<div dir="ltr"><div dir="ltr"><div class="gmail_default" style="font-size:small">I have given much thought to this question but as Karl Marx said, the point is to change it. Comments inline and at the end.</div></div><br><div class="gmail_quote"><div dir="ltr" class="gmail_attr">On Fri, Aug 20, 2021 at 8:30 PM R Perlman <<a href="mailto:radiajpc@gmail.com">radiajpc@gmail.com</a>> wrote:<br></div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><p style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px;margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Despite PGP and S/MIME having been designed zillions of years ago, it seems like end-to-end email encryption/integrity protection are not widely used. Which of the following is reasonably close to the truth? </span></span></span></p>
<ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Of course they are widely used. I'm just not aware.</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">Roughly 1-2 million accounts activated for both. Use is not negligible but far short of the over 4 billion users of email.</div></div><div><br></div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">The usability issues were not worked out. How would a user obtain a public key? How would a user get a certificate? How would a user know the public key of someone they are receiving from/sending to?</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">A real concern but the usability threshold is much harder. If you ask the user to make any effort whatsoever, you are lost. SSL/TLS works because it is completely transparent and zero effort on the user's part.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">The Mesh automates the process of device provisioning. So configuring Thunderbird to use S/MIME should be a one time 30 second affair. But that is not close to being enough.</div></div><div><br></div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">It never reached critical mass…there were never enough people who could receive encrypted email that it was worth trying to figure out how to send it.</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">A valid concern and this was made much worse by the VHS/Betamax format war. And that same issue is going to limit the growth of Signal/Telegram etc. and keep those in a significant but small community.</div></div><div> <br></div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Big companies do not want end-to-end encryption of email. They want to have middleboxes be able to scan for phishing links and perhaps they are legally required to keep records of all email sent to or from company email addresses.</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">Big companies do not want malware vectoring in. That is a slightly different concern. SMTP is worn out at this point. Middleboxes to scan spam are a kludge to deal with the fact that the protocol is default insecure. DKIM does not change that very much either. </div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">If you want to do end-to-end encryption, you have to deal with these issues and more. End to end means something very different in the enterprise context. If Alice sends an order to Bob by email and Bob falls under a bus, the corporation needs to read the email because the relationship is with them and not with Bob.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">Designers have to leave the libertarian 'its all about me, only me and nobody apart from me' behind.</div></div><div><br></div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px"><li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Even individual users need middleboxes to scan for spam and other services (such as maybe warning about dangerous links)</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">No, we have to abandon SMTP.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">Mesh messaging is access controlled. So every message Alice receives from Sue the Spammer is rejected. All that Sue can send that Alice will receive by default is a contact request in a highly constrained format and even that is subject to access control.</div><br></div><div><div class="gmail_default" style="font-size:small">By default, I would probably allow anyone who has attended an IETF meeting and checked in with their Mesh profile to send me mail messages. But I wouldn't allow just anyone to interrupt me with a voice call.</div></div><div> </div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Ordinary users just aren't worried about having their email seen by others, at least not enough to figure out how to get an email client that can do encryption, obtain a key, etc.</span></span></span></li></ul></div></div></div></blockquote><div class="gmail_default" style="font-size:small">And never will be. Ask nothing of the user.</div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Other solutions became popular, which (I think) involve a central server that a sender requests a secret key from, the sender encrypts with that secret key, and then the receiver needs to ask the central server for the key. I think if a big company is using such a product, it is implemented in a way that lets the company see plaintext of all email to/from that company's email addresses. </span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">These are expensive hacks that offer rather little actual security but they are widely used.</div></div><div> </div><blockquote class="gmail_quote" style="margin:0px 0px 0px 0.8ex;border-left:1px solid rgb(204,204,204);padding-left:1ex"><div dir="ltr"><div dir="ltr"><div style="box-sizing:border-box"><ul style="font-family:"Segoe UI",system-ui,"Apple Color Emoji","Segoe UI Emoji",sans-serif;font-size:14px">
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">People don't really know what different forms of "encrypted email" mean, so central-server-secret-key-style, vs end-to-end with user public keys, vs using TLS between mail transfer agents all count as "encrypted email"</span></span></span></li>
<li style="margin-bottom:13px"><span style="font-size:11pt"><span style="line-height:115%"><span style="font-family:Calibri,sans-serif">Something else?</span></span></span></li></ul></div></div></div></blockquote><div><div class="gmail_default" style="font-size:small">The whole complexity of PKI and deciding whether <a href="mailto:alice@example.com">alice@example.com</a> is 'Alice'.</div><br></div><div><div class="gmail_default" style="font-size:small">DNS makes a lousy basis for email addresses. Users need portable email addresses and SMTP just can't give them that. DNS names are ridiculously expensive and part of that is irreducible because DNS is bjorked.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">I think these are all fixable and will shortly be releasing code that I think starts on the road to a fix. But an infrastructure can only deploy if there is a deployment strategy and that means designing for deployment. The myopic IETF approach of 'lets make the smallest change possible' limits us to incremental changes that are too small to be worth it for the end user.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">I don't see any player in the market trying to develop an open system in this space. Signal, Telegram etc. all force you to use their service. That isn't open, it is a proprietary system offered for free while it builds an audience. My criteria for success:</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">* It has to be genuinely open, anyone can write a client, anyone can run their own service</div><div class="gmail_default" style="font-size:small"></div><div class="gmail_default" style="font-size:small">* User addresses (callsigns) must be portable between service providers and incur no renewal fees and be cheap to register (less than $0.10)</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">* It has to span the full range of security concerns, securing data at rest, asynchronous messaging (mail), synchronous (chat), voice, video. All with the same callsign (I also provide contact, password catalogs and 2nd factor authentication)</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">* It has to demand no additional effort on the part of the user.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">* It has to fit with real world user concerns. That is 'how do I give access to all our data on USB sticks to Fred who just joined the company', not 'how do I prevent the FBI from effecting a warrant for the material under any circumstance I can imagine'.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">* It should be as secure as we can make it without compromising any of the goals above.</div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small"><br></div><div class="gmail_default" style="font-size:small">I am just wrapping up the final pieces so the initial tool can demonstrate provisioning keys for SSH, S/MIME and OpenPGP. Hoping to launch very soon.</div><br></div><div> </div></div></div>