Comments for How do I send encrypted email?

Comment from Mark J on 2012-02-06

2012-02-06T10:09:10Z

@Chris
You can use a program like 7zip to create an encrypted self extracting zip file. This is a zip file with a .exe extension which contains the software internally to unzip and decrypt itself without external software.
7-zip file archiving utility

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Comment from Chris on 2012-02-05

2012-02-06T07:10:36Z

I'm looking for a means where I can encrypt an email message, send it to my son and he doesn't need to have the software installed on his computer to read it. He would only need to enter a password. Will something like this work? TIA

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Comment from Anjan on 2011-12-08

2011-12-08T23:27:59Z

I think it is very very absolutely important to protect ones email id and password. When one sends email from public hotspot, if the id and password are snatched as they make their way from ones laptop to the Access Point then the person loses his email forever. Happily Yahoo webMail encrypts id/passwd via SSL. If one is concerned about privacy of the message, he/she can use file attachment with "very strong" password. Ofcourse, you need a way to let the recipient know the password, and ofcourse you would not use the same email to give it to him. However, I am very happy to find that Gmail actualy use SSL encryption for password and message body. No other free webmail service does this. This is Grrreeeaaaaat! I just thought I would share this with you.

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Comment from Gina on 2011-09-15

2011-09-16T00:55:50Z

Hi Leo,
We are all aware of the risks involved in signing up for an email service provider and sending and receiving messages through these providers and making sure it is secure is of course of utmost importance to us, so we would choose to send personal and sensitive information via the most secure website and that would also mean paying for this service. Well, all the complexity of this should really be worth it..but what can you say about encrypt.me which offers us a very affordable cost (it's free at the moment which is great) and very simple to use! I think its closed loop system is safe enough to send very sensitive information without much hassle in signing up!
its definitely worth checking out!

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Comment from MM on 2011-07-12

2011-07-12T13:05:55Z

now GPG support is available in the new mozilla thunder bird.so I think there is no need to use command prompt.am I correct??..

The Enigmail extension has been available for a while and does make it easier, but only if you use Thunderbird.

14-Jul-2011

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Comment from Jon Lybrook on 2011-05-14

2011-05-15T02:48:05Z

Hi Leo,

Good overview about secure email, but you make no mention about strictly web-based services. Sniffing email may be uncommon, but you can bet Google is scanning and storing any data about you via Gmail if it helps beef up their giant marketing database about all of us. Communicating through an encrypted method that is not free is about the only way to ensure privacy. Word Secure (https://wordsecure.com) or similar services are essentially web-based apps that are secure on the sender and recipient end. GPG and PGP require 3rd party tools to be installed and configured on both the sender and recipient's end and are impractical, where as web-based solutions are all done over SSL, like with banking and ecommerce software. Unlike Gmail where it may be secure on one side but not both, web based encrypted solutions provide point-to-point protection.

Yes, there is a nominal cost to subscribe to these services Rick, but for people who value security it's a bargain compared to blowing your weekend figuring out convoluted 3rd party tools and convincing your clients and customers to also blow their weekends installing the same.

Jon Lybrook

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Comment from Selvan on 2011-03-10

2011-03-10T22:13:57Z

Is it possible to integrate this into Windows Live Mail?

Not that I'm aware of.

11-Mar-2011

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Comment from Selvan Poothamby on 2011-03-01

2011-03-01T15:49:12Z

Most of my recipients can't do this.

So I wonder if it's possible to act as the intended recipient using a bogus but legit e-mail account and generate the public/private key pair.

Then send the private key to them using and I keep and use their public key to send e-mail with attachments totaling less than 200 KB using WLM.

Is it doable?

You could do it and even use their email address instead of a bogus one. They would have to trust you as you would be able to open their encrypted emails. It's best to give them the key personally and not by email as there's a risk of key interception on the internet. If you aren't able to hand it to them you could mail them a cd, usb stick or a diskette.

04-Mar-2011

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Comment from Andy on 2010-12-16

2010-12-16T21:19:50Z

FYI there are services out the that do public private key encryption for you encryptshield.com is a free email encryption service for doing just what your talking about

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Comment from CompletelyPrivateFiles on 2010-10-27

2010-10-27T15:45:16Z

Public/private key encryption is very strong security, but requires a lot of steps, not to mention key management. I think that's one of the reasons it's found little adoption by the masses.

So many people try 'security through obscurity' and just send their sensitive data via email, hoping that no one's looking.

