Product Information Bulletin. Clearswift SECURE Gateway 4.7

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Product Information Bulletin Clearswift SECURE Email Gateway 4.7 November 2017

Copyright Published by Clearswift Ltd. 1995 2017 Clearswift Ltd. All rights reserved. The materials contained herein are the sole property of Clearswift Ltd unless otherwise stated. The property of Clearswift may not be reproduced or disseminated or transmitted in any form or by any means electronic, mechanical, photocopying, recording, or otherwise stored in any retrievable system or otherwise used in any manner whatsoever, in part or in whole, without the express permission of Clearswift Ltd. Information in this document may contain references to fictional persons, companies, products and events for illustrative purposes. Any similarities to real persons, companies, products and events are coincidental and Clearswift shall not be liable for any loss suffered as a result of such similarities. The Clearswift Logo and Clearswift product names are trademarks of Clearswift Ltd. All other trademarks are the property of their respective owners. Clearswift Ltd. (registered number 3367495) is registered in Britain with registered offices at 1310 Waterside, Arlington Business Park, Theale, Reading, Berkshire RG7 4SA, England. Users should ensure that they comply with all national legislation regarding the export, import, and use of cryptography. Clearswift reserves the right to change any part of this document at any time. Page 2 of 14

Contents Overview... 4 New Features... 4 Postfix MTA support... 4 TLS enhancements... 5 STIG hardening... 6 Bypass bad-data error conditions... 7 Sanitize and Redact JPEG image properties... 8 GDPR EU Regional (PII) Policies... 9 Message tracking... 10 Encryption Enhancements... 11 Property Name scanning enhancements... 11 Enhancement requests... 12 Bug fixes... 13 Availability... 13 Interoperability... 13 End of life... 13 Platform support... 14 Packaging... 14 Page 3 of 14

Overview This new release delivers a number of customer enhancement requests, as well as additional security features for the Clearswift SECURE Email Gateway. The new features are briefly summarized below, and examined in more detail on the following pages: Postfix TLS enhancements STIG hardening Bypass bad-data error conditions Sanitize and Redact JPEG image properties GDPR regional PII tokens Message Tracking Retention period Property Name scanning enhancements New Features Postfix MTA support Postfix offers defined interfaces to permit message interception to be simpler Postfix offers more features with good performance Considered a secure MTA for use in Military deployments Sendmail was originally developed in 1982 and, while it has been a common MTA, in recent years its popularity has declined compared to newer MTAs such as Postfix and Exim, which offer better performance and greater security. Top Mail Server Market Share One of the major drawbacks of Sendmail was its monolithic structure. Postfix is more modular with defined APIs permitting easier integration with content inspection technologies in the Gateway. If a security vulnerability is identified, patching Postfix becomes much easier Page 4 of 14

with these defined APIs, enabling customers systems to be made resilient in a much shorter timeframe. The APIs and the number of available Postfix extensions will allow Clearswift to introduce new and innovative features for many more years. TLS enhancements Opportunistic and Mandatory modes More flexible configurations for outbound connections Support for Subject Alternate Names By changing the MTA from Sendmail to Postfix, we provide a number of new features mainly for use in TLS and Address Rewriting. Most people will be using TLS. This has changed in this release so that you can now: Define a default TLS version for outbound connections then override the default version setting on a per-connection basis, which could be for one or more domains Define a default TLS cipher for outbound connections then override the default cipher setting on a per-connection basis, which could be for one or more domains Validate certificates by their Subject Alternate Name certificate details for outbound connections Granular Outbound connection TLS properties As part of the integration of Postfix, the Gateway interface has undergone cosmetic changes to make the deployment of TLS easier for customers. Page 5 of 14

STIG hardening Defined by DISA Guidelines for more secure deployments of standard COTS products (operating systems, web servers & databases) Automatically applied 55 recommendations implemented in 4.7 Ensuring system security is fully maintained against industry best practice is paramount. The Gateways now include conformance to a number of security recommendations created by the Defense Information Systems Agency (DISA), who have crafted the Security Technical Implementation Guides (STIGs). The STIGs contain technical guidance to "lock down" information systems/software that might otherwise be vulnerable to a malicious computer attack. In 4.7 there are 55 recommendations that have been applied, and each Gateway release will contain progressively more. These security recommendations are automatically applied on installation and upgrade, and customers can view the STIGs report by logging into the console and accessing the report here: /opt/csrh/stig/reports/cs-remediation-report.html The report is in HTML so it is advisable to get the file off the Gateway using FTP/SFTP or a similar process. Page 6 of 14

Example STIG report In most cases the Sysadmin will not notice any changes, but some of the more obvious ones are: NTP enabled by default on install and upgrade Increased auditing of user actions in Console and terminal windows New console (not SSH) message prior to login New logon message after login prior to the Console loading Bypass bad-data error conditions Allows customers to enable override file processing failures Bad-data rule split into processing failure and bad-data As part of message processing, the Clearswift Deep Content Inspection (DCI) engine will inspect the structure of the message and any attachments. If the DCI finds errors in the message structure caused by the mail-client that created the message or in the structure of an attachment, the Gateway will legitimately block the message as the errors could in fact be some type of new exploit that may affect the mail client (e.g. Outlook) or the tool used to open the attachment (e.g. Word). There will be some customers who are trying to send out data that might have been created using a 3 rd party PDF tool. Unfortunately, this application creates files with a structure that is technically incorrect and would be blocked by the Gateway, but can still be opened by most PDF clients. Therefore, customers can use the new Detect Malformed Data content rule to determine which file formats to block and which to ignore; in the example above, they would configure the policy to exclude PDF files from being held. Page 7 of 14

