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    Let's Encrypt Windows Server

    IT Discussion
    lets encrypt windows server 2016 ssl certificates
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    • WLS-ITGuyW
      WLS-ITGuy
      last edited by WLS-ITGuy

      I have a windows 2016 server running all my ManageEngine stuff. (Yes I have posted there as well).

      Can I use LE to secure ADManager, Servicedesk, Desktop Central, and Self Service? It is one URL ie: helpdesk dot website dot net

      I was reading this https://mangolassi.it/topic/18137/get-wildcard-ssl-certs-for-iis-on-windows-with-letsencrypt but it appears to be more about wildcard certs.

      scottalanmillerS 2 Replies Last reply Reply Quote 1
      • scottalanmillerS
        scottalanmiller @WLS-ITGuy
        last edited by

        @WLS-ITGuy said in Let's Encrypt Windows Server:

        I was reading this https://mangolassi.it/topic/18137/get-wildcard-ssl-certs-for-iis-on-windows-with-letsencrypt but it appears to be more about wildcard certs.

        That's what you use for IIS regardless of how many you need to cover.

        JaredBuschJ 1 Reply Last reply Reply Quote 1
        • scottalanmillerS
          scottalanmiller @WLS-ITGuy
          last edited by

          @WLS-ITGuy said in Let's Encrypt Windows Server:

          Can I use LE to secure ADManager, Servicedesk, Desktop Central, and Self Service? It is one URL ie: helpdesk dot website dot net

          Then the question is... can you use LE for... and then we need to know what Web Server those are running on. That you perceive it as multiple apps isn't a factor, it is just one website. That it is just one website would only matter if we lacked a multiple website option.

          But given the factors on Windows, all that matters is if it is IIS or a different web server. As long as it is IIS, you use the guide that I provided.

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

            Guide was tested just last week, too.

            1 Reply Last reply Reply Quote 1
            • JaredBuschJ
              JaredBusch @scottalanmiller
              last edited by

              @scottalanmiller said in Let's Encrypt Windows Server:

              @WLS-ITGuy said in Let's Encrypt Windows Server:

              I was reading this https://mangolassi.it/topic/18137/get-wildcard-ssl-certs-for-iis-on-windows-with-letsencrypt but it appears to be more about wildcard certs.

              That's what you use for IIS regardless of how many you need to cover.

              I don't believe that ME uses IIS directly.

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

                @JaredBusch said in Let's Encrypt Windows Server:

                @scottalanmiller said in Let's Encrypt Windows Server:

                @WLS-ITGuy said in Let's Encrypt Windows Server:

                I was reading this https://mangolassi.it/topic/18137/get-wildcard-ssl-certs-for-iis-on-windows-with-letsencrypt but it appears to be more about wildcard certs.

                That's what you use for IIS regardless of how many you need to cover.

                I don't believe that ME uses IIS directly.

                That's what matters most, not what apps it is or how many, but what app are we discussing for LE to be interfacing with.

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

                  You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                  JaredBuschJ 1 Reply Last reply Reply Quote 2
                  • JaredBuschJ
                    JaredBusch @scottalanmiller
                    last edited by

                    @scottalanmiller said in Let's Encrypt Windows Server:

                    You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                    This is what I do with my MESD deployment.

                    WLS-ITGuyW 1 Reply Last reply Reply Quote 3
                    • WLS-ITGuyW
                      WLS-ITGuy @JaredBusch
                      last edited by

                      @JaredBusch said in Let's Encrypt Windows Server:

                      @scottalanmiller said in Let's Encrypt Windows Server:

                      You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                      This is what I do with my MESD deployment.

                      Do you use Apache or NGNIX for that?

                      scottalanmillerS 1 Reply Last reply Reply Quote 0
                      • scottalanmillerS
                        scottalanmiller @WLS-ITGuy
                        last edited by

                        @WLS-ITGuy said in Let's Encrypt Windows Server:

                        @JaredBusch said in Let's Encrypt Windows Server:

                        @scottalanmiller said in Let's Encrypt Windows Server:

                        You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                        This is what I do with my MESD deployment.

                        Do you use Apache or NGNIX for that?

                        You "always" use Nginx for stand alone reverse proxies. That's what it is built for.

                        WLS-ITGuyW 1 Reply Last reply Reply Quote 0
                        • WLS-ITGuyW
                          WLS-ITGuy @scottalanmiller
                          last edited by

                          @scottalanmiller said in Let's Encrypt Windows Server:

                          @WLS-ITGuy said in Let's Encrypt Windows Server:

                          @JaredBusch said in Let's Encrypt Windows Server:

                          @scottalanmiller said in Let's Encrypt Windows Server:

                          You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                          This is what I do with my MESD deployment.

                          Do you use Apache or NGNIX for that?