Our company, CompletelyPrivateFiles, tries to strike a balance somewhere in between security and difficulty. We have a free browser-side email encryption solution called PointMX that ensures that your message is encrypted with 256-bit AES encryption before it leaves your computer. It's built with JavaScript so there's no Flash/Java dependency. It's best suited for smaller messages.

https://www.completelyprivatefiles.com/services/smx/

How it works:

You enter a secret passphrase that you will share somehow with the recipients of the message. A strong key is derived from the weaker passphrase (although you could use a 'strong random' passphrase if you wanted).

When you click Send your browser encrypts the message before leaving your computer and we email it for you.

We have no knowledge of your passphrase or key, and your message is encrypted as it travels the Internet's email servers.

The recipient(s) receive an email in their Inbox, and click to view the message. They must provide the passphrase in order for their browser to decrypt the message.

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Comment from Rick on 2010-10-21

2010-10-21T13:40:55Z

TL;DR! Who is ever going to use this feature if a free version is not easily available(read above, TL;DR, way too complex for the peops who send 99,999% of all e-mails) or you have to pay for it(Ha. Haha. Hahaha). Secure e-mail is a stillborn.

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Comment from Manoj Patil on 2010-09-21

2010-09-21T21:45:34Z

Excellent answer for GPG encryption warning message User this Key anyway y/N : : There is no assurance this key belongs to the named user
It is NOT certain that the key belongs to the person named in the user ID. If you *really* know what you are doing,
> you may answer the next question with yes.

> Use this key anyway? (y/N) y

I wanted to Run this script -silently without user interaction. your SOLUTION

gpg --always-trust --encrypt --recipient (receipient@yahoo.com) testfile.txt

did not ask for Y/n warning messge. Many many many Thanks , I was looking for simple solution.
where I am not creating any GPG keys , I just want to use key from other party and send the file encrypting their key in Nightly job.
This solution helped me , I was searching a lot for this .

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Comment from sahadev on 2010-08-24

2010-08-25T05:43:03Z

i can't understand about enscrypting and descrypting tha data so can't itbe written in simpler form

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Comment from Angus Bradley on 2010-08-04

2010-08-04T13:58:22Z

This is great, but PGP is a bit too complex for many - which is why we created http://safedrop.com - secure messages that self destruct. no techie knowledge required - and the recipient can *reply* securely as well!

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Comment from tomas on 2010-07-11

2010-07-11T13:38:53Z

I found a solution called WitchFile ( www.witchfile.com)

how about WitchFile ?

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Comment from Ram Narayan on 2010-06-20

2010-06-20T14:24:59Z

Use this portable PGP encryption based email client from Securebox.

http://www.securebox.co.nr

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Comment from John BM on 2010-05-22

2010-05-22T09:02:13Z

Check this link

http://www.fastpitchnetworking.com/pressrelease.cfm?PRID=41397

India based software company offers a dynamic encrypted emails solution

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Comment from Franco Russo on 2010-05-18

2010-05-19T02:29:10Z

077 emails, www.007emails.com offer a free encrypted message service with double encription, once the final recipient has read the Emails that you sent, that the Emails will self-destruct completely in less than seven seconds.

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Comment from opolis on 2010-04-30

2010-04-30T12:01:43Z

well, with opolis secure mail http://www.opolis.eu - a free service - messages are instantly encrypted and all required steps fully integrated. and, the sender decides what the recipient of a message is allowed to do with it ...

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Comment from ahmad on 2010-02-02

2010-02-02T21:11:41Z

to encrypt email visite
this site --- free

www.newatsys.com

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Comment from InstantCrypt on 2009-12-30

2009-12-30T22:25:05Z

Thanks Leo!

InstantCrypt, a free program that uses the above-described GnuPG (also called GPG) can be downloaded here:

www.instantcrypt.com

InstantCrypt is for entry-level and occasional users and lets you encrypt and decrypt e-mail without you having to go through the technicalities of GnuPG described above. You, and the person that you correspond with need InstantCrypt or a similar encryption program (such as PGP, GPG, or other programs using the OpenPGP standard). InstantCrypt runs on Windows only.

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Comment from Alexa Gerber on 2009-11-25

2009-11-25T13:40:44Z

I also have a encryption product. It basically just a software item. When you install it on your outlook there is a send secure button. You press that, a link is mailed to the recipient. A password is sms through to him and the recipient can then access the information. An email is then send through to the sender saying the package was delivered successfully. When the email is opened. The contact can either save the document, or as soon as it is closed it will be deleted immediately. You can download a 30 trail on www.securenvoy.co.za.

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Comment from Ed Gerck on 2009-11-15

2009-11-15T08:04:14Z

To send encrypted email with delivery notification and self-destruct, without requiring the recipient to setup or register, try free ZSentry Mail Basic at http://emailsecurity.zsentry.com/
(zsentry can also send using desktop email with SSL SMTP)

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Comment from Sally O'Boyle on 2009-03-27

2009-03-27T16:49:44Z

Thank you for your great post. Very informative. Unfortunately, GNU is impossible to use unless you can translate the install instructions. I can't. Not even close... Any other suggestions? I know about PGP and will end up buying that if there are no other ideas. Thanks!

