I thought it was some issues with the Windows 10 ISO so I gave up after a few times and didn't try again until recently when I tried Debian. Debian's installation interface (GUI) shows up and I'm able to go through it until the step of "Install the base system", and again there's almost a different message each time. Something like this.
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Debootstrap warning
Warning: Failure trying to run: chroot "/target" pkgk --force-depends --install /var/cache/apt/achives/libc6_2.28-10_amd64.deb
So I thought there might be some issue with the Guest OS trying to access the filesystem but I can't think of a reason why. VirtualBox was installed without any errors, even though I can't remember if I allowed the kernel extension via System Preferences > Security the first time I tried to install it or not. I guess I did, because this is what I see now
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~ » kextstat | grep -v com.apple
Index Refs Address Size Wired Name (Version) UUID <Linked Against>
160 0 0xffffff7f846a0000 0x4000 0x4000 com.intel.driver.EnergyDriver (3.7.0) 35E739F9-BF6C-3024-A67C-750711B3FB64 <8 6 5 3>
182 0 0xffffff7f84cd0000 0x185000 0x185000 at.obdev.nke.LittleSnitch (5430) 7462BC7A-1330-3F92-A73F-3FBFE331C74A <8 6 5 3 1>
202 3 0xffffff7f84e58000 0xf1000 0xf1000 org.virtualbox.kext.VBoxDrv (6.1.4) A45D7366-1795-31A8-94A2-99A0EE7C88E4 <8 6 5 3 1>
203 0 0xffffff7f84adc000 0x8000 0x8000 org.virtualbox.kext.VBoxUSB (6.1.4) C11F34A0-3FA8-3868-901F-3A4736209000 <202 186 61 8 6 5 3 1>
204 0 0xffffff7f84ae4000 0x5000 0x5000 org.virtualbox.kext.VBoxNetFlt (6.1.4) A30F158C-26AF-3122-812C-AAF76610D33D <202 8 6 5 3 1>
205 0 0xffffff7f84ae9000 0x6000 0x6000 org.virtualbox.kext.VBoxNetAdp (6.1.4) 41B7D036-09B0-3E04-900B-6C13201ACDEC <202 6 5 1>
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1. Remove the guest Debian and Windows, and try to create new ones again
2. Remove and reinstall Virtualbox, including newer version (6.1.4), and older version (6.0.18).
3. Remove Virtualbox and restart the mac, then reinstall Virtualbox
4. Update macOS to latest version (2 days ago) 10.15.4
5. Reinstall Virtualbox using both normal dmg file download, and homebrew cask
I don't see any crash logs (the guest OS didn't crash, just cannot continue the installation process), so I don't know what else I can provide. If there's anything, please let me know and I will provide it.
Any help to get this sorted out would be really appreciated!
Thank you!