<TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>

ether 96:83:d2:7b:d2:eb

inet6 fe80::1c9a:f5d:d6e8:69d5%en0 prefixlen 64 secured scopeid 0xe 

inet 172.20.10.7 netmask 0xfffffff0 broadcast 172.20.10.15

inet6 2600:381:cc19:9898:14c9:4c06:9b23:8e19 prefixlen 64 autoconf secured 

inet6 2600:381:cc19:9898:3852:cffb:f03:3019 prefixlen 64 autoconf temporary 

nd6 options=201<PERFORMNUD,DAD>

media: autoselect

status: active

awdl0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500

options=6460<TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>

ether 96:9d:07:43:98:3a

inet6 fe80::949d:7ff:fe43:983a%awdl0 prefixlen 64 scopeid 0x11 

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 96:9d:07:43:98:3a

inet6 fe80::949d:7ff:fe43:983a%llw0 prefixlen 64 scopeid 0x12 

nd6 options=201<PERFORMNUD,DAD>

media: autoselect (none)

utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380

inet6 fe80::712d:9970:ba8f:1705%utun1 prefixlen 64 scopeid 0x13 

nd6 options=201<PERFORMNUD,DAD>

utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000

inet6 fe80::3293:2922:402:f45d%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::306f:9eb1:1c1:a0e%utun4 prefixlen 64 scopeid 0x17 

nd6 options=201<PERFORMNUD,DAD>

utun5: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380

inet6 fe80::19c2:bb5d:d96d:cf16%utun5 prefixlen 64 scopeid 0x18 

nd6 options=201<PERFORMNUD,DAD>

utun6: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380

inet6 fe80::68d4:a859:37af:7113%utun6 prefixlen 64 scopeid 0x19 

nd6 options=201<PERFORMNUD,DAD>

utun7: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380

inet6 fe80::5f6f:9c57:928:57a0%utun7 prefixlen 64 scopeid 0x1a 

nd6 options=201<PERFORMNUD,DAD>

tap0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 1500

ether 5e:9b:af:17:7a:0a

inet 10.0.0.224 netmask 0xffffff00 broadcast 10.0.0.255

nd6 options=201<PERFORMNUD,DAD>

media: autoselect

status: active

open (pid 5994)


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


Non-Apple kexts that are loaded:


Index Refs Address            Size       Wired      Name (Version) UUID <Linked Against>

  282    0 0                  0x9e5      0x9e5      net.tunnelblick.tun (5.0) 5845BB14-660C-34B4-879F-D4D6277EBE4A <9 7 6 3>

  283    0 0                  0x913      0x913      net.tunnelblick.tap (5.0) 2F65AD5B-B8BE-371D-84E9-8194AAB4E815 <9 7 6 3>


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


Quit Log:


2026-01-10 08:59:41.612683 applicationShouldTerminate: termination because of Quit; delayed until 'shutdownTunnelblick' finishes)

2026-01-10 08:59:41.615067 shutDownTunnelblick: started.

2026-01-10 08:59:41.615697 shutDownTunnelblick: Starting cleanup.

2026-01-10 08:59:41.615962 cleanup: Entering cleanup

2026-01-10 08:59:41.616208 synchronized user defaults

2026-01-10 08:59:42.522780 shutDownTunnelblick: Cleanup finished.

2026-01-10 08:59:42.523888 Finished shutting down Tunnelblick; allowing termination


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


Traces Log:



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


Console Log:



2026-01-10 09:11:17.871089 *Tunnelblick: macOS 26.2 (25C56); Tunnelblick 8.1beta03 (build 6340); prior version 8.0 (build 6300)

2026-01-10 09:11:18.270011 *Tunnelblick: Attempting connection with client2; Set nameserver = 0x00000301; monitoring connection

2026-01-10 09:11:18.270146 *Tunnelblick: openvpnstart start client2.tblk 54900 0x00000301 0 3 0 0x0211c3f2 -ptADGNWradsgnw 2.6.14-openssl-3.5.1 <password>

2026-01-10 09:11:18.292071 *Tunnelblick: openvpnstart starting OpenVPN

2026-01-10 09:11:19.366537 WARNING: Compression for receiving enabled. Compression has been used in the past to break encryption. Sent packets are not compressed unless "allow-compression yes" is also set.

