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8 Securing Unstructured Data

Chapter 11 discusses the subject of securing data storage—how security can be
applied to the specific locations where data resides. That chapter focuses on the
static state of data (information) on a hard disk or in a database, but in the high-
bandwidth, mobile, and networked environments in which we work and live,
information rarely stays in one place. In a matter of microseconds, information
can be distributed to many locations and people around the world. In order to
secure this data, we must look beyond the simple confines of where information
can be stored and think more about how it is stored or, more accurately for this
chapter, how it is formatted.

Information is typically categorized as being in either a structured format or
an unstructured format. The meaning of these terms is subject to different
interpretations by divergent groups, so first we’ll address their meaning in the
context of our discussion of securing unstructured data. It also makes sense to
think in terms of which of three different states data is currently residing: at rest,
in transit, or in use. We’ll discuss that second. Finally, we’ll get to the primary
focus of the chapter, the different approaches to securing unstructured data.

Structured Data vs. Unstructured Data
For purposes of this book, we are not going to get into a detailed discussion about
whether, for example, the unstructured Excel spreadsheet actually contains very
structured data. In classic terms, structured data is data that conforms to some
sort of strict data model and is confined by that model. The model might define a
business process that controls the flow of information across a range of service-
oriented architecture (SOA) systems, for example, or it might define how data is
stored in an array in memory. But for most IT and security professionals,
structured data is the information that lives in the database and is organized
based on the database schema and associated database rules. This means two
important things to you as a security professional:

• Databases reside within a data center that is surrounded by brick walls, metal
cages, network firewalls, and other security mechanisms that allow you to
control access to the data.

• The data itself is structured in a manner that typically allows for easy
classification of the data. For example, you can identify a specific person’s
medical record in a database and apply security controls accordingly.

So, because you know what structured data looks like and where it resides,
you have tight control over who can access it. Security controls are relatively easy
to define and apply to structured data using either the built-in features of the
structure or third-party tools designed for the specific structure.

By contrast, unstructured data is much more difficult to manage and secure.
Unstructured data can live anywhere, in any format, and on any device, and can
move across any network. Consider, for example, a patient record that is
extracted from the database, displayed in a web page, copied from the web page
into a spreadsheet, attached to an e-mail, and then e-mailed to another location.
Simply describing the variety of networks, servers, storage, applications, and
other methods that were used to move the information beyond the database
could take an entire chapter.

Unstructured data has no strict format. Of course, our Word documents, e-
mails, and so on conform to standards that define their internal structure;
however, the data contained within them has few constraints. Returning to the
example of the patient record, suppose a user copies it from the web page into the
spreadsheet after altering its contents, maybe removing certain fields and
headers. As this information flows from one format to another, its original
structure has been effectively changed.

Figure 8-1 depicts some examples of how data can move around between
different locations, applications, and formats.

Figure 8-1 Unstructured data doesn’t respect security boundaries.

Securing information when stored as structured data is relatively
straightforward. But as a piece of information from the structured world moves

into the unstructured world—in different file formats, across networks you didn’t
expect it to traverse, stored in places you can’t control—you have less control.
Doesn’t sound good? Consider the fact that many analysts say 80 percent or more
of digital information in an organization is unstructured, and that the amount of
unstructured data is growing at a rate 10 to 20 times the rate of structured data.
Also consider the constant stream of news articles highlighting theft of
intellectual property, accidental loss of information, and malicious use of data, all
with unstructured data at the core of the problem. In 2010, the worldwide total of
unstructured data was estimated at roughly 1 million petabytes
(1,048,576,000,000 GB) and is considered to be increasing at a rate of 25 percent a
year. We clearly need to understand how we can secure unstructured data.

At Rest, in Transit, and in Use
Unstructured data can be in one of three states at any given time. It can be at rest,
sitting quietly on a storage device. It can also be in transit (sometimes referred to
as “in flight”), which means it is being copied from one location to another. Or, it
can be in use, in which case the data is actively open in some application. Take
for example a PDF file. It may be stored on a USB drive, in a state of rest. The
same PDF file may be copied from the USB device, attached to an e-mail, and sent
across the Internet. The PDF then moves across many states of transit as it is
copied from the USB device, to the e-mail server, and travels along networks from
inbox to inbox. Finally, a recipient of the e-mail actually opens the PDF, at which
point the unstructured data is in use—residing in memory, under the control of
an application (such as Adobe Reader), and being rendered to the user who can
interact with the information.

The goal of this chapter is to focus on the challenges of securing unstructured
data in all three of these states and to look at common technologies used to
protect access to, and control over, information. We will look at specific types of
technology and examine newer technologies, such as data loss prevention (DLP)
systems, to see where the trends are going.
The Challenge of Securing Unstructured Data
To illustrate the challenge of securing unstructured data, assume your
organization has an HR application that has a database which maintains
information about each employee, including their annual wage, previous
disciplinary action, and personal data, such as home address and Social Security
number. Like most modern HR applications, it is web based, so when an
authenticated user runs a report, the report is returned from the world of the
structured database into the unstructured world as it is delivered to the web
browser in HTML format. The user of the application can then easily copy and

paste this information from the web browser into an e-mail message and forward
the data onto someone else. As soon as that information is added to the body of
the e-mail, it loses all structure and association with the original application. The
user may also choose to copy and paste only some of the information, change
some of the information, or add new content to the original information. The
person to whom the user sends the e-mail may then copy and paste the
information into a spreadsheet alongside other data. That spreadsheet
information may be used to create a graphical representation of the information,
with some of the original text used as labels on the graph. Very quickly,
information can be changed, restructured, and stored in smaller data formats
such as e-mails, documents, images, videos, and so on.

