securing novell groupwise through ssl and s/mime

109
Securing Novell® GroupWise® through SSL and S/Mime Dirk Giles GroupWise Software Engineer [email protected] Mukesh Jethwani Novell WorldWide Support Engineer [email protected]

Upload: novell

Post on 10-May-2015

6.689 views

Category:

Technology


4 download

DESCRIPTION

Novell GroupWise has always been known for its security, but there's even more you can do. Attend this session to learn about areas that are frequently overlooked in the security of Novell GroupWise environments. With the help of product demonstrations, participants will learn how to implement secure LDAP authentication, how to enhance the security of GroupWise communication with SSL and how to roll out S/MIME to GroupWise users.

TRANSCRIPT

Page 1: Securing Novell GroupWise through SSL and S/MIME

Securing Novell® GroupWise® through SSL and S/Mime

Dirk Giles GroupWise Software [email protected]

Mukesh JethwaniNovell WorldWide Support [email protected]

Page 2: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.2

Agenda

• LDAP authentication and Novell® GroupWise® Post Offices

• Novell GroupWise Agents and SSL

– Certificate Generation

– Installing and Enabling SSL

– Securing GWIA and WebAccess agents

• Secure Internet Email with S/MIME

Page 3: Securing Novell GroupWise through SSL and S/MIME

LDAP Authentication

Page 4: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.4

Why Use LDAP Authentication?

• Uses user's directory password

– Minimizes password management requirements

– Supports password policies (Bind Mode)

– Less passwords for the user to remember

• Can authenticate to other LDAP directories

• Requires that users connect to the directory

– Note: Directory accounts without a password will not require a password, even with a High Security Post Office

Page 5: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.5

LDAP Authentication Planning

• LDAP Server information

– Use SSL or not?

> SSL key file

– IP Address or name of LDAP server

– LDAP port for LDAP server

– User authentication method

> Bind

> Compare

Page 6: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.6

LDAP Authentication Planning Part 2

• Use proxy user?

– Access the directory with limited rights

– Need distinguished name (DN)

– Need password

• Allow users to change password?

– Novell® GroupWise® Client Change Password dialog

Page 7: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.7

Export LDAP CertificateWhich One?

Page 8: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.8

Export LDAP CertificateCertificate Properties

Page 9: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.9

Export LDAP CertificateExport Wizard – No Private Key

Page 10: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.10

Export LDAP CertificateExport Wizard – Output Format and Filename

Page 11: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.11

LDAP Server ConfigurationNovell® GroupWise® System Tools

Page 12: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.12

LDAP Server ConfigurationLDAP Server List

Page 13: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.13

LDAP Server ConfigurationLDAP Server Options

Page 14: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.14

Post Office ConfigurationSecurity Settings

Page 15: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.15

Post Office ConfigurationLDAP Server Selection

Page 16: Securing Novell GroupWise through SSL and S/MIME

LDAP Authentication Demonstration

Page 17: Securing Novell GroupWise through SSL and S/MIME

Securing Novell® GroupWise® with SSL

Page 18: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.18

Novell® GroupWise® Security and SSL

• Enhances native messaging encryption

• Ensures secure communication between the Post Office Agent and clients

• Ensures secure communication between the Novell GroupWise agents

• Secures Web Console and WebAccess

Page 19: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.19

Where Do I Start?

1. Get a certificate!

– Generate a Certificate Signing Request (CSR)

> Each separate server should have its own

> Agents running on the same server can share

Page 20: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.20

Generate Certificate Signing RequestNovell® GroupWise® Generate CSR Utility (GWCSRGEN)

