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    Enabling RequireTLS on Exchange Send Connectors

    IT Discussion
    tls exchange exchange 2010 starttls email
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    • scottalanmillerS
      scottalanmiller @Dashrender
      last edited by

      @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

      @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

      @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

      https://i.imgur.com/Z0O4DcO.png

      This is a lawfirm. 😞

      With a local server not behind some spam service I bet.

      That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

      Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

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

        @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

        @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

        @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

        @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

        https://i.imgur.com/Z0O4DcO.png

        This is a lawfirm. 😞

        With a local server not behind some spam service I bet.

        That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

        Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

        it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

        scottalanmillerS coliverC 2 Replies Last reply Reply Quote 0
        • scottalanmillerS
          scottalanmiller @Dashrender
          last edited by

          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

          @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

          @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

          https://i.imgur.com/Z0O4DcO.png

          This is a lawfirm. 😞

          With a local server not behind some spam service I bet.

          That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

          Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

          it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

          Pretty much all businesses had this problem. Think about how often VPNs and MPLS and similar things exist. Very common. Think about any user that has a VPN connection at home, all use of VPN causes the issue. The use of VPNs specifically to disrupt GEO IP is semi-new, but the use of all VPN does it even when not intended and if anything, VPN usage is decreasing a lot as it is rarely needed today like it was in the past. In the early 2000s VPN use was extremely high.

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

            per request.

            So I can plainly say that Cox.net does not support startTLS, and they have told me plainly that they never will.

            Additionally, we have run into a bank, a union and a law office that didn't work by default. The bank and law office both indicated that they believed they had opportunistic TLS enabled - I showed them the telnet IP 25 output that disagrees with them. Both of these also have said they are working to make exceptions for my domain/email server/IP specifically to enable this (why???? why not just enable opportunistic TLS?) I haven't heard from the union yet.

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

              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

              @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

              @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

              https://i.imgur.com/Z0O4DcO.png

              This is a lawfirm. 😞

              With a local server not behind some spam service I bet.

              That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

              Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

              it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

              Hasn't HTTP over SSL been around longer then GeoIP tracking? We've had full on SSL VPNs since 1994 at least.

              JaredBuschJ DashrenderD scottalanmillerS 3 Replies Last reply Reply Quote 0
              • JaredBuschJ
                JaredBusch @coliver
                last edited by

                @coliver said in Enabling RequireTLS on Exchange Send Connectors:

                @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

                @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

                @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                https://i.imgur.com/Z0O4DcO.png

                This is a lawfirm. 😞

                With a local server not behind some spam service I bet.

                That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

                Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

                it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

                Hasn't HTTP over SSL been around longer then GeoIP tracking? We've had full on SSL VPNs since 1994 at least.

                They have not been in common usage.

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

                  @coliver said in Enabling RequireTLS on Exchange Send Connectors:

                  @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                  @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

                  @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                  @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

                  @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                  https://i.imgur.com/Z0O4DcO.png

                  This is a lawfirm. 😞

                  With a local server not behind some spam service I bet.

                  That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

                  Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

                  it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

                  Hasn't HTTP over SSL been around longer then GeoIP tracking? We've had full on SSL VPNs since 1994 at least.

                  Sure, but that's not really meant to obfuscate traffic on the internet, those are meant to get traffic into a private network, so GEO IPs wouldn't really matter in most cases.

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

                    Well, it looks like the law firm has fixed their issue.

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

                      @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                      Well, it looks like the law firm has fixed their issue.

                      OK another source checked for me.. looks like they fixed their opportunistic problems.

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

                        @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                        per request.

                        So I can plainly say that Cox.net does not support startTLS, and they have told me plainly that they never will.

                        They have a vested interest in being crappy. There is no reason for them to be more than minimally functional.

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

                          @coliver said in Enabling RequireTLS on Exchange Send Connectors:

                          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                          @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

                          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                          @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

                          @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                          https://i.imgur.com/Z0O4DcO.png

                          This is a lawfirm. 😞

                          With a local server not behind some spam service I bet.

                          That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

                          Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

                          it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

                          Hasn't HTTP over SSL been around longer then GeoIP tracking? We've had full on SSL VPNs since 1994 at least.

