I installed Tunnelblick and now my Mac won't boot?!

[Red Nicholson]

Hi everyone,  

So, this is embarrassing: I just installed the Tunnelblick client, in order to use the VPN service in my Orbi router.

I installed Tunnelblick (fine), downloaded the config file from my Orbi router (fine), installed the tan/tup extensions as prompted, and when prompted to reboot, did so. Now, my iMac (2019, Intel) is stuck in a continual loop reboot cycle. 

I can boot to a separate drive, but every time I boot to my main disk it just continues to reboot. 

I'm not sure what has happened here, but I'd really love your help so that I can get back to using my iMac!

NB: my main disk is an external USB-C drive, so it is possible to mount it and access/delete any files that you think could be causing the issue?

Thanks so much for your help

[Tunnelblick developer]

Nobody else seems to have had this problem, but here's my advice:

I suggest you try to boot in Safe Mode, which will prevent Tunnelblick's system extensions (kexts) from being used.

If it won't boot into Safe Mode, then the problem isn't with the Tunnelblick system extensions; you should probably contact Apple support [1]. They'll probably have you re-install macOS.

If it boots into Safe Mode OK, then first try to boot normally. (Safe Mode does repairs of other things which might be causing the problem.)

If it doesn't boot normally, boot into Safe Mode again, and delete any of the following files that exist:

/Library/Extensions/tunnelblick-tun.kext

/Library/Extensions/tunnelblick-tap.kext

/Library/Extensions/tun-notarized.kext

/Library/Extensions/tap-notarized.kext

(Which ones your system will have depends on what version of Tunnelblick you have and which version of macOS.)

You will need to authorize deleting them using a computer administrator username and password.

After that, boot into Safe Mode again to clean things up again, then boot normally.

Good luck, and please keep us posted with your results.

[1] As an alternative to Apple Support, you could boot into Recovery Mode and delete the system extensions from there. I think you can use Terminal from the Utilities menu and use the commands to delete the system extensions:

cd /Library/Extensions

rm -rf tunnelblick-tun.kext tunnelblick-tap.kext tun-notarized.kext tap-notarized.kext

[Red Nicholson]

Thank you for the advice and support. I was able to mount the external SSD (my main startup disk) and manually delete the Tunnelblick extensions and preference files. Unfortunately it would still not boot. I was even able to reinstall macOS Ventura on it through recovery mode, but still no luck. I'd then need to boot into the SATA drive, which provided me with a kernel panic report. I've pasted the kernel panic error message below. 

My only remaining option is to transfer data off the drive, erase it, and reinstall macOS. Very weird, because I'm aware no one else has had this problem! 🤷‍♂️

panic(cpu 1 caller 0xffffff8002085595): System KC UUID 6A42C612-C16E-8326-2A16-332C24FC7EB7 linked against 256B8BC4-F493-B59D-0D98-308D2DA37266, but CD86DD7D-A56A-2550-20C5-45A80CF73695 is loaded @OSKext.cpp:14204
Panicked task 0xffffff9b536d4038: 3 threads: pid 60: kernelmanagerd
Backtrace (CPU 1), panicked thread: 0xffffffa4ed2b5598, Frame : Return Address
0xfffffffeffdbf3c0 : 0xffffff8001a6f4fd
0xfffffffeffdbf410 : 0xffffff8001bc3c54
0xfffffffeffdbf450 : 0xffffff8001bb36d9
0xfffffffeffdbf4b0 : 0xffffff8001a0f951
0xfffffffeffdbf4d0 : 0xffffff8001a6f7dd
0xfffffffeffdbf5c0 : 0xffffff8001a6ee87
0xfffffffeffdbf620 : 0xffffff80021dceab
0xfffffffeffdbf710 : 0xffffff8002085595
0xfffffffeffdbf830 : 0xffffff8002083c2f
0xfffffffeffdbf860 : 0xffffff80020836de
0xfffffffeffdbf8e0 : 0xffffff80020924ee
0xfffffffeffdbfb00 : 0xffffff800209198c
0xfffffffeffdbfb60 : 0xffffff800208fa26
0xfffffffeffdbfbe0 : 0xffffff80020a3206
0xfffffffeffdbfc70 : 0xffffff8001ae9c1e
0xfffffffeffdbfcc0 : 0xffffff8001a4975a
0xfffffffeffdbfd60 : 0xffffff8001a604a2
0xfffffffeffdbfdd0 : 0xffffff8001a60b27
0xfffffffeffdbfef0 : 0xffffff8001b98f53
0xfffffffeffdbffa0 : 0xffffff8001a0fdb6