2026-01-10 09:11:19.367267 DEPRECATED OPTION: --cipher set to 'AES-128-CBC' but missing in --data-ciphers (AES-256-GCM:AES-128-GCM:CHACHA20-POLY1305). OpenVPN ignores --cipher for cipher negotiations. 

2026-01-10 09:11:19.367359 OpenVPN 2.6.14 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [MH/RECVDA] [AEAD]

2026-01-10 09:11:19.367365 library versions: OpenSSL 3.5.1 1 Jul 2025, LZO 2.10

2026-01-10 09:11:19.367819 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:54900

2026-01-10 09:11:19.367824 Need hold release from management interface, waiting...

2026-01-10 09:11:20.818030 *Tunnelblick: openvpnstart log:

     OpenVPN started successfully.

     Command used to start OpenVPN (one argument per displayed line):

          /Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.6.14-openssl-3.5.1/openvpn

          --daemon

          --log-append /Library/Application Support/Tunnelblick/Logs/-SLibrary-SApplication Support-STunnelblick-SShared-Sclient2.tblk-SContents-SResources-Sconfig.ovpn.769_0_3_0_34718706.54900.openvpn.log

          --cd /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources

          --machine-readable-output

          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 6340 8.1beta03 (build 6340)"

          --verb 3

          --config /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources/config.ovpn

          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources

          --verb 3

          --cd /Library/Application Support/Tunnelblick/Shared/client2.tblk/Contents/Resources

          --management 127.0.0.1 54900 /Library/Application Support/Tunnelblick/Mips/client2.tblk.mip

          --setenv IV_SSO webauth,crtext

          --management-query-passwords

          --management-hold

          --redirect-gateway def1

          --script-security 2

          --route-up "/Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh" -9 -a -d -f -m -o -p -w -ptADGNWradsgnw

          --down "/Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh" -9 -a -d -f -m -o -p -w -ptADGNWradsgnw

          --route-pre-down "/Library/Application Support/Tunnelblick/Tunnelblick.app/Contents/Resources/client.route-pre-down.tunnelblick.sh" -9 -a -d -f -m -o -p -w -ptADGNWradsgnw

2026-01-10 09:11:20.820827 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:49914

2026-01-10 09:11:20.836094 MANAGEMENT: CMD 'pid'

2026-01-10 09:11:20.836226 MANAGEMENT: CMD 'auth-retry interact'

2026-01-10 09:11:20.836248 MANAGEMENT: CMD 'state on'

2026-01-10 09:11:20.836268 MANAGEMENT: CMD 'state'

2026-01-10 09:11:20.836294 MANAGEMENT: CMD 'bytecount 1'

2026-01-10 09:11:20.841157 *Tunnelblick: Established communication with OpenVPN

2026-01-10 09:11:20.841771 *Tunnelblick: >INFO:OpenVPN Management Interface Version 5 -- type 'help' for more info

2026-01-10 09:11:20.842471 MANAGEMENT: CMD 'hold release'

2026-01-10 09:11:20.842681 WARNING: No server certificate verification method has been enabled.  See http://openvpn.net/howto.html#mitm for more info.

