Cannot open TUN/TAP dev VPN: No such file or directory (errno=2)

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Cody Ellis

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Dec 9, 2021, 4:11:05 PM12/9/21
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Running Monterey 12.01 and having issues connecting. Keep getting error: Cannot open TUN/TAP dev VPN: No such file or directory (errno=2)

I've installed and uninstalled the beta version and the current version of tunnelblick with no luck

we've tried

3.8.7Beta03
3.8.7a
3.8.8Beta02

Tunnelblick developer

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Dec 9, 2021, 4:36:59 PM12/9/21
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Please post the diagnostic info obtained by following the instructions at Read Before You Post.

Cody Ellis

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Dec 30, 2021, 5:51:25 PM12/30/21
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*Tunnelblick: macOS 12.0.1 (21A559); Tunnelblick 3.8.8beta03 (build 5790); prior version 3.8.8beta02 (build 5780); Admin user
git commit 5acbdf090ec649ca775fdbdb4ebb493cd501528e
The Tunnelblick.app process is not being translated (x86_64)
System Integrity Protection is enabled
Model: MacBookPro11,5

Configuration client1

"Sanitized" condensed configuration file for /Users/DipZdap/Library/Application Support/Tunnelblick/Configurations/client1.tblk:

client
dev tap
proto udp
dev-node VPN
remote 68.4.82.161 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 5


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

Files in client1.tblk:
      Contents/Resources/cli….crt
      Contents/Resources/ca.crt
      Contents/Resources/config.ovpn
      Contents/Resources/cli….key

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

Tunnelblick Kext Policy Data:

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

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

Configuration preferences:

-loadTun =
-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0
-lastConnectionSucceeded = 0

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

Wildcard preferences:

-notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0

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

Program preferences:

launchAtNextLogin = 1
tunnelblickVersionHistory = (
    "3.8.8beta03 (build 5790)",
    "3.8.7beta03 (build 5740)",
    "3.8.8beta02 (build 5780)",
    "3.8.7a (build 5770)"
)
statusDisplayNumber = 0
lastLaunchTime = 662597059.1663049
lastLanguageAtLaunchWasRTL = 0
connectionWindowDisplayCriteria = showWhenConnecting
maxLogDisplaySize = 102400
keyboardShortcutIndex = 1
updateCheckAutomatically = 1
NSWindow Frame ConnectingWindow = 1085 898 389 217 0 0 2560 1415
NSWindow Frame SUUpdateAlert = 970 762 620 398 0 0 2560 1415
detailsWindowFrameVersion = 5740
detailsWindowFrame = {{521, 347}, {920, 522}}
detailsWindowLeftFrame = {{0, 0}, {167, 402}}
detailsWindowViewIndex = 0
detailsWindowConfigurationsTabIdentifier = log
leftNavSelectedDisplayName = client1
AdvancedWindowTabIdentifier = connectingAndDisconnecting
haveDealtWithOldTunTapPreferences = 1
haveDealtWithAlwaysShowLoginWindow = 1
haveDealtWithOldLoginItem = 1
haveDealtWithAfterDisconnect = 1
SUEnableAutomaticChecks = 1
SUScheduledCheckInterval = 86400
SULastCheckTime = 2021-12-30 22:44:19 +0000
SUHasLaunchedBefore = 1

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

Forced preferences:

(None)

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

Deployed forced preferences:

(None)

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

Tunnelblick Log:

