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My accountant is now using the stupid “encrypted email” system Outlook has where it sends you a link to their server, which then emails you a password to login

My accountant is now using the stupid “encrypted email” system Outlook has where it sends you a link to their server, which then emails you a password to login to read the email. It’s so bloody clunky and annoying. It’s particularly stupid as I then don’t have a copy of the email myself, and they have disabled text selection on the webpage so I can’t even copy and paste it (easily)! I suppose it ensures that if the recipient isn’t using TLS with SMTP then it’s not sent unencrypted over the wire, but I suspect the vast majority of email servers are using TLS now. If someone hacks my email they have access to it anyway. I wish the system was intelligent enough to turn itself off if the recipient server has TLS, then I could almost support it as a concept. But if someone is watching your unencrypted connection to your mail server they can just follow the link and then watch the password being sent. So meh, stupid pointless thing.

pabs3 5y ago
Just use the browser dev tools to re-enable text selection? There must be a browser extension that can automate that too. Maybe even Greasemonkey would do.
- shakna 5y ago
  In Firefox, you can simply set a preference and scripts won't be able to disable copy/paste. Go to about:config, and search for dom.event.clipboardevents.enabled and disable it.
  - dbrgn 5y ago
    This will probably break many other use cases as well (e.g. services that allow pasting formatted text and will convert it to unformatted text, or pages like GitHub where you can paste an image into the edit area).
    - shakna 5y ago
      It shouldn't break either of those usecases (I gave GitHub a go and it certainly seems to work). Those functions tend to be handled by a different preference (dom.allow_cut_copy). The only service I am aware of that it does break is Google Docs, because they handle things in an odd manner. But as they received several bug reports for that since 2017, I wouldn't get your hopes up that it'll ever be fixed.
- samwillis 5y ago
  That’s exactly what I do, however I wouldn’t want to try and explain how to do it to my Parents. They are meticulous with their filing system and this would make it impossible. They would ultimately probably print more stuff out to save.
  - notriddle 5y ago
    1. Does Microsoft not disable printing, also? 2. If not, do your parents know how to print to PDF?
    - hulitu 5y ago
      Printing from a webpage on desktop is a PITA. On Android you don't have the option to print. Brave new world.
jabroni_salad 5y ago
Unfortunately, Rights Management is the hot thing of the minute. It doesn't make since for you since you are the ultimate destination, but in many cases we need to transmit information and also take steps to ensure that the recipient does not forward that data anywhere else without our permission. If we are going to still be responsible for the data's privacy after it leaves our network then we are just going to never let it leave our network. These unfriendly encryption mechanisms also let us actually retract a message if it was sent to the wrong person, a feature that is on the honor system in traditional implementations. On the user end all they know is that if they put [encrypt] in the subject they won't be written up by their compliance department. People really like not getting fired over clerical stuff so they over-use it.
- samwillis 5y ago
  So, I understand the motivation, it's the misguided implementation that's the problem. The only thing from your suggested requirements that actually works is the ability to "retract" an email before its been read. It can still be forwarded (after extracting from a badly implemented site). The "ensure the right person got it" password is stupid as its literally sending it to the same email address. The thing I find so bizarre about this is that lawyers/accountant etc. have been seeing out letters in the post forever and never had the desire to implement this level of security. Post can be intercepted, read by third parties and modified at will, just like unencrypted email. The only thing that's changed is that because there is supposedly the ability to do it someone has lobbied for there to be a mandate for it. Just because it "can be done" doesn't mean is should or that it achieves what the motivation was. If there is something that important that it can't be in the wrong hands then either do it in person or sent a courier with the signed for letter that requires id on delivery. These systems are nothing other than security theatre that's sold to the unknowledgeable as something they need, when the reality is it's a complete waste of everyones time. (except for the person selling it!)
  - kasey_junk 5y ago
    It would be extremely expensive to mechanize the dragnet stealing/modification of the post. I agree the current solutions for electronic communication are stupid but there is concern about the many vectors and attacker could get all the data. The fax only ones are the dumbest though because on both sides everyone is just using electronic documents.
implements 5y ago
> I suppose it ensures that if the recipient isn’t using TLS with SMTP then it’s not sent unencrypted over the wire, … I discovered setting up an old IP camera recently that it’s now very hard to send an unencrypted email via SMTP. Nearly all servers refuse to relay unauthenticated emails (no username and password), and only permit authentication if the connection is SSL or promoted to SSL via STARTTLS (ie encrypted). (I mention it because the camera wouldn’t cooperate or tell me what the problem was - ended up having to learn Wireshark and read the relevant RFCs re Authenticated SMTP).
- Karrot_Kream 5y ago
  I went through this process just the other day, setting up Postfix on a Zerotier network. Postfix lets you specify a "mynetworks" config option that lets you allow certain IP ranges. I added the Zerotier IPv6 assigned ranges to this list, disabled any form of TLS on the smtpd end, and was able to effectively turn off TLS. It was more annoying than I thought it would be but it makes sense given how few real world deployments lack TLS these days.

