TLS handshake will not complete in tunnelblick: incoming plaintext read error

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cmw...@g.rit.edu

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Jul 9, 2015, 11:51:50 AM7/9/15
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I am attempting to connect to a pfSense openVPN server using Tunnelblick 3.6beta06 as an administrator, but I am receiving a TLS handshake error each time I attempt to connect. I double checked the location of the tls key, as well as the contents of the key and they are correct on both the openVPN server, and on my local macbook. The log and configuration files have been posted below, any help would be appreciated.
 
*Tunnelblick: OS X 10.7.5; Tunnelblick 3.6beta06 (build 4346); Admin user

Configuration config

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

client
dev tap
proto tcp
remote 128.151.18.205 443
resolv-retry infinite
nobind
persist-key
persist-tun
ca ca.crt
cert C.crt
key C.key
ns-cert-type server
tls-auth ta.key 1
cipher AES-128-CBC
auth SHA1
comp-lzo
verb 5


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

Non-Apple kexts that are loaded:

Index Refs Address            Size       Wired      Name (Version) <Linked Against>
  112    3 0xffffff7f826dc000 0x58000    0x58000    org.virtualbox.kext.VBoxDrv (4.3.28) <7 5 4 3 1>
  113    0 0xffffff7f81d0e000 0x8000     0x8000     org.virtualbox.kext.VBoxUSB (4.3.28) <112 35 32 7 5 4 3 1>
  114    0 0xffffff7f817be000 0x5000     0x5000     org.virtualbox.kext.VBoxNetFlt (4.3.28) <112 7 5 4 3 1>
  115    0 0xffffff7f81ae2000 0x6000     0x6000     org.virtualbox.kext.VBoxNetAdp (4.3.28) <112 5 4 1>

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

There are no unusual files in config.tblk

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

Configuration preferences:

-lastConnectionSucceeded = 0

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

Wildcard preferences:


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

Program preferences:

launchAtNextLogin = 1
notOKToCheckThatIPAddressDidNotChangeAfterConnection = 0
askedUserIfOKToCheckThatIPAddressDidNotChangeAfterConnection = 1
tunnelblickVersionHistory = (
    "3.6beta06 (build 4346)"
)
statusDisplayNumber = 0
lastLaunchTime = 458148471.812864
connectionWindowDisplayCriteria = showWhenConnecting
maxLogDisplaySize = 102400
installationUID (not shown)
keyboardShortcutIndex = 1
updateCheckAutomatically = 1
updateSendProfileInfo = 1
NSWindow Frame SettingsSheetWindow = 372 98 829 424 0 0 1280 778
NSWindow Frame ConnectingWindow = 445 466 389 187 0 0 1280 778
detailsWindowFrameVersion = 4346
detailsWindowFrame = {{38, 151}, {1069, 596}}
detailsWindowLeftFrame = {{0, 0}, {196, 478}}
leftNavSelectedDisplayName = config
haveDealtWithSparkle1dot5b6 = 1
haveDealtWithOldTunTapPreferences = 1
haveDealtWithOldLoginItem = 1
SUEnableAutomaticChecks = 1
SUFeedURL = https://www.tunnelblick.net/appcast-b.rss
SUScheduledCheckInterval = 86400
SUSendProfileInfo = 1
SULastCheckTime = 2015-07-09 15:27:51 +0000
SULastProfileSubmissionDate = 2015-07-06 20:16:33 +0000
SUHasLaunchedBefore = 1
WebKitDefaultFontSize = 16
WebKitStandardFont = Times

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

Tunnelblick Log:

2015-07-09 11:28:05 *Tunnelblick: OS X 10.7.5; Tunnelblick 3.6beta06 (build 4346)
2015-07-09 11:28:06 *Tunnelblick: Attempting connection with config using shadow copy; Set nameserver = 1; monitoring connection
2015-07-09 11:28:06 *Tunnelblick: openvpnstart start config.tblk 1337 1 0 1 0 16754 -ptADGNWradsgnw 2.3.6
2015-07-09 11:28:07 *Tunnelblick: openvpnstart log:
     OpenVPN started successfully. Command used to start OpenVPN (one argument per displayed line):
    
          /Applications/Tunnelblick.app/Contents/Resources/openvpn/openvpn-2.3.6/openvpn
          --daemon
          --log
          /Library/Application Support/Tunnelblick/Logs/-SUsers-Scw-SLibrary-SApplication Support-STunnelblick-SConfigurations-Sconfig.tblk-SContents-SResources-Sconfig.ovpn.1_0_1_0_16754.1337.openvpn.log
          --cd
          /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
          --verb
          3
          --config
          /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
          --cd
          /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
          --management
          127.0.0.1
          1337
          --management-query-passwords
          --management-hold
          --script-security
          2
          --up
          /Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -a -d -f -m -w -ptADGNWradsgnw
          --down
          /Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -a -d -f -m -w -ptADGNWradsgnw
          --route-pre-down
          /Applications/Tunnelblick.app/Contents/Resources/client.route-pre-down.tunnelblick.sh -a -d -f -m -w -ptADGNWradsgnw