You might have a very well-defined security model controlling access to the
HR application and the database that contains the HR information. However, the
information needs to be delivered to people or applications for it to be
meaningful. If it gets delivered over a network, you can make sure that access to
the network is secure, yet when the information reaches the user, it can be
transformed into a thousand different formats and sent to dozens of other
applications and networks. Each of the locations where that information may
exist can be secured, and it may be possible to apply access controls to the file
share and control access to the data (content) repositories and the networks in
which they reside; however, your unstructured information may end up
anywhere and thus it is very hard to secure. In fact, it is hard to even locate,
identify, and classify information. Once that HR data ends up deep in an e-mail
thread which accidentally gets forwarded to the wrong audience, it no longer
resembles the well-defined structure of the original data residing in the database.
It has also been duplicated several times as it has traveled from the database to
the inbox of an unauthorized user.

Unstructured data changes are constantly occurring, and data ends up in
places you don’t expect, particularly as the Internet provides an unbelievably
large network of computers that excels in the transfer of unstructured data.
Enormous amounts of money and effort have been invested in building social
networking sites, file sharing and collaboration services, and peer-to-peer
applications that provide endless ways in which a piece of unstructured data can
be distributed within seconds to an audience of billions. It is little wonder that we
frequently read about examples of data loss—now that we’ve created so many
amazing ways to allow information to easily leave our protected borders, our
network controls to stop attackers from accessing our protected data are no
longer sufficient to keep it secure.

Approaches to Securing Unstructured Data

The problem of unstructured data has not gone unnoticed by the security
community; we have access to an array of technologies that are designed to
provide at least partial solutions to the problem of how to secure unstructured
data. While what follows is by no means a complete examination of all the
technologies available, we will examine the most commonly used technologies
and highlight the pros and cons of each. The key areas where unstructured data
can reside can be broken down into the following categories:

• Databases
• Applications
• Networks
• Computers
• Storage
• Physical world (printed documents)

The following sections describe techniques for security data in each of these
The database is the center of the data world. The majority of information you are
trying to secure was either created and inserted into, lives in, or has been
retrieved from a database. The most secure database in the world would be one
that nobody could access. It would have no keyboard attached, no network
connected, and no way to remove or add storage devices. Some would even argue
that the machine would also need to be powered off, located in a room without
doors, and be disconnected from any power source. Clearly it would also be the
world’s most useless database, as nobody would be able to actually use the data
stored on it. Therefore, for practical reasons, you have to secure the data within
the database while also allowing legitimate users and applications to access it.

The database was once considered the realm of structured data, but with new
developments in database technology, increasing amounts of unstructured data
are now stored in the database. For example, the database can be the storage
component of a content management system or an application that stores images,
videos, and other unstructured data.

Figure 8-2 shows the typical elements of a database system. In its most basic
form, the database is accessed over a network and a query is run against the
database service. This causes a database process to run and access the data store
to retrieve the queried data, which is then piped back over the network. The data
store can also export data into backups that are restored on development systems
or staging environments. Unstructured data can therefore reside in different
areas of the database—either at rest in the schema in the database data files, in
backups, or sometimes exported to other development or staging databases.

Database security is discussed in further detail in Chapter 12; however, in the
context of unstructured data protection, we are mainly concerned with
encryption, which is discussed next.

Figure 8-2 Information flows into and out of a database.
Encrypting Unstructured Data at Rest in the Database
The most common approach to securing the data in a database is encryption
(described in further detail as a general topic in Chapter 10). Encryption of data
that resides in a database can be approached in various ways:

• Encryption of the actual data itself such that it is stored in normal data files in an
encrypted state. The database doesn’t necessarily know (or care) whether or how
the data is encrypted, so it passes the encrypted data to the application to decrypt.

• Partial encryption of the database schema so that specific rows, columns, or
records are encrypted as a function of the storage of the data. In this case the
database handles the encryption of data and performs the decryption to the

• Full encryption of the database data files such that any information that resides
in them is encrypted.

In the first scenario, the data itself is encrypted. As far as the database is
concerned, it is just storing another big chunk of data. When dealing with
unstructured data, this usually means that the files have been explicitly
encrypted using some type of external technology.

The second and third scenarios are handled completely within the database
platform itself—data is encrypted at rest (and also sometimes in use as it resides
in the memory of the database processes). Oracle and Microsoft use the term
“transparent data encryption” when referring to this sort of data security
because, as far as the application accessing the data is concerned, the information

is unencrypted—the encryption is transparent to the application because the data
is decrypted before the application sees it. These solutions offer a variety of levels
of confidentiality for the data they are protecting. Essentially the goal is to allow
only database or application processes to have access to the decrypted data.
Depending on the method of encryption applied, database exports and backups
can be protected without additional technology. Often, data that needs to be used
in development environments can be declassified by using data masking
technologies that use scrambling or randomization to convert real data into fake
information that still has similar characteristics to the original information.

