Email and Encryption


  1. Do not use your work email address e.g. to pass on whistleblower material to politicians, journalists or bloggers.

    The Home Office (or other Government Department) , as your employer, is perfectly within its rights to analyse the log files of its own email systems. They do not need to wait for a "serious criminal investigation" which would require a Regulation of Investigatory Powers Act 2000 warrant signed by, wait for it, the Home Secretary, or as recently delegated under the Terrorism Act 2006, any nameless official that the Home Secretary delegates the renewal of long running intelligence agency or electronic interception warrants, which almost certainly include the "protection" of the Home Office IT systems themselves.

  2. If you are relatively very IT literate, you may be able to master how to send an email through a Mixmaster Anonymous Remailer chain, but, we suspect that the number of people who are confident enough to do this currently working at the Home Office and who might become whistleblowers is very small.

  3. Similarly, a whistleblower could use Pretty Good Privacy public key encryption, but again, this requires some effort to install the PGP software, on your own PC (not on your Home Office workstation !)

  4. PGP encryption could protect the content of of your correspondence with whoever you are whistleblowing to, but not the fact that your are in communication with say, David Davis, or the Sun newspaper or even a political blog.

  5. GPG - Gnu Privacy Guard is an open source version of PGP, compatible with most PGP keys (and vice versa), except for some of the old keys which used RSA public key and IDEA symmetric key algorithms, which the open source purists did not want to use, due to their patent status, despite "free for non-commercial use" licences.

  6. Unfortunately it is only Spy Blog and a few other technical security and privacy related blogs which publish a PGP Public Encryption Key, something which we encourage other bloggers, journalists and members of Parliament to do as well. - Spy Blog PGP public encryption key


A good compromise for the non-technical civil servant who wants to be a whistleblower could be a Hushmail account.

This has the advantage of being based in Canada, Ireland and the tax haven of Anguilla, and is a web based email system which uses the SSL/TLS encryption used to protect credit card and internet banking transactions from snoopers.

You may have to install the Sun version of the Java Runtime Environment if you have a recent version of Windows XP which no longer comes with Java installed by default.

  • Hushmail, as of mid-October 2006 now have a "No Java" or "Turn Java Off" option in their web page client. The encryption gets done at the server. The web browser to web server SSL/TLS https sessions remain, but are therefore at risk of a man-in-the-middle attack, whilst being immune from casual monitoring.

You can sign up for a free, anonymous Hushmail account, (with 2Mb of storage space) which needs to be accessed at least every 3 weeks to keep it active . You can pay about US $35 a year for a full account,which gives you a Gigabyte of email and document storage, and the very useful ability to create email aliases e.g., (but obviously this will leave a credit card trail with your name and address, unless you use the hard to trust e-gold payment system).

Hushmail to Hushmail traffic is strongly encrypted, but using Hushmail to say, email your Member of Parliament will be plaintext like other emails.

Hushmail do have a "pre-shared secret" challenge/response email system called Hushmail Express which can be useful for non-hushmail replies, but it is quite a bit less secure, although still a lot more secure than unencrypted email.

Whether or not it is safe for a whistleblower to use a Hushmail account from within their workplace, depends on the situation. Ideally this should be done from home or even a public cyber café etc. (unless the whistleblower feels that they are under directed surveillance i.e. being followed or observed).

Hushmail obviously complies with Canadian law

Hushmail have handed over emails probably stored in the online mailbox, and IP address logs as a result of a Canadian Court Order, at the request of the US authorities who were investigating a relatively minor anabolic steroid drug dealer.

Deleting your stored emails after you have read them, and always using the Java applet, still makes Hushmail more secure against electronic interception, than the more common web based email services.

See Wired magazine's investigation: Encrypted E-Mail Company Hushmail Spills to Feds

See also the April 2010 Wired article about the case of a senior US National Security Agency accused of leaking information to a Baltimore Sun newspaper reporter NSA Official Faces Prison for Leaking to Newspaper


Thomas Andrews Drake, 52, was a high-ranking NSA employee with access to signals intelligence documents when he repeatedly leaked classified information to the unnamed reporter, who ran stories based on the leaks between February 2006 and November 2007, the indictment alleges.

Fox News is reporting that the journalist was Siobhan Gorman, who worked at the time for the Baltimore Sun and is now a reporter with The Wall Street Journal, which is published by Fox parent corporation News Corp.