Page 21: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.21

Request the Certificate

• Submit the certificate signing request to a certificate authority

– Trusted Certificate Authorities

– Online submission mechanisms

– Create your own

Page 22: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.22

Create a Certificate

• Novell Certificate Server™ and Novell® eDirectory™

– ConsoleOne®

> Requires the Novell Certificate Server snap-in

– iManager

> Requires the Novell Certificate Server plug-in module

• YaST on Linux

– Novell Open Enterprise Server

– SUSE® Linux Enterprise Server

Page 23: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.23

Create a Certificate usingNovell Certificate Server™

• Enter certificate signing request

• Select key type and usage

• Select validity period

• Select output format and filename

Page 24: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.24

Issuing a Certificate with ConsoleOne®

Issue Certificate Wizard

Page 25: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.25

Issuing a Certificate with ConsoleOne®

Enter certificate signing request

Page 26: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.26

Issuing a Certificate with ConsoleOne®

Select key type and usage

Page 27: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.27

Issuing a Certificate with ConsoleOne®

Select validity period

Page 28: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.28

Issuing a Certificate with ConsoleOne®

Select output format and filename

Page 29: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.29

Issuing a Certificate with YaSTEnter Certificate Authority

Page 30: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.30

Issuing a Certificate with YaSTSelect Export to File

Page 31: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.31

Issuing a Certificate with YaSTSelect output format and filename

Page 32: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.32

Issuing a Certificate with YaSTSave certificate

Page 33: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.33

Issuing a Certificate with YaSTSave key

Page 34: Securing Novell GroupWise through SSL and S/MIME

Certificate Generation Demonstration

Page 35: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.35

Install the Certificate

2. Install the certificate!– Use ConsoleOne® to designate the certificate

and key paths– Enter the password of the key file

Page 36: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.36

Configure AccessNetwork Access Tab

3. Enable SSL and configure access– Disabled, Enabled, and Required– Internal versus External

Page 37: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.37

Equivalent Command Line Options

Page 38: Securing Novell GroupWise through SSL and S/MIME

GWPOA CertificateInstallation Demonstration

Page 39: Securing Novell GroupWise through SSL and S/MIME

Securing Novell® GroupWise® Internet Agent

Page 40: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.40

Securing the Novell® GroupWise® Internet Agent with SSL• Secure Connections to other SMTP hosts

• Secure Connections for POP/IMAP clients

• Secure Connections to WebConsole

– SSL Enabled or Required for the above?

Page 41: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.41

Securing the GWIA with SSLInstall the Certificate

Page 42: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.42

Securing the GWIA with SSLEnabling SSL

Page 43: Securing Novell GroupWise through SSL and S/MIME

Securing Novell® GroupWise®

Internet Agent Demonstration

Page 44: Securing Novell GroupWise through SSL and S/MIME

Securing Novell® GroupWise® WebAccess

Page 45: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.45

Securing WebAccess with SSL

• Securing WebAccess Agent - WebConsole

• Securing WebAccess Application (Apache/IIS)

Page 46: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.46

Securing WebAccess AgentInstall Certificate

Page 47: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.47

Securing WebAccess AgentEnabling SSL

Page 48: Securing Novell GroupWise through SSL and S/MIME

Securing WebAccess Agent Demonstration

Page 49: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.49

Securing WebAccess ApplicationLinux - Apache

• Modify /etc/sysconfig/apache– APACHE_SERVER_FLAGS=” SSL”

• Modify /etc/apache2/vhosts.d/vhost-ssl.conf

Page 50: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.50

Securing WebAccess ApplicationLinux - Apache

• Restart apache2 by typing “rcapache2 restart”

• If the Private Key has a password restarting apache will ask for the password during the restart. Follow the step listed below to remove the password from the Key file

– openssl rsa -in gw.key -out gwu.key

– Also protect gwu.key by making sure only root can read gwu.key by typing “chmod 700 gwu.key”

• Modify the /etc/apache2/vhosts.d/vhost-ssl.conf with the unencrypted key file

Page 51: Securing Novell GroupWise through SSL and S/MIME

Securing Apache on Linux Demonstration

Page 52: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.52

Securing WebAccess ApplicationNetWare® - Apache

• Apache on NetWare by default enables SSL but uses the internal Certificates

• Follow TID 3033173 to import Certificate from a Public CA to Novell® eDirectory™