2026-01-10 09:11:20.842695 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts

2026-01-10 09:11:20.846854 MANAGEMENT: >STATE:1768057880,RESOLVE,,,,,,

2026-01-10 09:11:20.982234 TCP/UDP: Preserving recently used remote address: [AF_INET]208.190.137.76:12974

2026-01-10 09:11:20.982430 Socket Buffers: R=[131072->131072] S=[131072->131072]

2026-01-10 09:11:20.982474 Attempting to establish TCP connection with [AF_INET]208.190.137.76:12974

2026-01-10 09:11:20.982502 MANAGEMENT: >STATE:1768057880,TCP_CONNECT,,,,,,

2026-01-10 09:11:21.056400 TCP connection established with [AF_INET]208.190.137.76:12974

2026-01-10 09:11:21.056632 TCPv4_CLIENT link local: (not bound)

2026-01-10 09:11:21.056681 TCPv4_CLIENT link remote: [AF_INET]208.190.137.76:12974

2026-01-10 09:11:21.056759 MANAGEMENT: >STATE:1768057881,WAIT,,,,,,

2026-01-10 09:11:21.146519 MANAGEMENT: >STATE:1768057881,AUTH,,,,,,

2026-01-10 09:11:21.146661 TLS: Initial packet from [AF_INET]208.190.137.76:12974, sid=b553e2fb 8600e5dc

2026-01-10 09:11:21.416024 VERIFY OK: depth=1, C=TW, ST=TW, L=Taipei, O=netgear, OU=netgear, CN=netgear, emailAddress=ma...@netgear.com

2026-01-10 09:11:21.416458 VERIFY OK: depth=0, C=TW, ST=TW, O=netgear, OU=netgear, CN=netgear, emailAddress=ma...@netgear.com

2026-01-10 09:11:21.707632 Control Channel: TLSv1.3, cipher TLSv1.3 TLS_CHACHA20_POLY1305_SHA256, peer certificate: 1024 bits RSA, signature: RSA-SHA256, peer temporary key: 253 bits X25519

2026-01-10 09:11:21.707732 [netgear] Peer Connection Initiated with [AF_INET]208.190.137.76:12974

2026-01-10 09:11:21.707768 TLS: move_session: dest=TM_ACTIVE src=TM_INITIAL reinit_src=1

2026-01-10 09:11:21.707902 TLS: tls_multi_process: initial untrusted session promoted to trusted

2026-01-10 09:11:22.931678 MANAGEMENT: >STATE:1768057882,GET_CONFIG,,,,,,

2026-01-10 09:11:22.931780 SENT CONTROL [netgear]: 'PUSH_REQUEST' (status=1)

2026-01-10 09:11:23.123247 PUSH: Received control message: 'PUSH_REPLY,sndbuf 393216,rcvbuf 393216,route 10.0.0.0 255.255.255.0,route-delay 5,route-gateway dhcp,ping 10,ping-restart 120,peer-id 0,cipher AES-256-GCM'

2026-01-10 09:11:23.123418 OPTIONS IMPORT: --sndbuf/--rcvbuf options modified

2026-01-10 09:11:23.123463 Socket Buffers: R=[131072->393216] S=[132288->393216]

2026-01-10 09:11:23.123482 OPTIONS IMPORT: route options modified

2026-01-10 09:11:23.123497 OPTIONS IMPORT: route-related options modified

2026-01-10 09:11:23.124231 TUN/TAP device /dev/tap0 opened

2026-01-10 09:11:23.124281 MANAGEMENT: >STATE:1768057883,ASSIGN_IP,,,,,,

2026-01-10 09:11:23.124708 Data Channel: cipher 'AES-256-GCM', peer-id: 0, compression: 'lzo'

2026-01-10 09:11:23.124736 Timers: ping 10, ping-restart 120

2026-01-10 09:11:23.279124 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:23.339133 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:23.825088 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:24.438786 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:24.520128 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:25.055660 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:25.669249 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:27.456513 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:27.519122 write to TUN/TAP : Input/output error (fd=-1,code=5)

2026-01-10 09:11:28.130667 NOTE: unable to redirect IPv4 default gateway -- VPN gateway parameter (--route-gateway or --ifconfig) is missing

2026-01-10 09:11:28.130763 WARNING: OpenVPN was configured to add an IPv4 route. However, no IPv4 has been configured for tap0, therefore the route installation may fail or may not work as expected.

