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    Best Practices - Securing your Windows Server 2016 VM on Vultr

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    fail2ban vultr iaas windows windows server windoes server 2016 security hosting reverse proxy vpn zerotier directaccess rds azure
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    • black3dynamiteB
      black3dynamite @bigbear
      last edited by

      @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

      Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

      Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

      Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

      Maybe a jump server could be an option?

      1 Reply Last reply Reply Quote 0
      • DashrenderD
        Dashrender @bigbear
        last edited by

        @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

        Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

        Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

        Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

        FYI, Direct Access (DA) is a VPN solution.

        bigbearB 1 Reply Last reply Reply Quote 1
        • scottalanmillerS
          scottalanmiller @bigbear
          last edited by

          @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

          Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

          VPN or VPN-like reverse proxy are basically the only possible options.

          1 Reply Last reply Reply Quote 0
          • bigbearB
            bigbear @Dashrender
            last edited by

            @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

            @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

            Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

            Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

            Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

            FYI, Direct Access (DA) is a VPN solution.

            Yes but that's not how MS markets it. Its a magical "always-on" connection. That does seem to be part of RRAS.... lol

            scottalanmillerS 1 Reply Last reply Reply Quote 0
            • bigbearB
              bigbear
              last edited by

              This https://rdpguard.com/ @scottalanmiller posted looks like something worth trying out first. Also appears to be actively developed. Anyone else using it?

              Mike DavisM 1 Reply Last reply Reply Quote 0
              • DashrenderD
                Dashrender @scottalanmiller
                last edited by

                @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                Yes at the moment it is exposed. The only difference on Azure is that the use a high level port instead of 3389.

                I would guess those who are scanning would also discover those higher number ports.

                Or do I create a Vultr firewall and restrict login attempts to particular IP address ranges?

                Well general rule of thumb is that RDP should never be exposed directly, it's not considered a secure protocol and it is the absolutely number one target of attacks because being exposed flags you as being on Windows (making you a high profile target because you are less likely to be properly secured), flagging you as not following security best practices (making you a high profile target because you are less likely to be properly secured) and lets people know that you are paying a premium over UNIX, so you have money to spend and something to lose (the poor can't consider Windows.) So if attackers see RDP, they go after it like crazy. And the expectation from the Microsoft side is that it will never be exposed to the Internet.

                This is where a proxy or VPN are expected, always. Not that those won't also get attacked, but they have a different exposure profile, provide another layer of defence, use stronger security, can fail closed, and provide stronger authentication. Same as we were discussing in the other thread about Exchange the other day.

                it does suck that that is the case. There is no reason that RDP should be any less secure than SSH. 😞

                1 Reply Last reply Reply Quote 0
                • scottalanmillerS
                  scottalanmiller @bigbear
                  last edited by

                  @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                  @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                  @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                  Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

                  Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

                  Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

                  FYI, Direct Access (DA) is a VPN solution.

                  Yes but that's not how MS markets it. Its a magical "always-on" connection. That does seem to be part of RRAS.... lol

                  MS says what it does and the description is EXACTLY a VPN. It's as VPN as VPN gets. No different than Pertino or ZeroTier.

                  DashrenderD 1 Reply Last reply Reply Quote 1
                  • DashrenderD
                    Dashrender @scottalanmiller
                    last edited by

                    @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                    @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                    @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                    @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                    Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

                    Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

                    Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

                    FYI, Direct Access (DA) is a VPN solution.

                    Yes but that's not how MS markets it. Its a magical "always-on" connection. That does seem to be part of RRAS.... lol

                    MS says what it does and the description is EXACTLY a VPN. It's as VPN as VPN gets. No different than Pertino or ZeroTier.

                    This was my point. There's no reason to list it separately from a VPN, because it is a VPN.

                    scottalanmillerS 1 Reply Last reply Reply Quote 1
                    • scottalanmillerS
                      scottalanmiller @Dashrender
                      last edited by

                      @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                      @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                      @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                      @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                      @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                      Have had some issues with it banning the servers external WAN address when behind NAT instead of the remote IP Address. Have been sifting through code but its not an active project, just a one time port.

                      Using the VULTR firewall to restrict all inbound traffic and to allow RDP sessions based on our office WAN IP has stopped the issues. However, I am still trying to decide how that helps my roaming users.

                      Outside of VPN or DirectAccess I am not sure what other secure access methods there could be. Looking for ideas.

                      FYI, Direct Access (DA) is a VPN solution.

