Tunnel blick idle time issues - Mac
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Anil Bagga
Nov 13, 2021, 11:08:48 PM11/13/21
to tunnelblick-discuss
I use version as mentioned in the diagnostics data below.
After connecting to VPN using Tunnelblick, I connect to my company server (Windows) using Microsoft Remote Desktop (MRD).
After connecting thru Tunnelblick, if I dont connect thru MRD immediately, I cannot connect although the connection status shows connected.
If I disconnect and connect MRD, I can login. Idle time disconnect in MRD is much longer.
How can this idle time of Tunnelblick be increased?
Anil Bagga
*Tunnelblick: macOS 12.0.1 (21A559); Tunnelblick 3.8.6beta04 (build 5705); prior version 3.8.4b (build 5602); Admin user
git commit 2298ea8e617432a99874ca6b423ac879ca06c202
The Tunnelblick.app process is not being translated (x86_64)
System Integrity Protection is enabled
Configuration anil.bagga__ssl_vpn_config
"Sanitized" condensed configuration file for /Users/anilbagga/Library/Application Support/Tunnelblick/Configurations/anil.bagga__ssl_vpn_config.tblk:
client
dev tun
proto udp
explicit-exit-notify
verify-x509-name "C=IN, ST=India, O=Harmony Plastics Pvt Ltd, OU=OU, CN=SophosApplianceCertificate_C1B0CC7KWCQBRF6, emailAddress=i...@harmonyplastics.com"
route remote_host 255.255.255.255 net_gateway
resolv-retry infinite
nobind
persist-key
persist-tun
<ca>
[Security-related line(s) omitted]
</ca>
<cert>
[Security-related line(s) omitted]
</cert>
<key>
[Security-related line(s) omitted]
</key>
auth-user-pass
cipher AES-128-CBC
auth SHA256
comp-lzo no
route-delay 4
verb 3
reneg-sec 0
remote 14.140.247.178 8443
remote 10.255.0.1 8443
================================================================================
Files in anil.bagga__ssl_vpn_config.tblk:
Contents/Resources/config.ovpn
================================================================================
Tunnelblick Kext Policy Data:
================================================================================
Configuration preferences:
-keychainHasUsernameAndPassword = 1
-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 1
-consecutiveSuccessfulIPAddressChanges = 5
-loginWindowSecurityTokenCheckboxIsChecked = 0
-lastConnectionSucceeded = 1
================================================================================
Wildcard preferences:
-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0
================================================================================
Program preferences:
skipWarningThatIPAddressDidNotChangeAfterConnection = 1
skipWarningAboutDnsProblems = 1
launchAtNextLogin = 1
tunnelblickVersionHistory = (
"3.8.6beta04 (build 5705)",
"3.8.4b (build 5602)",
"3.8.5 (build 5670)",
"3.8.6beta01 (build 5680)",
"3.8.5 (build 5670)",
"3.8.6beta01 (build 5680)",
"3.8.5 (build 5670)",
"3.8.4b (build 5602)",
"3.8.4a (build 5601)",
"3.8.4 (build 5600)"
)
lastLaunchTime = 658554086.263477
showConnectedDurations = 1
lastLanguageAtLaunchWasRTL = 0
connectionWindowDisplayCriteria = showWhenConnecting
maxLogDisplaySize = 102400
lastConnectedDisplayName = anil.bagga__ssl_vpn_config
keyboardShortcutIndex = 1
updateCheckAutomatically = 1
updateCheckBetas = 1
NSWindow Frame ConnectingWindow = 525 509 389 217 0 0 1440 875
NSWindow Frame SUUpdateAlert = 410 378 620 392 0 0 1440 875
detailsWindowFrameVersion = 5705
detailsWindowFrame = {{376, 272}, {920, 522}}
detailsWindowLeftFrame = {{0, 0}, {167, 402}}
detailsWindowViewIndex = 0
detailsWindowConfigurationsTabIdentifier = settings
leftNavSelectedDisplayName = anil.bagga__ssl_vpn_config
AdvancedWindowTabIdentifier = vpnCredentials
haveDealtWithOldTunTapPreferences = 1
haveDealtWithAlwaysShowLoginWindow = 1
haveDealtWithOldLoginItem = 1
haveDealtWithAfterDisconnect = 1
SUEnableAutomaticChecks = 1
SUScheduledCheckInterval = 86400
SULastCheckTime = 2021-11-14 03:41:27 +0000
SUHasLaunchedBefore = 1
SUSkippedVersion = 5730
================================================================================
Forced preferences:
(None)
================================================================================
Deployed forced preferences:
(None)
================================================================================
Tunnelblick Log:
2021-11-14 09:15:03.544196 *Tunnelblick: macOS 12.0.1 (21A559); Tunnelblick 3.8.6beta04 (build 5705); prior version 3.8.4b (build 5602)
2021-11-14 09:15:03.833707 *Tunnelblick: Attempting connection with anil.bagga__ssl_vpn_config using shadow copy; Set nameserver = 769; monitoring connection
2021-11-14 09:15:03.834143 *Tunnelblick: openvpnstart start anil.bagga__ssl_vpn_config.tblk 60863 769 0 1 0 34652464 -ptADGNWradsgnw 2.5.3-openssl-1.1.1k
2021-11-14 09:15:03.892157 *Tunnelblick: openvpnstart starting OpenVPN
2021-11-14 09:15:04.335330 DEPRECATED OPTION: --cipher set to 'AES-128-CBC' but missing in --data-ciphers (AES-256-GCM:AES-128-GCM). Future OpenVPN version will ignore --cipher for cipher negotiations. Add 'AES-128-CBC' to --data-ciphers or change --cipher 'AES-128-CBC' to --data-ciphers-fallback 'AES-128-CBC' to silence this warning.