2021-12-30 14:44:40.381336 *Tunnelblick: macOS 12.0.1 (21A559); Tunnelblick 3.8.8beta03 (build 5790); prior version 3.8.8beta02 (build 5780)
2021-12-30 14:44:40.690340 *Tunnelblick: Attempting connection with client1 using shadow copy; Set nameserver = 769; monitoring connection
2021-12-30 14:44:40.691195 *Tunnelblick: openvpnstart start client1.tblk 57245 769 0 1 0 34652530 -ptADGNWradsgnw 2.5.5-openssl-1.1.1m <password>
2021-12-30 14:44:40.749201 *Tunnelblick: openvpnstart starting OpenVPN
2021-12-30 14:44:44.152512 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.
2021-12-30 14:44:44.152871 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.
2021-12-30 14:44:44.153477 OpenVPN 2.5.5 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [LZ4] [PKCS11] [MH/RECVDA] [AEAD] built on Dec 23 2021
2021-12-30 14:44:44.153496 library versions: OpenSSL 1.1.1m  14 Dec 2021, LZO 2.10
2021-12-30 14:44:44.154674 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:57245
2021-12-30 14:44:44.154721 Need hold release from management interface, waiting...
2021-12-30 14:44:45.794784 *Tunnelblick: openvpnstart log:
     The system reported that the tap kext was loaded successfully
     OpenVPN started successfully.
     Command used to start OpenVPN (one argument per displayed line):
          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.5.5-openssl-1.1.1m/openvpn
          --daemon
          --log /Library/Application Support/Tunnelblick/Logs/-SUsers-SDipZdap-SLibrary-SApplication Support-STunnelblick-SConfigurations-Sclient1.tblk-SContents-SResources-Sconfig.ovpn.769_0_1_0_34652530.57245.openvpn.log
          --cd /Library/Application Support/Tunnelblick/Users/DipZdap/client1.tblk/Contents/Resources
          --machine-readable-output
          --setenv IV_GUI_VER "net.tunnelblick.tunnelblick 5790 3.8.8beta03 (build 5790)"
          --verb 3
          --config /Library/Application Support/Tunnelblick/Users/DipZdap/client1.tblk/Contents/Resources/config.ovpn
          --setenv TUNNELBLICK_CONFIG_FOLDER /Library/Application Support/Tunnelblick/Users/DipZdap/client1.tblk/Contents/Resources
          --verb 3
          --cd /Library/Application Support/Tunnelblick/Users/DipZdap/client1.tblk/Contents/Resources
          --management 127.0.0.1 57245 /Library/Application Support/Tunnelblick/Mips/client1.tblk.mip
          --management-query-passwords
          --management-hold
          --script-security 2
          --route-up /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -9 -a -d -f -m -w -ptADGNWradsgnw
          --down /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -9 -a -d -f -m -w -ptADGNWradsgnw
          --route-pre-down /Applications/Tunnelblick.app/Contents/Resources/client.route-pre-down.tunnelblick.sh -9 -a -d -f -m -w -ptADGNWradsgnw
2021-12-30 14:44:45.802992 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:57245
2021-12-30 14:44:45.841227 MANAGEMENT: CMD 'pid'
2021-12-30 14:44:45.841350 MANAGEMENT: CMD 'auth-retry interact'
2021-12-30 14:44:45.841395 MANAGEMENT: CMD 'state on'
2021-12-30 14:44:45.841436 MANAGEMENT: CMD 'state'
