Virtualbox and OpenVPN connections












2















I taking training on web application hacking and the professor is asking me to ssh to attack machine and do hacking.



I am using Kali Linux at home and using Virtualbox. The professor allows OpenVPN to connect. If I connect via OpenVPN to his platform with my Windows machine, shall I be able to use Kali? Will NAT take care VPN-related issues when I attack from Kali?



Once I ssh to attack machine, can I use kali over OpenVPN?










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migrated from security.stackexchange.com Jan 14 at 12:36


This question came from our site for information security professionals.



















  • That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

    – CD Rohling
    Jan 12 at 11:59











  • Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

    – schroeder
    Jan 14 at 12:33
















2















I taking training on web application hacking and the professor is asking me to ssh to attack machine and do hacking.



I am using Kali Linux at home and using Virtualbox. The professor allows OpenVPN to connect. If I connect via OpenVPN to his platform with my Windows machine, shall I be able to use Kali? Will NAT take care VPN-related issues when I attack from Kali?



Once I ssh to attack machine, can I use kali over OpenVPN?










share|improve this question













migrated from security.stackexchange.com Jan 14 at 12:36


This question came from our site for information security professionals.



















  • That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

    – CD Rohling
    Jan 12 at 11:59











  • Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

    – schroeder
    Jan 14 at 12:33














2












2








2








I taking training on web application hacking and the professor is asking me to ssh to attack machine and do hacking.



I am using Kali Linux at home and using Virtualbox. The professor allows OpenVPN to connect. If I connect via OpenVPN to his platform with my Windows machine, shall I be able to use Kali? Will NAT take care VPN-related issues when I attack from Kali?



Once I ssh to attack machine, can I use kali over OpenVPN?










share|improve this question














I taking training on web application hacking and the professor is asking me to ssh to attack machine and do hacking.



I am using Kali Linux at home and using Virtualbox. The professor allows OpenVPN to connect. If I connect via OpenVPN to his platform with my Windows machine, shall I be able to use Kali? Will NAT take care VPN-related issues when I attack from Kali?



Once I ssh to attack machine, can I use kali over OpenVPN?







vpn openvpn






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share|improve this question











share|improve this question




share|improve this question










asked Jan 12 at 7:24







Tajkia Hafiz











migrated from security.stackexchange.com Jan 14 at 12:36


This question came from our site for information security professionals.









migrated from security.stackexchange.com Jan 14 at 12:36


This question came from our site for information security professionals.















  • That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

    – CD Rohling
    Jan 12 at 11:59











  • Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

    – schroeder
    Jan 14 at 12:33



















  • That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

    – CD Rohling
    Jan 12 at 11:59











  • Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

    – schroeder
    Jan 14 at 12:33

















That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

– CD Rohling
Jan 12 at 11:59





That depends on the configuration of your VM. If you use NAT on your Network adapter it will do the trick.

– CD Rohling
Jan 12 at 11:59













Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

– schroeder
Jan 14 at 12:33





Although you are taking a cybersecurity course, and you are using Kali, this is actually a pure networking question and not a security question.

– schroeder
Jan 14 at 12:33










2 Answers
2






active

oldest

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1














It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.






share|improve this answer































    0















    So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?




    Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.






    share|improve this answer


























    • OpenVPN is being set up on the Windows host, not the Kali guest.

      – schroeder
      Jan 14 at 12:32











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    2 Answers
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    2 Answers
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    active

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    active

    oldest

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    1














    It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.






    share|improve this answer




























      1














      It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.






      share|improve this answer


























        1












        1








        1







        It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.






        share|improve this answer













        It all depends on your VirtualBox machine setup. NAT configuration in such an instance would relay all your traffic trough your OpenVPN configuration, while Bridged Adapter configuration would ignore your local OpenVPN setup if it’s not running in the router or switch software.







        share|improve this answer












        share|improve this answer



        share|improve this answer










        answered Jan 12 at 14:27









        Vilius PovilaikaVilius Povilaika

        1336




        1336

























            0















            So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?




            Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.






            share|improve this answer


























            • OpenVPN is being set up on the Windows host, not the Kali guest.

              – schroeder
              Jan 14 at 12:32
















            0















            So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?




            Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.






            share|improve this answer


























            • OpenVPN is being set up on the Windows host, not the Kali guest.

              – schroeder
              Jan 14 at 12:32














            0












            0








            0








            So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?




            Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.






            share|improve this answer
















            So if I connect via open VPN to his platform with my Windows machine, shall I able to use Kali? Does NAT will do take care VPN related issue when I attack from Kali?




            Your virtualbox should forward connection irrespective NAT/bridged mode, from kali. Your virtual machine will use the same routing as the host OS windows. It should just work fine.







            share|improve this answer














            share|improve this answer



            share|improve this answer








            edited Jan 14 at 14:44









            Community

            1




            1










            answered Jan 14 at 12:26







            BountySite




















            • OpenVPN is being set up on the Windows host, not the Kali guest.

              – schroeder
              Jan 14 at 12:32



















            • OpenVPN is being set up on the Windows host, not the Kali guest.

              – schroeder
              Jan 14 at 12:32

















            OpenVPN is being set up on the Windows host, not the Kali guest.

            – schroeder
            Jan 14 at 12:32





            OpenVPN is being set up on the Windows host, not the Kali guest.

            – schroeder
            Jan 14 at 12:32


















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