2021-11-14 09:15:04.335590 OpenVPN 2.5.3 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Jun 19 2021
2021-11-14 09:15:04.335649 library versions: OpenSSL 1.1.1k 25 Mar 2021, LZO 2.10
2021-11-14 09:15:04.337164 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:60863
2021-11-14 09:15:04.337193 Need hold release from management interface, waiting...
2021-11-14 09:15:05.097005 *Tunnelblick: openvpnstart log:
OpenVPN started successfully.
Command used to start OpenVPN (one argument per displayed line):
/Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.5.3-openssl-1.1.1k/openvpn
--daemon
--log /Library/Application Support/Tunnelblick/Logs/-SUsers-Sanilbagga-SLibrary-SApplication Support-STunnelblick-SConfigurations-Sanil.bagga__ssl_vpn_config.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_34652464.60863.openvpn.log
--cd /Library/Application Support/Tunnelblick/Users/anilbagga/anil.bagga__ssl_vpn_config.tblk/Contents/Resources
--machine-readable-output
--setenv IV_GUI_VER "net.tunnelblick.tunnelblick 5705 3.8.6beta04 (build 5705)"
--verb 3
--config /Library/Application Support/Tunnelblick/Users/anilbagga/anil.bagga__ssl_vpn_config.tblk/Contents/Resources/config.ovpn
--setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/anilbagga/anil.bagga__ssl_vpn_config.tblk/Contents/Resources
--verb 3
--cd /Library/Application Support/Tunnelblick/Users/anilbagga/anil.bagga__ssl_vpn_config.tblk/Contents/Resources
--management 127.0.0.1 60863 /Library/Application Support/Tunnelblick/hejcpmhbnfpdbdoofaphgicpokjkgkdnnnjpmljc.mip
--management-query-passwords
--management-hold
--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
2021-11-14 09:15:05.098695 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:60863
2021-11-14 09:15:05.116821 MANAGEMENT: CMD 'pid'
2021-11-14 09:15:05.116879 MANAGEMENT: CMD 'auth-retry interact'
2021-11-14 09:15:05.116921 MANAGEMENT: CMD 'state on'
2021-11-14 09:15:05.116954 MANAGEMENT: CMD 'state'
2021-11-14 09:15:05.117120 MANAGEMENT: CMD 'bytecount 1'
2021-11-14 09:15:05.117625 *Tunnelblick: Established communication with OpenVPN
2021-11-14 09:15:05.119197 *Tunnelblick: >INFO:OpenVPN Management Interface Version 3 -- type 'help' for more info
2021-11-14 09:15:05.121193 MANAGEMENT: CMD 'hold release'
2021-11-14 09:15:05.136975 *Tunnelblick: Obtained VPN username and password from the Keychain
2021-11-14 09:15:05.137789 MANAGEMENT: CMD 'username "Auth" "Anil.bagga"'
2021-11-14 09:15:05.137851 MANAGEMENT: CMD 'password [...]'