2015-07-09 11:28:06 us=899028 Current Parameter Settings:
2015-07-09 11:28:06 us=899266   config = '/Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn'
2015-07-09 11:28:06 us=899282   mode = 0
2015-07-09 11:28:06 us=899294   show_ciphers = DISABLED
2015-07-09 11:28:06 us=899307   show_digests = DISABLED
2015-07-09 11:28:06 us=899324   show_engines = DISABLED
2015-07-09 11:28:06 us=899337   genkey = DISABLED
2015-07-09 11:28:06 us=899349   key_pass_file = '[UNDEF]'
2015-07-09 11:28:06 us=899362   show_tls_ciphers = DISABLED
2015-07-09 11:28:06 us=899374 Connection profiles [default]:
2015-07-09 11:28:06 us=899387   proto = tcp-client
2015-07-09 11:28:06 us=899399   local = '[UNDEF]'
2015-07-09 11:28:06 us=899412   local_port = 0
2015-07-09 11:28:06 us=899424   remote = '128.151.18.205'
2015-07-09 11:28:06 us=899437   remote_port = 443
2015-07-09 11:28:06 us=899449   remote_float = DISABLED
2015-07-09 11:28:06 us=899461   bind_defined = DISABLED
2015-07-09 11:28:06 us=899473   bind_local = DISABLED
2015-07-09 11:28:06 us=899485   connect_retry_seconds = 5
2015-07-09 11:28:06 us=899497   connect_timeout = 10
2015-07-09 11:28:06 us=899510   connect_retry_max = 0
2015-07-09 11:28:06 us=899522   socks_proxy_server = '[UNDEF]'
2015-07-09 11:28:06 us=899535   socks_proxy_port = 0
2015-07-09 11:28:06 us=899547   socks_proxy_retry = DISABLED
2015-07-09 11:28:06 us=899560   tun_mtu = 1500
2015-07-09 11:28:06 us=899572   tun_mtu_defined = ENABLED
2015-07-09 11:28:06 us=899584   link_mtu = 1500
2015-07-09 11:28:06 us=899596   link_mtu_defined = DISABLED
2015-07-09 11:28:06 us=899609   tun_mtu_extra = 32
2015-07-09 11:28:06 us=899621   tun_mtu_extra_defined = ENABLED
2015-07-09 11:28:06 us=899633   mtu_discover_type = -1
2015-07-09 11:28:06 us=899645   fragment = 0
2015-07-09 11:28:06 us=899661   mssfix = 1450
2015-07-09 11:28:06 us=899674   explicit_exit_notification = 0
2015-07-09 11:28:06 us=899739 Connection profiles END
2015-07-09 11:28:06 us=899753   remote_random = DISABLED
2015-07-09 11:28:06 us=899766   ipchange = '[UNDEF]'
2015-07-09 11:28:06 us=899779   dev = 'tap'
2015-07-09 11:28:06 us=899791   dev_type = '[UNDEF]'
2015-07-09 11:28:06 us=899803   dev_node = '[UNDEF]'
2015-07-09 11:28:06 us=899816   lladdr = '[UNDEF]'
2015-07-09 11:28:06 us=899828   topology = 1
2015-07-09 11:28:06 us=899840   tun_ipv6 = DISABLED
2015-07-09 11:28:06 us=899853   ifconfig_local = '[UNDEF]'
2015-07-09 11:28:06 us=899865   ifconfig_remote_netmask = '[UNDEF]'
2015-07-09 11:28:06 us=899878   ifconfig_noexec = DISABLED
2015-07-09 11:28:06 us=899890   ifconfig_nowarn = DISABLED
2015-07-09 11:28:06 us=899902   ifconfig_ipv6_local = '[UNDEF]'
2015-07-09 11:28:06 us=899915   ifconfig_ipv6_netbits = 0
2015-07-09 11:28:06 us=899927   ifconfig_ipv6_remote = '[UNDEF]'
2015-07-09 11:28:06 us=899940   shaper = 0
2015-07-09 11:28:06 us=899952   mtu_test = 0
2015-07-09 11:28:06 us=899964   mlock = DISABLED
2015-07-09 11:28:06 us=899977   keepalive_ping = 0
2015-07-09 11:28:06 us=899989   keepalive_timeout = 0
2015-07-09 11:28:06 us=900001   inactivity_timeout = 0
2015-07-09 11:28:06 us=900014   ping_send_timeout = 0
2015-07-09 11:28:06 us=900026   ping_rec_timeout = 0
2015-07-09 11:28:06 us=900038   ping_rec_timeout_action = 0
2015-07-09 11:28:06 us=900050   ping_timer_remote = DISABLED
2015-07-09 11:28:06 us=900063   remap_sigusr1 = 0
2015-07-09 11:28:06 us=900075   persist_tun = ENABLED
2015-07-09 11:28:06 us=900087   persist_local_ip = DISABLED
2015-07-09 11:28:06 us=900099   persist_remote_ip = DISABLED
2015-07-09 11:28:06 us=900112   persist_key = ENABLED
2015-07-09 11:28:06 us=900124   passtos = DISABLED
2015-07-09 11:28:06 us=900136   resolve_retry_seconds = 1000000000
2015-07-09 11:28:06 us=900149   username = '[UNDEF]'
2015-07-09 11:28:06 us=900175   groupname = '[UNDEF]'
2015-07-09 11:28:06 us=900188   chroot_dir = '[UNDEF]'
2015-07-09 11:28:06 us=900200   cd_dir = '/Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources'
2015-07-09 11:28:06 us=900213   writepid = '[UNDEF]'
2015-07-09 11:28:06 us=900225   up_script = '/Applications/Tunnelblick.app/Contents/Resources/client.up.tunnelblick.sh -a -d -f -m -w -ptADGNWradsgnw'
2015-07-09 11:28:06 us=900238   down_script = '/Applications/Tunnelblick.app/Contents/Resources/client.down.tunnelblick.sh -a -d -f -m -w -ptADGNWradsgnw'
2015-07-09 11:28:06 us=900250   down_pre = DISABLED
2015-07-09 11:28:06 us=900262   up_restart = DISABLED
2015-07-09 11:28:06 us=900274   up_delay = DISABLED
2015-07-09 11:28:06 us=900286   daemon = ENABLED
2015-07-09 11:28:06 us=900299   inetd = 0
2015-07-09 11:28:06 us=900311   log = ENABLED
2015-07-09 11:28:06 us=900323   suppress_timestamps = DISABLED
2015-07-09 11:28:06 us=900335   nice = 0
2015-07-09 11:28:06 us=900347   verbosity = 5
2015-07-09 11:28:06 us=900359   mute = 0
2015-07-09 11:28:06 us=900371   status_file = '[UNDEF]'
2015-07-09 11:28:06 us=900383   status_file_version = 1
2015-07-09 11:28:06 us=900396   status_file_update_freq = 60
2015-07-09 11:28:06 us=900408   occ = ENABLED
2015-07-09 11:28:06 us=900420   rcvbuf = 65536
2015-07-09 11:28:06 us=900436   sndbuf = 65536
2015-07-09 11:28:06 us=900449   sockflags = 0
2015-07-09 11:28:06 us=900461   fast_io = DISABLED
2015-07-09 11:28:06 us=900473   lzo = 7
2015-07-09 11:28:06 us=900485   route_script = '[UNDEF]'
2015-07-09 11:28:06 us=900497   route_default_gateway = '[UNDEF]'
2015-07-09 11:28:06 us=900509   route_default_metric = 0
2015-07-09 11:28:06 us=900522   route_noexec = DISABLED
2015-07-09 11:28:06 us=900534   route_delay = 0
2015-07-09 11:28:06 us=900550   route_delay_window = 30
2015-07-09 11:28:06 us=900563   route_delay_defined = DISABLED
2015-07-09 11:28:06 us=900576   route_nopull = DISABLED
2015-07-09 11:28:06 us=900589   route_gateway_via_dhcp = DISABLED
2015-07-09 11:28:06 us=900602   max_routes = 100
2015-07-09 11:28:06 us=900614   allow_pull_fqdn = DISABLED
2015-07-09 11:28:06 us=900627   management_addr = '127.0.0.1'
2015-07-09 11:28:06 us=900639   management_port = 1337
