Cayman Islands: Penetration Testing And Web Application Security

Last Updated: 13 September 2011
Article by Micho Schumann

Many organizations perform penetration tests on their computer networks (also called ethical hacking). These tests are attempts to breach network defenses from the Internet in order to identify security weaknesses and implement remediation measures. Ethical hacking usually covers the corporate Web site and other systems that are visible from the public Internet. Web applications, which are widely used in the financial services industry, are often overlooked and should always be included when external testing is scheduled. 

The first step for an organization is usually to assess the external network defenses and systems to ensure that they are adequately protected against attacks. The corporate website for example is a prime target for attackers. An attacker that is able to break into the system that hosts the corporate website will then attempt to leverage that access to gain further access to the internal network and systems. Email, remote access nodes as well as any server which are publically accessible should be included in these tests.

Once the network has been tested as described above, organizations should turn their attention to Web applications. Web applications can be defined as applications that are usually accessed via a Web browser such as Internet Explorer or Mozilla Firefox. They give clients access to their portfolios, personal information and allow them to perform a variety of operations ranging from trading stock, changing contact information, paying various fees to purchasing merchandise. Even if they normally require a username and a password, Web applications can constitute a privileged gateway for digital intruders because they are often linked to corporate networks, databases and confidential data.

A hacker's strategy: Get legitimate access

A danger looms for organizations who grant online access to customers: the rogue client! A rogue client is an individual, who legitimately accesses a Web application and, once logged in, examines, probes and tests the application's limits and safeguards. For this, we offer an example: A rogue client logs in the web application. They are able to view their personal data, the status of their investments and perform transactions.

Up to here, there is nothing abnormal. The rogue client will then most likely attempt to gain full access to the client database, view data that belongs to other clients, gain administrative access or perform unauthorized transactions. Possible motivations are corporate espionage, retaliation or simply for bragging rights within the hacker community. In our experience, these types of breaches often go undetected. When a rogue client accesses information they are not supposed to have access to, the confidentiality and data integrity implications are enormous.

Test before launch

Always test the security of a Web application prior to it being made available to clients. If weaknesses are identified, changes can be made before the application is formally launched. When a web application is being developed, the programmers should always test for security weaknesses as part of their overall development process. However, once testing by the developers is completed, the web application should be formally tested for security by an independent third party such as a quality assurance team or an outside organization.

When the application undergoes changes or when a new version is produced, security testing should be performed once again to ensure that no new vulnerabilities were accidentally introduced with the addition of new code and functionalities. Finally, web applications should be retested on an annual basis, since previously unknown weaknesses may be discovered by security researchers and expose the web application to a breach.

Where to find help?

Unless an organization has a quality assurance team with adequate skills that is independent from the web application development team, a third party organization should usually be hired to assist with this critical task. When hiring a third party, organizations should meet with firms to clearly detail their needs and objectives. It is important to enquire about what methodology will be used and what reliance is placed on automated testing tools. One of the widely used web application testing methodologies is called OWASP, which is short for the Open Web Application Security Project and is largely recognized in the information security community.

A tried and true methodology will ensure that the tests cover an adequate scope to identify weaknesses which may be present. Furthermore, although automated tools are frequently used, web application security testing requires a significant amount of manual testing which must be matched with strong technical knowledge by those executing the tests. Manual testing by highly skilled web application testers will detect weaknesses that automated tools may miss and which could ultimately lead to a security breach.

The bottom line for businesses is that web applications offer practical and timely online solutions to clients but they also offer intruders a gateway into your network and confidential data. To mitigate these risks, organizations should thoroughly test these applications prior to their launch, when changes are implemented and on an annual basis. With appropriate testing, organizations can gain confidence that they are offering their clients a secure way to perform online operations and thus both parties benefit from the full potential of web applications.

Author information:

Micho holds a Masters degree in Information Systems as well as the titles of Certified Information Systems Auditor and Certified Information System Security Professional.  Micho has ten years of experience in Information Systems security and was previously with KPMG in Montreal, Canada for seven years prior to joining the Cayman Islands practice in 2007.

For further information about IT Security please contact Micho Schumann on +1 345 949 4800.

© 2011 KPMG, a Cayman Islands partnership and a member firm of the KPMG network of independent member firms affiliated with KPMG International Cooperative ("KPMG International"), a Swiss entity. All rights reserved.

