Tunnelblick won't connect

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Gracie Rittenberg

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Jul 16, 2025, 1:20:19 PMJul 16
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At my small business, we recently redesigned our website and transferred the domain from GoDaddy to Sqaurespace. Since the domain transfer has been in process, our Tunnelblick VPN won't connect and we cant do any work. Not sure how to fix it, I'm not tech savvy and our IT manager is in Europe. Diagnostic info below: 

*Tunnelblick: macOS 15.5 (24F74); Tunnelblick 6.0.1 (build 6161); prior version 4.0.1 (build 5971); Admin user
git commit ee61466db8206bff5d219f96ebef1141da115200
The Tunnelblick.app process is not being translated (arm64)
System Integrity Protection is enabled
Model: iMac21,2

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

Configuration Rittlit Server

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

remote rittlit.dyndns.org 34252
float
nobind
proto udp
dev tun
sndbuf 0
rcvbuf 0
keepalive 10 30
comp-lzo yes
auth-user-pass
client
auth SHA1
ignore-unknown-option cipher data-ciphers
cipher AES-128-CBC
data-ciphers AES-128-CBC
remote-cert-tls server
<ca>
[Security-related line(s) omitted]
</ca>
<cert>
[Security-related line(s) omitted]
</cert>
<key>
[Security-related line(s) omitted]
</key>

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

Files in Rittlit Server.tblk:
      Contents/Resources/config.ovpn

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

Configuration preferences:

-keychainHasUsernameAndPassword = 1
-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 1
-consecutiveSuccessfulIPAddressChanges = 5
-loginWindowSecurityTokenCheckboxIsChecked = 0
-lastConnectionSucceeded = 0

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

Wildcard preferences:

-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0

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

Program preferences:

TBUpdateVersionStringForDownloadedAppUpdate = 8.0 (build 6300)
launchAtNextLogin = 1
tunnelblickVersionHistory = (
    "6.0.1 (build 6161)",
    "4.0.1 (build 5971)"
)
lastLaunchTime = 774303674.245703
lastLanguageAtLaunchWasRTL = 0
connectionWindowDisplayCriteria = showWhenConnecting
maxLogDisplaySize = 102400
lastConnectedDisplayName = Rittlit Server
keyboardShortcutIndex = 1
updateCheckAutomatically = 1
NSWindow Frame ConnectingWindow = 925 783 389 217 0 0 2240 1235
NSWindow Frame SUStatusFrame = 920 842 400 135 0 0 2240 1235
NSWindow Frame SUUpdateAlert = 810 627 620 398 0 0 2240 1235
detailsWindowFrameVersion = 6161
detailsWindowFrame = {{8, 85}, {2224, 1142}}
detailsWindowLeftFrame = {{0, 0}, {414.5, 1022}}
detailsWindowViewIndex = 0
detailsWindowConfigurationsTabIdentifier = log
leftNavOutlineViewExpandedDisplayNames = (
    "Global/",
    "Global/Shared/"
)
leftNavSelectedDisplayName = Rittlit Server
haveDealtWithOldTunTapPreferences = 1
haveDealtWithAlwaysShowLoginWindow = 1
haveDealtWithOldLoginItem = 1
haveDealtWithAfterDisconnect = 1
SUEnableAutomaticChecks = 1
SUScheduledCheckInterval = 86400
SULastCheckTime = 2025-07-15 20:21:14 +0000
SUHasLaunchedBefore = 1

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

Forced preferences:

(None)

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

Deployed forced preferences:

(None)

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

Tunnelblick Kext Policy Data:



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

Tunnelblick Log:

2025-07-16 13:12:43.897712 *Tunnelblick: macOS 15.5 (24F74); Tunnelblick 6.0.1 (build 6161); prior version 4.0.1 (build 5971)
2025-07-16 13:12:44.722721 *Tunnelblick: Attempting connection with Rittlit Server using shadow copy; Set nameserver = 0x00000301; monitoring connection
2025-07-16 13:12:44.723264 *Tunnelblick: openvpnstart start Rittlit\ Server.tblk 51515 0x00000301 0 1 0 0x0210c130 -ptADGNWradsgnw 2.6.13-openssl-3.0.16 <password>
2025-07-16 13:12:44.784519 *Tunnelblick: openvpnstart starting OpenVPN
2025-07-16 13:12:45.290875 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.
2025-07-16 13:12:45.295090 OpenVPN 2.6.13 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [MH/RECVDA] [AEAD]
2025-07-16 13:12:45.295142 library versions: OpenSSL 3.0.16 11 Feb 2025, LZO 2.10
2025-07-16 13:12:45.296266 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:51515
2025-07-16 13:12:45.296281 Need hold release from management interface, waiting...
2025-07-16 13:12:45.989451 *Tunnelblick: openvpnstart log:
     OpenVPN started successfully.
     Command used to start OpenVPN (one argument per displayed line):
          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.6.13-openssl-3.0.16/openvpn
          --daemon
          --log-append /Library/Application Support/Tunnelblick/Logs/-SUsers-Sgracerittenberg-SLibrary-SApplication Support-STunnelblick-SConfigurations-SRittlit Server.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_34652464.51515.openvpn.log
          --cd /Library/Application Support/Tunnelblick/Users/gracerittenberg/Rittlit Server.tblk/Contents/Resources
          --machine-readable-output
          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 6161 6.0.1 (build 6161)"
          --verb 3
          --config /Library/Application Support/Tunnelblick/Users/gracerittenberg/Rittlit Server.tblk/Contents/Resources/config.ovpn
          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/gracerittenberg/Rittlit Server.tblk/Contents/Resources
          --verb 3
          --cd /Library/Application Support/Tunnelblick/Users/gracerittenberg/Rittlit Server.tblk/Contents/Resources
          --management 127.0.0.1 51515 /Library/Application Support/Tunnelblick/Mips/Rittlit Server.tblk.mip
          --setenv IV_SSO webauth,crtext
          --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
2025-07-16 13:12:46.006671 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:50016
2025-07-16 13:12:46.083114 MANAGEMENT: CMD 'pid'
2025-07-16 13:12:46.083176 MANAGEMENT: CMD 'auth-retry interact'
2025-07-16 13:12:46.083206 MANAGEMENT: CMD 'state on'
2025-07-16 13:12:46.083233 MANAGEMENT: CMD 'state'
2025-07-16 13:12:46.084230 MANAGEMENT: CMD 'bytecount 1'
2025-07-16 13:12:46.087441 *Tunnelblick: Established communication with OpenVPN
2025-07-16 13:12:46.092735 *Tunnelblick: >INFO:OpenVPN Management Interface Version 5 -- type 'help' for more info
2025-07-16 13:12:46.093410 MANAGEMENT: CMD 'hold release'
2025-07-16 13:12:46.097430 *Tunnelblick: Obtained VPN username and password from the Keychain
2025-07-16 13:12:46.098131 MANAGEMENT: CMD 'username "Auth" "annr"'
2025-07-16 13:12:46.098186 MANAGEMENT: CMD 'password [...]'
2025-07-16 13:12:46.098290 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2025-07-16 13:12:46.125316 MANAGEMENT: >STATE:1752685966,RESOLVE,,,,,,
2025-07-16 13:12:46.193517 TCP/UDP: Preserving recently used remote address: [AF_INET]72.89.95.221:34252