2015-07-09 11:28:06 us=900652   management_user_pass = '[UNDEF]'
2015-07-09 11:28:06 us=900665   management_log_history_cache = 250
2015-07-09 11:28:06 us=900678   management_echo_buffer_size = 100
2015-07-09 11:28:06 us=900691   management_write_peer_info_file = '[UNDEF]'
2015-07-09 11:28:06 us=900704   management_client_user = '[UNDEF]'
2015-07-09 11:28:06 us=900716   management_client_group = '[UNDEF]'
2015-07-09 11:28:06 us=900729   management_flags = 6
2015-07-09 11:28:06 us=900742   shared_secret_file = '[UNDEF]'
2015-07-09 11:28:06 us=900755   key_direction = 2
2015-07-09 11:28:06 us=900767   ciphername_defined = ENABLED
2015-07-09 11:28:06 us=900780   ciphername = 'AES-128-CBC'
2015-07-09 11:28:06 us=900792   authname_defined = ENABLED
2015-07-09 11:28:06 us=900805   authname = 'SHA1'
2015-07-09 11:28:06 us=900817   prng_hash = 'SHA1'
2015-07-09 11:28:06 us=900830   prng_nonce_secret_len = 16
2015-07-09 11:28:06 us=900843   keysize = 0
2015-07-09 11:28:06 us=900855   engine = DISABLED
2015-07-09 11:28:06 us=900868   replay = ENABLED
2015-07-09 11:28:06 us=900881   mute_replay_warnings = DISABLED
2015-07-09 11:28:06 us=900894   replay_window = 64
2015-07-09 11:28:06 us=900906   replay_time = 15
2015-07-09 11:28:06 us=900919   packet_id_file = '[UNDEF]'
2015-07-09 11:28:06 us=900931   use_iv = ENABLED
2015-07-09 11:28:06 us=900944   test_crypto = DISABLED
2015-07-09 11:28:06 us=900957   tls_server = DISABLED
2015-07-09 11:28:06 us=900969   tls_client = ENABLED
2015-07-09 11:28:06 us=900995   key_method = 2
2015-07-09 11:28:06 us=901008   ca_file = 'ca.crt'
2015-07-09 11:28:06 us=901021   ca_path = '[UNDEF]'
2015-07-09 11:28:06 us=901033   dh_file = '[UNDEF]'
2015-07-09 11:28:06 us=901045   cert_file = 'Craig.crt'
2015-07-09 11:28:06 us=901058   priv_key_file = 'Craig.key'
2015-07-09 11:28:06 us=901071   pkcs12_file = '[UNDEF]'
2015-07-09 11:28:06 us=901083   cipher_list = '[UNDEF]'
2015-07-09 11:28:06 us=901095   tls_verify = '[UNDEF]'
2015-07-09 11:28:06 us=901108   tls_export_cert = '[UNDEF]'
2015-07-09 11:28:06 us=901120   verify_x509_type = 0
2015-07-09 11:28:06 us=901133   verify_x509_name = '[UNDEF]'
2015-07-09 11:28:06 us=901145   crl_file = '[UNDEF]'
2015-07-09 11:28:06 us=901158   ns_cert_type = 1
2015-07-09 11:28:06 us=901171   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901183   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901196   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901208   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901221   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901234   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901246   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901259   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901271   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901283   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901296   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901308   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901321   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901333   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901346   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901358   remote_cert_ku[i] = 0
2015-07-09 11:28:06 us=901370   remote_cert_eku = '[UNDEF]'
2015-07-09 11:28:06 us=901383   ssl_flags = 0
2015-07-09 11:28:06 us=901399   tls_timeout = 2
2015-07-09 11:28:06 us=901411   renegotiate_bytes = 0
2015-07-09 11:28:06 us=901424   renegotiate_packets = 0
2015-07-09 11:28:06 us=901447   renegotiate_seconds = 3600
2015-07-09 11:28:06 us=901459   handshake_window = 60
2015-07-09 11:28:06 us=901471   transition_window = 3600
2015-07-09 11:28:06 us=901482   single_session = DISABLED
2015-07-09 11:28:06 us=901494   push_peer_info = DISABLED
2015-07-09 11:28:06 us=901506   tls_exit = DISABLED
2015-07-09 11:28:06 us=901518   tls_auth_file = 'ta.key'
2015-07-09 11:28:06 us=901530   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901542   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901554   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901566   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901579   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901590   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901602   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901614   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901626   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901638   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901650   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901662   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901674   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901686   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901698   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901710   pkcs11_protected_authentication = DISABLED
2015-07-09 11:28:06 us=901723   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901735   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901747   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901759   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901771   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901795   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901807   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901820   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901832   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901844   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901856   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901868   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901880   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901892   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901904   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901917   pkcs11_private_mode = 00000000