2021-11-14 09:15:05.138147 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2021-11-14 09:15:05.139653 TCP/UDP: Preserving recently used remote address: [AF_INET]14.140.247.178:8443
2021-11-14 09:15:05.139714 Socket Buffers: R=[786896->786896] S=[9216->9216]
2021-11-14 09:15:05.139727 UDP link local: (not bound)
2021-11-14 09:15:05.139739 UDP link remote: [AF_INET]14.140.247.178:8443
2021-11-14 09:15:05.139761 MANAGEMENT: >STATE:1636861505,WAIT,,,,,,
2021-11-14 09:15:05.157677 MANAGEMENT: >STATE:1636861505,AUTH,,,,,,
2021-11-14 09:15:05.157755 TLS: Initial packet from [AF_INET]14.140.247.178:8443, sid=56e9f903 984474b7
2021-11-14 09:15:05.460903 VERIFY OK: depth=1, C=IN, ST=India/ Rajasthan, L=Udaipur, O=Harmony Plastics Pvt Ltd, OU=OU, CN=Sophos_CA_C1B0CC7KWCQBRF6, emailAddress=i...@harmonyplastics.com
2021-11-14 09:15:05.461552 VERIFY X509NAME OK: C=IN, ST=India, O=Harmony Plastics Pvt Ltd, OU=OU, CN=SophosApplianceCertificate_C1B0CC7KWCQBRF6, emailAddress=i...@harmonyplastics.com
2021-11-14 09:15:05.461610 VERIFY OK: depth=0, C=IN, ST=India, O=Harmony Plastics Pvt Ltd, OU=OU, CN=SophosApplianceCertificate_C1B0CC7KWCQBRF6, emailAddress=i...@harmonyplastics.com
2021-11-14 09:15:06.571253 Control Channel: TLSv1, cipher SSLv3 DHE-RSA-AES256-SHA, peer certificate: 2048 bit RSA, signature: RSA-SHA256
2021-11-14 09:15:06.571347 [SophosApplianceCertificate_C1B0CC7KWCQBRF6] Peer Connection Initiated with [AF_INET]14.140.247.178:8443
2021-11-14 09:15:07.792764 MANAGEMENT: >STATE:1636861507,GET_CONFIG,,,,,,
2021-11-14 09:15:07.792970 SENT CONTROL [SophosApplianceCertificate_C1B0CC7KWCQBRF6]: 'PUSH_REQUEST' (status=1)
2021-11-14 09:15:08.950476 PUSH: Received control message: 'PUSH_REPLY,route-gateway 10.81.234.5,sndbuf 0,rcvbuf 0,ping 45,ping-restart 180,route 10.1.1.15 255.255.255.255,route 10.1.1.15 255.255.255.255,route 10.1.1.9 255.255.255.255,route 10.1.1.11 255.255.255.255,route 10.1.1.10 255.255.255.255,topology subnet,route remote_host 255.255.255.255 net_gateway,ifconfig 10.81.234.7 255.255.255.0'
2021-11-14 09:15:08.950705 OPTIONS IMPORT: timers and/or timeouts modified
2021-11-14 09:15:08.950749 OPTIONS IMPORT: --sndbuf/--rcvbuf options modified
2021-11-14 09:15:08.950799 Socket Buffers: R=[786896->786896] S=[9216->9216]
2021-11-14 09:15:08.950830 OPTIONS IMPORT: --ifconfig/up options modified
2021-11-14 09:15:08.950860 OPTIONS IMPORT: route options modified
2021-11-14 09:15:08.950922 OPTIONS IMPORT: route-related options modified
2021-11-14 09:15:08.950956 Using peer cipher 'AES-128-CBC'
2021-11-14 09:15:08.951096 Outgoing Data Channel: Cipher 'AES-128-CBC' initialized with 128 bit key
2021-11-14 09:15:08.951128 Outgoing Data Channel: Using 256 bit message hash 'SHA256' for HMAC authentication
2021-11-14 09:15:08.951146 Incoming Data Channel: Cipher 'AES-128-CBC' initialized with 128 bit key
2021-11-14 09:15:08.951200 Incoming Data Channel: Using 256 bit message hash 'SHA256' for HMAC authentication
2021-11-14 09:15:08.952910 Opened utun device utun3
2021-11-14 09:15:08.952936 MANAGEMENT: >STATE:1636861508,ASSIGN_IP,,10.81.234.7,,,,
2021-11-14 09:15:08.952961 /sbin/ifconfig utun3 delete
ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2021-11-14 09:15:08.960486 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2021-11-14 09:15:08.960531 /sbin/ifconfig utun3 10.81.234.7 10.81.234.7 netmask 255.255.255.0 mtu 1500 up
2021-11-14 09:15:08.964222 /sbin/route add -net 10.81.234.0 10.81.234.7 255.255.255.0
add net 10.81.234.0: gateway 10.81.234.7
2021-11-14 09:15:13.204376 MANAGEMENT: >STATE:1636861513,ADD_ROUTES,,,,,,
