Recently Vagrant ssh stopped working and I can't figure out why. It's 
probably a local setting that's messed up, so that's why I'm posting here 
instead of on the Github bug tracker.

Software Versions:
Host OS: Win 10 Pro x64 with PowerShell
Guest OS: doesn't really matter
Vagrant: 2.2.4
Virtual Box: 5.2.26

To reproduce:
$ vagrant init ubuntu/cosmic64
$ vagrant up

Ends with:

> ==> default: Waiting for machine to boot. This may take a few minutes...
>     default: SSH address: 127.0.0.1:2222
>     default: SSH username: vagrant
>     default: SSH auth method: private key
> Timed out while waiting for the machine to boot. This means that
> Vagrant was unable to communicate with the guest machine within
> the configured ("config.vm.boot_timeout" value) time period.
>
> If you look above, you should be able to see the error(s) that
> Vagrant had when attempting to connect to the machine. These errors
> are usually good hints as to what may be wrong.
>
> If you're using a custom box, make sure that networking is properly
> working and you're able to connect to the machine. It is a common
> problem that networking isn't setup properly in these boxes.
> Verify that authentication configurations are also setup properly,
> as well.
>
> If the box appears to be booting properly, you may want to increase
> the timeout ("config.vm.boot_timeout") value.
>


When running ssh:

$ vagrant ssh --debug


DEBUG virtualbox_5_2:   - [1, "ssh", 2222, 22, "127.0.0.1"]
 INFO subprocess: Starting process: 
["C:\\HashiCorp\\Vagrant\\embedded\\usr\\bin/ssh.EXE"]
DEBUG subprocess: Selecting on IO
DEBUG subprocess: stderr: usage: ssh [-46AaCfGgKkMNnqsTtVvXxYy] [-b 
bind_address] [-c cipher_spec]
           [-D [bind_address:]port] [-E log_file] [-e escape_char]
           [-F configfile] [-I pkcs11] [-i identity_file]
           [-J [user@]host[:port]] [-L address] [-l login_name] [-m 
mac_spec]
           [-O ctl_cmd] [-o option] [-p port] [-Q query_option] [-R address]
           [-S ctl_path] [-W host:port] [-w local_tun[:remote_tun]]
           [user@]hostname [command]
DEBUG subprocess: Waiting for process to exit. Remaining to timeout: 32000
DEBUG subprocess: Exit status: 255
 INFO ssh: Invoking SSH: C:\HashiCorp\Vagrant\embedded\usr\bin/ssh.EXE 
["[email protected]", "-p", "2222", "-o", "LogLevel=FATAL", "-o", 
"Compression=yes",
"-o", "DSAAuthentication=yes", "-o", "IdentitiesOnly=yes", "-o", 
"StrictHostKeyChecking=no", "-o", "UserKnownHostsFile=/dev/null", "-i", 
"C:/Users/Bart/.vag
rant.d/insecure_private_key"]
DEBUG safe_exec: Converting command and arguments to common UTF-8 encoding 
for exec.
DEBUG safe_exec: Command: 
`"C:\\HashiCorp\\Vagrant\\embedded\\usr\\bin/ssh.EXE"` Args: 
`["[email protected]", "-p", "2222", "-o", "LogLevel=FATAL", "-o", "C
ompression=yes", "-o", "DSAAuthentication=yes", "-o", "IdentitiesOnly=yes", 
"-o", "StrictHostKeyChecking=no", "-o", "UserKnownHostsFile=/dev/null", 
"-i", "C
:/Users/Bart/.vagrant.d/insecure_private_key"]`
DEBUG safe_exec: Converted - Command: 
`"C:\\HashiCorp\\Vagrant\\embedded\\usr\\bin/ssh.EXE"` Args: 
`["[email protected]", "-p", "2222", "-o", "LogLevel=FATA
L", "-o", "Compression=yes", "-o", "DSAAuthentication=yes", "-o", 
"IdentitiesOnly=yes", "-o", "StrictHostKeyChecking=no", "-o", 
"UserKnownHostsFile=/dev/nul
l", "-i", "C:/Users/Bart/.vagrant.d/insecure_private_key"]`

When I open Virtual Box, the box runs without issues. I can show the GUI 
and log in the tty. It seems to be just ssh that's not working. 

I've also tried:
- Uninstall and reinstall Vagrant
- Cleaned up environment vars (initially it was using git's ssh), now it's 
enforced with VAGRANT_PREFER_SYSTEM_BIN
- Checked if the ssh service was running in Ubuntu, and if I can ping the 
host OS. Both seems fine.

I've run out of ideas. Any other suggestions I could try?

Thanks!





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