2015-07-09 11:28:06 us=901929   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=901941   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=901953   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=901964   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=901976   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=901988   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902000   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902012   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902024   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902036   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902048   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902060   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902072   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902084   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902096   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902108   pkcs11_cert_private = DISABLED
2015-07-09 11:28:06 us=902120   pkcs11_pin_cache_period = -1
2015-07-09 11:28:06 us=902132   pkcs11_id = '[UNDEF]'
2015-07-09 11:28:06 us=902144   pkcs11_id_management = DISABLED
2015-07-09 11:28:06 us=902172   server_network = 0.0.0.0
2015-07-09 11:28:06 us=902186   server_netmask = 0.0.0.0
2015-07-09 11:28:06 us=902203   server_network_ipv6 = ::
2015-07-09 11:28:06 us=902216   server_netbits_ipv6 = 0
2015-07-09 11:28:06 us=902229   server_bridge_ip = 0.0.0.0
2015-07-09 11:28:06 us=902242   server_bridge_netmask = 0.0.0.0
2015-07-09 11:28:06 us=902255   server_bridge_pool_start = 0.0.0.0
2015-07-09 11:28:06 us=902269   server_bridge_pool_end = 0.0.0.0
2015-07-09 11:28:06 us=902281   ifconfig_pool_defined = DISABLED
2015-07-09 11:28:06 us=902294   ifconfig_pool_start = 0.0.0.0
2015-07-09 11:28:06 us=902307   ifconfig_pool_end = 0.0.0.0
2015-07-09 11:28:06 us=902320   ifconfig_pool_netmask = 0.0.0.0
2015-07-09 11:28:06 us=902332   ifconfig_pool_persist_filename = '[UNDEF]'
2015-07-09 11:28:06 us=902345   ifconfig_pool_persist_refresh_freq = 600
2015-07-09 11:28:06 us=902357   ifconfig_ipv6_pool_defined = DISABLED
2015-07-09 11:28:06 us=902369   ifconfig_ipv6_pool_base = ::
2015-07-09 11:28:06 us=902382   ifconfig_ipv6_pool_netbits = 0
2015-07-09 11:28:06 us=902394   n_bcast_buf = 256
2015-07-09 11:28:06 us=902406   tcp_queue_limit = 64
2015-07-09 11:28:06 us=902417   real_hash_size = 256
2015-07-09 11:28:06 us=902429   virtual_hash_size = 256
2015-07-09 11:28:06 us=902441   client_connect_script = '[UNDEF]'
2015-07-09 11:28:06 us=902453   learn_address_script = '[UNDEF]'
2015-07-09 11:28:06 us=902465   client_disconnect_script = '[UNDEF]'
2015-07-09 11:28:06 us=902477   client_config_dir = '[UNDEF]'
2015-07-09 11:28:06 us=902489   ccd_exclusive = DISABLED
2015-07-09 11:28:06 us=902503   tmp_dir = '/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/'
2015-07-09 11:28:06 us=902516   push_ifconfig_defined = DISABLED
2015-07-09 11:28:06 us=902529   push_ifconfig_local = 0.0.0.0
2015-07-09 11:28:06 us=902542   push_ifconfig_remote_netmask = 0.0.0.0
2015-07-09 11:28:06 us=902566   push_ifconfig_ipv6_defined = DISABLED
2015-07-09 11:28:06 us=902579   push_ifconfig_ipv6_local = ::/0
2015-07-09 11:28:06 us=902592   push_ifconfig_ipv6_remote = ::
2015-07-09 11:28:06 us=902606   enable_c2c = DISABLED
2015-07-09 11:28:06 us=902618   duplicate_cn = DISABLED
2015-07-09 11:28:06 us=902630   cf_max = 0
2015-07-09 11:28:06 us=902642   cf_per = 0
2015-07-09 11:28:06 us=902656   max_clients = 1024
2015-07-09 11:28:06 us=902668   max_routes_per_client = 256
2015-07-09 11:28:06 us=902681   auth_user_pass_verify_script = '[UNDEF]'
2015-07-09 11:28:06 us=902693   auth_user_pass_verify_script_via_file = DISABLED
2015-07-09 11:28:06 us=902705   port_share_host = '[UNDEF]'
2015-07-09 11:28:06 us=902717   port_share_port = 0
2015-07-09 11:28:06 us=902729   client = ENABLED
2015-07-09 11:28:06 us=902741   pull = ENABLED
2015-07-09 11:28:06 us=902754   auth_user_pass_file = '[UNDEF]'
2015-07-09 11:28:06 us=902768 OpenVPN 2.3.6 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [PKCS11] [MH] [IPv6] built on Jun 12 2015
2015-07-09 11:28:06 us=902787 library versions: OpenSSL 1.0.2c 12 Jun 2015, LZO 2.09
2015-07-09 11:28:06 us=903537 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:1337
2015-07-09 11:28:06 us=904082 Need hold release from management interface, waiting...
2015-07-09 11:28:06 *Tunnelblick: openvpnstart starting OpenVPN
2015-07-09 11:28:07 *Tunnelblick: Established communication with OpenVPN
2015-07-09 11:28:07 us=631138 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:1337
2015-07-09 11:28:07 us=657374 MANAGEMENT: CMD 'pid'
2015-07-09 11:28:07 us=657681 MANAGEMENT: CMD 'state on'
2015-07-09 11:28:07 us=657830 MANAGEMENT: CMD 'state'
2015-07-09 11:28:07 us=658059 MANAGEMENT: CMD 'bytecount 1'
2015-07-09 11:28:07 us=658203 MANAGEMENT: CMD 'hold release'
2015-07-09 11:28:07 us=658652 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-07-09 11:28:07 us=659973 Control Channel Authentication: using 'ta.key' as a OpenVPN static key file
2015-07-09 11:28:07 us=660236 Outgoing Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2015-07-09 11:28:07 us=660362 Incoming Control Channel Authentication: Using 160 bit message hash 'SHA1' for HMAC authentication
2015-07-09 11:28:07 us=660501 LZO compression initialized
2015-07-09 11:28:07 us=660731 Control Channel MTU parms [ L:1592 D:168 EF:68 EB:0 ET:0 EL:0 ]
2015-07-09 11:28:07 us=660910 Socket Buffers: R=[262140->65536] S=[131070->65536]
2015-07-09 11:28:07 us=661409 Data Channel MTU parms [ L:1592 D:1450 EF:60 EB:135 ET:32 EL:0 AF:3/1 ]
2015-07-09 11:28:07 us=661576 Local Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_CLIENT,comp-lzo,keydir 1,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-client'
2015-07-09 11:28:07 us=661685 Expected Remote Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_SERVER,comp-lzo,keydir 0,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-server'
2015-07-09 11:28:07 us=661922 Local Options hash (VER=V4): '29f6c8b2'
2015-07-09 11:28:07 us=662035 Expected Remote Options hash (VER=V4): '3d4363c6'
2015-07-09 11:28:07 us=662156 Attempting to establish TCP connection with [AF_INET]128.151.18.205:443 [nonblock]