pabs3 5y ago

Just use the browser dev tools to re-enable text selection? There must be a browser extension that can automate that too. Maybe even Greasemonkey would do.

shakna 5y ago
In Firefox, you can simply set a preference and scripts won't be able to disable copy/paste. Go to about:config, and search for dom.event.clipboardevents.enabled and disable it.
- dbrgn 5y ago
  This will probably break many other use cases as well (e.g. services that allow pasting formatted text and will convert it to unformatted text, or pages like GitHub where you can paste an image into the edit area).
  - shakna 5y ago
    It shouldn't break either of those usecases (I gave GitHub a go and it certainly seems to work). Those functions tend to be handled by a different preference (dom.allow_cut_copy). The only service I am aware of that it does break is Google Docs, because they handle things in an odd manner. But as they received several bug reports for that since 2017, I wouldn't get your hopes up that it'll ever be fixed.
samwillis 5y ago
That’s exactly what I do, however I wouldn’t want to try and explain how to do it to my Parents. They are meticulous with their filing system and this would make it impossible. They would ultimately probably print more stuff out to save.
- notriddle 5y ago
  1. Does Microsoft not disable printing, also? 2. If not, do your parents know how to print to PDF?
  - hulitu 5y ago
    Printing from a webpage on desktop is a PITA. On Android you don't have the option to print. Brave new world.

jabroni_salad 5y ago

Unfortunately, Rights Management is the hot thing of the minute. It doesn't make since for you since you are the ultimate destination, but in many cases we need to transmit information and also take steps to ensure that the recipient does not forward that data anywhere else without our permission. If we are going to still be responsible for the data's privacy after it leaves our network then we are just going to never let it leave our network. These unfriendly encryption mechanisms also let us actually retract a message if it was sent to the wrong person, a feature that is on the honor system in traditional implementations. On the user end all they know is that if they put [encrypt] in the subject they won't be written up by their compliance department. People really like not getting fired over clerical stuff so they over-use it.

samwillis 5y ago
So, I understand the motivation, it's the misguided implementation that's the problem. The only thing from your suggested requirements that actually works is the ability to "retract" an email before its been read. It can still be forwarded (after extracting from a badly implemented site). The "ensure the right person got it" password is stupid as its literally sending it to the same email address. The thing I find so bizarre about this is that lawyers/accountant etc. have been seeing out letters in the post forever and never had the desire to implement this level of security. Post can be intercepted, read by third parties and modified at will, just like unencrypted email. The only thing that's changed is that because there is supposedly the ability to do it someone has lobbied for there to be a mandate for it. Just because it "can be done" doesn't mean is should or that it achieves what the motivation was. If there is something that important that it can't be in the wrong hands then either do it in person or sent a courier with the signed for letter that requires id on delivery. These systems are nothing other than security theatre that's sold to the unknowledgeable as something they need, when the reality is it's a complete waste of everyones time. (except for the person selling it!)
- kasey_junk 5y ago
  It would be extremely expensive to mechanize the dragnet stealing/modification of the post. I agree the current solutions for electronic communication are stupid but there is concern about the many vectors and attacker could get all the data. The fax only ones are the dumbest though because on both sides everyone is just using electronic documents.

implements 5y ago

> I suppose it ensures that if the recipient isn’t using TLS with SMTP then it’s not sent unencrypted over the wire, … I discovered setting up an old IP camera recently that it’s now very hard to send an unencrypted email via SMTP. Nearly all servers refuse to relay unauthenticated emails (no username and password), and only permit authentication if the connection is SSL or promoted to SSL via STARTTLS (ie encrypted). (I mention it because the camera wouldn’t cooperate or tell me what the problem was - ended up having to learn Wireshark and read the relevant RFCs re Authenticated SMTP).

Karrot_Kream 5y ago
I went through this process just the other day, setting up Postfix on a Zerotier network. Postfix lets you specify a "mynetworks" config option that lets you allow certain IP ranges. I added the Zerotier IPv6 assigned ranges to this list, disabled any form of TLS on the smtpd end, and was able to effectively turn off TLS. It was more annoying than I thought it would be but it makes sense given how few real world deployments lack TLS these days.