ObserveIT v.7.0.

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Introduction and Installation Guide
 ObserveIT Introduction and Installation Guide

Contents
Introduction .............................................................................................................................. 3
Product Version ....................................................................................................................... 3
Trial Limitations ....................................................................................................................... 4
System Requirements ............................................................................................................. 4
ObserveIT “All-in-One” Management Server............................................................................................ 5
ObserveIT Windows Agent ....................................................................................................................... 6
Unix/Linux Agent....................................................................................................................................... 6
Mac OSX Agent ......................................................................................................................................... 7
Web Categorization Module ..................................................................................................................... 8
Architecture Overview ............................................................................................................. 9
Important Considerations.......................................................................................................10
ObserveIT component network interaction ........................................................................................... 10
Permissions Required for all Computers ................................................................................................ 10
Firewall Permissions................................................................................................................................ 10
Privacy and Legal Considerations............................................................................................................ 10
Installation Package Overview ...............................................................................................11
Using PowerShell ....................................................................................................................18
Installing SQL Express ...........................................................................................................19
Configure SQL Express to Accept TCP/IP Connections ......................................................23
Installing the ObserveIT Software..........................................................................................25
Installing an ObserveIT Agent on a Microsoft Windows-based Computer .........................29
Installing an ObserveIT Agent on a *NIX-based Computer ..................................................33
Installing an ObserveIT Agent on a Mac Computer ..............................................................34
Verifying Successful User Activity Recording ......................................................................35
Copyright .................................................................................................................................36

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Introduction
The ObserveIT User Behavior Monitoring and Analytics platform is designed to help security,
incident response, infrastructure, compliance, and legal teams easily identify and eliminate
Insider threat. This document describes the steps necessary to set up and effectively deploy the
ObserveIT software for a self-guided trial.

Product Version
ObserveIT version v.7.0.0. features a number of major improvements over version 6.7.2.

This document was written for ObserveIT Enterprise version 7.0.0. This document uses screenshots and
procedures written for Windows Server 2012 R2 and SQL Express Server 2012.

Major Product Enhancements in 7.0.0

Increased visibility, insights into activity, preventing malicious actions, key-logging alerts, and a
new UI.
User Activity Profile
• Obtain an aggregated view of user activity by aggregating user actions, application
usage, and credential use
• View user active and idle time, most commonly used applications, and new websites that
have never been visited before
Web Console UI Rebranding
• New UI marries old and new functionality under a single interface
• Improved response and load time alongside improvements to stability and visual acuity
Insider Threat Library (ITL), Alert, and Report Improvement
• New 200 out-of-the-box alert rules
• New out-of-the-box reports and updated sample reports
• Keyword based alerting for detecting commands, abuse, or data exfiltration
Preventative Actions
• Prevent the launch of suspicious applications and block inappropriate use within allowed
applications
• Log off users from systems and prevent interactive access to sensitive servers
Expand to more platforms
• New Mac agent MacOS Sierra 10.12
• Windows Server 2016
• MS-SQL Database 2016
• RHEL 7.2 support

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Trial Limitations
ObserveIT will provide an Not for resale (NFR) license viable for a 15-day trial period. All self-
guided trials are limited in license scope to:
• 1 Windows Terminal Server License
• 2 Windows Server Licenses
• 5 Windows Desktop Licenses
• 5 Mac Desktop Licenses
• 5 Linux/Unix Multi-Purpose Licenses

System Requirements
Before running the ObserveIT install package, please review the necessary minimum
requirements.

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ObserveIT “All-in-One” Management Server

Prior to installation, you must have at least 1 virtual Windows Server with the following
specifications and components:
ObserveIT Server side Minimum System Requirements
Components

ObserveIT Hardware Requirements

Application Server • 2 dual-core fast CPU
• 8 GB RAM
Web Console Server
• 60 GB free hard disk space (OS)
Web Categorization • 1 Gigabit Ethernet adapter
Module
Software Requirements
Database Server • Operating system: Windows Server 2012 R2
• .NET Framework 3.5.1 and .NET Framework 4.5.2
• SQL Express 2012/2014 (database engine, Full-Text
Search, and SQL Server Management Studio)
• IIS 7.5/8.5 with ".NET Extensibility 3.5",”ASP”, "[Link]
3.5",
• "IIS 6.0 Management Compatibility" with all
subcomponents and "IIS Management Scripts and Tools"
• Domain member (preferred) with typical server
configuration
• Local administrator’s permissions
• SYSADMIN permissions on the SQL instance
• Mixed-mode SQL authentication

Note: It is the responsibility of the customer to provide all hardware/virtual machines, storage and all
networking requirements for the test environment to be ready for the installation of the ObserveIT
platform.