• Modify SYS:\APACHE2\CONF\HTTPD.CONF file

– SecureListen 443 “SSL CertificateDNS”

• Restart apache by typing ap2webdn and ap2webup

Page 53: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.53

Securing WebAccess ApplicationWindows 2008 - IIS

Page 54: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.54

Securing WebAccess ApplicationWindows 2008 - IIS

Page 55: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.55

Securing WebAccess ApplicationWindows 2008 - IIS

Page 56: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.56

Securing WebAccess ApplicationWindows 2008 - IIS

Page 57: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.57

Securing WebAccess ApplicationWindows 2008 - IIS

Page 58: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.58

Securing WebAccess ApplicationWindows 2008 - IIS

Sign the CSR using ConsoleOne® and issue the certificate in a der format

OR

Send the CSR to the Public CA and get the Certificate

Page 59: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.59

Securing WebAccess ApplicationWindows 2008 - IIS

Page 60: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.60

Securing WebAccess ApplicationWindows 2008 - IIS

Page 61: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.61

Securing WebAccess ApplicationEnabling SSL

Page 62: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.62

Securing WebAccess ApplicationEnabling SSL

Page 63: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.63

Securing WebAccess ApplicationEnabling SSL

Page 64: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.64

Securing WebAccess ApplicationEnabling SSL

Page 65: Securing Novell GroupWise through SSL and S/MIME

Securing IIS on Windows Demonstration

Page 66: Securing Novell GroupWise through SSL and S/MIME

Secure Internet Email with S/MIME

Page 67: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.67

Secure Internet Email with S/MIME

• What is S/MIME

– Digital Signature– Encryption (Symmetric vs Asymmetric)

• Advantages and Disadvantages

• Creating and Importing User Certificates (Public Key and Private Key)

• Exchanging Public Keys/Certificates

• Encrypting/Decrypting Mails

Page 68: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.68

What is S/MIME?

• S/MIME is an acronym for Secure/Multipurpose Internet Mail Extensions

• It is a standard for Public Key Encryption and signing of MIME Data. In simple terms, it is used for Digitally signing a message and/or Encrypting a message

– Digital Signature

– Encryption

Page 69: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.69

Digital Signature

• Signature – A signature in simple terms is a handwritten depiction of someone's name or a nickname that a person writes on documents as a proof of identity and intent

• Digital Signature is an electronic signature used to authenticate the identity of the sender of a message and possibly to ensure that the original content of the message or document that has been sent is unchanged. The ability to ensure that the original signed message arrived means that the sender cannot easily repudiate it later.

Page 70: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.70

Encryption

• Encryption – A process of transforming information using an information to make it unreadable to anyone except those possessing special knowledge

• Two types of Encryption

– Symmetric vs Asymmetric?

Page 71: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.71

Symmetric vs Asymmetric

• Symmetric– Same key is used for Encryption and Decryption

• Asymmetric

– Separate keys are used for Encryption and Decryption

Page 72: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.72

Advantages/Disadvantages

• Advantages

– Authenticity and Protection of the Message

• Disadvantages

– Not all email software handles S/MIME signatures

– S/MIME Encryption is currently not available for the Novell® GroupWise® Linux, Mac, or WebAccess clients

Page 73: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.73

Creating and Importing User Certificates (Public Key and Private Key)