2025-07-16 13:12:46.193627 Socket Buffers: R=[786896->786896] S=[9216->9216]
2025-07-16 13:12:46.193660 UDPv4 link local: (not bound)
2025-07-16 13:12:46.193688 UDPv4 link remote: [AF_INET]72.89.95.221:34252
2025-07-16 13:12:46.193746 MANAGEMENT: >STATE:1752685966,WAIT,,,,,,
2025-07-16 13:13:16.748889 [UNDEF] Inactivity timeout (--ping-restart), restarting
2025-07-16 13:13:16.749745 SIGUSR1[soft,ping-restart] received, process restarting
2025-07-16 13:13:16.749841 MANAGEMENT: >STATE:1752685996,RECONNECTING,ping-restart,,,,,
2025-07-16 13:13:16.753670 *Tunnelblick: Delaying HOLD release for 1.000 seconds
2025-07-16 13:13:17.758265 MANAGEMENT: CMD 'hold release'
2025-07-16 13:13:17.758456 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2025-07-16 13:13:17.763853 MANAGEMENT: >STATE:1752685997,RESOLVE,,,,,,
2025-07-16 13:13:17.769235 TCP/UDP: Preserving recently used remote address: [AF_INET]72.89.95.221:34252
2025-07-16 13:13:17.769429 Socket Buffers: R=[786896->786896] S=[9216->9216]
2025-07-16 13:13:17.769466 UDPv4 link local: (not bound)
2025-07-16 13:13:17.769496 UDPv4 link remote: [AF_INET]72.89.95.221:34252
2025-07-16 13:13:17.769577 MANAGEMENT: >STATE:1752685997,WAIT,,,,,,
2025-07-16 13:13:47.668122 [UNDEF] Inactivity timeout (--ping-restart), restarting
2025-07-16 13:13:47.669909 SIGUSR1[soft,ping-restart] received, process restarting
2025-07-16 13:13:47.669977 MANAGEMENT: >STATE:1752686027,RECONNECTING,ping-restart,,,,,
2025-07-16 13:13:47.673037 *Tunnelblick: Delaying HOLD release for 1.000 seconds
2025-07-16 13:13:48.679804 MANAGEMENT: CMD 'hold release'
2025-07-16 13:13:48.680017 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2025-07-16 13:13:48.685772 MANAGEMENT: >STATE:1752686028,RESOLVE,,,,,,
2025-07-16 13:13:48.691021 TCP/UDP: Preserving recently used remote address: [AF_INET]72.89.95.221:34252
2025-07-16 13:13:48.691196 Socket Buffers: R=[786896->786896] S=[9216->9216]
2025-07-16 13:13:48.691232 UDPv4 link local: (not bound)
2025-07-16 13:13:48.691262 UDPv4 link remote: [AF_INET]72.89.95.221:34252
2025-07-16 13:13:48.691359 MANAGEMENT: >STATE:1752686028,WAIT,,,,,,
2025-07-16 13:14:18.162468 [UNDEF] Inactivity timeout (--ping-restart), restarting
2025-07-16 13:14:18.164471 SIGUSR1[soft,ping-restart] received, process restarting
2025-07-16 13:14:18.164548 MANAGEMENT: >STATE:1752686058,RECONNECTING,ping-restart,,,,,
2025-07-16 13:14:18.168373 *Tunnelblick: Delaying HOLD release for 1.000 seconds
2025-07-16 13:14:19.175345 MANAGEMENT: CMD 'hold release'
2025-07-16 13:14:19.175571 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2025-07-16 13:14:19.181136 MANAGEMENT: >STATE:1752686059,RESOLVE,,,,,,
2025-07-16 13:14:19.220906 TCP/UDP: Preserving recently used remote address: [AF_INET]72.89.95.221:34252
2025-07-16 13:14:19.221076 Socket Buffers: R=[786896->786896] S=[9216->9216]
2025-07-16 13:14:19.221113 UDPv4 link local: (not bound)
2025-07-16 13:14:19.221144 UDPv4 link remote: [AF_INET]72.89.95.221:34252
2025-07-16 13:14:19.221263 MANAGEMENT: >STATE:1752686059,WAIT,,,,,,
2025-07-16 13:14:43.674763 *Tunnelblick: Disconnecting; notification window disconnect button pressed
2025-07-16 13:14:43.980679 *Tunnelblick: Disconnecting using 'kill'
2025-07-16 13:14:44.698682 event_wait : Interrupted system call (fd=-1,code=4)
2025-07-16 13:14:44.714626 SIGTERM[hard,] received, process exiting
2025-07-16 13:14:44.718867 MANAGEMENT: >STATE:1752686084,EXITING,SIGTERM,,,,,
2025-07-16 13:14:45.723990 *Tunnelblick: Expected disconnection occurred.