The biggest problem with the latter two scenarios is that the unstructured data
is only secured while it resides in some part of the database files. When the data
needs to be accessed, it is delivered, usually in unencrypted form, to the querying
application. At that point it’s beyond the reach of any database encryption
Implementing Controls to Restrict Access to Unstructured Data
In scenarios where the database handles encryption of data and sends the
querying applications the data automatically decrypted, controlling who or what
can connect to the database and perform those queries becomes very important;
this is where database access controls play a key role in restricting access to data.
The approaches that are used by different databases vary, from authentication
with a simple username and password to gain access to a database schema, to a
complex set of rules that define for various levels of data classification who can
access what, from where, at what time, and using what application. Chapter
12 discusses this subject in further detail, along with other aspects of database
security. Often, as access rules become more complex, they provide opportunities
and requirements to determine increasingly complex structures of data
classification and control access to data at a granular level.

The credentials used to authenticate and provide authorization to access data
can either be stored within the database platform or reside within an external
identity directory. This enables the security of data to be associated with the
enterprise directory store, thus creating an easier method for managing the
access control model by using the existing access control infrastructure. For
example, you may have in your identity directory a range of groups with
memberships that reflect access to, say, sales, engineering, and research data. The
capability to associate database permissions with such groups and have logic in
the application return certain records based on those permissions provides a
very effective means of controlling access. By simply moving a user from one
group to another, you impact the access control mechanisms in the application
through to the database.

All the investment in configuring controls to restrict access to the database
still relies on trust that the process that is allowed to access the data is legitimate,
or that the data continues to be secured after it leaves the database.
Securing Data Exports
Many databases provide functionality for the mass export of data into other
databases. This presents security challenges. You may have encrypted the
database files and, using an encrypted backup platform, tied down user access
from the application through to the tables in the database, yet the owner of the
schema of data may still have a range of tools at their disposal to extract and
export data en mass. This activity is often the legitimate transfer of sets of data to
other systems for development purposes. For example, suppose an outsourcing
company is working on new features in your organization’s application and
requires data to work with to test its application changes. A quick e-mail or phone
call by the outsourcing team to the application owner to request an export of a
particular data set, and, bam, in a matter of seconds, a set of your organization’s
data now resides within another system that you have little to no control over.

From an unstructured data perspective, this can be a significant problem,
because the information that resides in database files can be easily shipped from
location to location. For example, the database may well have a set of access
controls that apply only to the production instance and not other instances such
as test and development. In that case, as the data is exported to test or
development, you may lose those controls. That would be equivalent (in the flat-
file world) to copying an entire file share containing hundreds of folders, with
each folder containing confidential files, to some other file share without proper
permissions. All that data suddenly becomes unprotected. Fortunately for people
concerned about the security of those files, that rarely happens. But in the real
world, database exports from one environment to another do occur frequently.

Encryption can be applied at the export phase. This usually is a different
mechanism from that used for the encryption of data in the schema or the
encryption applied to system-wide database backups. When exporting data, it is
usually possible to provide a passphrase to use as the key for the one-time
encryption of a specific data export. This allows sets of data to be protected in
transit because the encrypted export and passphrase are shared separately when
communicated to the user importing the data into their own system.
Challenges in Current Database Security Solutions
Although databases have been around since the late 1970s, they still top the list of
targets for attack. And, as noted earlier, the amount of unstructured data in the
database is constantly increasing. Why is this? Recently, developers have
incorporated into database platforms some clever features that make the storage

of unstructured data more efficient. Take for example de-duplication, a technique
where multiple copies of the same document are automatically detected and
stored only once, with a reference to the original for each copy. Consider a
database that is the back-end storage for a content management system. You may
have a sales presentation uploaded by many different users, and storing 20
copies of the same file would significantly increase storage requirements. By
using de-duplication, you could considerably reduce your storage requirements.
The database may also be able to perform data compression before the database
encrypts the data at rest. So, with more unstructured data residing in the
database, the database becomes a more attractive target for attack. Direct attacks
to the database, indirect attacks via the application, loss of backup tapes, and
poorly managed exports of sensitive data are all common threats today.

The database security methods previously mentioned are all necessary to
provide a reasonable level of security while the data is resident in the database.
However, at some point the data (both structured and unstructured) has to come
out of the database to be presented to trusted applications. That’s really the whole
point of a database—not to store data forever, but to allow that data to be queried
and given to other applications. Those other applications often contain their own
weaknesses and are configured and managed differently, resulting in the
potential for a lack of consistent data protection if those applications are not
properly secured. Thus, we must follow the flow of information as it continues its
Unstructured data is typically created in either of two ways: through user activity
on their workstations, or as applications access and manipulate structured data
and reformat it into a document, e-mail, or image. The number of applications is
growing at an amazing rate. With cloud development platforms, it is now a
relatively trivial task to create a collection of data from a wide variety of sources
and consolidate it into a new application. For the purpose of this chapter, our
focus is on web applications. There are many other types of applications, from a
suite of Microsoft Office products to client/server applications that do not
leverage any web-based technology. However, web applications are by far the
most common network-connected application, and their client is non-specific—
it’s a web browser. As such, securing web applications is the greatest challenge.
Secure application development is discussed in more detail in Chapters 26 and 27,
and controlling the behavior of already-written applications is covered
in Chapter 30.