2021-12-30 14:44:45.841473 MANAGEMENT: CMD 'bytecount 1'
2021-12-30 14:44:45.842163 *Tunnelblick: Established communication with OpenVPN
2021-12-30 14:44:45.846143 *Tunnelblick: >INFO:OpenVPN Management Interface Version 3 -- type 'help' for more info
2021-12-30 14:44:45.847783 MANAGEMENT: CMD 'hold release'
2021-12-30 14:44:45.848538 WARNING: No server certificate verification method has been enabled.  See http://openvpn.net/howto.html#mitm for more info.
2021-12-30 14:44:45.848574 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2021-12-30 14:44:45.933092 TCP/UDP: Preserving recently used remote address: [AF_INET]68.4.82.161:12974
2021-12-30 14:44:45.933165 Socket Buffers: R=[786896->786896] S=[9216->9216]
2021-12-30 14:44:45.933184 UDP link local: (not bound)
2021-12-30 14:44:45.933197 UDP link remote: [AF_INET]68.4.82.161:12974
2021-12-30 14:44:45.933248 MANAGEMENT: >STATE:1640904285,WAIT,,,,,,
2021-12-30 14:44:46.331460 MANAGEMENT: >STATE:1640904286,AUTH,,,,,,
2021-12-30 14:44:46.331518 TLS: Initial packet from [AF_INET]68.4.82.161:12974, sid=88e08355 5fd343ba
2021-12-30 14:44:46.621294 VERIFY OK: depth=1, C=TW, ST=TW, L=Taipei, O=netgear, OU=netgear, CN=netgear, emailAddress=ma...@netgear.com
2021-12-30 14:44:46.621948 VERIFY OK: depth=0, C=TW, ST=TW, O=netgear, OU=netgear, CN=netgear, emailAddress=ma...@netgear.com
2021-12-30 14:44:46.908033 Control Channel: TLSv1, cipher SSLv3 DHE-RSA-AES256-SHA, peer certificate: 1024 bit RSA, signature: RSA-SHA256
2021-12-30 14:44:46.908080 [netgear] Peer Connection Initiated with [AF_INET]68.4.82.161:12974
2021-12-30 14:44:48.004773 MANAGEMENT: >STATE:1640904288,GET_CONFIG,,,,,,
2021-12-30 14:44:48.004860 SENT CONTROL [netgear]: 'PUSH_REQUEST' (status=1)
2021-12-30 14:44:53.199147 SENT CONTROL [netgear]: 'PUSH_REQUEST' (status=1)
2021-12-30 14:44:58.512544 SENT CONTROL [netgear]: 'PUSH_REQUEST' (status=1)
2021-12-30 14:44:59.621269 PUSH: Received control message: 'PUSH_REPLY,route 192.168.1.0 255.255.255.0,route-delay 5,route-gateway dhcp,ping 10,ping-restart 120,route 192.168.1.1 255.255.255.0 192.168.1.1'
2021-12-30 14:44:59.621392 OPTIONS IMPORT: timers and/or timeouts modified
2021-12-30 14:44:59.621409 OPTIONS IMPORT: route options modified
2021-12-30 14:44:59.621419 OPTIONS IMPORT: route-related options modified
2021-12-30 14:44:59.621431 Using peer cipher 'AES-128-CBC'
2021-12-30 14:44:59.621562 Outgoing Data Channel: Cipher 'AES-128-CBC' initialized with 128 bit key
2021-12-30 14:44:59.621605 Outgoing Data Channel: Using 160 bit message hash 'SHA1' for HMAC authentication
2021-12-30 14:44:59.621619 Incoming Data Channel: Cipher 'AES-128-CBC' initialized with 128 bit key
2021-12-30 14:44:59.621631 Incoming Data Channel: Using 160 bit message hash 'SHA1' for HMAC authentication
2021-12-30 14:44:59.622249 MANAGEMENT: Client disconnected
2021-12-30 14:44:59.622275 Cannot open TUN/TAP dev VPN: No such file or directory (errno=2)
2021-12-30 14:44:59.622286 Exiting due to fatal error
2021-12-30 14:45:06.887346 *Tunnelblick: Expected disconnection occurred.