Example Exclude PDF files from Message Processing Failures Sanitize and Redact JPEG image properties Allows redaction of image properties Allows sanitization (removal) of image properties Included as part of Data Redaction / Document Sanitization Licenses Previously, the Redaction and Document Sanitization features were limited to Text, Documents, Message bodies, and Web Pages. This version allows customers with the appropriate license to inspect image meta data and optionally redact items or remove properties. This is particularly important to organizations where: the exact location the picture was taken is sensitive the time that the picture was taken is sensitive, or the device used to take the picture is sensitive Page 8 of 14

Example Image meta data showing GPS location where picture was taken The Redaction features can redact specific text from the properties, or some or all of the image meta data may be removed. Example Image properties following redaction of the text iphone GDPR EU Regional (PII) Policies Consistent set of PII tokens to cover Passport, Social Security / Driving License and National Identity (where applicable) Covering 28 countries With heavy penalties for Data Loss under the regulations of GDPR, coming into force in May 2018, customers need to ensure that Personal Identifiable Information (PII) data is controlled. Page 9 of 14

Austria Belguim Bulgaria Croatia Cyprus Czech Republic Denmark Estonia Finland France Germany Greece Hungary Ireland Italy Latvia Lithuania Luxembourg Malta Netherlands Poland Portugal Romania Slovakia Slovenia Spain Sweden UK Passport Social Security Driving License Identity Card 4.6 4.7 PII Tokens added in 4.7 Clearswift products have been extended to support a much wider range of entries, allowing a greater chance to protect employee and customer data from being lost. Message tracking Can be extended to support storing 2 years worth of data Shows inbound TLS traffic Show Log output different as Postfix log file is different from Sendmail Customers can now extend their Tracking and Report retention settings to hold up to 2 years worth of data. This will increase the amount of disk space used by the system, and reports over extended periods of time may have an effect on system performance. When a message was tracked in previous versions, Message Tracking would only show whether TLS was used for outbound connections. It has now been extended to show when a connection is received, if it came over TLS. Page 10 of 14

Encryption Enhancements Uses cryptographic message syntax for better compatibility with other solutions Default S/MIME signature algorithm now SHA256 The SECURE Email Gateway now uses Cryptographic Message Syntax (CMS) by default for S/MIME message processing to provide better compatibility with other cryptographic solutions and advancing compliance requirements. The default for the S/MIME signature algorithm has been changed from SHA1 to SHA256. The new setting is more secure and affects signature processing as well as certificate generation. However, if you have used the Gateway UI to create a CA for S/MIME you may need to recreate it following this change in order to ensure a consistent use of the new algorithm throughout the whole certificate chain. Property Name scanning enhancements Allows customers to search through document/image properties without having to know the exact name Can search all properties except a named property for text Page 11 of 14

In situations where you know that text could exist in a property, but are unsure which property it may be stored, you can simply add a! character in the property name used by the Analyze Properties content rule. For example, to scan all properties to check for the term Secret you can use a single! character. If you want to scan for content in properties, but not the Author property, the! character can be used to negate that property value. Enhancement requests The following customer reported enhancement requests have been implemented in this release. ER# MAIL-6572 MAIL-5307 MAIL-7891 Summary Extension of Retention Time within the Tracking and Report Settings Message Tracking not showing TLS for inbound message Allow peering using NIC not reserved for Web UI use Page 12 of 14

MAIL-7194 MAIL-11104 MAIL-6542 MAIL-6737 MAIL-7561 MAIL-1532 Support the of wildcard in Connection profile for Certificate Subject Validation Add regional keyboard layouts for Greek, Turkey, Norway and Japan Reclassify Action Support for mmap files TLS Handshake failed email not send in clear text Support address rewriting with partially-wild carded users Bug fixes A number of client-reported bugs have been fixed in this release. Please see the release notes for more information. Availability Phase Date General Availability November 2017 Interoperability It is possible 1 to peer a Version 4.7 Gateway with an existing Version 3.x Gateway, although it will not be possible to share policy due to the different levels of functionality in the later products. It will be possible to import a 3.8 configuration into a V4.6 system thus saving deploying a V4.0 (or 4.1 to 4.3) and then upgrading that to V4.7. End of life This release will signal the start of the SEG 4.5 end of life program. Version 4.5 s EOL program will last 12 months (as defined in the Support Services handbook) and will reach end of life on 7 th November 2018. 1 In order to peer a V4.4 or later with SEG 3.8 does require some modification of the TLS ciphers used for Peer communications Page 13 of 14

Platform support Clients with low memory and low disk space systems might find their hardware is no longer suitable and will need to refresh their hardware / virtual systems especially if they intend setup 2 years worth of Message Tracking. Clearswift recommends that systems have a minimum of 4 GB RAM, multi-core processors that support 64bit instructions and over 250 Gb+ of disk space for low volume production environments. For customers with a greater workload the recommended minimum would be 6-8 GB RAM, single or dual multi-core processors and 250Gb+ of redundant disk storage. Packaging This release will NOT be available as a patch for all systems running 3.x to automatically download. Clients using 4.0 to 4.6 will be able to upgrade their system through the Admin Server Console. Clients who want to migrate from 3.x must install a new system and migrate their existing configuration to the new system. They will typically deploy the solution in a test mode initially and then deploy a production system. Clients will be able to import a V3.8.* policy file to replicate their policy or a V3.8.* full system backup if they want to import reporting data, quarantine messages, logs, and policy. To make the installation process easier, clients will be able to request professional services from Clearswift to assist in the deployment of this new version. Page 14 of 14