2015-07-09 11:28:07 us=662272 MANAGEMENT: >STATE:1436455687,TCP_CONNECT,,,
2015-07-09 11:28:08 us=663652 TCP connection established with [AF_INET]128.151.18.205:443
2015-07-09 11:28:08 us=664578 TCPv4_CLIENT link local: [undef]
2015-07-09 11:28:08 us=665636 TCPv4_CLIENT link remote: [AF_INET]128.151.18.205:443
2015-07-09 11:28:08 us=665799 MANAGEMENT: >STATE:1436455688,WAIT,,,
                                        WRThu Jul  9 11:28:08 2015 us=669186 MANAGEMENT: >STATE:1436455688,AUTH,,,
2015-07-09 11:28:08 us=669486 TLS: Initial packet from [AF_INET]128.151.18.205:443, sid=869715af 2d8bce29
                                        WWWWRRRWRRRWWRWRWRRWWRWRWRRWWRWRWRThu Jul  9 11:28:08 2015 us=685470 VERIFY ERROR: depth=0, error=self signed certificate: C=US, ST=State, L=Locality, O=pfSense webConfigurator Self-Signed Certificate, emailAddress=ad...@pfSense.localdomain, CN=pfSense-559a8e35a90d9
2015-07-09 11:28:08 us=685977 TLS_ERROR: BIO read tls_read_plaintext error: error:14090086:SSL routines:ssl3_get_server_certificate:certificate verify failed
2015-07-09 11:28:08 us=686136 TLS Error: TLS object -> incoming plaintext read error
2015-07-09 11:28:08 us=686240 TLS Error: TLS handshake failed
2015-07-09 11:28:08 us=686443 Fatal TLS error (check_tls_errors_co), restarting
2015-07-09 11:28:08 us=686583 TCP/UDP: Closing socket
2015-07-09 11:28:08 us=687186 SIGUSR1[soft,tls-error] received, process restarting
2015-07-09 11:28:08 us=687437 MANAGEMENT: >STATE:1436455688,RECONNECTING,tls-error,,
2015-07-09 11:28:08 us=770197 MANAGEMENT: CMD 'hold release'
2015-07-09 11:28:08 us=770420 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-07-09 11:28:08 us=770574 Re-using SSL/TLS context
2015-07-09 11:28:08 us=770688 LZO compression initialized
2015-07-09 11:28:08 us=770912 Control Channel MTU parms [ L:1592 D:168 EF:68 EB:0 ET:0 EL:0 ]
2015-07-09 11:28:08 us=771097 Socket Buffers: R=[262140->65536] S=[131070->65536]
2015-07-09 11:28:08 us=771347 Data Channel MTU parms [ L:1592 D:1450 EF:60 EB:135 ET:32 EL:0 AF:3/1 ]
2015-07-09 11:28:08 us=771480 Local Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_CLIENT,comp-lzo,keydir 1,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-client'
2015-07-09 11:28:08 us=771586 Expected Remote Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_SERVER,comp-lzo,keydir 0,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-server'
2015-07-09 11:28:08 us=771702 Local Options hash (VER=V4): '29f6c8b2'
2015-07-09 11:28:08 us=771814 Expected Remote Options hash (VER=V4): '3d4363c6'
2015-07-09 11:28:08 us=771927 Attempting to establish TCP connection with [AF_INET]128.151.18.205:443 [nonblock]
2015-07-09 11:28:08 us=772034 MANAGEMENT: >STATE:1436455688,TCP_CONNECT,,,
2015-07-09 11:28:09 us=772897 TCP connection established with [AF_INET]128.151.18.205:443
2015-07-09 11:28:09 us=773342 TCPv4_CLIENT link local: [undef]
2015-07-09 11:28:09 us=773461 TCPv4_CLIENT link remote: [AF_INET]128.151.18.205:443
2015-07-09 11:28:09 us=773646 MANAGEMENT: >STATE:1436455689,WAIT,,,
                                        WRThu Jul  9 11:28:09 2015 us=780248 MANAGEMENT: >STATE:1436455689,AUTH,,,
2015-07-09 11:28:09 us=780543 TLS: Initial packet from [AF_INET]128.151.18.205:443, sid=dccda6c5 5e55eff2
                                        RRWRRRWWRWRRRWWRWRRRWWRWRRThu Jul  9 11:28:09 2015 us=793044 VERIFY ERROR: depth=0, error=self signed certificate: C=US, ST=State, L=Locality, O=pfSense webConfigurator Self-Signed Certificate, emailAddress=ad...@pfSense.localdomain, CN=pfSense-559a8e35a90d9
2015-07-09 11:28:09 us=793330 TLS_ERROR: BIO read tls_read_plaintext error: error:14090086:SSL routines:ssl3_get_server_certificate:certificate verify failed
2015-07-09 11:28:09 us=793540 TLS Error: TLS object -> incoming plaintext read error
2015-07-09 11:28:09 us=793691 TLS Error: TLS handshake failed
2015-07-09 11:28:09 us=794064 Fatal TLS error (check_tls_errors_co), restarting
2015-07-09 11:28:09 us=794271 TCP/UDP: Closing socket
2015-07-09 11:28:09 us=794461 SIGUSR1[soft,tls-error] received, process restarting
2015-07-09 11:28:09 us=794610 MANAGEMENT: >STATE:1436455689,RECONNECTING,tls-error,,
2015-07-09 11:28:09 us=870250 MANAGEMENT: CMD 'hold release'
2015-07-09 11:28:09 us=870716 NOTE: the current --script-security setting may allow this configuration to call user-defined scripts
2015-07-09 11:28:09 us=871066 Re-using SSL/TLS context
2015-07-09 11:28:09 us=871188 LZO compression initialized
2015-07-09 11:28:09 us=871356 Control Channel MTU parms [ L:1592 D:168 EF:68 EB:0 ET:0 EL:0 ]
2015-07-09 11:28:09 us=871517 Socket Buffers: R=[262140->65536] S=[131070->65536]
2015-07-09 11:28:09 us=871748 Data Channel MTU parms [ L:1592 D:1450 EF:60 EB:135 ET:32 EL:0 AF:3/1 ]
2015-07-09 11:28:09 us=871890 Local Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_CLIENT,comp-lzo,keydir 1,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-client'
2015-07-09 11:28:09 us=871995 Expected Remote Options String: 'V4,dev-type tap,link-mtu 1592,tun-mtu 1532,proto TCPv4_SERVER,comp-lzo,keydir 0,cipher AES-128-CBC,auth SHA1,keysize 128,tls-auth,key-method 2,tls-server'
2015-07-09 11:28:09 us=872109 Local Options hash (VER=V4): '29f6c8b2'
2015-07-09 11:28:09 us=872220 Expected Remote Options hash (VER=V4): '3d4363c6'
2015-07-09 11:28:09 us=872331 Attempting to establish TCP connection with [AF_INET]128.151.18.205:443 [nonblock]
2015-07-09 11:28:09 us=872437 MANAGEMENT: >STATE:1436455689,TCP_CONNECT,,,
2015-07-09 11:28:10 *Tunnelblick: Disconnecting; VPN Details… window disconnect button pressed
2015-07-09 11:28:10 *Tunnelblick: Disconnecting using 'kill'
2015-07-09 11:28:10 us=395419 TCP/UDP: Closing socket
2015-07-09 11:28:10 us=395717 SIGTERM[hard,init_instance] received, process exiting
2015-07-09 11:28:10 us=395831 MANAGEMENT: >STATE:1436455690,EXITING,init_instance,,
2015-07-09 11:28:11 *Tunnelblick: No 'post-disconnect.sh' script to execute
2015-07-09 11:28:11 *Tunnelblick: Expected disconnection occurred.