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

Down log:

(Not found)
================================================================================

Previous down log:

(Not found)
================================================================================

Network services:

An asterisk (*) denotes that a network service is disabled.
Display Ethernet
MiFi 5510
Display Ethernet 2
Display Ethernet 3
Thunderbolt Ethernet
Display FireWire 3
Display FireWire 2
Display FireWire
Wi-Fi
Thunderbolt Bridge

Wi-Fi Power (en0): Off

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

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
en3: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
        options=50b<RXCSUM,TXCSUM,VLAN_HWTAGGING,AV,CHANNEL_IO>
        ether 38:c9:86:44:e9:13
        nd6 options=201<PERFORMNUD,DAD>
        media: autoselect (none)
        status: inactive
en4: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
        options=50b<RXCSUM,TXCSUM,VLAN_HWTAGGING,AV,CHANNEL_IO>
        ether 0c:4d:e9:c2:c9:be
        nd6 options=201<PERFORMNUD,DAD>
        media: autoselect (none)
        status: inactive
en5: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
        options=50b<RXCSUM,TXCSUM,VLAN_HWTAGGING,AV,CHANNEL_IO>
        ether 38:f9:d3:12:ae:3a
        inet6 fe80::107c:a9e8:156c:54b0%en5 prefixlen 64 secured scopeid 0x6
        inet6 2600:8802:c0d:9e00:1469:4c64:79ad:17a prefixlen 64 autoconf secured
        inet6 2600:8802:c0d:9e00:70fd:3e36:c722:f05e prefixlen 64 deprecated autoconf temporary
        inet 192.168.0.83 netmask 0xffffff00 broadcast 192.168.0.255
        inet6 fddd:1ff0:2069:1:1c99:cef3:dda1:6c03 prefixlen 64 deprecated autoconf secured
        inet6 2600:8802:c0d:9e00:7cff:b837:8bf6:66b4 prefixlen 64 autoconf temporary
        nd6 options=201<PERFORMNUD,DAD>
        media: autoselect (1000baseT <full-duplex,flow-control,energy-efficient-ethernet>)
        status: active
en0: flags=8823<UP,BROADCAST,SMART,SIMPLEX,MULTICAST> mtu 1500
        options=400<CHANNEL_IO>
        ether ac:bc:32:c9:c9:0f
        nd6 options=201<PERFORMNUD,DAD>
        media: autoselect (<unknown type>)
        status: inactive
en1: flags=8963<UP,BROADCAST,SMART,RUNNING,PROMISC,SIMPLEX,MULTICAST> mtu 1500
        options=460<TSO4,TSO6,CHANNEL_IO>
        ether 82:17:05:19:69:40
        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 82:17:05:19:69:41
        media: autoselect <full-duplex>
        status: inactive
bridge0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
        options=63<RXCSUM,TXCSUM,TSO4,TSO6>
        ether 82:17:05:19:69:40
        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 8 priority 0 path cost 0
        member: en2 flags=3<LEARNING,DISCOVER>
                ifmaxaddr 0 port 9 priority 0 path cost 0
        nd6 options=201<PERFORMNUD,DAD>
        media: <unknown type>
        status: inactive
p2p0: flags=8802<BROADCAST,SIMPLEX,MULTICAST> mtu 2304
        options=400<CHANNEL_IO>
        ether 0e:bc:32:c9:c9:0f
        media: autoselect
        status: inactive
awdl0: flags=8902<BROADCAST,PROMISC,SIMPLEX,MULTICAST> mtu 1484
        options=400<CHANNEL_IO>
        ether 36:d9:c9:08:0f:d6
        nd6 options=201<PERFORMNUD,DAD>
        media: autoselect
        status: inactive
llw0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
        options=400<CHANNEL_IO>
        ether 36:d9:c9:08:0f:d6
        nd6 options=201<PERFORMNUD,DAD>
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1380
        inet6 fe80::3d5:a07f:27bf:6f68%utun0 prefixlen 64 scopeid 0xe
        nd6 options=201<PERFORMNUD,DAD>
utun1: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 2000
        inet6 fe80::bf7a:7674:bd01:c084%utun1 prefixlen 64 scopeid 0xf
        nd6 options=201<PERFORMNUD,DAD>
utun2: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1000
        inet6 fe80::ce81:b1c:bd2c:69e%utun2 prefixlen 64 scopeid 0x10
        nd6 options=201<PERFORMNUD,DAD>

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

Non-Apple kexts that are loaded:

Index Refs Address            Size       Wired      Name (Version) UUID <Linked Against>
  156    0 0xffffff7f99724000 0x4000     0x4000     com.kairos.driver.DuetDisplay (2) ACE0314B-69A7-3100-9155-3B4B6C96B2EC <118 7 6 3>
  157    0 0xffffff7f997c5000 0x3000     0x3000     com.logmein.driver.LogMeInSoundDriver (4.1.89f63) B1738EC7-AA7B-38B7-AD32-52FB7AF97212 <132 7 6 3>

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

Quit Log:

2021-12-30 14:44:06.692762 cleanup: Entering cleanup
2021-12-30 14:44:06.693382 synchronized user defaults
2021-12-30 14:44:07.755901 applicationShouldTerminate: termination for unknown reason, probably Command-Q; delayed until 'shutdownTunnelblick' finishes)
2021-12-30 14:44:07.760254 shutDownTunnelblick: started.
2021-12-30 14:44:07.760813 shutDownTunnelblick: Starting cleanup.
2021-12-30 14:44:07.761242 cleanup: Entering cleanup
2021-12-30 14:44:07.761682 shutDownTunnelblick: Cleanup already being done.
2021-12-30 14:44:07.762302 Finished shutting down Tunnelblick; allowing termination

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

Traces Log:


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

Console Log:

Tunnelblick developer

unread,
Dec 30, 2021, 8:44:35 PM12/30/21
to tunnelblick-discuss
Remove the line "dev-node VPN" from your OpenVPN configuration file.

You should also update to macOS 12.1.
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