                          Depends, yes we've had HTTPS commonly for a very long time and GeoIP detection is common only relatively recently. But in some ways, we've had GeoIP tracking since the first IPs were assigned. The first six sites were tracked by IP. So in some ways we've had GeoIP since day one. But it was long, long ago that it stopped working. Same with SS7 (PSTN). My home phone in 1997 was listed as a different city than I lived in (listed as Webster, NY; lived in Greece, NY) and my IP address was likewise off a bit.

                          So all networks have this issue, even ones that predate the Internet by decades. The nature of a network is that you can't know where the endpoint is.

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

                            My hotel room here in Dallas is coming up as Toronto as well.

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

                              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                              @coliver said in Enabling RequireTLS on Exchange Send Connectors:

                              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                              @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

                              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                              @JaredBusch said in Enabling RequireTLS on Exchange Send Connectors:

                              @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                              https://i.imgur.com/Z0O4DcO.png

                              This is a lawfirm. 😞

                              With a local server not behind some spam service I bet.

                              That's hard to say. I do know that their SMTP out IP address was GEO tagged as coming from Europe, so my spam filter used to block them, but I have to remind myself that Geo tracking IPs is pretty unreliable these days...

                              Always were. Any use of a VPN completely defeats GEO IP tracking and VPNs predate GEO IP tracking. The idea that it's a new problem makes it more confusing.

                              it's not a new problem, but ubiquitous use of VPN by consumers is a pretty new situation so I don't think it broke all that much, businesses that ran into the issue, might have had more clout to get things resolve with paid services they used that were business services.

                              Hasn't HTTP over SSL been around longer then GeoIP tracking? We've had full on SSL VPNs since 1994 at least.

                              Sure, but that's not really meant to obfuscate traffic on the internet, those are meant to get traffic into a private network, so GEO IPs wouldn't really matter in most cases.

                              Private network and obfuscating traffic are the same thing there.

                              1 Reply Last reply Reply Quote 0
                              • MattSpellerM
                                MattSpeller
                                last edited by

                                Did you break your cox?

                                I'll get my coat and show myself out....

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

                                  OK, we've had two sites get themselves fixed, the law firm and the bank - the both now accept TLS.

                                  The two consumer class ISP emails - Cox.net and inebraska.com have both in no uncertain terms indicated that they will NOT support TLS.

                                  I've been required to setup a bypass for one of them, currently it appears I can only do a bypass at a domain level, not the email address level - I'm still looking, but if you are aware of a way to add an email address bypass only to the outbound connector on Exchange 2010, please share.

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

                                    That second one looks like a code for "drunk Nebraska"

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

                                      That's awesome that two agreed to fix the issue.

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

                                        @Dashrender said in Enabling RequireTLS on Exchange Send Connectors:

                                        OK, we've had two sites get themselves fixed, the law firm and the bank - the both now accept TLS.

                                        The two consumer class ISP emails - Cox.net and inebraska.com have both in no uncertain terms indicated that they will NOT support TLS.

                                        I've been required to setup a bypass for one of them, currently it appears I can only do a bypass at a domain level, not the email address level - I'm still looking, but if you are aware of a way to add an email address bypass only to the outbound connector on Exchange 2010, please share.

                                        Does this not break your HIPAA compliance, as users will be able to send to this domain unencrypted? Thus defeating the entire purpose?

                                        Tell your CEO that if you do this, then you have to pay for some third party service for secure delivery. Their call to waste the money. Not yours.

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

                                          @scottalanmiller said in Enabling RequireTLS on Exchange Send Connectors:

                                          That's awesome that two agreed to fix the issue.

                                          Actually I consider it sad - When I explained the problem to one, they flat out told me - yes we do. I offered to send screen shots of the ehlo response - oh hold on... tappy tappity, tap tap.. huh.. hmm... Ok... oh .. what IP are you coming from? I tell them... more waiting.. oh ok try now... tada! it worked....

                                          The other one responded to my original inquiry claiming that they had opportunistic enabled by default for anyone, I sent them the screen shots, an hour later - OK please try it - tada!

                                          They are both now offering opportunistic TLS - I tried from multiple locations with different domains and they now always offer startTLS. So yeah.. they now offer a bit more security.

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

                                            @Dashrender also they got busted running in house, insecure email. Probably a lot of unsecured things that they thought they could make a quick buck running shoddily in house.

                                            DashrenderD 1 Reply Last reply Reply Quote 1
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