CryptoMailer User Guide
Contents
1. CryptoMailer Uninstall Warming During the uninstall of CroptoM ailer you will loose your passwords To avoid this CryptoM aller allows you to export them What do vou wish to do 7 CryptoMailer User Guide Copyright TheGreenBow 2009 Contacts Contacts 38 6 Contacts 6 1 Contacts Information and update are available at www thegreenbow com Technical support by email at support thegreenbow com Sales support by email at sales thegreenbow com CryptoMailer User Guide Copyright TheGreenBow 2009 Secure Strong Simple TheGreenBow Security Software Copyright TheGreenBow 20092. TheGreenBow CryptoMailer User Guide Contact support thegreenbow com Website www thegreenbow com Copyright TheGreenBow 2009 CryptoMailer User Guide Copyright TheGreenBow 2009 All rights reserved No parts of this work may be reproduced in any form or by any means graphic electronic or mechanical including photocopying recording taping or information storage and retrieval systems without the written permission of the publisher Products that are referred to in this document may be either trademarks and or registered trademarks of the respective owners The publisher and the author make no claim to these trademarks While every precaution has been taken in the preparation of this document the publisher and the author assume no responsibility for errors or omissions or for damages resulting from the use of information contained in this document or from the use of programs and source code that may accompany it In no event shall the publisher and the author be liable for any loss of profit or any other commercial damage caused or alleged to have been caused directly or indirectly by this document Printed f vrier 2009 in San Francisco Table of Contents Part I Introduction 2 1 WAV and HOW tO enc D ea nee ee 2 2 F diUleS ili 3 Part Il Getting Started 6 i InSsfallation lei dia FEIENNDEERTSRDERPESERTENSEESSERN 6 2 Installation Problems sese ssssscsss sees s sese sees seene e
3. e allows to View or Decrypt the file when receiving encrypted file as shown below tE Private ppt Note CryptoMailer does not allow to add a file into an encrypted file i e received via email If so the following warning window will popup You can not include the file C Users cl Desktop file max because it is an encrypted file 4 7 Adding a text message The text area can be used to enter a message memo in addition to the filesyou want to encrypt This text message will be encrypted together with the files before sending by email All cut copy paste operations are allowed in the text area CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 24 4 8 No further distribution please See at staff meeting John Cut Copy Paste Delete Select All Right to left Reading order Show Unicode control characters Insert Unicode control character Password Pa Open IME Reconversion When the Answer button is activated after receiving an encrypted email the text area reproduces the text of the sender with the gt sign and indicates the names of the files received gt gt Please find our presentations gt for our customers Encrypt Decrypt Send View Depending on the context CryptoMailer proposes several actions via several buttons e Decrypt file when receiving an email e When replying to an encrypted email e When sen
4. 12 C3 CryptoMailer Activation O Software Actrration Step 2 of 2 Processing Activation Software successtully activated C3 CryptoMailer Activation O Software Activation Step 2 of 2 Processing Activation A Activation Error Activation error code 54 Cannot connect to the activation server Check if no firewall filters the activation communication ar if MOU are using a Proxy In case of network connection problem during activation error 53 or 54 you can return to previous page to configure a proxy CryptoMailer User Guide Copyright TheGreenBow 2009 Activation 13 C3 CryptoMailer Activation O Software Activation Step 1 of 2 Welcome in the Software Actrvation Process To activate this software please enter your license number and your email in the fields below then click on Activate Licenze number 123456 78904AB CDEF12 345678 Email address mymail company com le g malltacompany com Warning this email address 12 used to send you the activation confirmation Please make sure itis a corect address a To configure a proxy click here To configure the proxy enter the proxy address and port access in the window below The address of the proxy may be either an IP address or DNS The port is a number between 0 and 65535 Typically the value of the port 80 HTTP port K Proxy Configuration If you are Using a Proxy Server to conn