Application security can be categorized into the following groups:

• Application access controls that ensure an identity is authenticated and
authorized to view the protected data, to which that identity is authorized, via the

• Network and session security to ensure the connection between the database,
application, and user is secure

• Auditing and logging of activity to provide reporting of valid and invalid
application activity

• Application code and configuration management that ensure code and changes to
the application configuration are secure

This list simplifies application security into some high-level concepts that
allow us to focus on the basic fundamentals of application security. Securing
applications is one of the most important ways to protect data, because
applications are the interface between the end user and the data. As a result a
great deal of the security investment is devoted to the development of the
application. Some companies, such as Microsoft, have a strict software
development lifecycle (SDLC) program to ensure applications are built in a secure
fashion. This approach is often called “secure by design” because security is a key
part of the software development process rather than a set of configurations
applied to the application as an afterthought. When you purchase an application
from a vendor, these aspects of security are typically out of your control;
therefore, you must choose your vendor wisely. If your organization is
developing its own applications, you must ensure that your developers have a
reasonable (and verifiable) level of knowledge about building secure
applications. Preparing for the Certified Information Systems Security
Professional (CISSP) certification exam is often a good starting point to give any
developer grounding in security and the implications to application
development. Chapter 27 of this book describes secure software development in
further detail.
Application Access Controls
Once an application is deployed and running, the first event in the chain of
events leading to access of your unstructured data is when a user attempts to
gain access to the application. Most enterprise-oriented applications have the
ability to integrate with existing identity management infrastructure, which is
considered a best practice. This allows users to authenticate by using credentials
that are already familiar to them. Single sign-on (SSO) mechanisms are typically
beneficial for applications because they provide usability and security and
simplify password management. Once a user has completed the authentication
phase, the application must determine what the user is authorized to do by using

the access control model within the application, which defines who can access
which information or resources.
Network and Session Security
After the application has authenticated the user and knows which data the user is
authorized to access, it must deliver that information when prompted. A wide
range of protocols can be used to secure the transmission of data from the
database to the application and from the application to the end user. A common
protocol for securing data transmissions is Secure Sockets Layer/Transport Layer
Security (SSL/TLS), which encrypts traffic delivered from the server to the client.
Some authentication solutions also extend the security features of authentication
to only allow certain trusted clients. This could, for instance, take the form of
allowing access to the application only by clients using a secure VPN channel or
using a computer that has a certain security patch level and antivirus/anti-
malware instance running. All these technologies are trying to assert a level of
trust for the communication between the application and the client.
Auditing and Logging
Similar to a database, applications can also provide a variety of options for
auditing and logging. This may take place in the code within the application itself,
or the application web server may provide prebuilt auditing functionality that is
available to the application. Again, as with a database, the audit data itself needs
to be secured, as the information being recorded may also be regarded as
sensitive. Security is not limited to protecting the confidentiality of audit data,
though; it extends to protection of audit data from unauthorized changes—that is,
ensuring data integrity. Someone who attacks a system will often attempt to hide
their tracks, and being able to manipulate the audit files is often a very effective
way to remove any evidence of an attack.
Application Code and Configuration Management
It is important to ensure that code and application configuration changes
preserve the security controls and settings and don’t introduce new
vulnerabilities, a configuration management system can be used. Configuration
management systems provide a repository for storing previous versions of
software, as well as controls for the workflow of reviews and approvals needed to
enforce compliance with an organization’s security policies.

Many large applications can also be configured to work with governance, risk
management, and compliance (GRC) software that has fine-grained knowledge of
the application assets as well as the policies the organization wishes to comply
with, providing reporting that verifies compliance with policy. A good example of
a GRC solution in action is ensuring that a doctor who is permitted to prescribe
drugs doesn’t also have the ability to dispense them (separation of duties). GRC

solutions are embedded tightly with applications and can also work alongside
identity management solutions.
Challenges in Current Application Security Solutions
Applications are among the biggest generators of unstructured content, and the
aforementioned security mechanisms highlight the need for a sufficient level of
security to ensure that only authorized users are able to access an application,
pursuant to the principle of least privilege. Securing this trusted connection
ensures that content is delivered to the end user confidentially.

Application security is the most mature and robust area of data security,
because it’s been around longer and has received more attention than other areas
such as networks and computers. The big application vendors who create the sort
of software that runs many large corporations have invested significant time and
effort to secure these applications. Large consulting firms have been built on
their expertise in deploying these applications in secure configurations, and the
applications are surrounded by technologies that secure the communication of
information into and out of the application. Yet in the same manner that a
database has to move information from its secured world and give it to a trusted
application, the application must secure access to, and the transmission of, data
to the end user. A user may well be using the correct authentication credentials
and accessing from a secure network, and may only be given data that is relevant
to their role, but ultimately they are getting access to information that, with
today’s browser-based web applications, they can very easily remove from the
secure confines of the application into the totally unknown and unprotected
world of unstructured content.

This is why organizations continue to experience data loss. Security may be
implemented at the application level, yet once the information goes beyond the
application, there is little or no control over it. As soon as the data is copied
beyond your controlled network, you lose the ability to protect the information.
Data moves from the protected realm of the database into the application and on
to the end user. Sometimes this communication occurs via a local process, but
often the application and database reside on different servers connected via a
network. The end users are rarely on the same computer that the application and
server reside on. Therefore, the security of the network itself is another area that
we must examine. However, because several other chapters of this book focus on
the subject of network security, the scope of this section is limited to mentioning
some of the technologies designed to secure unstructured data on the network.
These technologies are discussed in more depth in other chapters.

Network security technologies have developed into complex systems that are
able to analyze traffic and detect threats. Network intrusion prevention systems
(NIPSs; see Chapter 18) actively monitor the network for malicious activity and,
upon detection, prevent intrusion into the network. Malware protection
technologies prevent Trojans from deploying and planting back doors on your
trusted network clients. The newest polymorphic advanced persistent threats
(APTs), which steal data, provide back doors to attackers, and cause denial of
service (DoS) attempts, can be blocked using solutions that detect illegitimate
traffic and deny it.