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ObserveIT Windows Agent

The Windows Agent is a user-mode executable that binds to every user session. As soon as a
user logs into a monitored server, the Agent begins recording based on the configured recording
policy.
The ObserveIT Windows Agent can be installed on any supported Windows-based operating
system (server or desktop) that you want to monitor. For the trial, it is recommended that you
manually install the Agent on each system to get familiar with the setup steps required.

Operating System Minimum System Requirements

Microsoft Windows Hardware Requirements
• 2.4 GHz or faster Intel or AMD processor
• 2 GB RAM or more
• At least 1 GB free hard disk space
• 100 Mb/1Gb Ethernet adapter (1 Gigabit link speed
recommended)

Software Requirements
• Microsoft Windows Server 2008/2008 R2/2012/2012 R2,
Windows Vista, Windows 7, Windows 8/8.1, Windows 10 (It is
recommended that you always use the latest service pack for
your operating system)
• .NET Framework (version 3.5.1 and 4.5.2 must always be
installed)

Note: Local Administrator’s permissions required to install the agent.

Unix/Linux Agent
The *NIX Agent runs in user mode and is triggered when an interactive session is created on a
monitored machine (connected via SH, Telnet, Rlogin, etc.) It records user activity inside the
sessions, including interactive user activity and system functions such as OPEN, EXEC,
CHMOD and others.
The ObserveIT agent can be installed on all Unix or Linux-based systems which require
monitoring. The Unix or Linux Agent installer is a self-extracting file which includes the package
and an installation script.
You can deploy ObserveIT Agents on the following Unix/Linux-based operating systems:
▪ Solaris ▪ AIX
▪ HP-UX ▪ RHEL/CentOS
▪ Oracle Linux ▪ SLES (SuSE Linux Enterprise Server)
▪ Ubuntu ▪ Debian
▪ Amazon Linux

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Example: CentOS/RHEL Expanded Requirements

RHEL/CentOS ▪ 4.8-4.9, 5.6-5.11, 6.0-6.7;

Supported Versions i386/x86_64
▪ 7.0-7.2; x86_64

Note: If you require additional *NIX minimum requirements please review our detailed documentation.

Mac OSX Agent

The ObserveIT mac Agent software can be installed on any supported Mac Platform. The
software is a user mode package that will record interactive actions on Mac desktops and
laptops. The agent also supports VNC for remote connections and fast user switch for recording
multiple users.
The ObserveIT agent can be installed on all Mac based systems which require monitoring. The
Agent installer is a self-extracting file which includes the package and an installation script.
Mac agent is part of the launchd agent binary. Mac agent is guarded by the Apple OS (launchd).
Each session has it's own logger (including fast switch and VNC connections).

Operating System Minimum System Requirements

Mac OSX Hardware Requirements
• 1.6 GHz or faster Intel Core processor
• 4 GB RAM or more
• At least 1 GB free hard disk space
• 100 Mb/1Gb Ethernet adapter (1 Gigabit link speed
recommended)
• VNC support for remote connections
• Fast user switch for recording multiple users

Software Requirements
• OSX 10.10 Yosemite
• OSX 10.11 El Capitan
• MacOS Sierra 10.12
• On MacOS Sierra 10.12 the logger permissions must be
granted manually through system perferences.

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Web Categorization Module

In ObserveIT 6.7 a Web Categorization module has been added to the ObserveIT feature set to
alert administrators on inappropriate or dangerous site visitation. ObserveIT will be able to
detect and alert on users visiting illegal, phishing, or harmful sites.
We chose 28 categories that are most commonly associated with exposure and risk.
Some of the categories include: Malicious Ad sites, gambling, gaming, illegal drugs, infected
watering holes, remote proxies, and phishing.
The purpose of the web categorization is to act as a first layer of notification for organizations
that have not configured a content filtering platform. Secondly, ObserveIT can be used as
mitigation strategy for users who have intentionally bypassed an existing content filtering
system.