                      Yes but that's not how MS markets it. Its a magical "always-on" connection. That does seem to be part of RRAS.... lol

                      MS says what it does and the description is EXACTLY a VPN. It's as VPN as VPN gets. No different than Pertino or ZeroTier.

                      This was my point. There's no reason to list it separately from a VPN, because it is a VPN.

                      Exactly. It's the middle of the VPN field.

                      1 Reply Last reply Reply Quote 0
                      • A
                        Alex Sage @bigbear
                        last edited by

                        @bigbear said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                        Or do I create a Vultr firewall and restrict login attempts to particular IP address ranges?

                        This.

                        1 Reply Last reply Reply Quote 0
                        • dafyreD
                          dafyre
                          last edited by

                          Or you could use the Vultr firewall to block everything and use something like ZeroTier as the VPN component.

                          scottalanmillerS 1 Reply Last reply Reply Quote 0
                          • scottalanmillerS
                            scottalanmiller @dafyre
                            last edited by

                            @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                            Or you could use the Vultr firewall to block everything and use something like ZeroTier as the VPN component.

                            Yup, any VPN will work, but ZT has a lot of cool flexibility.

                            DashrenderD 1 Reply Last reply Reply Quote 0
                            • scottalanmillerS
                              scottalanmiller
                              last edited by

                              With ZT, you can use the AD on the RDS server to provide AD to the end points as well.

                              1 Reply Last reply Reply Quote 0
                              • DashrenderD
                                Dashrender @scottalanmiller
                                last edited by

                                @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                Or you could use the Vultr firewall to block everything and use something like ZeroTier as the VPN component.

                                Yup, any VPN will work, but ZT has a lot of cool flexibility.

                                Sure, but brings long DNS issues, that Pertino had to solve with an AD client "fix."

                                dafyreD 1 Reply Last reply Reply Quote 0
                                • dafyreD
                                  dafyre @Dashrender
                                  last edited by dafyre

                                  @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                  @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                  @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                  Or you could use the Vultr firewall to block everything and use something like ZeroTier as the VPN component.

                                  Yup, any VPN will work, but ZT has a lot of cool flexibility.

                                  Sure, but brings long DNS issues, that Pertino had to solve with an AD client "fix."

                                  If it's juts one server, you don't need the DNS bits. 😄 Just point everybody at the IP address.

                                  Edit: Or use a HOSTS file.

                                  DashrenderD 1 Reply Last reply Reply Quote 0
                                  • DashrenderD
                                    Dashrender @dafyre
                                    last edited by

                                    @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                    @Dashrender said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                    @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                    @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                    Or you could use the Vultr firewall to block everything and use something like ZeroTier as the VPN component.

                                    Yup, any VPN will work, but ZT has a lot of cool flexibility.

                                    Sure, but brings long DNS issues, that Pertino had to solve with an AD client "fix."

                                    If it's juts one server, you don't need the DNS bits. 😄 Just point everybody at the IP address.

                                    Edit: Or use a HOSTS file.

                                    With AD, you'll need DNS to find specific record types. It's true that a hosts file might solve most of the issues though.

                                    1 Reply Last reply Reply Quote 1
                                    • bigbearB
                                      bigbear
                                      last edited by

                                      In regards to ZT it might work, reminds me a lot of Himachi.

                                      Since the remote client wouldn't be part of the domain DNS wouldn't be a concern. It would be less exposure to risk than RDPGuard (which I am still gonna try first).

                                      1 Reply Last reply Reply Quote 0
                                      • scottalanmillerS
                                        scottalanmiller
                                        last edited by

                                        ZT is really nice.

                                        dafyreD 1 Reply Last reply Reply Quote 0
                                        • dafyreD
                                          dafyre @scottalanmiller
                                          last edited by

                                          @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                          ZT is really nice.

                                          And did we mention free for up to 100 devices?

                                          scottalanmillerS 1 Reply Last reply Reply Quote 0
                                          • scottalanmillerS
                                            scottalanmiller @dafyre
                                            last edited by

                                            @dafyre said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                            @scottalanmiller said in Best Practices - Securing your Windows Server 2016 VM on Vultr:

                                            ZT is really nice.

                                            And did we mention free for up to 100 devices?

                                            On the hosted version, and free unlimited if you host yourself (which isn't cost effective as the cost of a VM is as high as the cost of the service.)

                                            dafyreD 1 Reply Last reply Reply Quote 0
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