All of the network security techniques described in Part IV of this book can be
used to secure network communications. However, network security solutions
are not able to protect information that has already left the network; they can
only detect the unauthorized transmission of data and deny it from going any
Challenges in Current Network Security Solutions
Again, as with application security for unstructured data, the biggest challenge
with network security for unstructured data is that once a trusted user or client is
connected to the network, the network will freely pass to that user or client any
information they are authorized to access. You might be using advanced
techniques to monitor traffic flows, but to enable business, you still need to allow
information to flow. For example, suppose you need to secure information in
collaboration with a new business partner. Suppose further that you’ve created a
secure network between the two businesses and integrated it with the identity
management systems to only authenticate legitimate users at the partner
business to access your networked applications. Over this network will flow
many pieces of valuable information, securely. However, when that information
reaches the partner, it will no longer be bound within your nicely secured
network and may exist in the clear, meaning it can be easily lost or misused. If
something goes wrong, such as loss of data, you may have nothing but audit
records showing who from the partner business accessed that data. Those may be
useful in figuring out what went wrong, but any measures you take in response
will always be reactive, after the damage has already been done.

Two growing trends in the modern business environment are to move to
cloud-based services and to expand external collaboration in the form of
outsourcing, partner alliances, and increased customer access to company
information. This has resulted in the creation of various methods for connecting
your corporate network to several sources, further complicating the problem of
security. Data flows across networks to the application and from the application

over the network to the database. Network security solutions should be used to
provide the best possible protection to this data.
Once a legitimate user has securely connected across the network to the
application to access data residing in the database, the information is ultimately
presented in a web page that is rendered by a web browser. From there, the user
can move the data to an unstructured and unprotected location, such as a PDF file
or an Excel spreadsheet, and then download and store the data on the local drive
of a desktop workstation. Therefore, the security on the computer from which the
user interacts with the application and resulting unstructured content becomes
critical. Essentially, the computer is the front line in the battleground of
information security today.

Servers are usually limited in number and physically under your control, or at
least under the control of your cloud services provider. Networks and their
gateways are also limited in number and usually within your control. But end-
user computers may number in the hundreds or thousands and may often be
beyond your security control. Furthermore, those computers may be running a
large number of platforms, a wide variety of OS versions, and a wide variety of
software, and may be used by a wide variety of people. Everything we do with
information happens on the computer, which means the security of that
computer is critical to the ongoing security of your information. Within the
context of the security of unstructured content on computers, we will focus on
only a few areas:

• Ensuring that only legitimate users can access the computer (identity access

• Controlling the flow of information over network interfaces and other
information connection points (USB, DVD, etc.)

• Securing data residing at rest on the computer
Identity Access Control
All operating systems have some form of user access control. The most basic (and
common) form is a username and password combination that is validated against
a local identity store. Successfully authenticated users are then granted a session
to the system, which then manages access to resources, typically by using an
access control list (ACL). In business environments, computers under the control
of the organization are configured to authenticate and grant sessions to users
whose identities are stored in a centralized identity management system. The
most prevalent identity management system is Microsoft Active Directory, which
natively manages access to Windows clients but is also often extended to the

management of Unix-based workstations. (Access control is covered in further
detail in Chapter 7.)

It is this identity that is associated with any unstructured data on the system.
Unfortunately, once a piece of unstructured data resides on a computer, any
security mechanism that controls access to it on the system is longer effective.
Thus, the identity that is used in the computer access may have little effect on the
actual access controls to local content. Some technologies are able to shrink the
access control layer to the content itself, and that is the subject of the following
Controlling the Flow of Data over Networks and Connected Devices
Once a user is authenticated and provided with a session, they are able to
proceed to access the network, read data on the local hard disk, and connect USB
and other storage devices and transfer data to and from the computer. Privileges
to perform these actions are implemented by the local computer, which in turn,
with technologies like Active Directory, conforms to a central policy that defines
what users are able to do on their desktops.

From the unstructured data perspective, all these connections are simply
pipes through which information can travel, from one to the next. Each pipe may
have its own security model, but each model applies security to the unstructured
data only while it travels through the associated pipe.
Securing Data at Rest
Once they are logged in to a computer, most users in organizational
environments start working with data that is often stored locally on the host
device. It might, for example, take the form of a Word document saved from an e-
mail to the desktop; or it might be a PDF file cached by your browser as it
displays it from a web page. Even smartphones are computers that are able to
store massive amounts of data and run business software that allows the use of
unstructured data. Security for storage devices, as described in Chapter 11,
becomes important at this stage.
Challenges in Current Computer Security Solutions
Computers represent the interaction of humans and computers. Much effort goes
into creating a level of trust between the person and the computer. Usernames,
passwords, security token keys, smart cards, fingerprint scanners, various
biometric devices, and other mechanisms all attempt to ensure the computer
knows that the person is who they claim to be. Yet once this trust has been
established, information is allowed to flow freely. This trust in the human at the
keyboard often fails. Humans send e-mails by accident, lose USB keys, print
confidential information and leave it lying around, and sometimes even steal
data intentionally.