2021-11-14 09:15:13.204548 /sbin/route add -net 14.140.247.178 192.168.1.1 255.255.255.255
add net 14.140.247.178: gateway 192.168.1.1
2021-11-14 09:15:13.209968 /sbin/route add -net 10.1.1.15 10.81.234.5 255.255.255.255
add net 10.1.1.15: gateway 10.81.234.5
2021-11-14 09:15:13.215160 /sbin/route add -net 10.1.1.15 10.81.234.5 255.255.255.255
route: writing to routing socket: File exists
add net 10.1.1.15: gateway 10.81.234.5: File exists
2021-11-14 09:15:13.220829 /sbin/route add -net 10.1.1.9 10.81.234.5 255.255.255.255
add net 10.1.1.9: gateway 10.81.234.5
2021-11-14 09:15:13.225094 /sbin/route add -net 10.1.1.11 10.81.234.5 255.255.255.255
add net 10.1.1.11: gateway 10.81.234.5
2021-11-14 09:15:13.227794 /sbin/route add -net 10.1.1.10 10.81.234.5 255.255.255.255
add net 10.1.1.10: gateway 10.81.234.5
2021-11-14 09:15:13.230422 /sbin/route add -net 14.140.247.178 192.168.1.1 255.255.255.255
route: writing to routing socket: File exists
add net 14.140.247.178: gateway 192.168.1.1: File exists
09:15:13 *Tunnelblick: **********************************************
09:15:13 *Tunnelblick: Start of output from client.up.tunnelblick.sh
09:15:15 *Tunnelblick: NOTE: No network configuration changes need to be made.
09:15:15 *Tunnelblick: WARNING: Will NOT monitor for other network configuration changes.
09:15:15 *Tunnelblick: WARNING: Will NOT disable IPv6 settings.
09:15:15 *Tunnelblick: DNS servers '192.168.1.1' will be used for DNS queries when the VPN is active
09:15:15 *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.
09:15:15 *Tunnelblick: Flushed the DNS cache via dscacheutil
09:15:15 *Tunnelblick: /usr/sbin/discoveryutil not present. Not flushing the DNS cache via discoveryutil
09:15:15 *Tunnelblick: Notified mDNSResponder that the DNS cache was flushed
09:15:15 *Tunnelblick: Not notifying mDNSResponderHelper that the DNS cache was flushed because it is not running
09:15:15 *Tunnelblick: End of output from client.up.tunnelblick.sh
09:15:15 *Tunnelblick: **********************************************
2021-11-14 09:15:15.562766 WARNING: this configuration may cache passwords in memory -- use the auth-nocache option to prevent this
2021-11-14 09:15:15.562802 Initialization Sequence Completed
2021-11-14 09:15:15.562852 MANAGEMENT: >STATE:1636861515,CONNECTED,SUCCESS,10.81.234.7,14.140.247.178,8443,,
2021-11-14 09:15:16.775847 *Tunnelblick: Routing info stdout:
route to: 192.168.1.1
destination: 192.168.1.1
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 1197
stderr:
2021-11-14 09:15:16.776465 *Tunnelblick: Warning: DNS server address 192.168.1.1 is not a public IP address and is not being routed through the VPN.
================================================================================
Down log:
09:14:59 *Tunnelblick: **********************************************
09:14:59 *Tunnelblick: Start of output from client.down.tunnelblick.sh
09:15:00 *Tunnelblick: WARNING: Not restoring network settings because no saved Tunnelblick DNS information was found.
09:15:00 *Tunnelblick: Flushed the DNS cache with dscacheutil -flushcache
09:15:00 *Tunnelblick: Notified mDNSResponder that the DNS cache was flushed
09:15:00 *Tunnelblick: End of output from client.down.tunnelblick.sh
09:15:00 *Tunnelblick: **********************************************
================================================================================
Previous down log:
13:00:38 *Tunnelblick: **********************************************
13:00:38 *Tunnelblick: Start of output from client.down.tunnelblick.sh
13:00:39 *Tunnelblick: WARNING: Not restoring network settings because no saved Tunnelblick DNS information was found.