5. e Rule1 Use a long password at least 6 characters 10 is the perfect length that could ease brute force attacks e Rule2 Do not be limited to lower case alphabetic characters Use upper and lower case characters numbers special characters 8 or accents C e Rule3 Avoiding the use of words or names related to your private life name of daughter date of birth or too conventional password admin toto etc that could ease dictionary attacks 4 5 Password Management This window is accessible either via Password button on the main interface or through the menu Configuration gt Password list The Password management allows to add delete import and export passwords contact contactia company com 1 Adding a password Click on the New button CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 20 Hew password Mame Password gt Confirm Email inda company com e Enter the Name used to represent the password in the list The password itself will never be displayed This Name is typically the recipient s name e Enterthe password in the Password and then enter it twice in Confirm field See also rules of security in the composition of the password e Enterthe email address that will be used to send email This email will be automatically included in the recipient of the encrypted email This field is optional
6. the secret to decipher them MAXI CUSISTECH 05 994 0016 1 7132E916 ba Y EHSHt UO IE 9 Tale ol C ALGO ERCVEA 1 Maa D gt EOaE FILEDocument tet Ir nog Du fol 2063Ms 250Pi 071 p dxwCE 00 114 m snigti b i No liz t h DCN O AMD AGE arm pi ELL A tAit We a 460418 8 Je SEA led Pr OYWTiOwAgIr WILT phar ptei Liel loe rPLi Oye E tuyuim JA Pi lv Jr 4d ABg An iks sJIh Wrapett GpprAvst jaa EKL BQ y pea i218t 45 i Ega 11 658 Es MS JATSPDEIZ SI YwAAOU 1 1_ Ezivt ti gt How to encrypt Whenever a file is encrypted by CryptoMailer a random key is created This key is protected by a protection key derived from a user password This password can be chosen from the list or entered manually This way the same document encrypted several times with the same password gives different results It is therefore impossible to decrypt a document for someone who does not know the password Brute force To find the password a method of brute force can be used This method consists of trying all possible strings So depending on complexity of the password the brute force method is quickly becoming useless due to the extremely high number of combinations to test Assuming the password k5L y P To find this password composed of eight characters an attacker must try all possible codes between 1 and 8 characters to have the chance to find it Consider that there are 112 charac
7. Mailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 22 Save in E a 9 da E ey Esl Name Date modified IE Contacts 6 18 2007 8 04 PM File I Desktop 1 7 2009 11 29 AM File Documents 1 7 2009 8 11 AM File I Downloads 12 23 2008 11 51 File IE Favorites 6 19 2007 4 55PM File PH Links 8 17 2007 11 45 AM File MS Music 6 19 2007 4 58 PM File Pictures 12 22 2008 5 39 AM File CA A ee d B R d Save as type CryptoMailer Contacts File dat 5 Import one or several passwords CryptoMailer can import passwords These passwords had to be exported by CryptoMailer software To import passwords click on Import button select the file containing the passwords CryptoMailer then asks the password used to encrypt the file Gi Import Contacts dat A password i required to import this new contact file Password Ga Passwords contained in the file are then added to the list of the passwords 4 6 List of attachments The list of attachments area shows all the files you have added to be encrypted as shown below CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 93 1 Add one or several files to the list e using a simple drag amp drop of your file onto the window anywhere e using the Browse button 2 Contextual menu with right click on any files e allows to Remove the file from the list when sending encrypted files
8. an be opened e By double clicking the file CryptoMailer will open its decryption interface e By right clicking on the file and selecting the menu Decrypt CryptoMailer will decrypt the CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 33 file on the disk If the password used to encrypt the file is part of the list of passwords CryptoMailer immediately decrypts the file without asking the password to the user CryptoMailer User Guide Copyright TheGreenBow 2009 Un installation Un installation 35 5 Un installation 5 1 Un installation Uninstalling CryptoMailer can be done via the Windows Start menu or via the Windows Control Panel 1 Windows Start menu e Select Programs gt TheGreenBow gt CryptoMailer then CryptoMailer uninstallation de TheGreenBow CryptoMailer C3 CryptoMailer 4 51 Bi CryptoMailer help 2 Uninstall CryptoMailer 4 Back 2 Windows Control Panel e Select Add Remove Programs e Select CryptoMailer and click Add Remove e Validate uninstallation windows CryptoMailer Uninstall Uninstalling warns the user that he risks losing all its keys It may then as shown below e Stop the uninstallation and export its passwords e Continue uninstalling without saving the passwords e Cancel uninstallation CryptoMailer User Guide Copyright TheGreenBow 2009 Un installation 36