Consistently securing information in use on computers is one of the biggest
challenges facing the information security community today. Yet the computer is
the perfect place to start educating the end user on the importance of security.
There are mature solutions for different aspects of computer security. Anti-
malware technologies have been on the market for over a decade, and storage
encryption is in a fairly well-defined space. The challenge is to integrate the
various endpoint technologies to accurately support your security policies.
Storage (Local, Removable, or Networked)
Once on the computer, information either exists in a dynamic state, in the
memory of a running process (for example, with a web browser or software
application), or is stored in an unstructured form on the hard disk or a removable
drive (for example, in a file located in a local folder).

Storage is one of the most effective areas of unstructured data security and is
often the one which receives the most attention after a data loss incident. Storage
security solutions mainly deal with data at rest, but sometimes stored data exists
in another state, either in transit or in use. An example of this is the contents of a
PDF file that is stored in RAM and paged to the disk by the operating system. Is
this data at rest or in use? (An interesting court case that hinged on the
distinction between “at rest” and “in use” was mentioned in Chapter 3.) Typically,
storage security solutions focus on encryption or access control. These subjects
are covered in more detail in Chapter 7, but let’s consider the strengths and
weaknesses of encryption (detailed in Chapter 10) further before we move on.
Encryption of Storage
The most common “go to” security tactic for anyone who has suffered a data
breach, failed an audit, or just wants to be proactive is to “encrypt everything”
because that seems to be the easiest and most comprehensive approach. This is
mainly because databases, network storage, content management systems, and
computers ultimately end up storing data on storage devices like hard disk arrays
or USB flash memory, so encrypting these locations is an obvious solution.
Methods of encryption on storage devices fall into two categories:

• Disk encryption (either hardware based or software based)
• File-system encryption

Disk Encryption Hardware disk encryption is totally transparent to the
operating system and, therefore, to applications and users on the computer. This
means storing a piece of unstructured data on the disk is simple and requires no
change to the operating system, the application, or the content format.

Some form of authentication must take place before any data on the drive can
be decrypted and read. When full disk encryption is performed using software,
the operating system must have some form of unencrypted partition from which

to boot and in turn authenticate the system to gain access to the cryptographic
keys to decrypt the main encrypted disks.

Both hardware and software methods provide the encryption of data as it is
written to disk across the entire disk. The methods are totally transparent to the
processes (other than, of course, those in the operating system that may be
managing the encryption/ decryption), and as data is read from disk, it is seen by
applications in its decrypted state. One downside of hardware-based disk
encryption is that the management of the cryptographic keys can be difficult.
File-System Encryption Another method of encrypting data at rest is to
implement the functionality in the file system itself. This means that the methods
may vary depending on the operating system in use. Typically, the main
difference is that file and folder encryption only secures files and folders, not the
metadata. In other words, an unauthorized person is able to list the files, view the
filenames, and see the user and group ownerships, but they cannot actually
access the files themselves without the cryptographic keys. (An exception is the
ZFS file system, which does encrypt metadata.)

File-system encryption, like disk encryption, only applies when the content
resides in a location that is encrypted. If the data is moved from the encrypted
disk to a disk that’s unencrypted, it is no longer protected.
Challenges in Current Storage Security Solutions
Storage encryption and access controls are common in many organizations, yet
occurrences of data loss continue to increase, even from environments that have
these types of solutions. As mentioned, encryption only works at the source.

Storage access controls are clearly necessary. You need a level of control over
users’ access to information on local computers or networked file shares.
However, the limitations of these access controls are very quickly reached.
Imagine the simple scenario of two folders on a network file share, “All Company
– Public” and “Confidential – Engineering.” You may have defined a tight set of
engineering groups who have access to the latter, while allowing anyone in the
company, maybe even outsiders, to access the former. It only takes the single act
of a trusted engineer to accidentally store a few confidential documents in the
“All Company – Public” folder to render the access controls for that information
completely ineffective. Location-based access controls like this only provide
control for the location where the information resides; information moves
everywhere, but the security defined at the location does not travel with it.
Data Printed into the Physical World
A lot of time and effort is devoted to finding solutions for securing unstructured
data in the digital world; however, data loss incidents due to the loss or
inappropriate disposal of paper documents must also be considered—that is,

finding solutions for how to secure information in the hardcopy world.
Considering data in paper form as unstructured content is also another way to
visualize how structured data can easily pass into the unstructured world. You
print it out.

Encryption typically doesn’t help when printing information because the
information needs to be readable to humans. Instead, methods such as
watermarks and redaction are used. Watermarks leave identifying data (like a
background image or word) in the printed copies in an attempt to alert users to
the importance of the information and try to reduce the chances they are
negligent with the data. Redaction is the process of editing or blacking out certain
text in a document such that certain sensitive parts of a document are not visible.
Redaction often applies to the visibility of both the digital document and the
resulting printed version. Risks are introduced when information is not redacted
sufficiently, or the wrong data is redacted. For example, the U.S. Transportation
Security Administration (TSA) in 2009 posted a PDF online that had been redacted
in an ineffective way such that the blacked-out areas could be easily viewed
simply by copying the content and pasting it into another document.

The computer industry has been promising the paperless office for many
years, and although we collectively generate a great deal less paper than we used
to, paper has definitely not gone away. Many data breach incidents are the result
of poor disposal of physical paper records.

