Extend Windows Server Trial: 240 Days - A Complete Guide

Maximizing the Utility of Microsoft Evaluation Software
Microsoft's evaluation releases represent a significant benefit for IT professionals and developers. They provide access to fully functional software for testing, demonstration, and development purposes without incurring licensing costs.
However, these evaluation versions are inherently time-restricted. Consequently, maximizing the operational lifespan of an evaluation release is crucial to fully leverage its capabilities.
Extending the Windows Server 2008 R2 Evaluation Period
This guide details the process of extending the usage duration of the Windows Server 2008 R2 evaluation release to its absolute limit.
By following the outlined steps, you can ensure a prolonged period for thorough testing and evaluation before needing to transition to a licensed version.
The ability to maintain a functional evaluation environment for an extended timeframe is particularly beneficial for complex deployments and long-term testing scenarios.
Important Note: While these methods extend the evaluation period, they do not circumvent licensing requirements. A valid license must be obtained for continued use beyond the extended evaluation timeframe.
Successfully extending the evaluation period allows for comprehensive assessment of the software's features and compatibility within your specific infrastructure.
This proactive approach to evaluation ensures informed decision-making regarding software adoption and investment.
Understanding Windows Server 2008 R2 Evaluation
Upon activation, the Windows Server 2008 R2 evaluation or trial period is set to 180 days. Following this period, a legitimate license key is necessary to continue operation; otherwise, the server will automatically power down after one hour of use.
Like many Microsoft products needing activation, Windows Server 2008 R2 provides an initial grace period. This allows for unrestricted use for a short time before activation becomes mandatory.
Grace Period Details
Specifically, the evaluation version offers a 10-day grace period. This period can be reset, or "re-armed," up to five times.
Successfully utilizing all five resets extends the total available usage time by an additional 60 days.
This method of extending the evaluation period is entirely permissible and is, in fact, supported by Microsoft.
The process described is designed to be automated, requiring minimal intervention after initial setup.
Extending the Windows Server Grace Period
The initial procedure, designated "Reset Activation Timer," leverages all five available 10-day grace periods. Each execution of this task represents a unique, date-specific invocation. The inaugural call should be scheduled ten days following the initial system startup, with each subsequent call occurring ten days after the preceding one.
It's important to note that we've incorporated utilities to facilitate the calculation of this timing, which will be detailed later in this document.

The core of this process involves executing the "slmgr.vbs" script with the -rearm parameter, followed by a system restart.

Consequently, the activation countdown is reset.
Please observe that the screenshot illustrates a value of 8; however, in a typical scenario, the countdown would have reached zero prior to this point.

The timer is then restored to its initial value of 10 days.

Server Activation Procedures
Following the exhaustion of all reset and rearm commands, the server must be activated. This process is initiated through the "Activate Server" task.
It is recommended that this task be scheduled for execution ten days after the most recent invocation of the "Reset Activation Timer" task.
The activation itself is accomplished by utilizing the "slmgr.vbs" script once more, but this time employing the -ato parameter. This parameter triggers the activation process, and a subsequent system reboot is required.
Ultimately, successful activation results in a server instance with a time-limited lifespan of 180 days.
Importing Pre-defined Scheduled Tasks
Although the necessary scheduled tasks can be created manually, we've provided them in an importable XML format for increased convenience. Links to these files are available in the section below.
To begin the import process, launch Task Scheduler. Then, within the Task Scheduler Library, right-click and choose the "Import Task" option.

Navigate to the folder containing the extracted Tasks and select the desired XML file.
Upon selection, it will be necessary to adjust the account under which the task executes to align with your server’s configuration. Within the "Create Task" dialog box – which appears after choosing a task – click the "Change User or Group" button.

Type "administrator" into the field and then click "Check Names" followed by "OK".

The effective account should now display the Administrator account specific to your system.

Applying the task settings will prompt you to enter the Administrator password.

This process must be repeated for each of the XML task files you wish to import.
Configuring the Scheduled Tasks
Adjusting the Dates
A primary adjustment required is updating the dates associated with each scheduled task. To simplify this process, a utility has been included within the downloaded package to compute the precise dates for each task. Execute the ActivationDates_RunMe.bat file from the extracted archive, and you will observe output similar to the example provided.
Modify the dates of the corresponding scheduled tasks to optimize the utilization period.

Expiry Notification Emails
Server activation will cease after 240 days. While the remaining time can be checked within the server’s settings, it’s easy to overlook this after eight months. Therefore, a scheduled task is provided to automatically send daily email reminders as the expiration date nears.

However, for this functionality to operate, Blat – a command-line email application – must be configured on your system.
Configuration is straightforward; download Blat and extract its contents to the C:\Windows directory (or a location included in your system's PATH environment variable). Then, from the command line, establish the sending properties:
BLAT -install <email server> <sender email address>
For instance, to configure Blat to transmit email via the server "smtp.myemail.com" using the address "notify@myemail.com", the command would be:
BLAT -install smtp.myemail.com notify@myemail.com
With Blat configured, navigate to the Actions tab within the task and edit the action.

Within the "Add arguments" line, scroll to the end and update the value following the "-to" parameter with the email address where warnings should be delivered. You can also modify the email's message body and subject here.

After applying your changes, test the email task by accessing the main Scheduled Task Library, right-clicking the email warning task, and selecting "Run".

If successful, an email should be received at the specified address.

By default, this action will execute daily, beginning 10 days before the server’s expiration.
Links
Activation tools for the server can be obtained from How-To Geek, providing resources including XML files for Scheduled Tasks and utilities for date computations.
Microsoft offers the Windows Server 2008 R2 Evaluation version for download.
Additional Resources
The Blat command-line email tool is available for download and can be utilized for automated email notifications.
These resources facilitate server setup and management, offering tools for activation, evaluation, and communication.
Utilizing these downloads can streamline the process of deploying and testing a Windows Server 2008 R2 environment.
The provided links offer direct access to essential software components for server administration.
Specifically, the How-To Geek resources are valuable for automating tasks and managing server schedules.
Furthermore, Blat provides a flexible solution for integrating email functionality into server-side scripts and applications.
Accessing the Windows Server 2008 R2 Evaluation allows for a comprehensive assessment of the operating system's capabilities.
These tools collectively support a robust and efficient server deployment workflow.