Prerequisites for Installing the Website Categorization Module

In order to download the initial data and receive updates directly from NetSTAR cloud service,
your machine (that is, the server on which the Website Categorization module is installed) must
have Internet access.
Make sure that port number 443 is open, and that the URL [Link]
[Link]/gcfus/[Link] (that the module needs to access NETSTAR for initial data download and
daily database updates) is not blocked by the Firewall.
8 GB minimum memory requirement is recommended. If you install the Website Categorization
module on a machine with less than 8 GB RAM, the first time that the module detects the
categorized browsed URLs, alerts will not be generated. Upon subsequent browsing, alerts will
be generated on these URLs.

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Architecture Overview

Figure 1 - "All-In-One" Architecture Diagram

The ObserveIT software application is comprised of the following components:

• ObserveIT Windows, *NIX, and Mac agents

• ObserveIT Web Categorization Module
• ObserveIT Application Server
• ObserveIT Web Console
• ObserveIT Database Server

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Important Considerations
ObserveIT component network interaction
1. Each monitored desktop or server runs the ObserveIT Agent which is installed locally on
the computer.
2. The Agent captures information about user activity, secures it, and sends it to the
Application Server.
3. If high availability is a requirement and there is more than one Application Server, they
should be load balanced by using either a software or hardware-based device. In that
case the Agents will communicate with the load balancer’s virtual IP (VIP).
4. The Application Server analyzes and compresses received data, then it stores it by
splitting the textual data in the SQL Server database.
5. An administrator can connect to the Web Console Web-based interface using a web
browser, and search for, replay, run reports and inspect alerts based on the captured
user activity.
6. Any component of the data transfer or data storage process can be encrypted, if
needed.
Permissions Required for all Computers
1. All computers are members of the same Active Directory domain
2. Logon permissions to these computers with administrative permissions
3. Permissions to access the SQL Server database engine (SYSADMIN permissions)
4. Full network connectivity

Firewall Permissions
On default configuration ObserveIT agents utilize HTTP port 4884 to communicate with the
application Server and the Application Server uses port 1433 to communicate with the
Database server. If firewalls are enabled, please make sure to create firewall permissions fo
these ports.
Opening the firewall ports can be done via Command prompt using the following rules:
1. For Agent to App Server: netsh advfirewall firewall add rule name="OIT Application
Server (TCP 4884)" dir=in action=allow protocol=TCP localport=4884
2. For App Server to Database: netsh advfirewall firewall add rule name="SQL Server (TCP
1433)" dir=in action=allow protocol=TCP localport=1433

Privacy and Legal Considerations

If the ObserveIT software will be deployed in a production environment, consider the
implications of installing monitoring software within your organization. Make sure that you
seek all proper management approval and consent.

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Installation Package Overview

After you have downloaded the ObserveIT installation package you will need to extract the
contents. Following this step go ahead and move the file folder over to the prepared test server.
Once the installation package is transferred, look inside. You will find the following file folders:

Figure 2 - Installation Folder Contents

✓ DB – Contains the setup files for the 4 ObserveIT SQL databases

✓ DB_Analytics – Contains the setup files for the ObserveIT analytics database
✓ Docs – Contains several helpful setup, benchmark, and integration documents
✓ Insider Threat Library – Contains the exported rule library for duplication and review
✓ Integrations and APIs – Contains examples of ObserveIT API and integrations
✓ Mac Agent – Contains the Mac agent install binaries
✓ SQLExpress – Installation package for SQLExpress for the purpose of the trial (you can use
your own instance of SQL in lieu of SQL Express if you prefer)
✓ Typical Install – ObserveIT one-click installation scripts and data
✓ Unix-Linux Agent – Various unix/linux agent install packages
✓ Utilities – Several useful tools such as the ObserveIT field-marking utility and Statistics
collector
✓ Web – Contains the web console and application server packages
✓ WebsiteCat – Contains the new ObserveIT web categorization module
✓ WinAgent32bit – Contains the ObserveIT windows agent for 32 bit systems
✓ Winagent64bit - Contains the ObserveIT windows agent for 64 bit systems
✓ READ [Link] – Contains system minimum requirements and helpful notes
✓ [Link] – Self-contained one-click ObserveIT installer that will be used for this trial