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

"Sanitized" full configuration file

##############################################
# Sample client-side OpenVPN 2.0 config file #
# for connecting to multi-client server.     #
#                                            #
# This configuration can be used by multiple #
# clients, however each client should have   #
# its own cert and key files.                #
#                                            #
# On Windows, you might want to rename this  #
# file so it has a .ovpn extension           #
##############################################

# Specify that we are a client and that we
# will be pulling certain config file directives
# from the server.
client

# Use the same setting as you are using on
# the server.
# On most systems, the VPN will not function
# unless you partially or fully disable
# the firewall for the TUN/TAP interface.
dev tap
;dev tun

# Windows needs the TAP-Win32 adapter name
# from the Network Connections panel
# if you have more than one.  On XP SP2,
# you may need to disable the firewall
# for the TAP adapter.
;dev-node MyTap

# Are we connecting to a TCP or
# UDP server?  Use the same setting as
# on the server.
proto tcp
;proto udp

# The hostname/IP and port of the server.
# You can have multiple remote entries
# to load balance between the servers.
remote X.X.X.X 443
;remote my-server-2 1194

# Choose a random host from the remote
# list for load-balancing.  Otherwise
# try hosts in the order specified.
;remote-random

# Keep trying indefinitely to resolve the
# host name of the OpenVPN server.  Very useful
# on machines which are not permanently connected
# to the internet such as laptops.
resolv-retry infinite

# Most clients don't need to bind to
# a specific local port number.
nobind

# Downgrade privileges after initialization (non-Windows only)
;user nobody
;group nobody

# Try to preserve some state across restarts.
persist-key
persist-tun

# If you are connecting through an
# HTTP proxy to reach the actual OpenVPN
# server, put the proxy server/IP and
# port number here.  See the man page
# if your proxy server requires
# authentication.
;http-proxy-retry # retry on connection failures
;http-proxy [proxy server] [proxy port #]

# Wireless networks often produce a lot
# of duplicate packets.  Set this flag
# to silence duplicate packet warnings.
;mute-replay-warnings

# SSL/TLS parms.
# See the server config file for more
# description.  It's best to use
# a separate .crt/.key file pair
# for each client.  A single ca
# file can be used for all clients.
ca ca.crt
cert C.crt
key C.key

# Verify server certificate by checking
# that the certicate has the nsCertType
# field set to "server".  This is an
# important precaution to protect against
# a potential attack discussed here:
https://urldefense.proofpoint.com/v2/url?u=http-3A__openvpn.net_howto.html-23mitm&d=BQICAg&c=kbmfwr1Yojg42sGEpaQh5ofMHBeTl9EI2eaqQZhHbOU&r=Inw718_LZnUK
#
# To use this feature, you will need to generate
# your server certificates with the nsCertType
# field set to "server".  The build-key-server
# script in the easy-rsa folder will do this.
ns-cert-type server