According to the indictment, Drake exchanged hundreds of e-mails with the reporter, and the two met in the Washington, D.C., area half a dozen times. Drake also researched stories for the journalist, sending e-mail to other NSA employees asking questions, and accessing classified documents to obtain information.

Drake even "reviewed, commented on, and edited drafts, near final and final drafts" of the reporter's articles, according to the government.


Drake opened a Hushmail e-mail account to contact Gorman, and volunteered to provide information about the NSA. Drake instructed the reporter to open her own Hushmail account so they could communicate covertly.

Hushmail is a Canada-based encrypted e-mail service that allows account holders to communicate securely with a client-side Java encryption applet. But Threat Level previously reported that the company has subverted its own encryption to help U.S. and Canadian authorities gain access to customer e-mail, in response to court orders. It's unclear if the FBI used that capability in investigating Drake.

Gorman agreed that information gathered from Drake would be attributed in articles to a "senior intelligence official" and that Drake would never be her only source for information.


The fact that a senior NSA official chose to trust Hushmail for his whistleblowing activities, is some sort of endorsement.

The proviso that he should not be the only source for any newspaper articles, is a wise one for whistleblowers dealing with the mainstream media.

However, perhaps "hundreds of emails" exchanged for more than a year, was rather too much use of that particular channel of communications ?

Presumably the FBI were snooping on all of the Baltimore Sun journalists, in order to try to track down the source of the NSA internal leaks ?

Hushmail and PGP

If you encrypt or sign and encrypt a message using your own PGP or GPG software, and then also use Hushmail to encrypt and or digitally sign your PGP message block inline in the body of the email, rather than as an attachment, this seems to cause problems for some versions of GPG software, due to an extra "-" and and extra " " space at the start of the encrypted block. Windows PGP software handles this ok, but various Linux open source and Apple versions of GPG do not. Either dispense with using Hushmail's digital signing, if you are already encrypting and signing with your local PGP key, or put any such messages or files into attachments rather than the inline body of the email message.

Please note: Hushmail only recognizes digital signatures on text messages that are signed using the Cleartext Signature Framework as described in RFC2440 section 7. Thus when sending to a Hushmail account you must sign the message first, generating a cleartext signed message, and then encrypt the result. If you encrypt and sign a message in a single step (the default for many PGP applications), the signature will not be recognized.

Gmail sessions are now encrypted by default

In response to the Chinese government hacking attacks on human rights activists Google gmaill accounts, the search engine giant has now (January 2010) switched on https:// SSL / TLS encryption by default.

See The Register article Google flips default switch for always-on Gmail crypto

Google mail also understands STARTTLS encryption between mail servers, so, for example a Gmail to Hushmail message will be encrypted all the way through, making interception by anyone other than the US or Canadian authorities unlikely.

Note that you Gmail Inbox and Sent folder, will still be unencrypted, and will be keyword searched by Google search engine software for Advertising Keyword (or Government watchlist) purposes.

Encryption does not mean Anonymity

Sending an email message which has been encrypted with PGP, or through a fully encrypted email service like Hushmail, or (now) mostly) encrypted one like Gmail, should preserve the Privacy of what is being sent, but it does not necessarily protect the anonymity of the whistleblower i.e. the when and to whom it was sent.

Neither Gmail to Hushmail, nor any other email system is immune from Communications Traffic Data retention, snooping and analysis i.e. which email account communicated with which other account, at what date and time, and how big a message was sent (which may be indicative of attached whistleblower documents etc.)

Obviously if you pay for an email service, especially through a Credit Card, then there will be a financial audit trail leading back to you.

Luckily, many "free" email accounts are available (with obviously limited functionality compared with the paid ones).

It is possible to set up a free Hushmail or Gmail or Hotmail or Yahoo mail etc. account, even through anonymising proxy services or Tor.

Such accounts based outside of the United Kingdom , and so make it more of an effort for the UK authorities to snoop on such email systems legally, especially during a whistleblower leak investigation, which does not qualify as being serious enough to invoke the national security ofr serious organised crime proportionality test under the Regulation of Investigatory Powers Act 2000 section 81 General interpretation

(3) Those tests are--

(a) that the offence or one of the offences that is or would be constituted by the conduct is an offence for which a person who has attained the age of twenty-one and has no previous convictions could reasonably be expected to be sentenced to imprisonment for a term of three years or more;

(b) that the conduct involves the use of violence, results in substantial financial gain or is conduct by a large number of persons in pursuit of a common purpose.