Physically printed copies of documents can pose risks just as great as those
posed by their digital counterparts. A user could print a spreadsheet and send it
via fax or mail to an unauthorized party. No information security technology that
exists in the digital domain is ever going to detect, secure, and control access to
the information when it is printed on paper. You can identify every single place
that digital information is going to live and encrypt those locations, but that
encryption has no effect on a paper-based copy. Thus, the best practices for
handling printed documents are limited to restriction of the contents printed,
along with reliance on human vigilance.

Before being printed, all confidential documents should have any non-
essential contents hidden or deleted, so unnecessary confidential information is
not included in the printout.

All printed confidential documents should have a front cover page, so their
contents are not visible from a casual glance. Also ensure that all pages have page
numbers (so any missing pages can be detected) and watermarks along with
headers and footers identifying the confidentiality level of the document.

Each copy of an entire document should be labeled, to aid in tracking each
copy. And confidential printouts should never be taken home, to a restaurant or

any public place, or anywhere outside of the controlled environment they’re
meant to be in.

Confidential documents should be printed to a private printer, whenever
possible, instead of to shared printers located in common areas. When this is not
possible, the person who prints the material should go directly to the printer,
watch it print, and collect the output immediately. Confidential documents should
never be left unattended, even for a short time.

All paper documents containing confidential information should be locked in
a secured container such as a desk drawer or file cabinet. They should never be
left sitting on top of a desk, even for a short time.

When no longer needed, documents should be immediately shredded or
placed in a secure container for a shredding service to destroy. The quality of
shredding is important—older “strip shredders” that simply cut pages into
individual strips are surprisingly easy to put back together. Crosscut shredders
cut in more than one direction, resulting in diamond-shaped pieces that are much
more difficult to reconstruct.

The Handbook for Safeguarding Sensitive Personally Identifiable
Information published by the U.S. Department of Homeland Security provides
some further guidelines for secure handling of hardcopy:

• When faxing data, make the recipient aware that a fax is about to be sent, so the
recipient will be aware that they need to go collect the fax right away.

• When sending mail, verify that the correct recipient received the delivery. Also
make sure the envelope is opaque so the contents inside are not visible. Use
tracking information to see where the delivery goes, via a delivery service that
provides Return Receipt, Certified or Registered mail, or a tracking service.

Finally, and as always, common sense should be used by the people who
handle paper copies of documents, because so much of document security is
dependent on human behaviors. People handing out confidential documents
need to make sure they know who they are giving copies to, and keep track of
those copies. They should also be responsible for collecting and destroying those
copies when done. A good example is a handout used in a meeting as a reference.
After the meeting is concluded, the meeting organizer should make sure to take
back the handouts, and remind everyone about their confidentiality. How do you
enforce good behaviors like this? The best way is to ingrain the desired behaviors
in the overall culture of the environment, through consistent messaging and
repetition via a security awareness program (as was discussed further in Chapter

Newer Approaches to Securing Unstructured
The previous sections of this chapter described various techniques for securing
unstructured data in individual environments, which may be thought of as “point
solutions.” These techniques emerged from security requirements of individual
use cases, and each is focused on the capabilities and limitations of the
environment to which it pertains. Newer approaches to unstructured data
security are broader in scope, more data-centric, and less platform-dependent.
The following sections describe these newer approaches, and how they can be
used to complement the security capabilities mentioned above.
Data Loss Prevention (DLP)
Data loss prevention (DLP) refers to a relatively new group of technologies
designed to monitor, discover, and protect data. You might also hear this
technology referred to as data leak prevention—and sometimes it’s also referred
to with the word protection instead of prevention. In any case, DLP is like a
“firewall for your data.” There is a wide variety of DLP solutions on the market,
which typically can be broken down into three types:

• Network DLP Usually a network appliance that acts as a gateway between major
network perimeters (most commonly between your corporate network and the
Internet). Network DLP monitors traffic that passes through the gateway in an
attempt to detect sensitive data and do something about it, typically block it from
leaving the network.

• Storage DLP Software running either on an appliance or directly on the file
server, performing the same functions as network DLP. Storage DLP scans
storage systems looking for sensitive data. When found, it can delete it, move it to
quarantine, or simply notify an administrator.

• Endpoint DLP Software running on endpoint systems that monitors operating
system activity and applications, watching memory and network traffic to detect
inappropriate use of sensitive information.

Network, storage, and endpoint DLP are often used together as part of a
comprehensive DLP solution to meet some or all of the following objectives:

• Monitoring Passive monitoring and reporting of network traffic and other
information communication channels such as file copies to attached storage

• Discovery Scanning local or remote data storage and classifying information in
data repositories or on endpoints

• Capture Storage of reconstructed network sessions for later analysis and
classification/policy refinement

• Prevention/blocking Prevention of data transfers based on information from the
monitoring and discovery components, either by interrupting a network session
or by interacting with a computer via local agents to stop the flow of information

DLP solutions may comprise a mixture of the above, and almost all DLP
solutions leverage some form of centralized server where policies are configured
to define what data should be protected and how.
Challenges in DLP Solutions
If the DLP solution isn’t monitoring a particular storage device or network
segment, or if a particular file doesn’t have the right policy associated with it,
then the DLP solution cannot enforce the right level of protection. This means
that every network segment, file server, content management system, and
backup system must be covered by a component of the DLP technology along
with proper classification of all documents critical to its success. Proper
configuration of the DLP environment and policies is a big task, and overlooking
one (or more) aspects can undermine the whole system.

