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    Why Let’s Encrypt is a really, really, really bad idea…

    Scheduled Pinned Locked Moved IT Discussion
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    • DustinB3403D
      DustinB3403
      last edited by

      What's worthwhile about automation like LE is that if the root CA was compromised, LE would simply revoke all certificates and create a new CA and issuance would begin again.

      He's acting like if someone isn't clicking "buy" that security is more vulnerable.

      1 Reply Last reply Reply Quote 3
      • JaredBuschJ
        JaredBusch
        last edited by

        @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

        What's worthwhile about automation

        Except that is not what the idiot was talking about with fire and forget.

        He was assuming people were setting it up and not renewing things.

        Which means stupid users and has nothing to do with the technology.

        1 Reply Last reply Reply Quote 2
        • DashrenderD
          Dashrender
          last edited by

          (Certificate expiration, with no one paying attention, is why no one at Equifax knew they had been hacked for months.)

          What? is that true? Equifax was hacked because they had an expired cert on their website - that doesn't compute.

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

            I'd love it if he's define 'fire and forget' it's to ambiguous to really know for sure.

            1 Reply Last reply Reply Quote 1
            • ObsolesceO
              Obsolesce @Dashrender
              last edited by

              @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

              (Certificate expiration, with no one paying attention, is why no one at Equifax knew they had been hacked for months.)

              What? is that true? Equifax was hacked because they had an expired cert on their website - that doesn't compute.

              I thought they were hacked because of CVE-2017-5638?

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

                @Obsolesce said in Why Let’s Encrypt is a really, really, really bad idea…:

                CVE-2017-5638

                Frankly I have no clue how they where hacked - but please, tell me how someone gets their servers hacked by having an expired cert on it?

                Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                right??

                DustinB3403D 1 Reply Last reply Reply Quote 0
                • DustinB3403D
                  DustinB3403 @Dashrender
                  last edited by DustinB3403

                  @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                  Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                  right??

                  Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                  DashrenderD 1 Reply Last reply Reply Quote 0
                  • DashrenderD
                    Dashrender @DustinB3403
                    last edited by

                    @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                    @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                    Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                    right??

                    Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                    eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                    but again, and expired cert is not the same as having the public

                    DustinB3403D 1 Reply Last reply Reply Quote 0
                    • DustinB3403D
                      DustinB3403 @Dashrender
                      last edited by DustinB3403

                      @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                      @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                      @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                      Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                      right??

                      Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                      eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                      but again, and expired cert is not the same as having the public

                      No I'm saying if as a user you went to bankofamerica.com and tried to login as your user account, a MiM could capture that information and login themselves.

                      Stolen creds at that point.

                      DashrenderD 1 Reply Last reply Reply Quote 0
                      • DashrenderD
                        Dashrender @DustinB3403
                        last edited by

                        @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                        Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                        right??

                        Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                        eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                        but again, and expired cert is not the same as having the public

                        No I'm saying if as a user you went to bankofamerica.com and tried to login as your user account, a MiM could capture that information and login themselves.

                        Stolen creds at that point.

                        @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                        @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                        Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                        right??

                        Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                        eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                        but again, and expired cert is not the same as having the public

                        No I'm saying if as a user you went to bankofamerica.com and tried to login as your user account, a MiM could capture that information and login themselves.

                        Stolen creds at that point.

                        This assumes that the Cert is the only encryption happening

                        ObsolesceO 1 Reply Last reply Reply Quote 0
                        • ObsolesceO
                          Obsolesce @Dashrender
                          last edited by

                          @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                          Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                          right??

                          Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                          eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                          but again, and expired cert is not the same as having the public

                          No I'm saying if as a user you went to bankofamerica.com and tried to login as your user account, a MiM could capture that information and login themselves.

                          Stolen creds at that point.

                          @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @DustinB3403 said in Why Let’s Encrypt is a really, really, really bad idea…:

                          @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                          Even if someone somehow got the private key for the cert, that doesn't let them breach the server, that only allows them to breach the communications between that server and a client.
                          right??

                          Yes, this doesn't get the person onto said server, it just allows someone to play MiM, which in practice could get the MiM onto the target server as the originating user.

                          eh? what originating user? you mean that being an MiM could allow them to get the admin creds and then log in as the admin? Ok I guess I could see that.

                          but again, and expired cert is not the same as having the public

                          No I'm saying if as a user you went to bankofamerica.com and tried to login as your user account, a MiM could capture that information and login themselves.

                          Stolen creds at that point.

                          This assumes that the Cert is the only encryption happening

                          Your https connection to a web server, the cert is the what is used to encrypt your connection. It has nothing to do with server security in any other sense.

                          1 Reply Last reply Reply Quote 1
                          • Emad RE
                            Emad R @Curtis
                            last edited by

                            @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                            https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                            This guy...

                            Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                            DashrenderD stacksofplatesS DustinB3403D 3 Replies Last reply Reply Quote 0
                            • DashrenderD
                              Dashrender @Emad R
                              last edited by

                              @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                              @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                              https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                              This guy...

                              Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                              Are you saying to spend money just because you can?

                              C 1 Reply Last reply Reply Quote 0
                              • C
                                Curtis @Dashrender
                                last edited by

                                @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                                Are you saying to spend money just because you can?