# If a tls-auth key is used on the server
# then every client must also have the key.
tls-auth ta.key 1

# Select a cryptographic cipher.
# If the cipher option is used on the server
# then you must also specify it here.
cipher AES-128-CBC

auth SHA1

# Enable compression on the VPN link.
# Don't enable this unless it is also
# enabled in the server config file.
comp-lzo

# Set log file verbosity.
verb 5


# End of file


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

ifconfig output:

lo0: flags=8049<UP,LOOPBACK,RUNNING,MULTICAST> mtu 16384
    options=3<RXCSUM,TXCSUM>
    inet6 fe80::1%lo0 prefixlen 64 scopeid 0x1
    inet 127.0.0.1 netmask 0xff000000
    inet6 ::1 prefixlen 128
gif0: flags=8010<POINTOPOINT,MULTICAST> mtu 1280
stf0: flags=0<> mtu 1280
en0: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    options=27<RXCSUM,TXCSUM,VLAN_MTU,TSO4>
    ether 34:15:9e:32:ce:46
    media: autoselect
    status: inactive
en1: flags=8863<UP,BROADCAST,SMART,RUNNING,SIMPLEX,MULTICAST> mtu 1500
    ether 58:b0:35:84:03:bd
    inet6 fe80::5ab0:35ff:fe84:3bd%en1 prefixlen 64 scopeid 0x5
    inet 10.5.10.98 netmask 0xffffc000 broadcast 10.5.63.255
    media: autoselect
    status: active
p2p0: flags=8843<UP,BROADCAST,RUNNING,SIMPLEX,MULTICAST> mtu 2304
    ether 0a:b0:35:84:03:bd
    media: autoselect
    status: inactive

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

Console Log:

2015-07-09 09:04:02 Tunnelblick[353] Set program update feedURL to https://www.tunnelblick.net/appcast-b.rss
2015-07-09 09:04:05 Tunnelblick[353] DEBUG: Updater: systemVersion 10.7.5 satisfies minimumSystemVersion 10.4.0
2015-07-09 09:04:05 Tunnelblick[353] DEBUG: Updater: systemVersion 10.7.5 satisfies minimumSystemVersion 10.4.0
2015-07-09 09:15:50 tunnelblickd[480] Status = 252 from tunnelblick-helper command 'compareShadowCopy config'
2015-07-09 09:15:50 Tunnelblick[353] tunnelblickd status from compareShadowCopy: 252
2015-07-09 09:15:54 Tunnelblick[353] Beginning installation or repair
2015-07-09 09:15:54 authexec[486] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 09:15:55 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 09:15:54. 3 arguments: 0x0001
                                            /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                            /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       Copied /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                           to /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                       Renamed /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                            to /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed ownership of /Library/Application Support/Tunnelblick/Users/cw/config.tblk and its contents from 502:80 to 0:0
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ca.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.key
                                       Tunnelblick installer finished without error
2015-07-09 09:15:55 Tunnelblick[353] Created or updated secure (shadow) copy of configuration file /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
2015-07-09 09:15:56 tunnelblickd[480] Status = 251 from tunnelblick-helper command 'start config.tblk 1337 1 0 1 0 16754 -ptADGNWradsgnw 2.3.6'
2015-07-09 09:15:56 Tunnelblick[353] tunnelblickd status from start: 251
2015-07-09 09:19:07 tunnelblickd[504] Status = 252 from tunnelblick-helper command 'compareShadowCopy config'
2015-07-09 09:19:07 Tunnelblick[353] tunnelblickd status from compareShadowCopy: 252
2015-07-09 09:19:10 Tunnelblick[353] Beginning installation or repair
2015-07-09 09:19:10 authexec[508] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 09:19:11 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 09:19:10. 3 arguments: 0x0001
                                            /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                            /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       Copied /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                           to /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                       Renamed /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                            to /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed ownership of /Library/Application Support/Tunnelblick/Users/cw/config.tblk and its contents from 502:80 to 0:0
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ca.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.key
                                       Tunnelblick installer finished without error
2015-07-09 09:19:11 Tunnelblick[353] Created or updated secure (shadow) copy of configuration file /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
2015-07-09 09:19:12 tunnelblickd[504] Status = 251 from tunnelblick-helper command 'start config.tblk 1337 1 0 1 0 16754 -ptADGNWradsgnw 2.3.6'
2015-07-09 09:19:13 Tunnelblick[353] tunnelblickd status from start: 251
2015-07-09 09:22:15 Tunnelblick[353] Converting/Installing /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn: File '/Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn' is missing.
2015-07-09 09:22:39 tunnelblickd[522] Status = 252 from tunnelblick-helper command 'compareShadowCopy config'
2015-07-09 09:22:39 Tunnelblick[353] tunnelblickd status from compareShadowCopy: 252
2015-07-09 09:23:05 Tunnelblick[353] Beginning installation or repair
2015-07-09 09:23:05 authexec[527] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 09:23:06 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 09:23:05. 2 arguments: 0x2001
                                            /Users/cweaver/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       removed /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       removed /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Tunnelblick installer finished without error
2015-07-09 09:23:06 Tunnelblick[353] Uninstalled configuration file /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
2015-07-09 09:23:25 Tunnelblick[353] Converting/Installing /Users/cw/Desktop/newConfig/config.ovpn at line 88: Copied ca.crt
2015-07-09 09:23:25 Tunnelblick[353] Changed permissions from 700 to 740 on /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk/Contents/Resources/ca.crt
2015-07-09 09:23:25 Tunnelblick[353] Converting/Installing /Users/cw/Desktop/newConfig/config.ovpn at line 89: Copied C.crt
2015-07-09 09:23:25 Tunnelblick[353] Changed permissions from 700 to 740 on /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk/Contents/Resources/C.crt
2015-07-09 09:23:25 Tunnelblick[353] Converting/Installing /Users/cw/Desktop/newConfig/config.ovpn at line 90: Copied C.key
2015-07-09 09:23:25 Tunnelblick[353] Changed permissions from 700 to 740 on /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk/Contents/Resources/C.key
2015-07-09 09:23:25 Tunnelblick[353] Converting/Installing /Users/cw/Desktop/newConfig/config.ovpn at line 107: Copied ta.key
2015-07-09 09:23:25 Tunnelblick[353] Changed permissions from 666 to 740 on /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk/Contents/Resources/ta.key
2015-07-09 09:23:25 Tunnelblick[353] Converting/Installing /Users/cw/Desktop/newConfig/config.ovpn: Converted OpenVPN configuration
2015-07-09 09:23:32 Tunnelblick[353] Beginning installation or repair
2015-07-09 09:23:32 authexec[536] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 09:23:33 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 09:23:32. 3 arguments: 0x0001
                                            /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                            /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk
                                       Copied /private/var/folders/tb/wr4sybb57x165vflq090gy700000gp/T/Tunnelblick-dKBl8h/config.tblk
                                           to /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk.temp
                                       Renamed /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk.temp
                                            to /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       Changed ownership of /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk and its contents from 502:20 to 502:80
                                       Copied /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                           to /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                       Renamed /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                            to /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed ownership of /Library/Application Support/Tunnelblick/Users/cw/config.tblk and its contents from 502:80 to 0:0
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ca.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/Craig.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/Craig.key
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ta.key
                                       Created secure (shadow) copy of config.tblk
                                       Tunnelblick installer finished without error
2015-07-09 09:26:32 tunnelblickd[546] Status = 252 from tunnelblick-helper command 'compareShadowCopy config'
2015-07-09 09:26:32 Tunnelblick[353] tunnelblickd status from compareShadowCopy: 252
2015-07-09 09:26:35 Tunnelblick[353] Beginning installation or repair
2015-07-09 09:26:35 authexec[551] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 09:26:36 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 09:26:35. 3 arguments: 0x0001
                                            /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                            /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       Copied /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                           to /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                       Renamed /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                            to /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed ownership of /Library/Application Support/Tunnelblick/Users/cw/config.tblk and its contents from 502:80 to 0:0
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ca.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.key
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ta.key
                                       Tunnelblick installer finished without error
2015-07-09 09:26:36 Tunnelblick[353] Created or updated secure (shadow) copy of configuration file /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
2015-07-09 10:52:12 tunnelblickd[1083] Status = 252 from tunnelblick-helper command 'compareShadowCopy config'
2015-07-09 10:52:13 Tunnelblick[353] tunnelblickd status from compareShadowCopy: 252
2015-07-09 10:52:16 Tunnelblick[353] Beginning installation or repair
2015-07-09 10:52:16 authexec[1098] executing /Applications/Tunnelblick.app/Contents/Resources/installer
2015-07-09 10:52:17 Tunnelblick[353] Installation or repair succeeded; Log:
                                       Tunnelblick installer started 2015-07-09 10:52:16. 3 arguments: 0x0001
                                            /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                            /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                       Copied /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
                                           to /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                       Renamed /Library/Application Support/Tunnelblick/Users/cw/config.tblk.temp
                                            to /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed ownership of /Library/Application Support/Tunnelblick/Users/cw/config.tblk and its contents from 502:80 to 0:0
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents
                                       Changed permissions from 750 to 755 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ca.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/config.ovpn
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.crt
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/C.key
                                       Changed permissions from 740 to 700 on /Library/Application Support/Tunnelblick/Users/cw/config.tblk/Contents/Resources/ta.key
                                       Tunnelblick installer finished without error
2015-07-09 10:52:17 Tunnelblick[353] Created or updated secure (shadow) copy of configuration file /Users/cw/Library/Application Support/Tunnelblick/Configurations/config.tblk
2015-07-09 11:21:58 [0x0-0x1e01e].org.mozilla.firefox[494] onclick@https://groups.google.com/forum/#!forum/tunnelblick-discuss:1:17
2015-07-09 11:25:58 Tunnelblick[353] applicationShouldTerminate: termination because of Quit; delayed until 'shutdownTunnelblick' finishes
2015-07-09 11:25:59 Tunnelblick[353] Finished shutting down Tunnelblick; allowing termination
2015-07-09 11:27:50 Tunnelblick[1181] Set program update feedURL to https://www.tunnelblick.net/appcast-b.rss
2015-07-09 11:27:52 Tunnelblick[1181] DEBUG: Updater: systemVersion 10.7.5 satisfies minimumSystemVersion 10.4.0
2015-07-09 11:27:52 Tunnelblick[1181] DEBUG: Updater: systemVersion 10.7.5 satisfies minimumSystemVersion 10.4.0


jkbull...gmail.com

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Jul 9, 2015, 12:22:22 PM7/9/15
to tunnelbli...@googlegroups.com, cmw...@g.rit.edu, cmw...@g.rit.edu


On Thursday, July 9, 2015 at 11:51:50 AM UTC-4, <> wrote:
I am attempting to connect to a pfSense openVPN server using Tunnelblick 3.6beta06 as an administrator, but I am receiving a TLS handshake error each time I attempt to connect. I double checked the location of the tls key, as well as the contents of the key and they are correct on both the openVPN server, and on my local macbook. The log and configuration files have been posted below, any help would be appreciated.

Here's the specific error message (well, as specific as OpenSSL gets):

2015-07-09 11:28:08 us=685977 TLS_ERROR: BIO read tls_read_plaintext error: error:14090086:SSL routines:ssl3_get_server_certificate:certificate verify failed
 
It means that, well, the certificate failed verification. You can search for the reasons that might happen, but you are probably better off just regenerating the keys and certificates. Further help might be available on a pfSense forum, or somewhere that deals with however you generated the public key infrastructure.


cmw...@g.rit.edu

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Jul 9, 2015, 2:04:37 PM7/9/15
to tunnelbli...@googlegroups.com, cmw...@g.rit.edu
I just created a new certificate authority and regenerated the keys and certificates, but I am receiving the same error still. I will continue searching the pfSense forum.
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