9. ding an email CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 95 e When opening an encrypted file e When decrypting an encrypted file e When viewing an encrypted file 1 Send an encrypted email By clicking Send the default messaging software open an email window all files from the list and text are grouped into a single encrypted file and attached to that email The email is fully formatted ready to be sent The email is set with the recipient email address his name if configured in the list of passwords email subject as encrypted file a signature in the email body and the encrypted file attached as shown below file max File Edit View Options Tools Help JARA Send Contacts Spell Attach Security Save From mymail company com nts 45 mycontact company com Subject File encrypted with CryptoMailer To decrypt the attached files download Cryptomailer software for free from http www thegreenbow com cryptomailer The signature in the email body can be changed at any time To change it you need to modify mail txt available in the CryptoMailer install directory Note The messaging software that CryptoMailer starts is the one defined by default in Windows To see which one is set as default go to Control Panel gt Internet Options gt Programs tab then Internet Programs gt Settings 2 Decrypt an encrypted file CryptoMailer Us
10. e Click OK 2 Delete one or several password To remove a password select one or several passwords from the list and click Delete To prevent the user to accidentally delete passwords the next window asks for confirmation 3 Modify password To change a password double click on any password into the list or select it and click Modify Each field can be changed individually CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 21 Modify Password Mame Linda Password Confirm ka Email inda company com 4 Export one or several passwords CryptoMailer allows you to export all or part of the list of passwords in order to share them more easily As the export is secured with specific password communicating a list of password can even be done by email To export passwords select one or several of them from the list and click on Export CryptoMailer asks for your password that will be used to encrypt the file exported It is possible to export only passwords selected Selected or all passwords All Password export Enter the password to protect the exported file then choose all or selected if you want to export all pour passworde or only those selected Password 262 ed Hide password Se safety rules concerning the composition of the password Select directory to save the export file called emicontacts dat by default Crypto
11. e number an orange banner shows the number of days remaining About CryptoMailer ft TheGreenBow CryptoMailer Copyright E TheGreenBow 2009 WIN thegreenbow com V 4 51 002 Check for Update License 123456 789046 CDEF12 345678 Email mumal icompan com Powered by The Green Bowl 4 10 Access control Access to CryptoMailer can be restricted by a password To enable password protection select the Configuration gt Access Control See also rules of security in the composition of the password CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 30 C3 CryptoMailer A Crypto ailer Access Control Ie Activate the CruptoMailer User Authentication Current i Mer Fe Confirm 5 Enter your password and click Ok In case the password has been set already click Modify A confirmation or warning window pops up 4 The password ts different from the confirmation 8 Please retry with a new password Warning There is no way to retrieve lost password 4 11 Options CryptoMailer options are the following e Always on top e Ask before quiting e Encryption algorithm AES or 3DES CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 31 To access Options go to Configuration gt Options Ask before quitting Cryptography Encryption algorithm AE C 4 12 Drag amp Drop To encryp
12. ect to the Internet please enter below the address and the port of this Proxy Server Proxy address I 92 168 100 17 Proxy Port g CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer Using CryptoMailer 15 4 4 1 Using CryptoMailer Launching CryptoMailer software can be launched in several ways 1 from the desktop by double clicking on its icon TheGreenBow CryptoMailer 2 from quick launch on the taskbar CryptoMailer 3 from Windows Start menu gt Programs gt TheGreenBow gt CryptoMailer p TheGreenBow CryptoMailer gt G CryptoMailer 4 51 EE CryptoMailer help C Uninstall CryptoMailer 4 Back Start Search 4 via double click on any encrypted file with max extension A Filet 1 mas a File max 5 via right click on a file and selecting Encrypt and Send or Encrypt i e contextual menu CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 16 confidential doc Edit New Print Convert to Adobe PDF Convert to Adobe PDF and EMail Combine supported files in Acrobat eP Pe Encrypt and send Encrypt El Scan Open With 4 2 Navigating CryptoMailer Once started CryptoMailer presents several areas Mens Contextual Help List of attachments Browse files to attach Text editor accompanyi
