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    Let's Encrypt Windows Server

    IT Discussion
    lets encrypt ssl certificates windows server 2016
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    • WLS-ITGuy
      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.

      scottalanmiller 2 Replies Last reply Reply Quote 1
      • scottalanmiller
        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.

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

            Guide was tested just last week, too.

            1 Reply Last reply Reply Quote 1
            • JaredBusch
              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.

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

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

                  JaredBusch 1 Reply Last reply Reply Quote 2
                  • JaredBusch
                    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-ITGuy 1 Reply Last reply Reply Quote 3
                    • WLS-ITGuy
                      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?

                      scottalanmiller 1 Reply Last reply Reply Quote 0
                      • scottalanmiller
                        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-ITGuy 1 Reply Last reply Reply Quote 0
                        • WLS-ITGuy
                          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?

                          scottalanmiller 1 Reply Last reply Reply Quote 0
                          • scottalanmiller
                            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.

                            Dashrender 1 Reply Last reply Reply Quote 0
                            • Dashrender
                              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
                              • JaredBusch
                                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-ITGuy scottalanmiller 2 Replies Last reply Reply Quote 1
                                • WLS-ITGuy
                                  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 :(

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

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

                                        scottalanmiller 1 Reply Last reply Reply Quote 0
                                        • scottalanmiller
                                          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-ITGuy 1 Reply Last reply Reply Quote 0
                                          • WLS-ITGuy
                                            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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