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Comment from Sam on 2008-11-07

2008-11-07T20:03:12Z

I like the info of your website but I am trying to eliminate the prompt but when i type gpg --sign-key "name" it gave me this error
pub 1024D/41AFECB4 created: 2004-01-29 expires: never usage: SCA
trust: full validity: unknown
sub 1024g/693C2BF1 created: 2004-01-29 expires: never usage: E
[ unknown] (1). "keyname"

gpg: no default secret key: secret key not available

Key not changed so no update needed.

please help.

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Comment from Dave on 2008-09-23

2008-09-24T01:56:05Z

I would like to be able to use this program to send emails to and from my PDA. Is this possible? If so, can you please walk me through how to set this up. (I know nothing about programming).

Thank You,
Dave

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Comment from Clint on 2008-07-23

2008-07-23T15:39:47Z

In the above section Encrypting Data you mentioned "There are ways to confirm and avoid this message: Use this key anyway? (y/N) y� Can you please provide more details?

Thanks,
Clint

It's been a while, but I believe the approach is that after you import the public key you sign it to confirm that it is what it claims to be. Check the GPG/PGP docs for more on this.

-Leo

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Comment from Bob Janacek on 2008-02-26

2008-02-26T20:18:57Z

Or you can just use an service like http://www.certifiedmail.com and do away with key mumbo jumbo altogether.

And if you happen to have an X.509 certificate, you can still sign the message and send it to the recipient securely. The signing cert will be displayed to the recipient for non-repudiation, but the encryption happens without needing each recipient to have their own keys.

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Comment from RAGHUMADHULLA on 2007-08-16

2007-08-16T13:16:13Z

A LOT OF THANKS.REALLY IT IS EASILY UNDERSTANDABLE MANNER. IAM VERY PROUD TO VISIT YOUR SITE AND ALSO WILL BE LEARN MORE THINGS FROM YOUR SITE.VERRRRRRRRRY THANKS.

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Comment from Ingo on 2007-04-04

2007-04-04T08:17:24Z

You can avoid the assurance or trust problem by adding " --always-trust" to the command when encrypting... worked for me anyway ;)

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Comment from Matt on 2007-03-22

2007-03-22T13:46:49Z

This comment explains a way to avoid the message in the article stating "there is no assurance key belongs to the named user". Whether it is the "best" or even a good way is beyond my knowledge but I thought I would share what I have learned. As always with "all things secure", use at your liability!

I was receiving this message too when trying to use an imported public key from PGP (commercial "equivalent" of GnuPGP) on my GnuPGP machine. I ended up generating a key on GnuPGP and then "signing" the PGP key with my generated (and trusted) GnuPGP key with the following command:

gpg --sign-key "key name"

It prompted me with the following message:

"Are you sure that you want to sign this key with your key "my GnuPGP key name"

Really sign? (y/N)"

To which I responded "y".

To which it required the passphrase to unlock the secret key for my GnuPGP key.

To which I supplied.

I then ran the command to update my trust database:

gpg --update-trustdb

To which it found the PGP key (signed) but with no defined "trust" value. So it gave me the following:

"Please decide how far you trust this user to correctly verify other users' keys (by looking at passports, checking fingerprints from different sources, etc.)

1 = I don't know or won't say
2 = I do NOT trust
3 = I trust marginally
4 = I trust fully
s = skip this key
q = quit"

To which I answered (4) and was no longer prompted with the statement "...there is no assurance key belongs to the named user..."

Hope this helps others. If there's a way to do this without generating a local private key and using that to sign the public key and someone knows, please let me/us know.

Thanks.

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Comment from Mark on 2007-02-15

2007-02-15T10:07:08Z

I've used GPG for a while to secure important data stored on my PC. I haven't really used it in earnest for email encryption, though. The main reason is that it's a bit too cumbersome for most people to use. I'm now advocating a product called Private Post (http://www.privatepost.com/) to my friends and customers. It is fairly easy to install, bolts into Outlook and Outlook Express and provides an Explorer extended menu for encrypting files etc. locally as well as in emails.

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Comment from Leo Notenboom on 2007-02-09

2007-02-10T03:17:25Z

-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

It's been a while since I did it, but if I recall correctly it involves:

- - making sure that you actually have the proper key

- - signing that key youself

Signing it essentially tells gpg that "yes, I've verified that they key
belongs to who it claims to".