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Installing IIS and Associated Roles

You can install IIS 8.0 on Windows Server 2012, or IIS 8.5 on Windows Server 2012 R2, using:

• Server Manager
• Powershell

To install IIS 8.x on Windows Server 2012/R2 using Server Manager

1. Open the Server Manager.
2. Click Roles, and click Add Roles.
3. In the Add Roles and Features Wizard, in the Server Roles page, select the Web Server
(IIS) option, and click Next.

Figure 3 - Selecting the Web Server (IIS) Role

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Figure 4 - Confirm Adding Web Server Features

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4. In the Features Wizard, select .NET Framework 3.5 Features.

Figure 5 - .NET Framework 3.5 Features

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5. Scroll down to the Management Tools folder in the Roles list, and select the Application
Development Role.
Make sure that the following roles are selected:
o .NET Extensibility 3.5
o .NET Extensibility 4.5
o ASP .NET 3.5
o ASP .NET 4.5
o ISAPI Extensions
o ISAPI Filters

Figure 6 - ObserveIT requires .NET 3.5 and 4.5 to run

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o Scroll down to Management Tools and select the following [Link] 6 Management
Compatability
o IIS 6 Scripting Tools
o IIS 6 WMI Compataibility

Figure 7 - IIS 6 Compatibility is necessary for running the interactive installer

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6. Confirm that the following roles have been selected prior to installation of the components.

Figure 8 - The roles do not require a server reboot

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Using PowerShell
To install IIS 8.0 and relevant components on Windows Server 2012 R2 using PowerShell
Open a PowerShell prompt with elevated credentials, and type the following command:
Import-Module ServerManager

Type the following command in one line. You can copy the command and paste it in the
PowerShell window.

Install-WindowsFeature Web-Server, Web-WebServer, Web-Common-Http,

Web-Default-Doc, Web-Dir-Browsing, Web-Http-Errors, Web-Static-
Content, Web-Health, Web-Http-Logging, Web-Performance, Web-Stat-
Compression, Web-Security, Web-Filtering, Web-App-Dev, Web-Net-Ext,
Web-Net-Ext45, Web-Asp, Web-Asp-Net, Web-Asp-Net45, Web-ISAPI-Ext,
Web-ISAPI-Filter, Web-Mgmt-Tools, Web-Mgmt-Console, Web-Mgmt-Compat,
Web-Metabase –IncludeManagementTools

If it is not installed, you will also need to install the .NET Framework 3.5 Features. Open a
Command Prompt, and type the following command in one line:
Add-WindowsFeature NET-Framework-Features, NET-Framework-Core

Close the PowerShell window. You do not need to reboot server.

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Installing SQL Express

If you already have your own SQL instance, disregard this step and go to the next section,
“Installing the ObserveIT platform”.

1. Navigate to the SQLExpress folder and to begin installation, run the SQL setup as an
administrator.

1. Select “New SQL Server stand-alone installation or add features to an existing

installation”, a new dialogue box will open up with additional prompts.

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2. Click through the Microsoft update, product updates, install setup files, and install rules.
Once you get to Installation Type make sure to click on the “Perform a new installation
of SQL Server 2014”.

3. Accept the license terms and move on to the Express features to install. The features
required for ObserveIT are the Database Engine Services, Full-text and Semantic
Extractions for Search, and the Management Tools – Basic and Complete, click
Next.

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4. You can choose to either leave the instance name on default or name it as needed. In
the example below the SQL instance is named “TestObserveIT”.

5. Click through Server Configuration leaving the settings on default. On the Database
Engine Configuration, switch the Authentication Mode to Mixed Mode and set a
password for your Server Authentication (SA) account.

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Note: On this screen you can also change the Data Directories path and FILESTREAM options.

6. On the “Reporting Services Configuration” leave options as default and click Next.

7. Click “Next and the Installation Progress” will begin. When it is finished review any
warning or alerts and move on to the next step.

