Evil-winrm error on connection to host

Off-topic
1

Hi, I am receiving an error that i have been unable to fix and find a solution for online.
I am running on OS: Ubuntu 22.04 LTS x86_64.
I am able to connect if i run the same command via kali or the docker file supplied in the evil-winrm git repo. Any solution to this issue would be greatly appreciated!

evil-winrm -u administrator -p badminton -i 10.129.239.174

Evil-WinRM shell v3.3

Info: Establishing connection to remote endpoint

Error: An error of type OpenSSL::Digest::DigestError happened, message is Digest initialization failed: initialization error

Error: Exiting with code 1
4 Likes
2

I too am running into this error.

3

@LordOfr0 Did you find the solution in the past 15 days?

4

Yes it is related to this issue Lab Access Openvpn certificate verify failed

If you fix this it will fix the evil-winrm issue

5

Strange. I’m using the starting machines, and it looks like tls-cipher "DEFAULT:@SECLEVEL=0" is already there. Don’t think it matters, but tried without quotes as well.

client
dev tun
proto udp
remote edge-us-starting-point-1-dhcp.hackthebox.eu 1337
resolv-retry infinite
nobind
persist-key
persist-tun
remote-cert-tls server
comp-lzo
verb 3
cipher AES-128-CBC
tls-cipher "DEFAULT:@SECLEVEL=0"
auth SHA256
key-direction 1

Tried different VPN servers, tried re-installing evil-winrm, ruby, etc.

6

try older openvpn version 2.51 e.g.

1 Like
7

Sadly, that didn’t work either. I’ll have to try a few other things.

8

I gave up and just used a docker image. Spent way too much time trying to solve this, so found a workaround.

9

Hi, have you got any solution to this?

10

after infinite frustration, scouring the web, noting the addition to .ovpn file == no positive results…

I jumped into Discord and asked, a user ended up responding, explaining its a known issue and suggested a full update on Kali. Upon updating, winrm worked smoothly, just as the write-up.

Link to Kali update doc: https://www.kali.org/docs/general-use/updating-kali/

11

This is alarmingly hacky, but it works for this case.

1.) pip install pywinrm
2.) run python3 to open up a prompt
3.) Run the following

import winrm
session = winrm.Session('10.129.67.232', auth=('administrator','badminton'), transport='ntlm')
session.run_ps("whoami").std_out

If you get an md4 error, refer to: this link.

Then simply re-run the final line replacing “whoami” with your command (You can also change run_ps to run_cmd to execute cmd commands instead of ps ones)

For the flag, do:

session.run_cmd("type C:\\Users\\mike\Desktop\\flag.txt").std_out

A bit hacky, but it’s a solution for this box.

1 Like
12

In my case issue was evil-winrm was using ruby 2.7 but mine ruby path was set to ruby 3.0
so go to and change ruby3 to ruby2.7 temporarily

cd /usr/bin/
cp ruby ruby.bk
cp -f ruby2.7 ruby

and run evil-winrm this will solve the issue.
after executing to reverb changes

cd /usr/bin/
cp -f ruby.bk ruby
13

In my case evil-winrm was using ruby2.7 but my default path for ruby was set to 3.0 so temporarily change it.

cd /usr/bin
cp ruby ruby.bk
cp -f ruby2.7 ruby

and now run evil-winrm it will work.
to revert back changes

cp -f ruby.bk ruby
1 Like
14

Add those lines to /etc/ssl/openssl.cnf

[provider_sect]
default = default_sect
legacy = legacy_sect

[default_sect]
activate = 1

[legacy_sect]
activate = 1

It will activate md4 for openssl.

15 Likes
15

this fixes it… ty /bow

1 Like
16

Thankyou, this fixed it for me!

1 Like
17

I’m using ubuntu, not kali. I gave up on making evil-winrm work on ubuntu. I used docker instead.

Here is the docker command I used…

docker run --rm -ti --name evil-winrm  oscarakaelvis/evil-winrm -i 10.129.111.232 -u Administrator -p 'password'
1 Like
18

I wrote the solution for M1/M2 users here.

19

Workaround: edit /etc/ssl/openssl.cnf by adding legacy = legacy_sect under default = default_sect in order to appear as:

[openssl_init]
providers = provider_sect

# List of providers to load
[provider_sect]
default = default_sect
legacy = legacy_sect

and by uncommenting #activate = 1 under [default_sect] and adding [legacy_sect] and activate = 1 under them in order to appear as:

[default_sect]
activate = 1
[legacy_sect]
activate = 1
6 Likes
20

Thanks!! this works for me!