• Administrator– Creates the Public Key and Private Key

• Users– Export the Private Key and the Public Key

• Users– Import the Public Key and Private Key into the Client

Page 74: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.74

Creating User CertificatesLogin to iManager as admin

Page 75: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.75

Creating User CertificatesCreate Certificate for users

Page 76: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.76

Creating User CertificatesCreate Certificate for users

Page 77: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.77

Creating User CertificatesCreate Certificate for users

Page 78: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.78

Creating User CertificatesCreate Certificate for users

Page 79: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.79

Creating User CertificatesCreate Certificate for users

Page 80: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.80

Creating User CertificatesCreate Certificate for users

Page 81: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.81

Importing User CertificatesAdministrator sets the URL

Page 82: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.82

Importing User CertificatesAdministrator sets the URL

Page 83: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.83

Importing User CertificatesAdministrator sets the URL

Page 84: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.84

Importing User CertificatesUser Imports the Certificate

Page 85: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.85

Importing User CertificatesUser Imports the Certificate

Page 86: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.86

Importing User CertificatesUser Imports the Certificate

Page 87: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.87

Importing User CertificatesUser Imports the Certificate

Page 88: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.88

Importing User CertificatesUser Imports the Certificate

Page 89: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.89

Importing User CertificatesUser Imports the Certificate

Page 90: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.90

Importing User CertificatesUser Imports the Certificate

Page 91: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.91

Importing User CertificatesUser Imports the Certificate

Page 92: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.92

Importing User CertificatesUser Imports the Certificate

Page 93: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.93

Importing User CertificatesUser Imports the Certificate

Page 94: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.94

Importing User CertificatesUser Imports the Certificate

Page 95: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.95

Importing User CertificatesUser Imports the Certificate

Page 96: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.96

Importing User CertificatesUser Imports the Certificate

Page 97: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.97

Importing User CertificatesUser Imports the Certificate

Page 98: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.98

Importing User CertificatesUser Imports the Certificate

Page 99: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.99

Exchanging Public Keys/Certificates

• Sender– Sends a digitally signed message

• Receiver– Receiver receives the digitally signed message along with the

Certificate

Page 100: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.100

Exchanging Public KeySender sends Digitally Signed Message

Page 101: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.101

Exchanging Public KeysReceiver receives Digitally Signed Message along with the sender's Certificate

Page 102: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.102

Encrypting/Decrypting Mails

• Sender (Original Receiver)– Encrypts an email using the Receivers Certificate

• Receiver (Original Sender)– Decrypts it using his/her Private Key

Page 103: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.103

Exchanging Public KeysSend Encrypted Message

Page 104: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.104

Exchanging Public KeysReceive Encrypted Message

Page 105: Securing Novell GroupWise through SSL and S/MIME

© Novell, Inc. All rights reserved.105

Overview

• User1 sends a digitally signed message to User2

• User2 receives the digitally signed message along with the certificate

• Now User2 can send an encrypted message to User1

• User1 decrypts the message with the Private Key

Page 106: Securing Novell GroupWise through SSL and S/MIME

S/MIME Demonstration

Page 107: Securing Novell GroupWise through SSL and S/MIME

Questions?

Page 108: Securing Novell GroupWise through SSL and S/MIME
Page 109: Securing Novell GroupWise through SSL and S/MIME

Unpublished Work of Novell, Inc. All Rights Reserved.This work is an unpublished work and contains confidential, proprietary, and trade secret information of Novell, Inc. Access to this work is restricted to Novell employees who have a need to know to perform tasks within the scope of their assignments. No part of this work may be practiced, performed, copied, distributed, revised, modified, translated, abridged, condensed, expanded, collected, or adapted without the prior written consent of Novell, Inc. Any use or exploitation of this work without authorization could subject the perpetrator to criminal and civil liability.

General DisclaimerThis document is not to be construed as a promise by any participating company to develop, deliver, or market a product. It is not a commitment to deliver any material, code, or functionality, and should not be relied upon in making purchasing decisions. Novell, Inc. makes no representations or warranties with respect to the contents of this document, and specifically disclaims any express or implied warranties of merchantability or fitness for any particular purpose. The development, release, and timing of features or functionality described for Novell products remains at the sole discretion of Novell. Further, Novell, Inc. reserves the right to revise this document and to make changes to its content, at any time, without obligation to notify any person or entity of such revisions or changes. All Novell marks referenced in this presentation are trademarks or registered trademarks of Novell, Inc. in the United States and other countries. All third-party trademarks are the property of their respective owners.