13. er Guide Copyright TheGreenBow 2009 Using CryptoMailer 26 The user can decrypt an encrypted message located on a drive The Decrypt button allows to select the directory where to decrypt the file in A password is required to decrypt the file Password Note When decrypting a file text message in the text area will be saved into a file called file txt in the same directory 3 Reply to an encrypted email When the Answer button is activated after receiving an encrypted email the text area reproduces the text of the sender with the gt sign and indicates the names of the files received gt gt Please find our presentations gt for our customers 4 Encrypt a file on the disk It is possible to encrypt a file on the disk via a right click on the document and then click on Encrypt CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 97 Open Edit New Print Convert to Adobe PDF Convert to Adobe PDF and EMail Combine supported files in Acrobat EP of Encrypt and send Encrypt Scan Open With K Note CryptoMailer do encrypt directories 5 Viewing to an encrypted email It is possible to view encrypted file via right click on it and click on View Open R View Decrypt Open With K Software will ask password to decrypt this file or it will find automatically in the contact list if
14. exists already C3 View f le max A password is required to view the file Password ie 6 Opening CryptoMailer to see which document and text have been received It is possible to open CryptoMailer with an encrypted file to see what text and document it contains via double click on the encrypted file and click on Open CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 28 4 9 About The About menu is accessible through the menu the main interface It provides information about the software e The software release number e The license number and email when software is activated e Check for Update can check on the TheGreenBow website the availability of an software update About CryptoMailer Copyright TheGreenBow 2009 a thegreenbow com V 4 531 002 Check for Update License 123456 789046 CDEF12 345678 Email mumal icompan com Powered by The Green Bowl If the software is in evaluation period an orange banner shows the number of days remaining CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 29 About CryptoMailer da Pox Software under evaluation 23 days remaining TheGreenBow CryptoMailer Pi Copyright TheGreenbow 2009 many thegreenbow com Y 4 51 002 Check for Update Licenze Evaluation version Powered by The Green Bowl If the software uses a temporary licens
15. ng memo Choice of password Id password Used A See also e Menus e List of attachments e Adding a text message e Choice of password e Action button like Send CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 17 4 3 4 4 Menus 1 File Menu The File menu is a contextual menu e During decryption of email the File menu proposes to Decrypt as into a directory e Inthe email encryption the File menu proposes Encrypt as into a directory The File gt New menu can also empty the text and the file areas 2 Configuration Menu The Configuration menu allows the following features e Access to Password lisi e Protection CryptoMailer software with Access Control e CryptoMailer Options settigns 3 2 Menu The menu allows the following features Access to Help Access to online support Online Software Activation this menu disappears once activated About windows Password choice CryptoMailer has an intuitive management of passwords The choice of a password is immediately accessible from the Password button on the main interface To use a password simply select from the list The drop down menu associated with the Password button offers at any moment e A list of already defined passwords CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 18 e To acccess to the managemen
16. nnenen enen ennenen nenen 8 Part III Activation 10 AS AP AA 10 2 SO Ware ACUVALON aes arse iaia 11 Part IV Using CryptoMailer 15 E A nn iaia 15 2 Navigaling CryptoMalleft clinici 16 3 MENUS S basti n 17 A PassWOrd CHOICE AAA 17 5 Password Management sms diaria 19 BRET CT 22 7 Adding A a MesSade es ee R S 23 8 Encrypt Decrypt Send VIEW LL 24 Y ADOUL ciale 28 10 ACCESS CONTO uscar ic 29 11 Opliions ree O di See neo eer ee nee 30 12 DO S Db TEH 31 13 Ore ai gt 40 Meal lla 31 14 Receiving an encrypted file by email rr 32 15 Opening an encrypted file sssss sss venier eenn 32 Part V Un installation 35 TUN IAS TA MA ON HHT 35 Part VI Contacts 38 1 CONMCS lai 38 Index 0 CryptoMailer User Guide Introduction Introduction 2 1 Introduction 1 1 Why and how to encrypt Why encrypting emails The emails you send today are transmitted over the Internet machine to machine without any protection or privacy exactly like postcards Thus your colleagues your email administrator your access provider equipment which provide for the transit of data over the Internet the provider of your correspondent his email administrator his Staff all those equipments or people may read your emails Using CryptoMailer your messages will be encrypted So your messages can be intercepted but they are unreadable except for your recipient who holds