2026-01-10 09:11:28.130796 MANAGEMENT: >STATE:1768057888,ADD_ROUTES,,,,,,

                           09:11:28 *Tunnelblick:  **********************************************

                           09:11:28 *Tunnelblick:  Start of output from client.up.tunnelblick.sh

                           09:11:28 *Tunnelblick:  Primary network service: Wi-Fi

                           WARNING: $route_vpn_gateway is empty

                           09:11:30 *Tunnelblick:  Using DHCP because route_vpn_gateway = '' and there tap0 has no IP configuration

                           09:11:30 *Tunnelblick:  Did 'ipconfig set "tap0" DHCP'

                           09:11:30 *Tunnelblick:  Configuring tap DNS via DHCP asynchronously

                           09:11:30 *Tunnelblick:  End of output from client.up.tunnelblick.sh

                           09:11:30 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

                           09:11:30 *Tunnelblick:  **********************************************

2026-01-10 09:11:30.346489 Initialization Sequence Completed

2026-01-10 09:11:30.346511 MANAGEMENT: >STATE:1768057890,CONNECTED,SUCCESS,,208.190.137.76,12974,172.20.10.7,49915

                           09:11:31 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

                           09:11:32 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

                           09:11:33 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

                           09:11:34 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

2026-01-10 09:11:31.459627 *Tunnelblick: Warning: Could not obtain a list of DNS addresses that are expected

2026-01-10 09:11:31.565858 *Tunnelblick: Routing info stdout:

   route to: 172.20.10.1

destination: 172.20.10.1

  interface: en0

      flags: <UP,HOST,DONE,LLINFO,WASCLONED,IFSCOPE,IFREF,ROUTER>

 recvpipe  sendpipe  ssthresh  rtt,msec    rttvar  hopcount      mtu     expire

       0         0         0         0         0         0      1500      1186 

stderr:


2026-01-10 09:11:31.566331 *Tunnelblick: Warning: DNS server address 172.20.10.1 is not a public IP address and is not being routed through the VPN.



2026-01-10 09:11:31.672138 *Tunnelblick: Routing info stdout:

   route to: fe80::6431:35ff:fe6a:7c64%en0

2026-01-10 09:11:34.924547 Extracted DHCP router address: 10.0.0.1

                           09:11:35 *Tunnelblick:  Sleeping for 1 seconds to wait for DHCP to finish setup.

                           09:11:36 *Tunnelblick:  Retrieved from DHCP/BOOTP packet: name server(s) [ 10.0.0.1 ], search domain(s) [ ] and SMB server(s) [ ] and using default domain name [ openvpn ]

                           09:11:36 *Tunnelblick:  Not aggregating ServerAddresses because running on macOS 10.6 or higher

                           09:11:36 *Tunnelblick:  Prepending 'openvpn' to search domains '' because the search domains were not set manually (or are allowed to be changed) and 'Prepend domain name to search domains' was selected

                           09:11:38 *Tunnelblick:  Saved the DNS and SMB configurations so they can be restored

                           09:11:38 *Tunnelblick:  Changed DNS ServerAddresses setting from 'fe80::6431:35ff:fe6a:7c64%en0 172.20.10.1' to '10.0.0.1'

                           09:11:38 *Tunnelblick:  Changed DNS SearchDomains setting from '' to 'openvpn'

                           09:11:38 *Tunnelblick:  Changed DNS DomainName setting from '' to 'openvpn'

                           09:11:38 *Tunnelblick:  Did not change SMB NetBIOSName setting of ''

                           09:11:38 *Tunnelblick:  Did not change SMB Workgroup setting of ''

                           09:11:38 *Tunnelblick:  Did not change SMB WINSAddresses setting of ''

                           09:11:38 *Tunnelblick:  DNS servers '10.0.0.1' will be used for DNS queries when the VPN is active

                           09:11:38 *Tunnelblick:  NOTE: The DNS servers do not include any free public DNS servers known to Tunnelblick. This may cause DNS queries to fail or be intercepted or falsified even if they are directed through the VPN. Specify only known public DNS servers or DNS servers located on the VPN network to avoid such problems.