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

Installer log:

2025-03-04 12:08:32.097612: Tunnelblick installer getuid() = 501; geteuid() = 0; getgid() = 20; getegid() = 20
currentDirectoryPath = '/'; 1 arguments:
     0x0101
2025-03-04 12:08:32.100568: Determined username 'gracerittenberg' from getuid(): 501
2025-03-04 12:08:32.102033: renamex_np() tests succeeded for /Applications
2025-03-04 12:08:32.103985: renamex_np() tests succeeded for /Library/Application Support/Tunnelblick
2025-03-04 12:08:32.106717: renamex_np() tests succeeded for /Users/gracerittenberg/Library/Application Support/Tunnelblick/Configurations
2025-03-04 12:08:32.107306: Created directory /Users/gracerittenberg/Library/Application Support/Tunnelblick/TBLogs with owner 0:80 and permissions 750
2025-03-04 12:08:32.107477: Changed ownership of /Users/gracerittenberg/Library/Application Support/Tunnelblick/TBLogs from 0:80 to 501:80
2025-03-04 12:08:32.109521: Replaced /Library/LaunchDaemons/net.tunnelblick.tunnelblick.tunnelblickd.plist
2025-03-04 12:08:32.326699: Used launchctl to load tunnelblickd
2025-03-04 12:08:32.334966: Tunnelblick installer succeeded

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

Down log:

17:05:32 *Tunnelblick:  **********************************************
17:05:32 *Tunnelblick:  Start of output from client.down.tunnelblick.sh
17:05:32 *Tunnelblick:  WARNING: Skipping further processing because the computer is shutting down.
17:05:32 *Tunnelblick:           No down-prefix.sh, down-suffix.sh, or post-disconnect.sh scripts were run.
17:05:32 *Tunnelblick:  End of output from client.down.tunnelblick.sh
17:05:32 *Tunnelblick:  **********************************************

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

Previous down log:

12:20:08 *Tunnelblick:  **********************************************
12:20:08 *Tunnelblick:  Start of output from client.down.tunnelblick.sh
12:20:09 *Tunnelblick:  Cancelled monitoring system configuration changes
12:20:09 *Tunnelblick:  Restored State:DNS
12:20:09 *Tunnelblick:  Removed Setup:DNS
12:20:09 *Tunnelblick:  Removed State:SMB
12:20:09 *Tunnelblick:  Restored DNS and SMB settings
12:20:10 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Ethernet"
12:20:10 *Tunnelblick:  Re-enabled IPv6 (automatic) for "AX88179A"
12:20:10 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Thunderbolt Bridge"
12:20:10 *Tunnelblick:  Re-enabled IPv6 (automatic) for "Wi-Fi"
12:20:11 *Tunnelblick:  Flushed the DNS cache with dscacheutil -flushcache
12:20:11 *Tunnelblick:  Notified mDNSResponder that the DNS cache was flushed
12:20:11 *Tunnelblick:  Up to six 'No such key' messages may appear next and may be ignored.
12:20:12 *Tunnelblick:  End of output from client.down.tunnelblick.sh
12:20:12 *Tunnelblick:  **********************************************

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

Network services:

An asterisk (*) denotes that a network service is disabled.
Ethernet
AX88179A
Thunderbolt Bridge
Wi-Fi