17. nstallation The installation of CryptoMailer done in launching the installation software C3 CryptoMailer Setup Installation lanquage Choose the installation language The installation of CryptoMailer takes into account a previous version already installed The configuration of the previous software release passwords license number etc is automatically preserved by installing the new release CryptoMailer User Guide Copyright TheGreenBow 2009 Getting Started 7 C3 CryptoMailer Setup Welcome in the Crypto ailer installation This program ig going to install CryptoM aller 4 51 To start the installation click on Nest Important The installation automatically generates a secret bi key The secret is stored encrypted in the CryptoMailer installation directory in the file prv However it is recommended to save this secret on another medium disk drive USB key etc For any recovery of files the secret is mandatory before contacting our techsupport The installation ends with the option to launch and activate the software C3 CryptoMailer Setup Cryptoki aller Setup successfully completed CmpptoMaller is successfully installed on your computer lF you want to run the software please check the box below i Run Creptobd ailer CryptoMailer User Guide Copyright TheGreenBow 2009 Getting Started 2 2 Installation Problems During installation
18. pt anymore TOU can order the software to receive a license or activate the software if you already own a license Cancel CryptoMailer User Guide Copyright TheGreenBow 2009 Activation 11 Order to purchase a software license online Once purchased the software license is automatically and immediately sent by email See activation 3 2 Software Activation CryptoMailer software can be activated at any time including after the evaluation period from the menu of the main interface gt Software Activation Software Activation requires a license number and an email address used to send an activation confirmation Simply copy the license number then click on one of 4 input fields and paste Ctrl V the license number C3 CryptoMailer Activation O Software Activation Step 1 of 2 Welcome in the Software 4Actration Process To activate this software please enter your license number and your email in the fields below then click on Activate License number 123458 729048 CDEF12 345678 Email address mymail company com le g malltacompany com Warning this email address 12 used to send you the activation confirmation Please make sure itis a corect address The activation is an exchange with TheGreenBow Online Activation Server When this exchange succeeds the activation is complete CryptoMailer User Guide Copyright TheGreenBow 2009 Activation
19. t a file simply drag amp drop a file from Windows Explorer anywhere onto the CryptoMailer window The file will be added to the list of attachment 4 13 Contextual menu One or several files can be encrypted and sent by email via a right click as shown below Encrypt will encrypt the files in the same directory Encrypt and Send will open CryptoMailer with the files in the file area Decrypt will decrypt the files in the same directory View will open the document assuming the required password is already known in your password list If not a popup will ask for the password CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 32 T Convert to Adobe PDF Convert to Adobe PDF and EMail fi Combine supported files in Acrobat 1 Encrypt and send B Encrypt I u View SEI R Decrypt Open With K Open With K To encrypt a password need to be selected A password is required to encrypt the file Password 36263 es Hide password 4 14 Receiving an encrypted file by email When a message Is received in the email software opening the attachment automatically starts CryptoMailer with the text and list of files in the encrypted file If the password used to encrypt the file is part of the list of passwords CryptoMailer immediately decrypts the file without asking the password to the user 4 15 Opening an encrypted file A file encrypted locally on the hard disk c