13:00:39 *Tunnelblick: Flushed the DNS cache with dscacheutil -flushcache
13:00:39 *Tunnelblick: Notified mDNSResponder that the DNS cache was flushed
13:00:39 *Tunnelblick: End of output from client.down.tunnelblick.sh
13:00:39 *Tunnelblick: **********************************************
================================================================================
Network services:
An asterisk (*) denotes that a network service is disabled.
USB 10/100/1000 LAN
Wi-Fi
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 8c:85:90:b6:bf:ee
inet 192.168.1.12 netmask 0xffffff00 broadcast 192.168.1.255
media: autoselect
status: active
en2: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
options=460<TSO4,TSO6,CHANNEL_IO>
ether 82:0e:66:e5:40:00
media: autoselect <full-duplex>
status: inactive
en1: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
options=460<TSO4,TSO6,CHANNEL_IO>
ether 82:0e:66:e5:40:01
media: autoselect <full-duplex>
status: inactive
bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=63<RXCSUM,TXCSUM,TSO4,TSO6>
ether 82:0e:66:e5:40:01
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 6 priority 0 path cost 0
member: en2 flags=3<LEARNING,DISCOVER>
ifmaxaddr 0 port 5 priority 0 path cost 0
media: <unknown type>
status: inactive
p2p0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 2304
options=400<CHANNEL_IO>
ether 0e:85:90:b6:bf:ee
media: autoselect
status: inactive
awdl0: flags=8943<UP,BROADCAST,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1484
options=400<CHANNEL_IO>
ether 8e:23:40:38:3f:fe
inet6 fe80::8c23:40ff:fe38:3ffe%awdl0 prefixlen 64 scopeid 0x9
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 8e:23:40:38:3f:fe
inet6 fe80::8c23:40ff:fe38:3ffe%llw0 prefixlen 64 scopeid 0xa
nd6 options=201<PERFORMNUD,DAD>
media: autoselect
status: active
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
inet6 fe80::cd3d:fbd0:85ce:3db0%utun0 prefixlen 64 scopeid 0xb
nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
inet6 fe80::3743:9671:8454:dcd2%utun1 prefixlen 64 scopeid 0xc
nd6 options=201<PERFORMNUD,DAD>
utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1000
inet6 fe80::ce81:b1c:bd2c:69e%utun2 prefixlen 64 scopeid 0xd
nd6 options=201<PERFORMNUD,DAD>
utun3: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500
inet 10.81.234.7 --> 10.81.234.7 netmask 0xffffff00
================================================================================
Non-Apple kexts that are loaded:
Index Refs Address Size Wired Name (Version) UUID <Linked Against>
151 0 0xffffff7f996ea000 0x2000 0x2000 com.epson.driver.EPSONProjectorAudio (1.40) B946B28C-3FE2-AB4C-6FDB-605A5518FA6E <150 7 6 3 1>
152 0 0xffffff7f996ee000 0x2000 0x2000 com.epson.driver.EPSONProjectorMPPAudio (1.40) CD50A087-0252-8C0B-7F9F-682E32D8A99E <150 7 6 3 1>
================================================================================
Quit Log:
2021-11-13 14:54:20.398878 applicationShouldTerminate: termination because of shutdown; delayed until 'shutdownTunnelblick' finishes)
2021-11-13 14:54:20.453384 shutDownTunnelblick: started.
2021-11-13 14:54:20.454122 shutDownTunnelblick: Starting cleanup.
2021-11-13 14:54:20.454775 cleanup: Entering cleanup
2021-11-13 14:54:20.455666 synchronized user defaults
================================================================================
Console Log:
Tunnelblick developer
Nov 15, 2021, 10:44:14 AM11/15/21
to tunnelblick-discuss
Tunnelblick does not have a "timeout".
This:
Because of the way your VPN configuration is set up, Tunnelblick does nothing; OpenVPN does everything.
It is very unusual to have Tunnelblick bypassed this way because it means that DNS will probably not work properly when you are connected to the VPN. That may be related to the problem you are having.
My guess is that something is happening with DHCP, but it could also be a DNS problem, or a routing problem. Again, because the VPN is set up to not have Tunnelblick do anything about DNS, Tunnelblick can't even be used to help diagnose the problem. (Normally, Tunnelblick can help pinpoint the problem as a DNS problem or a routing problem.)
2021-11-14 09:15:13.230422 /sbin/route add -net 14.140.247.178 192.168.1.1 255.255.255.255
route: writing to routing socket: File exists
indicates that routing is not set up properly for your VPN. That's a problem with the OpenVPN configuration and/or the OpenVPN server's setup.
My advise is to consult OpenVPN experts. You can find some links on our Support page.
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