KPMG and the KPMG logo are registered trademarks of KPMG International Cooperative ("KPMG International"), a Swiss entity.

The content of this article is intended to provide a general guide to the subject matter. Specialist advice should be sought about your specific circumstances.

To print this article, all you need is to be registered on

Click to Login as an existing user or Register so you can print this article.

Some comments from our readers…
“The articles are extremely timely and highly applicable”
“I often find critical information not available elsewhere”
“As in-house counsel, Mondaq’s service is of great value”

Related Topics
Related Articles
Up-coming Events Search
Font Size:
Mondaq on Twitter
Register for Access and our Free Biweekly Alert for
This service is completely free. Access 250,000 archived articles from 100+ countries and get a personalised email twice a week covering developments (and yes, our lawyers like to think you’ve read our Disclaimer).
Email Address
Company Name
Confirm Password
Mondaq Topics -- Select your Interests
 Law Performance
 Law Practice
 Media & IT
 Real Estate
 Wealth Mgt
Asia Pacific
European Union
Latin America
Middle East
United States
Worldwide Updates
Registration (you must scroll down to set your data preferences)

Mondaq Ltd requires you to register and provide information that personally identifies you, including your content preferences, for three primary purposes (full details of Mondaq’s use of your personal data can be found in our Privacy and Cookies Notice):

  • To allow you to personalize the Mondaq websites you are visiting to show content ("Content") relevant to your interests.
  • To enable features such as password reminder, news alerts, email a colleague, and linking from Mondaq (and its affiliate sites) to your website.
  • To produce demographic feedback for our content providers ("Contributors") who contribute Content for free for your use.

Mondaq hopes that our registered users will support us in maintaining our free to view business model by consenting to our use of your personal data as described below.

Mondaq has a "free to view" business model. Our services are paid for by Contributors in exchange for Mondaq providing them with access to information about who accesses their content. Once personal data is transferred to our Contributors they become a data controller of this personal data. They use it to measure the response that their articles are receiving, as a form of market research. They may also use it to provide Mondaq users with information about their products and services.

Details of each Contributor to which your personal data will be transferred is clearly stated within the Content that you access. For full details of how this Contributor will use your personal data, you should review the Contributor’s own Privacy Notice.

Please indicate your preference below:

Yes, I am happy to support Mondaq in maintaining its free to view business model by agreeing to allow Mondaq to share my personal data with Contributors whose Content I access
No, I do not want Mondaq to share my personal data with Contributors

Also please let us know whether you are happy to receive communications promoting products and services offered by Mondaq:

Yes, I am happy to received promotional communications from Mondaq
No, please do not send me promotional communications from Mondaq
Terms & Conditions (the Website) is owned and managed by Mondaq Ltd (Mondaq). Mondaq grants you a non-exclusive, revocable licence to access the Website and associated services, such as the Mondaq News Alerts (Services), subject to and in consideration of your compliance with the following terms and conditions of use (Terms). Your use of the Website and/or Services constitutes your agreement to the Terms. Mondaq may terminate your use of the Website and Services if you are in breach of these Terms or if Mondaq decides to terminate the licence granted hereunder for any reason whatsoever.

Use of

To Use you must be: eighteen (18) years old or over; legally capable of entering into binding contracts; and not in any way prohibited by the applicable law to enter into these Terms in the jurisdiction which you are currently located.

You may use the Website as an unregistered user, however, you are required to register as a user if you wish to read the full text of the Content or to receive the Services.

You may not modify, publish, transmit, transfer or sell, reproduce, create derivative works from, distribute, perform, link, display, or in any way exploit any of the Content, in whole or in part, except as expressly permitted in these Terms or with the prior written consent of Mondaq. You may not use electronic or other means to extract details or information from the Content. Nor shall you extract information about users or Contributors in order to offer them any services or products.