                          You "always" use Nginx for stand alone reverse proxies. That's what it is built for.

                          For those following along at home...Am I building a VM of NGNIX or installing NGNIX on the windows box?

                          scottalanmillerS 1 Reply Last reply Reply Quote 0
                          • scottalanmillerS
                            scottalanmiller @WLS-ITGuy
                            last edited by

                            @WLS-ITGuy said in Let's Encrypt Windows Server:

                            @scottalanmiller said in Let's Encrypt Windows Server:

                            @WLS-ITGuy said in Let's Encrypt Windows Server:

                            @JaredBusch said in Let's Encrypt Windows Server:

                            @scottalanmiller said in Let's Encrypt Windows Server:

                            You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                            This is what I do with my MESD deployment.

                            Do you use Apache or NGNIX for that?

                            You "always" use Nginx for stand alone reverse proxies. That's what it is built for.

                            For those following along at home...Am I building a VM of NGNIX or installing NGNIX on the windows box?

                            A VM. You don't want web serving on Windows, that's never good.

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

                              @scottalanmiller said in Let's Encrypt Windows Server:

                              @WLS-ITGuy said in Let's Encrypt Windows Server:

                              @scottalanmiller said in Let's Encrypt Windows Server:

                              @WLS-ITGuy said in Let's Encrypt Windows Server:

                              @JaredBusch said in Let's Encrypt Windows Server:

                              @scottalanmiller said in Let's Encrypt Windows Server:

                              You can always put a reverse proxy in front, using something like Nginx, and put the cert there.

                              This is what I do with my MESD deployment.

                              Do you use Apache or NGNIX for that?

                              You "always" use Nginx for stand alone reverse proxies. That's what it is built for.

                              For those following along at home...Am I building a VM of NGNIX or installing NGNIX on the windows box?

                              A VM. You don't want web serving on Windows, that's never good.

                              A waste of a license at the min - but it's so much worse than that.

                              1 Reply Last reply Reply Quote 0
                              • JaredBuschJ
                                JaredBusch
                                last edited by

                                @WLS-ITGuy By the way, there is a great tool for LE on IIS. Just not useful for you since ME does not use IIS last I knew.

                                WLS-ITGuyW scottalanmillerS 2 Replies Last reply Reply Quote 1
                                • WLS-ITGuyW
                                  WLS-ITGuy @JaredBusch
                                  last edited by

                                  @JaredBusch said in Let's Encrypt Windows Server:

                                  @WLS-ITGuy By the way, there is a great tool for LE on IIS. Just not useful for you since ME does not use IIS last I knew.

                                  That is what I am seeing 😞

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

                                    @JaredBusch said in Let's Encrypt Windows Server:

                                    @WLS-ITGuy By the way, there is a great tool for LE on IIS. Just not useful for you since ME does not use IIS last I knew.

                                    That's what I use, here is my doc on that:

                                    https://mangolassi.it/topic/18137/get-wildcard-ssl-certs-for-iis-on-windows-with-letsencrypt/

                                    1 Reply Last reply Reply Quote 0
                                    • scottalanmillerS
                                      scottalanmiller @WLS-ITGuy
                                      last edited by

                                      @WLS-ITGuy said in Let's Encrypt Windows Server:

                                      @JaredBusch said in Let's Encrypt Windows Server:

                                      @WLS-ITGuy By the way, there is a great tool for LE on IIS. Just not useful for you since ME does not use IIS last I knew.

                                      That is what I am seeing 😞

                                      Not a big deal, you likely want a solid reverse proxy anyway. Nginx is not a big deal to set up or maintain.

                                      1 Reply Last reply Reply Quote 0
                                      • WLS-ITGuyW
                                        WLS-ITGuy
                                        last edited by

                                        @JaredBusch you don't have any issues with agents checking in or pushing out updates with the RP?

                                        scottalanmillerS 1 Reply Last reply Reply Quote 0
                                        • scottalanmillerS
                                          scottalanmiller @WLS-ITGuy
                                          last edited by

                                          @WLS-ITGuy said in Let's Encrypt Windows Server:

                                          @JaredBusch you don't have any issues with agents checking in or pushing out updates with the RP?

                                          What would be the concern?

                                          WLS-ITGuyW 1 Reply Last reply Reply Quote 0
                                          • WLS-ITGuyW
                                            WLS-ITGuy @scottalanmiller
                                            last edited by

                                            @scottalanmiller said in Let's Encrypt Windows Server:

                                            @WLS-ITGuy said in Let's Encrypt Windows Server:

                                            @JaredBusch you don't have any issues with agents checking in or pushing out updates with the RP?

                                            What would be the concern?

                                            Curious more than anything.

                                            1 Reply Last reply Reply Quote 0
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