Wikipedia article on STARTTLS

STARTTLS is an extension to plain text communication protocols. It offers a way to upgrade a plain text connection to an encrypted (TLS or SSL) connection instead of using a separate port for encrypted communication.

STARTTLS for IMAP and POP3 is defined in RFC 2595, for SMTP in RFC 2487, and in RFC 4642 for NNTP.

A typical email header between two email servers which are using STARTLS encryption would include lines such as:

(using TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits))
(No client certificate requested)

EnigmaMail and OpenPGP

There is an easy to install plugin for the Mozilla Thunderbird email client called EnigmaMail. which is ,as it describes itself quite a "simple interface for OpenPGP email security"

This needs a copy of the Open Source version of the PGP software, available as a free free download from the Gnu Privacy Guard website.. Obviously there is source code for you to compile your own binary executable programs, and cryptographic checksums to show if the software has been tampered with etc.

However, for most of the people who are reading this article, there is GnuPG 1.4.10b compiled for Microsoft Windows. which is also easy to install.

The EnigmaMail setup wizard allows you to quickly generate a reasonable settings for generating your email encryption and signing key, and the software works well to import the PGP public keys of your correspondents, or to look them up on public PGP keyservers.

If you have difficulty in accessing the official websites for this software, then copies of the EnigmaMail plugin for Thunderbird 3.0 and the GnuPG software for Windows are available for download here.

General tips about encrypted email

  1. Remember that the Subject line of your email or the original Filename of any Attachment may not be encrypted, and may betray clues to a whistleblower leak investigation. Use something neutral for both of these, e.g. Attachment .doc , Attachment2.doc etc.

  2. Do not leave the Subject line Blank. Do not use anything that looks like spam e.g. "Viagra" or "Designer Watches" or "Poker" or "Important - Please read immediately" etc. as it might well be filtered out before it gets to your intended recipient.

  3. For extra security, do not store or write down your Email password or Encryption / Decryption passphrase, but memorise it.

  4. Choose a Strong Password or passphrase.

  5. As with many other web based services, if your Web Email service offers a "Forgotten Password" or Password Recovery or Reset option, then make sure that Answers to the Challenge / Response Questions are at least as strong as your actual password e.g. if the Question is "What is your mother's maiden name ?", you usually do not actually have to reply truthfully, or with a very short , easily guessed or easily password cracked answer. US Vice-Presidential candidate Sarah Palin's Yahoo email accounts were illegally accessed in this way in 2008.

Stored Email inbox and outbox

The laws in the UK and the USA and other countries, which protect unwarranted interception of email communications, are very specific,and really only apply to the actual email message in transit.

If your email is stored as a draft, awaiting to be sent, or copies are left undeleted in your inbox or outbox, either on your personal computer or on, for example a web based email service on like Hotmail, then the Police and Intelligence agencies do not usually need to get an Interception warrant, especially if they physically "seize" copies of the personal computer or email server hard disk storage systems for analysis.

Paradoxically, as was shown in the recent proper legal Operation Algebra investigation into child rape criminals in Scotland, shows that the UK authorities do not actually need to apply for any Court Order or get a warrant signed by the Home Secretary in order to get access to Foreign based email systems, e.g. Microsoft's Hotmail, based in California, USA.

See Spy Blog Operation Algebra child rape convictions in Scotland: open WiFi tracking, digital camera image forensics

Rennie's identity was revealed only after DI's Hood's team had invoked the International Mutual Assistance Treaty, which enabled Scottish investigators to request assistance from their American counterparts. An intervention by the FBI enabled the Edinburgh detectives to place a "preservation order " effectively freezing all the contacts, chatlogs and emails recorded on kplover's email account at the Microsoft offices in San Jose

i.e. although a Court Order in California was involved, this was entirely handled by the US authorities after the self-authorised Mutual Legal Assistance Treaty request by the Lothian & Borders Police, in secret, with no independent judicial oversight in the UK.

Obviously this is not much of a issue when dealing with serious criminals, but exactly the same mechanisms, and lack of privacy safeguards would come into play if a "whistleblower leak" inquiry was being handled by the UK Police or other Government agencies.

It would be wise for any whistleblower to make sure that they do not store copies of emails which they send or receive, to or from, journalists or bloggers or politicians or external ombudsmen or regulators etc. within their normal email or web mail systems.

Any copies which whistleblowers need to keep, should be in separate, strongly encrypted storage.

There is a technique, which might be effective if a particular email system is not under active surveillance at the time, which has been used since the very start of web based email systems, and which has been used (sometimes unsuccessfully) by terrorist suspects.