DLP only makes point-in-time decisions. Consider, for example, a DLP policy
that allows users to send confidential data to a trusted partner. Six months later
the organization decides this partner is too expensive, and sets up an agreement
with another, cheaper partner. You then reconfigure the DLP policy to reflect this
change in the business relationship, but the DLP solution has no ability to affect
all the information that has flowed to the old partner. Data may now reside with
a partner who will soon be signing an agreement with your competitor.

The way in which a DLP solution deals with policy violations has limitations.
Prevention is part of its name, and for good reason—when a user is copying a file
or e-mail, the DLP solution prevents copying of information that it deems
illegitimate. This may initially seem like a good outcome, but what if your CEO is
giving an important presentation and wants to copy a file to an unencrypted USB
stick to share a marketing presentation with the board of directors? DLP might
block that. What if you want to e-mail an important document to your home e-
mail address to work on over the weekend? Nope, DLP blocks it and informs the
IT security group. While DLP has many advantages, it may impact business
processes and productivity if all possible scenarios are not considered.

DLP is also capable of generating a certain number of false positives (and false
negatives), which makes fully implementing all blocking/prevention components
a risky exercise. Even when the accuracy of policy enforcement is very high,
organizations often find the disruption to business so high that they prefer a
monitoring-only implementation.

Despite these problems, DLP is still an excellent tool for hunting down and
monitoring the movement of sensitive data. It can provide very valuable insight

into the information flows within the network and, at a minimum, can highlight
where illegitimate activity takes place or where sensitive information is stored in
open file shares. The reports from DLP network monitoring and discovery
components provide a useful feedback loop: identifying compliance “hot spots”
and poor working practices, mapping the proliferation of sensitive content
throughout (and beyond) your enterprise, and enabling organizations to tune
their existing access control systems. But keep in mind that you will need to add
additional trained staff to reap all of the benefits of the DLP solution. A significant
increase in workload is required to examine and act on all the alerts coming from
the DLP solution, including false alerts.
Information Rights Management (IRM)
Information rights management (IRM) is a relatively new technology that builds
protection directly into the data files, regardless of where they are stored and
where they are transmitted and used. IRM evolved from digital rights
management (DRM), which is used in the entertainment industry to protect music
and movies and apply protection to all kinds of data. IRM uses a combination of
encryption and access controls to allow authorized users to open files, and to
block unauthorized users. With IRM, files are encrypted using strong encryption
techniques. When a request is made to open the file and decrypt the data,
software is required to check with a central authentication server (usually
somewhere on the Internet) and, via a reliable handshake mechanism, determine
whether the requesting user is allowed to unlock the data.

IRM solutions go even further than providing access to the data; they control
the ability to copy, paste, modify, forward, print, or perform any other function
that a typical end user would want to perform. This provides a granular level of
control over files that can’t be provided by any other single security technology.
Thus, IRM can be a valuable tool in the security toolbox. Continue to the next
chapter to learn much more about this promising technology.

As defined in this chapter, unstructured data is any collection of electronic
information that does not follow a strict format (and therefore lacks any inherent
security controls). Unstructured data by itself is wide open and unprotected. This
data may reside in databases, applications, networks, computers, storage, and
even the physical world. And, it is growing at a pace faster than that of structured
data, which typically has inherent security controls.

Structured data is relatively easy to secure compared to unstructured data,
which exists in three states at various times: at rest, in transit, and in use.
Unstructured data is found in applications, networks, computers, storage systems,

and even inside structured databases. And once that data is printed into the
physical world, it can no longer be controlled by the software-based security
technologies applied to the original source data. This chapter provided an
overview of a range of security technologies for securing unstructured data in all
of these locations, including the limitations of those technologies.

With regard to applications, we discussed the use of access controls, network
and session security, auditing and logging, and configuration management to
protect unstructured data at rest. For the network, we identified that you can use
all of the network security technologies described in Part IV of this book to
protect data in transit. On computers, we covered ensuring that only authorized
users can access the data, controlling the flow of that data, and securing the data
at rest on the computer. On storage systems, we mentioned access controls and
discussed encryption in more detail. We looked at securing unstructured data
within databases through the use of encryption. In the physical world, we
reviewed the challenges and best practices for handling paper copies of
confidential information. And finally, we talked about two newer technology
solutions: data loss prevention (DLP), and information rights management (IRM)
as solutions to protecting unstructured data.

There is a common thread to these technologies and what they attempt to
achieve: ensuring that only authenticated and authorized users can access
secured data, and that bypassing the access control protecting that data isn’t easy.
These technologies also share a common challenge: they need to be implemented
in the proper places, and even when they are, if the information travels beyond
your perimeter of control, you lose control over that information and visibility of
where it goes thereafter. As with most security models, layering of various
security controls helps to close the gap by providing a defense-in-depth approach
to security.

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Securing Vote Data at Poll Stations, In the Wire and Data at Rest. VDM Verlag,
ICON Group International. The 2011–2016 Outlook for Information Data Loss
Prevention (DLP) Appliances in the United States. ICON Group International, 2011.
Kenan, Kevin. Cryptography in the Database: The Last Line of Defense. Addison-
Wesley, 2005.
National Institute of Standards and Technology. NIST Special Publication 800-111:
Guide to Storage Encryption Technologies for End User Devices. NIST,

Photopoulos, Constantine. Managing Catastrophic Loss of Sensitive Data. Syngress,
U.S. Department of Homeland Security. Handbook for Safeguarding Sensitive
Personally Identifiable
U.S. Government. Guide to Storage Encryption Technologies for End User Devices.
Books, LLC, 2011.

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