Leo
-----BEGIN PGP SIGNATURE-----
Version: GnuPG v1.4.6 (MingW32)

iD8DBQFFzTkiCMEe9B/8oqERAqWfAJ9AEbgr3OvW6Xt0aXGavJCf0ydT1QCfRS0/
EnYiNJC91aX5gHNlCBx01RI=
=oHeH
-----END PGP SIGNATURE-----

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Comment from Paul Tregunno on 2007-02-09

2007-02-09T16:35:19Z

You mentioned below that there are ways to avoid the question "use this key anyway?" when encrypting. I would appreciate further information on how:

Now they're ready to encrypt. That looks like this (encrypting the example file "example.xls"):

c:\>gpg -a --encrypt -r example@ask-leo.com example.xls
gpg: 1B917E56: There is no assurance this key belongs to the named user

pub 2048g/1B917E56 2006-03-08 Leo A. Notenboom
Primary key fingerprint: 8A4F 770F D037 D414 F4E6 B95C 6E89 72A3 874A 3EC1
Subkey fingerprint: 215A 55C8 C88A 2587 4E64 995C 5EFC 7E3F 1B91 7E56

It is NOT certain that the key belongs to the person named
in the user ID. If you *really* know what you are doing,
you may answer the next question with yes.

Use this key anyway? (y/N) y
Note the dire warning about making sure you know who's key you're dealing with. There are ways to confirm and avoid this message, but for now to keep things simple, we'll simply note that the Primary Key fingerprint listed here matches the fingerprint that was listed when you created the key, and answer "Yes".

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Comment from Rodrigo on 2006-11-10

2006-11-10T17:06:27Z

Hi, can I avoid the message "It is NOT certain that the key belongs to the person named in the user ID. If you *really* know what you are doing, you may answer the next question with yes.
" on encrypt?

thanks

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Comment from Christer on 2006-10-03

2006-10-03T13:51:20Z

You wrote:
Note the dire warning about making sure you know who's key you're dealing with. There are ways to confirm and avoid this message, but for now to keep things simple, we'll simply note that the Primary Key fingerprint listed here matches the fingerprint that was listed when you created the key, and answer "Yes".

How do I avoid the message?

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Comment from Leo A. Notenboom on 2006-07-31

2006-07-31T23:46:49Z

You need to make sure that the directory that GPG.EXE is installed in is in your PATH, or if you don't know what that is, make sure that you CD (Change Directoru) to that directory. For example:

CD "\program files\gnupg"

if that's where the program is located, and then the gpg command should work from there.

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Comment from Phil on 2006-07-31

2006-07-31T16:11:09Z

I don't know why, but I couldn't get Command Prompt to recognise 'gpg --gen-key'. I went to their sight(GnuPG) and non of the links that it looked like I needed to use seemed to work. I tryed for a long time too. Whats Up? I am new but I'm not totally brain dead... I hope. What am I doing wrong? I have been trying to work out this mail thing for way to long of a time. Hours of wasted time just going around in circles. Big Brother won't let us have private mail anymore? I am getting real bugged at Big Brother!

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Comment from Leo A. Notenboom on 2006-03-09

2006-03-09T18:15:31Z

Thanks on the typo. Fixed.

And yes, you raise a recurring theme that applies to any and all computers and data: if it's not physically serure - it's not secure.

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Comment from John on 2006-03-09

2006-03-09T17:33:17Z

Just a typo...
"meaning that an authorized person gets a copy,"

I presume that you mean an UNauthorized person.
---
and a comment...

At the end of the day, your client could toss the data on a CD and hand it to the nice FedEx/UPS/Mail person.

Sensitive data is only as secret as the trust you put in the transfer medium.

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Comment from Leo A. Notenboom on 2006-03-09

2006-03-09T17:05:54Z

Outlook and Outlook Express's security works fine, I'm sure. But it's not compatible, that I'm aware of, with other mailers or with GPP/PGP. The Outlook/OE solution has you purchasing digital certificates from Verisign, and using those to encrypt and/or sign your email.

PGP still exists, but they're also not free any more. GPG is a compatible, free, opensource alternative.

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Comment from Rodney on 2006-03-09

2006-03-09T11:59:24Z

What about the encryption built inot Outlook Express under tools... options... security? Doesn't that work ok?

What ever happened to PGP? I know it was bought, discontinued then restarted. Has it been discontinued again?

Rodney

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Comment from Leo on 2006-03-08

2006-03-08T21:36:01Z

Actually those are both *significantly* less secure. (Word in particular.)

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Comment from Ronny on 2006-03-08

2006-03-08T21:33:08Z

You can avoid all this by putting the information in a zip file that is compressed with a password. It's less secure than the above but usually good enough. You can also put it in a Word document and save that with a password. This is less secure still but very easy.

To get the password to your client, just use the phone.

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