20. t of passwords List to add change or delete a password e To enter a password manually without picking it from the password list Manual 1 Choosing a password in the list CryptoMailer will store an unlimited number of passwords Once stored see Management oasswords they are not readable You can associate the name of email recipient you are going to send email to Saving passwords and recipient names allows the software to find automatically the right password for each decryption when decryption is requested 2 Entering password manually menu Manual When the mode Manual is selected the box on the right button becomes active and allows to enter a password manually without picking it from the password list The length of the password is unlimited All the characters are allowed uppercase lowercase numbers special characters or accents Moreover the mix of characters is one of the safety rules in the composition for a password This mode is useful when the user does not wish to keep track of this particular password in the future Please find attached the confidential presentations Password Hide password 3 Rules composition of a password To ensure a good level of safety in protecting access to software or data encryption it is recommended to follow certain rules of composition of a password CryptoMailer User Guide Copyright TheGreenBow 2009 Using CryptoMailer 19
21. ters easily accessible by a computer keyboard the tiny capital letters numbers accented characters punctuation and other symbols There is no less than 2 5 x 10e 16 codes of eight characters 25 million billion Assuming that the pirate has a system of computers that allows him to test and verify a million codes per second it will have nearly 800 years to test all possible codes CryptoMailer User Guide Copyright TheGreenBow 2009 Introduction 3 1 2 Dictionary For obvious reasons there are few people who choose a password like k5L y P The hackers thus prefer another method called Dictionary attacks In a dictionary attack hackers do not test a sequence of random characters but likely channels all words of the English language names names and their combination with some figures e g Virginia and Jerusalem will be systematically tested and probably virginie35 too Such dictionaries exist in all languages and are fairly easy to find on the internet Therefore assuming that the dictionary includes 50000 words it would need a sentence of at least 3 words to obtain a satisfactory level of security Indeed there are 2 5 billion possible combinations of two words among 50000 With a computer system capable of achieving 1 million operations per second it will take less than 42 minutes to test them all Anyway even if the string is longer strongly holidays protects much less that k5L y P B
22. the CryptoMailer files and directories are created It may happen that some files could not be created if they already exist If so the user will be displayed a warning popup window with the file name Finish the installation delete that file and start the software installation over again CryptoMailer User Guide Copyright TheGreenBow 2009 Activation Activation 10 3 Activation 3 1 Evaluation period CryptoMailer software should be activated before the end of his evaluation period 30 days Without activation the software CryptoMailer continues to operate beyond its evaluation period but can not encrypt anymore It can only decrypt During the evaluation period the following window pops up for each encryption Warning 30 days remaining before the end of the evaluation period At the end of this period this software won t be able to encrypt It will enable only to decrypt f have a license number want to activate CryptoMailer Enter your licenze number to automatically activate Crypto ailer This procedure only takes a few seconds Do you need a licenze number 7 Buy it online want to continue the evaluation of Cryptok ailer Once the evaluation period has expired the following message appears when the user wants to perform encryption C3 CryptoMailer Evaluation er Evaluation Period Over four evaluation period ls over This software can now only decrypt files It cannot encry
23. ut without doubt strongly holidays provides an adequate level of protection for day to day operations Recommendations It is recommended that meet certain safety rules concerning the composition of passwords Features CryptoMailer is a tool for encryption of files and messages designed around simplicity of use Less than a minute after installation you send your first encrypted email CryptoMailer is accessible to encrypt via drag amp drop of a file by the contextual menu of Windows Explorer or by automatic opening from any messaging software CryptoMailer encrypts a 3DES or AES 128bit lists of files with short text message CryptoMailer User Guide Copyright TheGreenBow 2009 Introduction 4 Please find attached the confidential presentations h 4 S wate ata ata ata ata ata aa aa Confirm i Hide password CryptoMailer is designed to work with any messaging software e g Outlook Lotus Notes Netscape Messenger Eudora Pegasus etc Summary Attach short text message Work with any messaging software Integration into Windows drag amp drop context menu Contact and password management Encryption 3DES AES 128 bit Compression Automatic identification password used Multi file encryption Import export of passwords Access Control CryptoMailer User Guide Copyright TheGreenBow 2009 Getting Started Getting Started 6 2 Getting Started 2 1 I
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