Interestingly, this is another security issue with STARTTLS. The whole concept of first establishing an unencrypted connection and only then upgrading to encryption is fragile in multiple ways. Admittedly, this is a pet peeve of mine, as I've co-authored a paper about it. I wonder why mailbox.org does not recommend that users switch from STARTTLS to implicit TLS for SMTP/POP3/IMAP, as this would mitigate such issues…
Mailbox.org discovers unencrypted password transmission in myMail
21–30 of 30 posts
Re: Mailbox.org discovers unencrypted password transmission in myMail
#22Interestingly, this is another security issue with STARTTLS. The whole concept of first establishing an unencrypted connection and only then upgrading to encryption is fragile in multiple ways. Admittedly, this is a pet peeve of mine, as I've co-authored a paper about it. I wonder why mailbox.org does not recommend that users switch from STARTTLS to implicit TLS for SMTP/POP3/IMAP, as this would mitigate such issues…
Re: Mailbox.org discovers unencrypted password transmission in myMail
#23Interestingly, this is another security issue with STARTTLS. The whole concept of first establishing an unencrypted connection and only then upgrading to encryption is fragile in multiple ways. Admittedly, this is a pet peeve of mine, as I've co-authored a paper about it. I wonder why mailbox.org does not recommend that users switch from STARTTLS to implicit TLS for SMTP/POP3/IMAP, as this would mitigate such issues…
And the mess I had unavoidably made around the sockets and starttls just made that worse. And there was no real way to unit test it.
Re: Mailbox.org discovers unencrypted password transmission in myMail
#24Earlier quoted context omitted.
the OS won't let you do that reliably unless the user also keeps opening the app. background processing is heavily limited for the right reasons.
iOS does that, maybe, but Android doesn’t. The mail client I use on my Android phone notifies me in a timely fashion when new mail arrives, often in less than a second. It just uses IMAP’s IDLE command to wait for new mail. If the connection drops it can just open a new one.
Does it occur to you that there are so many different variants of Android and they all do their own thing regarding background processes? It is so complicated that you can find websites like this https://dontkillmyapp.com/
Re: Mailbox.org discovers unencrypted password transmission in myMail
#25Interestingly, this is another security issue with STARTTLS. The whole concept of first establishing an unencrypted connection and only then upgrading to encryption is fragile in multiple ways. Admittedly, this is a pet peeve of mine, as I've co-authored a paper about it. I wonder why mailbox.org does not recommend that users switch from STARTTLS to implicit TLS for SMTP/POP3/IMAP, as this would mitigate such issues…
Another nice one is that implicit TLS is SNI routable (and thus much easier to route) -- this is the main reason for me, and I wish the standard had been updated to encourage more people to try 465 (or have a way to specify port in DNS records for example). Huge missed opportunity.
Re: Mailbox.org discovers unencrypted password transmission in myMail
#26Interestingly, this is another security issue with STARTTLS. The whole concept of first establishing an unencrypted connection and only then upgrading to encryption is fragile in multiple ways. Admittedly, this is a pet peeve of mine, as I've co-authored a paper about it. I wonder why mailbox.org does not recommend that users switch from STARTTLS to implicit TLS for SMTP/POP3/IMAP, as this would mitigate such issues…
Thank you for writing this, I use it as a reference when explaining the difference STARTTLS and implicit TLS and why people should choose one over the other. Another nice one is that implicit TLS is SNI routable (and thus much easier to route) -- this is the main reason for me, and I wish the standard had been updated to encourage more people to try 465 (or have a way to specify port in DNS records for example). Huge…
https://www.fastmail.help/hc/en-us/articles/360060591153-Man... under "Client email auto-discovery"
Though support for these are...
Re: Mailbox.org discovers unencrypted password transmission in myMail
#27Earlier quoted context omitted.
Thank you for writing this, I use it as a reference when explaining the difference STARTTLS and implicit TLS and why people should choose one over the other. Another nice one is that implicit TLS is SNI routable (and thus much easier to route) -- this is the main reason for me, and I wish the standard had been updated to encourage more people to try 465 (or have a way to specify port in DNS records for example). Huge…
> or have a way to specify port in DNS records for example https://www.fastmail.help/hc/en-us/articles/360060591153-Man... under "Client email auto-discovery" Though support for these are...
It does look like they are actually for clients (i.e. MUAs doing IMAP & Submission), not for relay (i.e. MTAs doing SMTP/SMTPS).
I've used MTA-STS and XML to enable auto-config for my stuff:
https://vadosware.io/post/thunderbird-autoconfig-for-your-se...
Oh and it looks like MTA-STS might be the solution:
https://en.wikipedia.org/wiki/Simple_Mail_Transfer_Protocol#...
Turns out there's an excellent guide by the UK government:
https://www.ncsc.gov.uk/collection/email-security-and-anti-s...
https://www.security.gov.uk/guidance/email-guidance/mta-sts/...
Relevant RFC:
Re: Mailbox.org discovers unencrypted password transmission in myMail
#28I'd never heard of myMail. Turns out it's a mobile only MUA made by a Russian company ( https://en.wikipedia.org/wiki/Mail.Ru ) and they were seen collecting people's usernames and passwords and using those logins to read people's messages from their own servers almost a decade ago ( https://old.reddit.com/r/Android/comments/20u712/beware_myma... )
>they were seen collecting people's usernames and passwords and using those logins to read people's messages from their own servers almost a decade ago To be fair microsoft's outlook ios and android clients does the same thing with external providers (like if you used it with fastmail). It is a common practice and something to be aware of when choosing an email app. EDIT: I'm specifically answering this comment. As f…
Mixed in were many logins from an IP address owned by the Microsoft campus at times when I would have been asleep. The account is a backup, and I don't have that mailbox attached to any apps. I emailed their security team asking what was going on but never got a response. After changing the password all the access was stopped. Though I should go back and re-check.
Re: Mailbox.org discovers unencrypted password transmission in myMail
#29Earlier quoted context omitted.
iOS does that, maybe, but Android doesn’t. The mail client I use on my Android phone notifies me in a timely fashion when new mail arrives, often in less than a second. It just uses IMAP’s IDLE command to wait for new mail. If the connection drops it can just open a new one.
"Android doesn't" Does it occur to you that there are so many different variants of Android and they all do their own thing regarding background processes? It is so complicated that you can find websites like this https://dontkillmyapp.com/
Re: Mailbox.org discovers unencrypted password transmission in myMail
#30Earlier quoted context omitted.
>they were seen collecting people's usernames and passwords and using those logins to read people's messages from their own servers almost a decade ago To be fair microsoft's outlook ios and android clients does the same thing with external providers (like if you used it with fastmail). It is a common practice and something to be aware of when choosing an email app. EDIT: I'm specifically answering this comment. As f…
Collecting credentials and reading mail from server is standard practice across hosts of email clients, since it’s the only way to get push notification working. If you don’t trust their server you probably shouldn’t use their client anyway.
In some countries this is "unauthorised access to computing systems".
But Google and co. are above the law anyway.