In your use of the Website and/or Services you shall: comply with all applicable laws, regulations, directives and legislations which apply to your Use of the Website and/or Services in whatever country you are physically located including without limitation any and all consumer law, export control laws and regulations; provide to us true, correct and accurate information and promptly inform us in the event that any information that you have provided to us changes or becomes inaccurate; notify Mondaq immediately of any circumstances where you have reason to believe that any Intellectual Property Rights or any other rights of any third party may have been infringed; co-operate with reasonable security or other checks or requests for information made by Mondaq from time to time; and at all times be fully liable for the breach of any of these Terms by a third party using your login details to access the Website and/or Services

however, you shall not: do anything likely to impair, interfere with or damage or cause harm or distress to any persons, or the network; do anything that will infringe any Intellectual Property Rights or other rights of Mondaq or any third party; or use the Website, Services and/or Content otherwise than in accordance with these Terms; use any trade marks or service marks of Mondaq or the Contributors, or do anything which may be seen to take unfair advantage of the reputation and goodwill of Mondaq or the Contributors, or the Website, Services and/or Content.

Mondaq reserves the right, in its sole discretion, to take any action that it deems necessary and appropriate in the event it considers that there is a breach or threatened breach of the Terms.

Mondaq’s Rights and Obligations

Unless otherwise expressly set out to the contrary, nothing in these Terms shall serve to transfer from Mondaq to you, any Intellectual Property Rights owned by and/or licensed to Mondaq and all rights, title and interest in and to such Intellectual Property Rights will remain exclusively with Mondaq and/or its licensors.

Mondaq shall use its reasonable endeavours to make the Website and Services available to you at all times, but we cannot guarantee an uninterrupted and fault free service.

Mondaq reserves the right to make changes to the services and/or the Website or part thereof, from time to time, and we may add, remove, modify and/or vary any elements of features and functionalities of the Website or the services.

Mondaq also reserves the right from time to time to monitor your Use of the Website and/or services.


The Content is general information only. It is not intended to constitute legal advice or seek to be the complete and comprehensive statement of the law, nor is it intended to address your specific requirements or provide advice on which reliance should be placed. Mondaq and/or its Contributors and other suppliers make no representations about the suitability of the information contained in the Content for any purpose. All Content provided "as is" without warranty of any kind. Mondaq and/or its Contributors and other suppliers hereby exclude and disclaim all representations, warranties or guarantees with regard to the Content, including all implied warranties and conditions of merchantability, fitness for a particular purpose, title and non-infringement. To the maximum extent permitted by law, Mondaq expressly excludes all representations, warranties, obligations, and liabilities arising out of or in connection with all Content. In no event shall Mondaq and/or its respective suppliers be liable for any special, indirect or consequential damages or any damages whatsoever resulting from loss of use, data or profits, whether in an action of contract, negligence or other tortious action, arising out of or in connection with the use of the Content or performance of Mondaq’s Services.


Mondaq may alter or amend these Terms by amending them on the Website. By continuing to Use the Services and/or the Website after such amendment, you will be deemed to have accepted any amendment to these Terms.

These Terms shall be governed by and construed in accordance with the laws of England and Wales and you irrevocably submit to the exclusive jurisdiction of the courts of England and Wales to settle any dispute which may arise out of or in connection with these Terms. If you live outside the United Kingdom, English law shall apply only to the extent that English law shall not deprive you of any legal protection accorded in accordance with the law of the place where you are habitually resident ("Local Law"). In the event English law deprives you of any legal protection which is accorded to you under Local Law, then these terms shall be governed by Local Law and any dispute or claim arising out of or in connection with these Terms shall be subject to the non-exclusive jurisdiction of the courts where you are habitually resident.

You may print and keep a copy of these Terms, which form the entire agreement between you and Mondaq and supersede any other communications or advertising in respect of the Service and/or the Website.

No delay in exercising or non-exercise by you and/or Mondaq of any of its rights under or in connection with these Terms shall operate as a waiver or release of each of your or Mondaq’s right. Rather, any such waiver or release must be specifically granted in writing signed by the party granting it.

If any part of these Terms is held unenforceable, that part shall be enforced to the maximum extent permissible so as to give effect to the intent of the parties, and the Terms shall continue in full force and effect.

Mondaq shall not incur any liability to you on account of any loss or damage resulting from any delay or failure to perform all or any part of these Terms if such delay or failure is caused, in whole or in part, by events, occurrences, or causes beyond the control of Mondaq. Such events, occurrences or causes will include, without limitation, acts of God, strikes, lockouts, server and network failure, riots, acts of war, earthquakes, fire and explosions.

By clicking Register you state you have read and agree to our Terms and Conditions