Process name corresponding to current thread (0xffffffa4ed2b5598): kernelmanagerd
Boot args: -bsdmgroot

Mac OS version:
22F82

Kernel version:
Darwin Kernel Version 22.5.0: Mon Apr 24 20:51:50 PDT 2023; root:xnu-8796.121.2~5/RELEASE_X86_64
Kernel UUID: 7E997BC9-2104-3D4D-9AAE-17BD7A3FEC2D
roots installed: 0
KernelCache slide: 0x0000000001600000
KernelCache base:  0xffffff8001800000
Kernel slide:      0x00000000016dc000
Kernel text base:  0xffffff80018dc000
__HIB  text base: 0xffffff8001700000
System model name: iMac19,2 (Mac-63001698E7A34814)
System shutdown begun: NO
Panic diags file available: NO (0xe00002bc)
Hibernation exit count: 0

System uptime in nanoseconds: 10358687838
Last Sleep:           absolute           base_tsc          base_nano
  Uptime  : 0x00000002696d0ba8
  Sleep   : 0x0000000000000000 0x0000000000000000 0x0000000000000000
  Wake    : 0x0000000000000000 0x0000001a2bc5ea86 0x0000000000000000
Compressor Info: 0% of compressed pages limit (OK) and 0% of segments limit (OK) with 0 swapfiles and OK swap space
Zone info:
  Zone map: 0xffffff901f8b2000 - 0xffffffb01f8b2000
  . PGZ   : 0xffffff901f8b2000 - 0xffffff90208b3000
  . VM    : 0xffffff90208b3000 - 0xffffff94ed319000
  . RO    : 0xffffff94ed319000 - 0xffffff9686be5000
  . GEN0  : 0xffffff9686be5000 - 0xffffff9b5364b000
  . GEN1  : 0xffffff9b5364b000 - 0xffffffa0200b1000
  . GEN2  : 0xffffffa0200b1000 - 0xffffffa4ecb17000
  . GEN3  : 0xffffffa4ecb17000 - 0xffffffa9b957e000
  . DATA  : 0xffffffa9b957e000 - 0xffffffb01f8b2000
  Metadata: 0xfffffffebe06a000 - 0xfffffffede06a000
  Bitmaps : 0xfffffffede06a000 - 0xfffffffedf86a000
  Extra   : 0 - 0

