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Write your email, save as PDF, encrypt it in a RAR, 7z etc, then attach and send... and send the person the password for the archive via out-of-band method, ie SMS.

Clunky, but definitely works!

:p
 
This is what happens when your security protocols are super complicated. I also would never rely on email for secure or even reliable messaging.
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Exactly my reaction. "Some of your emails may be insecure. So remove this software so that they're all insecure." ??

(Bigger question - why the hell are we still using insecure, spam-tastic email? It's astonishing that no mainstream secure alternative, with disposable addresses has really gained much traction.)

I remember going through an exhaustive security audit for a client (covering hosting, backup policy, security policies, incident management etc.) as they were sending us personal user information. Once we passed, they emailed it to us.... o_O
The issue is you reveal your password to attackers, which is worse than revealing the contents of your emails if you know they aren't encrypted.
Edit: I was wrong. The flaw is when you read the email, not when you send. So it's best to not read any encrypted emails until this is fixed. https://www.csoonline.com/article/3...d-smime-users-of-serious-vulnerabilities.html
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The workaround is to uncheck "Load Remote Content In Messages" from the Viewing preferences in Mail.

If you care at all about security this shouldn't be checked in the first place (cause you don't want to be auto-loading all HTML email's and their potential security holes, you should just be auto-loading things as plain text from a security perspective).

Fix is coming soon according to the GPGtools folks, perhaps folks are over-reacting?
Mail should really do this by default. The easiest exploit I know of is to include "tracking pixels" in spam so spammers know their messages are being read. iMessage is also guilty of loading remote content in received messages, but it doesn't do that if the sender isn't in your contacts, so I guess it's fine.
 
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Hmm.... security protocol creates a vulnerability. To protect yourself, stop encrypting your emails???

Interesting.

hehe..

I was waiting for something like this to come out..

Not to be a negative here, but sometimes it forces users to think "It may not be that trusting so why trust it 100% ?"

I never trust anything that much, no many how good it is. All software has/can vulnerabilities, even it we assume its secure always like PGP

We always trust something first, until its broken, where as i do the reverse.. "I assume its probably broken always". or ways in.

Too bad no one thinks like that anymore.
 
The vector of the attack seems to be.

1. You send an encrypted email

2. The bad guy intercepts that email, changes it slightly by adding a http:// link with your crypto message connected to the link

3. The bad guy forwards the mail to any of the recipients or the original sender (i.e. anyone who can decrypt the mail)

4. If any of the recipients ( including you) have html enabled, the email client will decrypt the message then execute the http link to the server (that the bad guys owns)

5. Due to a bug, the html link will actually contain the decrypted text. This will generate a ‘page not found’ error on the bad guys http server but the server will log the full request (including the decrypted text) hence allowing them to read the message.

6. This works because your (or your recipients) email clients decrypt the message first, then executed html.

Then there are variants of this. Even if you disable html links, if any of your recipients don’t, the bad guy can still read the message as they will get the malformed html request.
 
I work for a company that had done something similar. Send out an email stating that email was down. Of course we didn't see that notice until they resolved the problem. :p
The corporate world is full of these examples. But, it's not confined to email. Some 30+ years ago, a store I worked at sold VCRs that included instructions on how to hook up the VCR ... and the instructions were on videotape.
 
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Write your email, save as PDF, encrypt it in a RAR, 7z etc, then attach and send... and send the person the password for the archive via out-of-band method, ie SMS.

Clunky, but definitely works!

:p
Well kinda... brute force attacks on RAR/ZIP encrypted files are incredibly easy as there is no retry/lockout mechanism, so you can go as fast as your hardware will allow. A mid-range Intel processor can try 28 million passwords a second against a ZIP2 password protected file. GPU brute force tools can try 500 million passwords a seconds on a single home-user GPU. That means a 6 character ASCII password would be guessed in 28 minutes on a home PC.

If you scale that to the resources available to a serious agency trying to access your data... you'd be exposed in a matter of days no matter how long your password was.
 
Say
Well kinda... brute force attacks on RAR/ZIP encrypted files are incredibly easy as there is no retry/lockout mechanism, so you can go as fast as your hardware will allow. A mid-range Intel processor can try 28 million passwords a second against a ZIP2 password protected file. GPU brute force tools can try 500 million passwords a seconds on a single home-user GPU. That means a 6 character ASCII password would be guessed in 28 minutes on a home PC.

If you scale that to the resources available to a serious agency trying to access your data... you'd be exposed in a matter of days no matter how long your password was.

Just because you say "serious agency", that doesn't give them magic powers. If my passphrase is 3,000 chars long, as below, you better have a few trillion centuries to kill. I checked my passphrase (NOT my real one, of course) on:

https://www.grc.com/haystack.htm (the only man I trust in security)

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My view - use iMessage, FaceTime or Signal for reliable encrypted communication. If you want to send a long letter, type it up in Pages or Word or ... and then attach it to an iMessage. It will be end to end encrypted for you.

Think of email as sending a postcard - cute but zero privacy.

OR type in notes, text edit, word and copy/paste.
 
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