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Configure SQL Express to Accept TCP/IP Connections

By default, and to the frustration of many administrators new to SQL Express, the initial
configuration of SQLExpress comes with TCP/IP connections disabled, which is a
communication channel that the ObserveIT Application server requires to send data to the SQL
instance we created.
1. To enable “TCP/IP connections” hold down the Windows key and press R to initate a
Run window. Type the command associated with your version of SQLExpress and hit
OK:

SQL Server 2016:

[Link]
SQL Server 2014:
[Link]
SQL Server 2012:
[Link]
SQL Server 2008:
[Link]

2. Expand the “SQL Server Network Configuration” tab and select the Protocols for your
SQL Instance then on the right hand side right click on the “TCP/IP” protocol name and
select “Enable”.

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3. Confirm the successful installation of your SQL instance by opening SQL Server
Management Studio and logging in to your SQL instance with the Server Authentication
account.

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Installing the ObserveIT Software

Now that we have finished the installation of the SQL Server it is time to install ObserveIT.

1. Navigate back to the ObserveIT installation folder and run the [Link] as an
Administrator to launch the ObserveIT one-click installer.

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2. Configuring ObserveIT to install to the correct SQL Server requires you to put in the new
SQL instance that you have created. Since this is a local SQL instance you can use .\<SQL
Instance name>. Next in the SQL Server authentication section select “SQL Server” and
put in your Server Authentication (SA) credentials.

3. Under the Web Console selection, leave the ObserveIT Application (Port 4884) and select
whether or not you’d like to secure access to the web console.

Note: ObserveIT creates a self-signed certificate created in IIS. If you have your own
Digital Certificate you can use it to replace the self-signed cert after the installation.

4. Make sure you have your ObserveIT license ready (if not you can email
licenses@[Link]) and plug it into the “Insert License:” field.

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5. As the final step, hit on “I Agree” for the Terms of Service and click Install. The ObserveIT
install process will first deploy the ObserveIT databases, then the Application Server, Web
Console, and finally an ObserveIT agent.

Note: If the installation fails or does not go as expected, don’t worry! You are not alone. You should
reach out to one of our friendly support engineers at support@[Link].

6. Congratulations! You have completed the installation. The ObserveIT web console will
automatically launch.

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7. After closing the installation window, the ObserveIT web console opens automatically.
The login page appears, in which you can configure the initial admin password.

Note: You can refer to the User Guide located within the Web Console for configuration
and other useful settings.

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Installing an ObserveIT Agent on a Microsoft Windows-based

Computer
An ObserveIT agent must be installed on any computer that you want to monitor and record.
You can deploy as many ObserveIT Agents as required up to the trial licensing limit. For a small
number of monitored servers, it is recommended that you manually install the Agent on each
system to familiarize yourself with the process.
The following steps describe how to install an ObserveIT Agent on a Microsoft Windows-based
machine:

1. Navigate to the original ObserveIT installation folder and locate the two Windows Agent
installation folders. Copy the relevant file folders either manually to a target machine or
to an easily accessible network share.

• On a Windows 64-bit operating system, use the “WinAgent64bit” folder from the
ObserveIT installation folder.

• On a windows 32-bit operating system, use the “WinAgent32bit” folder from the
ObserveIT installation folder.

2. Once copied over, open the file folder and right-click the “[Link]” file, and select
“Run as Administrator” then click “Next”.

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3. Select “I accept” on the End-User License Agreement stage and click “Next”.

4. On the next screen fill-in the “Server” text box, type the name of the ObserveIT
Application Server. It is preferred that you use the server’s fully qualified domain name
(FQDN) or IP address.

Enter the TCP port number. By default, ObserveIT listens to TCP port 4884. When
accepting the default settings during the installation of the ObserveIT Application Server.
Click “Test Connection” to make sure that the communication is not obstructed by a
firewall (if there is no connection, refer to Firewall permissions under the Precautions
section on page 7)

If the configuration was correct, you will be notified that it was successful. Click “Ok”.

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5. It is recommended to select the “Custom installation” radial box so as to get familiar

with the custom settings then Click “Next”.