                           09:11:38 *Tunnelblick:  Flushed the DNS cache via dscacheutil

                           09:11:38 *Tunnelblick:  /usr/sbin/discoveryutil not present. Not flushing the DNS cache via discoveryutil

                           09:11:38 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed

                           09:11:38 *Tunnelblick:  Not notifying mDNSResponderHelper that the DNS cache was flushed because it is not running

                           09:11:38 *Tunnelblick:  Setting up to monitor system configuration with process-network-changes

destination: fe80::6431:35ff:fe6a:7c64%en0

  interface: en0

      flags: <UP,HOST,DONE,LLINFO,WASCLONED,IFSCOPE,IFREF,ROUTER>

 recvpipe  sendpipe  ssthresh  rtt,msec    rttvar  hopcount      mtu     expire

       0         0         0         0         0         0      1430         0 

stderr:


2026-01-10 09:11:31.672720 *Tunnelblick: Warning: DNS server address fe80::6431:35ff:fe6a:7c64%en0 is not a public DNS server known to Tunnelblick and is not being routed through the VPN

2026-01-10 09:11:36.837060 *Tunnelblick: This computer's apparent public IP address (166.196.110.74) was unchanged after the connection was made

Tim Gahagan

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Jan 10, 2026, 3:47:56 PM (2 days ago) Jan 10
to tunnelbli...@googlegroups.com, tunnelblick-discuss
Not sure this is a tunnelblick issue.

Just my suggestion since RDP notoriously has security bugs that are patch slow AF.
If you have admin rights, install rustdesk, the free alternative to anydesk. Open source, et al.
Test it. If works, use it. Then you eliminate the need for tunnelblick.

Your setup has 2 failure points tunnel and rdp.

Rustdesk has only one, its own all.

This is not helpful if you are married to tunnelblick, yes it should work, but you have no idea what external networks are blocking, so it’s a challenge. 

So I’d do some testing see if it works, read about it for yourself, and pivot if you can.

Just my opinion after maintaining remote connections for 20 years.

That being said, I’d never cast shade on tunnelblick, but OpenVPN is the server and that continues to be developed slowly. 
Routers that support it, even more slowly, too many CVE’s not patched quickly. So again my opinion, OpenVpn is no longer a reliable, secure solution.

It’s why I migrated close to 60 openvpn’s running on routers to Tailscale. The zero trust model is rock solid. And its overhead is tiny compared to openvpn. No generation of keys, deprivation of switches that used to work but don’t, on and on and on.

I used to be old school of if world leave alone, but in this day and age of 1000’s of penetration attacks a day, OpenVpn is just not up to the task of patching.

Again Tunnelblick is simply the client side and works very well, but it’s like taking a super car on a dirt road. The limitation is not the car it’s the road surface. The car is tunnelblick. The road is OpenVPN.

Just something to consider.

But try rust desk, and see if it works. If so it’s an rdp blocking issue.

Tim Gahagan

On Jan 10, 2026, at 9:54 AM, Chris Mueller <cjmue...@gmail.com> wrote:

Using Windows App to connect to my work laptop while traveling.  Successfully connected to VPN via Tunnelblick.  No issues while within my home network (VPN or not).
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Chris Mueller

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Jan 10, 2026, 10:07:00 PM (2 days ago) Jan 10
to tunnelbli...@googlegroups.com
Thanks. Tried rust desk. Doesn’t have the multiple monitor support that windows app excels at on the Mac but looks like a solid choice for a replacement. 

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