Wi-Fi Power (en1): 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
anpi1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=400<CHANNEL_IO>
ether ee:d1:44:93:6d:17
media: none
status: inactive
anpi0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=400<CHANNEL_IO>
ether ee:d1:44:93:6d:16
media: none
status: inactive
en0: flags=8823<UP,BROADCAST,SMART,SIMPLEX,MULTICAST> mtu 1500
options=428<VLAN_HWTAGGING,TSO4,CHANNEL_IO>
ether 9c:58:3c:9b:7b:70
nd6 options=201<PERFORMNUD,DAD>
media: autoselect (none)
status: inactive
en4: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=400<CHANNEL_IO>
ether ee:d1:44:93:6d:f6
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 ee:d1:44:93:6d:f7
nd6 options=201<PERFORMNUD,DAD>
media: none
status: inactive
en2: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
options=460<TSO4,TSO6,CHANNEL_IO>
ether 36:cc:9f:ff:60:c0
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:cc:9f:ff:60:c4
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:cc:9f:ff:60:c0
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: en2 flags=3<LEARNING,DISCOVER>
        ifmaxaddr 0 port 10 priority 0 path cost 0
member: en3 flags=3<LEARNING,DISCOVER>
        ifmaxaddr 0 port 11 priority 0 path cost 0
nd6 options=201<PERFORMNUD,DAD>
media: <unknown type>
status: inactive
ap1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=6460<TSO4,TSO6,CHANNEL_IO,PARTIAL_CSUM,ZEROINVERT_CSUM>
ether 2e:74:0a:a3:46:a7
nd6 options=201<PERFORMNUD,DAD>
media: autoselect (none)
status: inactive
en1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=400<CHANNEL_IO>
ether 0e:61:b7:4a:23:33
inet6 fe80::419:fbdf:b83e:12aa%en1 prefixlen 64 secured scopeid 0xd
inet 192.168.5.168 netmask 0xffffff00 broadcast 192.168.5.255
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 22:bd:72:61:f6:ec
inet6 fe80::20bd:72ff:fe61:f6ec%awdl0 prefixlen 64 scopeid 0xf
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 22:bd:72:61:f6:ec
inet6 fe80::20bd:72ff:fe61:f6ec%llw0 prefixlen 64 scopeid 0x10
nd6 options=201<PERFORMNUD,DAD>
media: autoselect (none)
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1500
inet6 fe80::7f0c:7dc3:7e5e:e85a%utun0 prefixlen 64 scopeid 0x11
nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
inet6 fe80::c347:4fc1:8f5f:50ff%utun1 prefixlen 64 scopeid 0x12
nd6 options=201<PERFORMNUD,DAD>
utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
inet6 fe80::f143:51ce:c636:946f%utun2 prefixlen 64 scopeid 0x13
nd6 options=201<PERFORMNUD,DAD>
utun3: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1000
inet6 fe80::ce81:b1c:bd2c:69e%utun3 prefixlen 64 scopeid 0x14
nd6 options=201<PERFORMNUD,DAD>
utun4: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
inet6 fe80::ff86:ded8:54ea:3d94%utun4 prefixlen 64 scopeid 0x15
nd6 options=201<PERFORMNUD,DAD>
utun5: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
inet6 fe80::90d9:a479:1c0f:6984%utun5 prefixlen 64 scopeid 0x16
nd6 options=201<PERFORMNUD,DAD>
en6: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
options=404<VLAN_MTU,CHANNEL_IO>
ether f8:e4:3b:d8:89:b0
nd6 options=201<PERFORMNUD,DAD>
media: autoselect (none)
status: inactive

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

Non-Apple kexts that are loaded:

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

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

Quit Log:

2025-07-15 15:16:48.813670 applicationShouldTerminate: termination because of Quit; delayed until 'shutdownTunnelblick' finishes)
2025-07-15 15:16:48.816223 shutDownTunnelblick: started.
2025-07-15 15:16:48.818661 shutDownTunnelblick: Starting cleanup.
2025-07-15 15:16:48.819035 cleanup: Entering cleanup
2025-07-15 15:16:48.819320 synchronized user defaults
2025-07-15 15:16:49.725542 shutDownTunnelblick: Cleanup finished.
2025-07-15 15:16:49.726497 Finished shutting down Tunnelblick; allowing termination

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

Traces Log:


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

Console Log:


Tunnelblick Developer

unread,
Jul 16, 2025, 1:42:10 PMJul 16
to tunnelblick-discuss
This, in the log:

     2025-07-16 13:12:46.193688 UDPv4 link remote: [AF_INET]72.89.95.221:34252
     2025-07-16 13:12:46.193746 MANAGEMENT: >STATE:1752685966,WAIT,,,,,,
     2025-07-16 13:13:16.748889 [UNDEF] Inactivity timeout (--ping-restart), restarting

means that when your computer tried to contact the VPN server at IP address 72.89.95.221 and port 34252, there was no response.

That means that there is not an OpenVPN server at that IP address responding on that port.  That IP address and port come from the OpenVPN configuration file on your Mac. (From the "remote rittlit.dyndns.org 34252" line. "rittlit.dyndns.org" resolves to 72.89.95.221, so your computer is trying to contact 72.89.95.221 port 34252.)

I don't know why DynDNS is being used; you have a valid domain (https://www.rittlit.com, which is at 198.49.23.144, which is a Squarespace addess) and I would think that you would be using that.

You really need to have your IT manager sort this out.

The only thing I can think of for you to try yourself is to edit the configuration file and change the "rittlit.dyndns.org" to "rittlit.com". That might work.
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