How to Extend Your Windows Server Trial (Legally)

June 1st, 2025 - Reading Time: 2-3 minutes

Windows Server trials are great for testing — until the dreaded “Evaluation Period Expired” message stops your setup cold. What if you could legally extend the trial period and buy yourself more time? Here’s how to do it using Microsoft’s own tools — no hacks, no cracks.

TL;DR

• You can extend the trial period up to 6 times, each for 180 days.
• Use the slmgr /rearm command.
• This works on Windows Server Evaluation editions only.
• It gives you up to 1080 extra days.

Step-by-Step Guide

1. Check Your Current Time Left

Open an elevated Command Prompt and run:

slmgr /dli

This tells you how many days are left or if the trial has expired.

2. Extend the Trial

Run:

slmgr /rearm

Then restart the server.
You now have another 180 days.

3. Repeat Up to 6 Times

You can do this up to 5 more times (total of 6).
To check how many rearms are left:

slmgr /dlv

4. After All Rearms Are Used

You’ll eventually hit 0 rearms. At this point, you either:

• Buy a license and activate via MAK/KMS
• Reinstall the OS for a fresh trial period (not ideal for live systems)

Legality & Ethics

Microsoft explicitly allows this for evaluation and test purposes.
Think of this as a grace period, not a loophole.

Conclusion

Using slmgr /rearm is a legit way to maximize your Windows Server evaluation time — especially helpful for labs, testing automation scripts, or preparing for certification exams.

Need even more time? Consider snapshotting the system after install or using automation to redeploy clean images.