                                I’ll PM you my address @Emad-R - feel free to send as much money as you would like 🙂

                                1 Reply Last reply Reply Quote 1
                                • stacksofplatesS
                                  stacksofplates @Emad R
                                  last edited by

                                  @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                  @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                                  https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                                  This guy...

                                  Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                                  Yeah I don't agree with that. The "warranties" that you get are literally useless and it's not possible to automate them. There is literally no upside to paying for one, even EV certs.

                                  Let's not forget that the TLS certs are not for ensuring it is a safe site. It's just a way to have an encrypted channel.

                                  Emad RE ingmarkoecherI 2 Replies Last reply Reply Quote 2
                                  • Emad RE
                                    Emad R @stacksofplates
                                    last edited by

                                    @stacksofplates said in Why Let’s Encrypt is a really, really, really bad idea…:

                                    @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                    @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                                    https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                                    This guy...

                                    Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                                    Yeah I don't agree with that. The "warranties" that you get are literally useless and it's not possible to automate them. There is literally no upside to paying for one, even EV certs.

                                    Let's not forget that the TLS certs are not for ensuring it is a safe site. It's just a way to have an encrypted channel.

                                    What about being Unique, or unlike the rest, wont that increase security. Like changing a port of SSH, the same method your not using a service that all the rest are using like Lets Encrypt, Thus by theory more secure.

                                    DashrenderD stacksofplatesS 2 Replies Last reply Reply Quote 0
                                    • DustinB3403D
                                      DustinB3403 @Emad R
                                      last edited by

                                      @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                      @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                                      https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                                      This guy...

                                      Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                                      So do you use any free and open source software, if so and you're making money you had better stop now and start paying someone for some software so you can make less money.

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

                                        @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                        @stacksofplates said in Why Let’s Encrypt is a really, really, really bad idea…:

                                        @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                        @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                                        https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                                        This guy...

                                        Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                                        Yeah I don't agree with that. The "warranties" that you get are literally useless and it's not possible to automate them. There is literally no upside to paying for one, even EV certs.

                                        Let's not forget that the TLS certs are not for ensuring it is a safe site. It's just a way to have an encrypted channel.

                                        What about being Unique, or unlike the rest, wont that increase security. Like changing a port of SSH, the same method your not using a service that all the rest are using like Lets Encrypt, Thus by theory more secure.

                                        Security through obscurity? Thats not security, that just leads people into a false sense of security. Sure it takes a bit more effort on the part of the hacker, but a determined hacker doesn't really care.

                                        The only point I really consider valid is the accountability aspect - but I'm not sure how much weight I can really give that single point. If LE is hacked, and the master key is stolen, they revoke it and start over, all of the automated systems (I hope) are able to get a new cert the next time they check in - which is very frequent typically, days/weeks normally, but at works are mere months compared to any typical CA, it could be three years if a cert was just purchased a bit before the breach.

                                        ObsolesceO 1 Reply Last reply Reply Quote 2
                                        • DustinB3403D
                                          DustinB3403
                                          last edited by DustinB3403

                                          Security through obscurity is the same as Security at Airports. It's Security Theater it's a means of trying to put on a show of security without actual security to deter people from attacking your site/airport/whatever.

                                          I'd much rather have a cert renew on demand for free or every few days for free than to wait 2-5 years before going to check if a new cert is required.

                                          1 Reply Last reply Reply Quote 0
                                          • ObsolesceO
                                            Obsolesce @Dashrender
                                            last edited by

                                            @Dashrender said in Why Let’s Encrypt is a really, really, really bad idea…:

                                            @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                            @stacksofplates said in Why Let’s Encrypt is a really, really, really bad idea…:

                                            @Emad-R said in Why Let’s Encrypt is a really, really, really bad idea…:

                                            @Curtis said in Why Let’s Encrypt is a really, really, really bad idea…:

                                            https://medium.com/swlh/why-lets-encrypt-is-a-really-really-really-bad-idea-d69308887801

                                            This guy...

                                            Actually he makes sense to me, if you have website that is generating good revenue you should spend on SSL

                                            Yeah I don't agree with that. The "warranties" that you get are literally useless and it's not possible to automate them. There is literally no upside to paying for one, even EV certs.

                                            Let's not forget that the TLS certs are not for ensuring it is a safe site. It's just a way to have an encrypted channel.

                                            What about being Unique, or unlike the rest, wont that increase security. Like changing a port of SSH, the same method your not using a service that all the rest are using like Lets Encrypt, Thus by theory more secure.

                                            Security through obscurity? Thats not security, that just leads people into a false sense of security. Sure it takes a bit more effort on the part of the hacker, but a determined hacker doesn't really care.

                                            The only point I really consider valid is the accountability aspect - but I'm not sure how much weight I can really give that single point. If LE is hacked, and the master key is stolen, they revoke it and start over, all of the automated systems (I hope) are able to get a new cert the next time they check in - which is very frequent typically, days/weeks normally, but at works are mere months compared to any typical CA, it could be three years if a cert was just purchased a bit before the breach.

                                            The crl is checked immediately by the browser, and will let you know the cert is revoked. I think most web browsers will make you do a manual step to bypass that to browse a website using a revoked ssl cert, if at all.

                                            DustinB3403D DashrenderD 2 Replies Last reply Reply Quote 0
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