last started kext at 3144222601: >DiskImages.SparseDiskImage 493.0.0 (addr 0xffffff8004144000, size 8192)
loaded kexts:
>DiskImages.SparseDiskImage 493.0.0
>DiskImages.ReadWriteDiskImage 493.0.0
>DiskImages.UDIFDiskImage 493.0.0
>DiskImages.RAMBackingStore 493.0.0
>DiskImages.HTTPBackingStore 493.0.0
>DiskImages.FileBackingStore 493.0.0
|SCSITaskUserClient 482.120.2
>!UMass!SInterfaceNub 554
>!AFileSystemDriver 3.0.1
@filesystems.tmpfs 1
@filesystems.lifs 1
@filesystems.hfs.kext 627.100.6
@BootCache 40
@!AFSCompression.!AFSCompressionTypeZlib 1.0.0
@!AFSCompression.!AFSCompressionTypeDataless 1.0.0d1
@filesystems.apfs 2142.120.7
>!ASDXC 3.4.2
|!ABCM5701Ethernet 11.0.0
>!ABCMWLANBusInterfacePCIeMac 1
>!AAHCIPort 378
@private.KextAudit 1.0
>!AACPIButtons 6.1
>!ARTC 2.0.1
>!ASMBIOS 2.1
>!AACPIEC 6.1
>!AAPIC 1.7
$!AUserConsent 1
@!ASystemPolicy 2.0.0
@nke.applicationfirewall 403
|IOKitRegistryCompatibility 1
|EndpointSecurity 1
@Dont_Steal_Mac_OS_X 7.0.0
@kec.Compression 1
@kec.!AEncryptedArchive 1
>DiskImages.KernelBacked 493.0.0
>usb.cdc 5.0.0
>usb.networking 5.0.0
>usb.!UHostCompositeDevice 1.2
>!AHPM 3.4.4
>!A!ILpssI2C!C 3.0.60
>!A!ILpssI2C 3.0.60
>!A!ILpssDmac 3.0.60
>!AThunderboltPCIDownAdapter 4.1.1
>!AThunderboltDPInAdapter 8.5.1
>!AThunderboltDPAdapter!F 8.5.1
>!ABSDKextStarter 3
|IOSurface 336.50.1
@filesystems.hfs.encodings.kext 1
>!ASyntheticGame!C 10.6.3
>!AXsanScheme 3
>!AThunderboltNHI 7.2.81
|IOThunderbolt!F 9.3.3
>!ABCMWLANCoreMac 1.0.0
|IO80211!F 1200.13.0
>IOImageLoader 1.0.0
>!AOLYHALMac 1
|IOSerial!F 11
>corecapture 1.0.4
|IOAHCIBlock!S 350.120.2
>!AEFINVRAM 2.1
|IOAHCI!F 301.100.1
>usb.!UXHCIPCI 1.2
>usb.!UXHCI 1.2
>usb.!UHostPacketFilter 1.0
|IOUSB!F 900.4.2
>!AEFIRuntime 2.1
>!ASMCRTC 1.0
|IOSMBus!F 1.1
|IOHID!F 2.0.0
|IOTimeSync!F 1150.2
|IOSkywalk!F 1.0
>mDNSOffloadUserClient 1.0.1b8
|IONetworking!F 3.4
>DiskImages 493.0.0
|IO!B!F 9.0.0
|IOReport!F 47
$quarantine 4
$sandbox 300.0
@kext.!AMatch 1.0.0d1
>!ASSE 1.0
>!AKeyStore 2
>!UTDM 554
|IOUSBMass!SDriver 235.100.2
|IOSCSIBlockCommandsDevice 482.120.2
|IO!S!F 2.1
|IOSCSIArchitectureModel!F 482.120.2
>!AFDEKeyStore 28.30
>!AEffaceable!S 1.0
>!ACyrus 1
>!AMobileFileIntegrity 1.0.5
$!AImage4 5.0.0
@kext.CoreTrust 1
>!ACredentialManager 1.0
|CoreAnalytics!F 1
>KernelRelayHost 1
|IOUSBHost!F 1.2
>!UHostMergeProperties 1.2
>usb.!UCommon 1.0
>!ABusPower!C 1.0
>!ASEPManager 1.0.1
>IOSlaveProcessor 1
>!AACPIPlatform 6.1
>!ASMC 3.1.9
|IOPCI!F 2.9
|IOACPI!F 1.4
>watchdog 1
@kec.pthread 1
@kec.Libm 1
@kec.corecrypto 12.0

[Tunnelblick developer]

What is the "SATA" drive you mention? The same as your external drive?

Are you able to boot into Safe Mode?

Did you try First Aid on the internal drive while in Recovery mode?

Did you try Apple Diagnostics on the computer?

I recommend you look at two  troubleshooting articles by Howard Oakley on his The Eclectic Light Company blog:

When your Mac can’t get to the login window

Identifying the state of your Mac: is it dead or alive? (the second half)