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6. Set the Recording Policy to Default Windows-based Policy. You can also change
other settings such as the installation folder, the registration state, and whether to hide
the agent from the Add/Remove Programs / Uninstall a Program applet in Control
Panel. When you finish configuration click Next.

7. Make note of the settings and click “Install”.

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1. When installation is complete, click ‘Finish” and note the Agent’s blue icon in the tray area.

Installing an ObserveIT Agent on a *NIX-based Computer

The Unix or Linux Agent installer is a self-extracting file which includes the package and an
installation script. All Unix/Linux Agent installation files are located at /opt/observeit/agent.
1. To install the *NIX agent navigate to the ObserveIT install folder, find the relevant
distribution .run file and copy it to the target server(s).

2. Log in to the target server with root permissions; or, alternatively, use
the pfexec command.

3. Run the ls –l command and verify that the file has execute permissions (-rwxr-xr-x).
Otherwise, use chmod +x for the Agent’s file name.

4. Run the command:

./observeit-agent-<*NIX_Distro>-<Dist_ver>-[Link].run -- -i -s <Application Server IP

address>
Installation output example:
Verifying archive integrity... Done.
Uncompressing ....
The oit package was not previously installed; performing clean install
Installing observeit agent
Successfully registered this machine and saved configuration

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After installing the Agent, you should check the Agent's registration and health status in the
ObserveIT web console.
Important Note!
1. If there are no execute permissions on the /tmp directory, installation will fail when the self-
extracting script attempts to deploy the packages. To prevent installation failure in this
case, run the installation command using the ––target option, as follows:

./observeit-agent-Ubuntu-12.04-precise-[Link].run --target /work/install -- -i -s [Link]

2. If there is insufficient space in the /tmp folder, then you need to redirect the installation to another
directory. In this case, include the –t option in the installation command, as follows:

./observeit-agent-Ubuntu-12.04-precise-[Link].run -- -i -s [Link] -t /work/tmp

where /work/tmp is the location of the new directory, if the /work/directory does not exist
you must create it manually.

Installing an ObserveIT Agent on a Mac Computer

The Mac Agent installer is a self-extracting file which includes the package and an installation
script. All Mac Agent installation files are located at /library/OIT/agent.
1. To install the ObserveIT Mac agent you must obtain the package and copy it your Mac
workstation.
2. Run the ls -l command and verify that the file has execute permissions (-rwxr-xr-x).
Otherwise, use chmod +x for the Agent’s file name.
3. Using the sudo (or equivalent) command, run the installation as follows:

Sudo ./ObserveIT-agent-OSX-[Link].run -- -i -s <ServerIP>:<Port>

Where <ServerIP> is the IP address or FQDN of the ObserveIT Application Server and
<Port> is the TCP port used by the ObserveIT Application Server

4. After successful installation, you can log in to the ObserveIT web Console and begin
recording sessions.

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Verifying Successful User Activity Recording

You should now be able to access the ObserveIT Web console from anywhere on your network
by navigating to the url: Https://<Server_Name_FQDN>/ObserveIT

1. By default ObserveIT will open up to the ObserveIT management console, you should
immediately see recorded sessions as well as the Trial duration at the top right of the
screen.

2. Go ahead and familiarze yourself with the layout of the console and expand the recorded
sessions by clicking the to make sure matadata is being collected. Then click on the
video replay button to verify session recording.

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Now you’re done! You should check out the Quick Help guide in the ObserveIT console as
well as the documents in the Installation Folder for configuration, usage, and setup.

Documentation Feedback
The following online documentation will provide you with guidance for specific aspects, including
system requirements and installation procedures:
[Link]

ObserveIT is engaged in a continuous effort to improve our documentation. Please help us by

sending your comments to: SE-USA@[Link].

Copyright
Copyright * 2016, ObserveIT Inc. All rights reserved.

The information in this document is subject to change without notice. No part of this document may be
reproduced, stored or transmitted in any form or by any means, electronic or mechanical, for any purpose
without the express written permission of:

ObserveIT Inc.

ObserveIT Inc. assumes no liability for any damages incurred, directly or indirectly, from any errors,
omissions or discrepancies between the software and the information contained in this document.

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