0
votes
2answers
37 views

Attaching the same file to two separate email, does it compromise security of the “message”

When using (Thunderbird and) GnuPG to send a PGP/MIME message to two separate recipients, with the text body different in both messages, but the same file attached to both of them, does this give an ...
31
votes
2answers
2k views

Why does PGP work with the CC field in e-mails?

I was wondering how PGP works with a CC. In my understanding, if I send an e-mail to foo@example.com and use baz@example.org in the CC, Enigmail would have to encrypt the e-mail once for every user ...
19
votes
6answers
1k views

Is there anything standing in the way of email encryption going mainstream? [closed]

PGP has been around for almost 20 years, but email encryption is not used by most 'regular people'. At the moment, with Snowden's NSA revelations (which should not be a huge surprise to anyone), the ...
2
votes
0answers
164 views

PGP-encrypted Email or SSL/TLS Webform for Responsible Disclosure Communication?

So it's a fairly simple question. When offering an avenue to security researchers for communication with us regarding disclosure of security vulnerabilities, what's the best way to do so? Assume we ...
2
votes
1answer
197 views

Which mail clients support PGP/MIME - is there an overview? [closed]

Does anyone know if there is a current overview (I only found ones from before 2006) which MUAs (mail clients) do support PGP/MIME? I wonder whether there still exist issues like "Outlook Express ...
7
votes
3answers
2k views

How (in)secure is POP/IMAP/SMTP

I'm making a few assumptions about basic email security, and I want to confirm or clarify some of these points to make sure I understand the big picture. Please correct me where I'm mistaken: The ...
4
votes
3answers
527 views

What is the most secure way to send emails using PGP?

I am a PGP beginner, having just downloaded GPG for OS X. I created my first pub/sec key for my email address and uploaded it to the public key server. GPG has several features available, namely: 1) ...
3
votes
6answers
209 views

Does an email signature increase security?

I'm using Thunderbird with Enigmail. It has both encrypt and sign options for sending PGP emails -- but why is an email signature needed? It just looks overkill to me! Alice and Bob can use PGP to ...
1
vote
1answer
83 views

Getting more users to use PGP [closed]

Does anyone know of browser Plugins that make Composing, sending, and reading email basically effortless? Mailvelope doesn't seem to be working with the floating compose boxes in Gmail currently. ...
2
votes
2answers
322 views

GPG good signature but Warning: untrusted signature

I'm having an issue with some of my clients being unable to open email attachments when I sign the messages. The error they get is something like (free translation): Error: cannot open. The ...
-2
votes
2answers
178 views

What was the Lavabit's backdoors to their customers' e-mails? [closed]

There has been some talk about the Lavabit's case. New info was published today, but not important. I'd like to know how Lavabit worked. First I thought they just did something with OpenPGP. Then I ...
1
vote
1answer
313 views

Why are the first 16 bits of the message digest not encrypted in PGP? [closed]

The first 16 bits of the message digest in a PGP signature are translated in the clear. As we know, sending something in clear text does not sound like a very good idea from a security point of view. ...
10
votes
3answers
702 views

Is off-the-record style encryption possible with email?

The instant messaging world has off-the-record encryption - which means you get authentication, encryption, and forward deniability. Key material is published after a session ends such that an ...
5
votes
7answers
1k views

Is PGP combined with a regular web-based email service secure?

With the disappearance of private email services like Lavabit and Tormail (http://www.dailydot.com/news/email-anonymous-hushmail-lavabit-nsa/) it seems that we will need to resort back to standard ...
4
votes
2answers
237 views

Security of PGP for Long-Term Storage

How secure are PGP/GPG encrypted mails? I realize that it's probably fine for regular e-mail scenarios, but what about the security over longer time periods (>30 years)? Is the 4096 bit limit for ...
-3
votes
2answers
163 views

Security and privacy in email and other communications [closed]

In the light of newly discovered events like the NSA's PRISM program, I'm really concerned about the privacy & security of my personal emails. Chances are governments already have backdoor access ...
2
votes
0answers
208 views

User friendly PGP email [closed]

Does there exist cross-platform email handlers following these basic guidelines based on some very limited experience? Generate new key at first startup, rather than asking the user if they have an ...
4
votes
1answer
235 views

Potential issues with Kim Dotcom's new proposed “encrypted webmail service”

Just spotted a Reddit thread about Kim Dotcom, of MegaUpload fame, planning to produce a secure webmail system that allows people to communicate securely, without the worry of having their messages ...
4
votes
1answer
269 views

Apart from the lack of native Oultook support, why should one prefer S/MIME over PGP/MIME for email?

From my (still quite subjective) point of view, GnuPG/PGP is superior to SSL (or more specifically, PGP/MIME over S/MIME; maybe in other areas SSL is the better choice), e.g. due to the support of ...
8
votes
1answer
920 views

GPG-encrypted mailing list and other approaches to safe communication

What is the best way to communicate privately on a mailing-list? Requiring each member of the list to have the public key of each other member, and encrypt their messages with those, is cumbersome to ...
4
votes
4answers
299 views

Securely publishing GPG keys

This is probably a stupid question/vaguely defined, but I need to ask it anyway. I want to put a public key for mail exchange on my website, such that even very powerful adversary with power to ...
9
votes
1answer
709 views

PGP: How is it possible for me to read a sent mail, encrypted by me with the recipient's public key?

I'm quite new to OpenPGP and am just starting to use it with Thunderbird. When I encrypt a mail with a recipient's public key, using Thunderbird + Enigmail + OpenPGP, and send it, I can find the ...
6
votes
2answers
208 views

Is DKIM needed for emails encrypted with OpenPGP?

DKIM seems to prove that a message came from where it claims to be from. However, OpenPGP encrypts the entire email and signs it which obviously proves it also came from the person it says it did. ...
4
votes
2answers
207 views

How to refuse delivering emails that are not signed by trusted PGP keys?

I'm fed up by spam and would like to have an email address that will only deliver mails signed by users I declared trusted. Some kind of purgatory for mails the signatures of which are trustworthy by ...
0
votes
2answers
442 views

Whether PGP is send over MIME?

If I am using PGP to encrypt mails whther it is send as a MIME (Multipurpose Internet Mail Extensions) message, and S/MIME and PGP are used for providing email security. When I send PGP message ...
9
votes
4answers
2k views

How do I encrypt the source and destination IP address, along with various parts of an email?

If the subject makes no sense to you, that's fine, it makes no sense to me. I've been tasked with securing emails sent from some devices, and I'm looking for advice on intelligent questions to ask to ...
14
votes
9answers
5k views

Encrypting email for gmail

My friend who is an accountant was asking me what the best way to exchange documents with clients. He was trying to tell me that just sending via email was sufficient and I told him he was insane. I ...
26
votes
4answers
14k views

How does PGP differ from S/MIME?

Is S/MIME an abstracted system for general MIME type encryption, whereas PGP is more for email? Why would I want to choose one over the other, or can I use both at the same time?
11
votes
2answers
2k views

Does my PGP key really need to match the e-mail address for which I'll be using it?

In considering whether or not I want to join the big web o' trust and put my keys on a key server, I got to thinking about how it would affect my e-mail address' exposure. I generally try to keep my ...