iPhone SE 13.4.1 with checkra1n 0.10.1 gives error code -31 on OSX 10.9.5

[Spedemix]

Tell us about your setup:

1. What iDevice are you using?

2. On what version of iOS is it?

3. What version of checkra1n are you using?

4. What is your host system (OS version? Hackintosh? VM? etc.)?

5. How are you connecting to the device (USB-A? USB-C? Apple/3rd party cable? Through a USB hub?)?

6. iPhone SE (A9)

7. 13.4.1

8. 0.10.1 (newest currently)

9. OSX Mavericks 10.9.5, hackintosh

10. Official Apple USB-A cable, no huds etc.

What are the steps to reproduce the issue?

1. attempt jailbreak using the gui version
2. put the phone succesfully in DFU mode using the instructions provided
3. get an error "Exploit failed (Error code: -31)" ...

What do you expect, and what is happening instead? Expectation: successful JB Reality: "Exploit failed (Error code: -31)"

Does the issue also occur if you tick "Safe Mode" in the checkra1n options? Yes

Any other info, error logs, screenshots, ...? If I put the phone in DFU mode on my own and run cli with verbose logging I get this:

sudo /Applications/checkra1n.app/Contents/MacOS/checkra1n --cli --verbose-logging --safe-mode
Password:
#
# Checkra1n beta 0.10.1
#
# Proudly written in nano
# (c) 2019-2020 Kim Jong Cracks
#
#========  Made by  =======
# argp, axi0mx, danyl931, jaywalker, kirb, littlelailo, nitoTV
# never_released, nullpixel, pimskeks, qwertyoruiop, sbingner, siguza
#======== Thanks to =======
# haifisch, jndok, jonseals, xerub, lilstevie, psychotea, sferrini
# Cellebrite (ih8sn0w, cjori, ronyrus et al.)
#==========================

 - [04/24/20 22:16:53] <Info>: Waiting for DFU devices
 - [04/24/20 22:16:53] <Verbose>: DFU mode device found
 - [04/24/20 22:16:53] <Info>: Exploiting
 - [04/24/20 22:16:53] <Verbose>: Attempting to perform checkm8 on 8003 1...
 - [04/24/20 22:16:53] <Info>: Checking if device is ready
 - [04/24/20 22:16:53] <Verbose>: == Checkm8 Preparation stage ==
 - [04/24/20 22:16:53] <Verbose>: DFU device disconnected
 - [04/24/20 22:16:53] <Verbose>: DFU mode device found
 - [04/24/20 22:16:53] <Info>: Setting up the exploit (this is the heap spray)
 - [04/24/20 22:16:53] <Verbose>: == Checkm8 Setup stage ==
 - [04/24/20 22:18:15] <Error>: [EXPLOIT:!] Failed issuing asynchronous upload! e00002c0 (error code: -27)
 - [04/24/20 22:18:15] <Info>: Right before trigger (this is the real bug setup)
 - [04/24/20 22:18:15] <Verbose>: Entered initial checkm8 state after 130112 steps, issuing DFU abort..
 - [04/24/20 22:18:15] <Error>: Timed out in state 1, assuming we are back to square one with this device. (error code: -31)
 - [04/24/20 22:18:15] <Verbose>: DFU device disconnected

FWIW I've succesfully JB'd this phone using bootra1n 0.10.1. However it'd still be nice to rejailbreak without the need to boot into a linux distro. Hence the report.

For the lulz I also tried bootra1n in a VM (with my OSX as host) but it didn't work as was to be expected; hangs when checkra1n tries to put the phone in DFU mode.

[zaapp-git]

Use version 0.10.0. https://assets.checkra.in/test/checkra1n%20beta%200.10.0.dmg

[Spedemix]

^^I tried version 0.10.0 (by enabling untested iOS versions since 13.4.1 is not supported).

Doesn't work. Gives me the same error code -31 as 0.10.1.

If I run it in --cli it gets stuck at this point:

/Applications/checkra1n.app/Contents/MacOS/checkra1n --cli --safe-mode --verbose-logging
#
# Checkra1n beta 0.10.0
#
# Proudly written in nano
# (c) 2019-2020 Kim Jong Cracks
#
#========  Made by  =======
# argp, axi0mx, danyl931, jaywalker, kirb, littlelailo, nitoTV
# never_released, nullpixel, pimskeks, qwertyoruiop, sbingner, siguza
#======== Thanks to =======
# haifisch, jndok, jonseals, xerub, lilstevie, psychotea, sferrini
# Cellebrite (ih8sn0w, cjori, ronyrus et al.)
#==========================

 - [05/16/20 23:28:24] <Info>: Waiting for DFU devices
 - [05/16/20 23:28:24] <Verbose>: DFU mode device found
 - [05/16/20 23:28:24] <Info>: Exploiting
 - [05/16/20 23:28:24] <Verbose>: Attempting to perform checkm8 on 8003 1...
 - [05/16/20 23:28:24] <Info>: Checking if device is ready
 - [05/16/20 23:28:24] <Verbose>: == Checkm8 Preparation stage ==
 - [05/16/20 23:28:24] <Verbose>: DFU device disconnected
 - [05/16/20 23:28:24] <Verbose>: DFU mode device found
 - [05/16/20 23:28:24] <Info>: Setting up the exploit (this is the heap spray)
 - [05/16/20 23:28:24] <Verbose>: == Checkm8 Setup stage ==

If I unplug the phone and plug it back in (the 5s trick) it continues with the following:

 - [05/16/20 23:33:56] <Error>: [EXPLOIT:!] Failed issuing asynchronous upload! e00002c0 (error code: -27)
 - [05/16/20 23:33:56] <Info>: Right before trigger (this is the real bug setup)
 - [05/16/20 23:33:56] <Verbose>: Entered initial checkm8 state after 3 steps, issuing DFU abort..
 - [05/16/20 23:33:56] <Error>: Timed out in state 1, assuming we are back to square one with this device. (error code: -31)
 - [05/16/20 23:33:56] <Verbose>: DFU device disconnected
 - [05/16/20 23:33:57] <Verbose>: DFU mode device found
 - [05/16/20 23:33:57] <Info>: Exploiting
 - [05/16/20 23:33:57] <Verbose>: Attempting to perform checkm8 on 8003 1...
 - [05/16/20 23:33:57] <Info>: Checking if device is ready
 - [05/16/20 23:33:57] <Verbose>: == Checkm8 Preparation stage ==
 - [05/16/20 23:33:57] <Verbose>: DFU device disconnected
 - [05/16/20 23:33:58] <Verbose>: DFU mode device found
 - [05/16/20 23:33:58] <Info>: Setting up the exploit (this is the heap spray)
 - [05/16/20 23:33:58] <Verbose>: == Checkm8 Setup stage ==

[Spedemix]

I just got myself a Macbook Air mid-2013, installed Mavericks on it and tried checkra1n 0.10.2 on it. I got the same error code -31 as with the hackintosh.

If I run --cli it hangs very much the same way as 0.10.0 I have described above.

Booting into bootra1n and running checkra1n from there in this MBA works flawlessly.

Thus it seems the problem is the operating system.