This involves composing an email message and storing it as a Draft, on the remote webmail server, but not actually Sending it. You then alert your recipient through some other means, e.g. a seemingly innocuous email message using a different account, or an SMS text message or some other sort of "Dead Letter Drop" signal (see Covert Channel Signals for Meetings or Dead Letter Drops

The intended recipient then logs into the same email account (you will have had to have shared the username and password credentials beforehand), in order to read and/or copy the information in the Draft. They will then Delete the Draft email when they have finished with it.

Ideally both the whistleblower and the recipient will have taken steps to hide their true IP Addresses as they access the web email site (see Tor - The Onion Router cloud of proxy servers, Open Proxy Servers, Virtual Private Networks etc.)

This technique can be used with many other systems, not just web email e.g. photo sharing or MP3 music sharing, and blogging websites etc.

RIPA and your Cryptographic De-cryption Keys

In the United Kingdom, the Regulation of Investigatory Powers ACt 200 Part III - Investigation of electronic data protected by encryption etc. has not been used against terrorists or drug smugglers etc., but it has been used against animal rights extremist activists and against mentally vulnerable people who stand up for their human right of privacy.

Any Police constable, can issue you with a RIPA section 49 notice, demanding either the plaintext of your encrypted files or messages, or the de-cryption key(s) so that they decrypt your intercepted emails, or encrypted computer files, which they have somehow got into their possession (either legally or illegally).

The legislation threatens you with up to 2 years in prison (and /or an unlimited fine) for not complying with such a section 49 notice, or up to 5 years in prison (and/or an unlimited fine), if the magic words "national security" are somehow weaseled into the investigation.

Tey can also impose secrecy over the fact or substance of a section 49 notice - a "tipping off" offence with a penalty of up to 5years and /or an unlimited fine.

This is all very deliberately vague and catch all.

It is a defence to claim that you have genuinely forgotten the PGP pass phrase, especially to an old Cryptographic key pair.

Appallingly for justice, the burden of proof falls on the accused, who has to prove his or her innocence, rather than be assumed to be innocent , with the prosecution having to prove guilt beyond reasonable doubt.

However, if you can show that you, as a human, rather than a machine, have never known the secret de-cryption key, e.g. for your SSL / TLS encrypted web browsing session, or the transient encrypted OpenPGP links between Tor server nodes or the STARTLS encryption between two email servers which you are not the systems administrator for or any other other ephermeral encryption, then you have a reasonable chance of defending yourself in Court.

Of course, your life will have been ruined by arrest / DNA sampling / Fingerprinting and criminal intelligence database records which are retained for ever, even if you are found not guilty in Court.

About this blog

We know that there are decent, honest, trustworthy individual politicians, civil servants, law enforcement, intelligence agency personnel and broadcast, print and internet journalists etc., who often feel powerless or trapped in the system. They need the assistance of external, detailed, informed, public scrutiny to help them to resist deliberate or unthinking policies, which erode our freedoms and liberties.

Some of these people will, in the public interest, act as whistleblowers, and may try to leak documents or information to the mainstream media, or to political blog websites etc.

Here are some Spy Blog "Hints and Tips", giving some basic preecautions, and some more obscure technical tips, which both whistleblowers, journalists, and bloggers need to be aware of, in order to help preserve the anonymity of whisteleblowing or other journalistic sources, especially in the United Kingdom, but applicable in other countries as well.

Whistleblower anonymity may not always be possible, or even necessary, forever into the future, but it is usuially crucial during at least the early stages of a "leak", whilst it is being evaluated by others, to see if it merits wider publication and publicity.

Email & PGP Contact

Please feel free to email your views about this blog, or news about the issues it tries to comment on.


Our PGP public encryption key is available for those correspondents who wish to send us news or information in confidence, and also for those of you who value your privacy, even if you have got nothing to hide.

You can download a free copy of the PGP encryption software from
(available for most of the common computer operating systems, and also in various Open Source versions like GPG).

We look forward to the day when UK Government Legislation, Press Releases and Emails etc. are Digitally Signed so that we can be assured that they are not fakes. Trusting that the digitally signed content makes any sense, is another matter entirely.


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CryptoParty London

CryptoParty London

Most months there is a CryptoParty London event. where some of these Hints and Tips and other techniques are demonstrated and taught.

Usually at:

Juju's Bar and Stage 15 Hanbury St, E1 6QR, London

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