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    SAMIT: Stop Using Secure Email

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    bbs email smtp security samit
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    • scottalanmillerS
      scottalanmiller @1337
      last edited by

      @Pete-S said in SAMIT: Stop Using Secure Email:

      @scottalanmiller said in SAMIT: Stop Using Secure Email:

      @JasGot said in SAMIT: Stop Using Secure Email:

      @scottalanmiller
      For regular e-mail (not "Secure E-Mail"), isn't the message traveling un-encrypted when it is moving MTA to MTA on port 25?

      If you use things like free cPanel email or your ISPs email or have your nephew deploy his own email server without hiring any IT people... it's plausible that someone will screw up the config and leave it unsecured or if you accidentally host your email with scammers or something. That's essentially true with any misconfigured system of any type.

      And even when misconfigured, most systems today will enable it by default. You'd have to run something unmaintained for a super long time or really go out of your way to do a bad job to have it come up in a new deployment.

      There's no reasonable case where a business (or an individual at home) would not have obvious access to a secure system and defy all reasonable recommendations for many years and demand to be intentionally insecure to make them be in a situation where they don't have security on their own end and only if sending data to an insecure second party would the data be at risk and when that happens, the encrypted channel is moot because the target itself is insecure so it doesn't matter.

      Yes, even scammers and spammers use TLS nowadays.

      The only time we ever receive emails that are not TLS encrypted have been same odd email notifications from ERP or LOB systems. Probably legacy systems.

      oh for sure, the only people we ever see on unencrypted email are senior citizens and doctors these days.

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

        @scottalanmiller said in SAMIT: Stop Using Secure Email:

        @Pete-S said in SAMIT: Stop Using Secure Email:

        @scottalanmiller said in SAMIT: Stop Using Secure Email:

        @JasGot said in SAMIT: Stop Using Secure Email:

        @scottalanmiller
        For regular e-mail (not "Secure E-Mail"), isn't the message traveling un-encrypted when it is moving MTA to MTA on port 25?

        If you use things like free cPanel email or your ISPs email or have your nephew deploy his own email server without hiring any IT people... it's plausible that someone will screw up the config and leave it unsecured or if you accidentally host your email with scammers or something. That's essentially true with any misconfigured system of any type.

        And even when misconfigured, most systems today will enable it by default. You'd have to run something unmaintained for a super long time or really go out of your way to do a bad job to have it come up in a new deployment.

        There's no reasonable case where a business (or an individual at home) would not have obvious access to a secure system and defy all reasonable recommendations for many years and demand to be intentionally insecure to make them be in a situation where they don't have security on their own end and only if sending data to an insecure second party would the data be at risk and when that happens, the encrypted channel is moot because the target itself is insecure so it doesn't matter.

        Yes, even scammers and spammers use TLS nowadays.

        The only time we ever receive emails that are not TLS encrypted have been same odd email notifications from ERP or LOB systems. Probably legacy systems.

        oh for sure, the only people we ever see on unencrypted email are senior citizens and doctors these days.

        I’d add smaller ISPs too.

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

          @scottalanmiller said in SAMIT: Stop Using Secure Email:

          but either party (or both) have the right to demand it.

          This can be interpreted simply as the client or MTA "requesting" an insecure connection, right?

          I see most WHM/cPanel servers configured for SSL/TLS but will always accept non encrypted messages from other MTA servers.

          Do you think it is safe (from an undelivered mail perspective) to refuse non-TLS connections from servers too?

          scottalanmillerS 3 Replies Last reply Reply Quote 0
          • scottalanmillerS
            scottalanmiller @Dashrender
            last edited by

            @Dashrender said in SAMIT: Stop Using Secure Email:

            @scottalanmiller said in SAMIT: Stop Using Secure Email:

            @Pete-S said in SAMIT: Stop Using Secure Email:

            @scottalanmiller said in SAMIT: Stop Using Secure Email:

            @JasGot said in SAMIT: Stop Using Secure Email:

            @scottalanmiller
            For regular e-mail (not "Secure E-Mail"), isn't the message traveling un-encrypted when it is moving MTA to MTA on port 25?

            If you use things like free cPanel email or your ISPs email or have your nephew deploy his own email server without hiring any IT people... it's plausible that someone will screw up the config and leave it unsecured or if you accidentally host your email with scammers or something. That's essentially true with any misconfigured system of any type.

            And even when misconfigured, most systems today will enable it by default. You'd have to run something unmaintained for a super long time or really go out of your way to do a bad job to have it come up in a new deployment.

            There's no reasonable case where a business (or an individual at home) would not have obvious access to a secure system and defy all reasonable recommendations for many years and demand to be intentionally insecure to make them be in a situation where they don't have security on their own end and only if sending data to an insecure second party would the data be at risk and when that happens, the encrypted channel is moot because the target itself is insecure so it doesn't matter.

            Yes, even scammers and spammers use TLS nowadays.

            The only time we ever receive emails that are not TLS encrypted have been same odd email notifications from ERP or LOB systems. Probably legacy systems.

            oh for sure, the only people we ever see on unencrypted email are senior citizens and doctors these days.

            I’d add smaller ISPs too.

            A few, but most small ISPs just use GMail. It's giant ISPs that do nefarious things at scale you have to worry about.

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

              @JasGot said in SAMIT: Stop Using Secure Email:

              This can be interpreted simply as the client or MTA "requesting" an insecure connection, right?

              Yes, or more appropriately, "demanding."

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

                @JasGot said in SAMIT: Stop Using Secure Email:

                Do you think it is safe (from an undelivered mail perspective) to refuse non-TLS connections from servers too?

                It depends on the circumstance. Do you want to do business with anyone or just people with a clue?

                As an IT company, we need insecure messages from clueless people because that's who needs to hire us. So accepting insecure messaging is a need of pretty much any marketing or sales team.

                But an IT engineering team could be locked down.

                But really, if you are in the business of communicating with people who don't have TLS allowed, you have bigger security problems than the email encryption. So I'd want to investigate the entire security picture rather than one minor aspect of it. Insecure email is rarely a big deal, people who are okay requiring insecure email are almost always a big deal.

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

                  @JasGot said in SAMIT: Stop Using Secure Email:

                  I see most WHM/cPanel servers configured for SSL/TLS but will always accept non encrypted messages from other MTA servers.

                  Basically everyone works that way because almost no one wants, by default, to refuse emails from clueless, insecure family members.

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

                    Also, accepting insecure email is different than allowing your organization to send insecure email.

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

                      @JaredBusch said in SAMIT: Stop Using Secure Email:

                      Also, accepting insecure email is different than allowing your organization to send insecure email.

                      Very true. Accepting things insecurely is better than sending them.

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

                        @scottalanmiller said in SAMIT: Stop Using Secure Email:

                        @JaredBusch said in SAMIT: Stop Using Secure Email:

                        Also, accepting insecure email is different than allowing your organization to send insecure email.

                        Very true. Accepting things insecurely is better than sending them.

                        I accept email in any way that it is sent. But all sent email is required to be TLS or it will not send. I have a couple of people that the boss cannot email because of it, as well as one prior customer that is still running an ancient ass GroupWise 6 email server. They email asking for one off support for their routers sometimes.

                        1 Reply Last reply Reply Quote 2
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