DTT

How to set up server 2019 on amazon web services

Published: February 17, 2019 (Updated: Feb 17, 2019)
#AWS #Windows Server 2019 #EC2

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Deploying Windows Server 2019 on AWS: The Ultimate Step-by-Step Guide!

Hi guys, Darren O’Neill here from Darren’s Tech Tutorials!

Welcome to another quick and practical guide. If you’ve been looking to harness the power of the cloud and need a robust testing environment, today we are walking through the process of setting up a brand new Windows Server 2019 instance on AWS (Amazon Web Services).

We’re going to cover everything from launching an EC2 instance to securing your connection and logging in via RDP. By the end of this tutorial, you’ll have a fully functional Windows Server 2019 environment running in the cloud.

Let’s dive in!

1. Getting Started: Logging In and Navigating to EC2

To begin, you’ll need an active AWS account and access to the management console.

  1. Log In: Navigate to the AWS Management Console and enter your credentials.
  2. Find Services: Once logged in, click on the Services dropdown menu at the top.
  3. Select EC2: Under the Compute section, click on EC2 (Elastic Compute Cloud). This dashboard manages all your virtual server instances.
  4. Launch an Instance: On the EC2 dashboard, look for and click the prominent blue button labeled Launch Instance.

2. Selecting the Windows Server 2019 AMI

The first step in launching your instance is selecting the appropriate operating system image (known as an Amazon Machine Image, or AMI).

  1. Search for the OS: In the search bar on the AMI selection page, type 2019 and press Enter.
  2. Select the Base Image: Scroll through the results until you find the Microsoft Windows Server 2019 Base image. Click Select.
  3. Choose Instance Type (Crucial for Free Tier!): On the next screen, you must select your instance type. To ensure you stay within the AWS Free Tier limits and avoid unexpected charges, make sure you choose the t2.micro instance type.
  4. Click Next: Configure Instance Details.

Pro Tip: If you select any instance type other than t2.micro and you are not already utilizing the Free Tier, you may be charged! Always confirm pricing before launching larger instances.

3. Configuring Storage, Tags, and Security

We will generally stick to the default network configurations, but we need to pay close attention to storage and security groups.

  1. Configure Instance Details: For this test environment, we will leave most details on the default settings (including the default VPC). Click Next: Add Storage.
  2. Add Storage: The default setting usually provides 30 GB of General Purpose SSD storage, which is sufficient for a basic server test. We will leave this default setting. Click Next: Add Tags.
  3. Add Tags: Tags are helpful for identification and organization. Click Add Tag.
    • Key: Name
    • Value: Windows 2019 Server
  4. Click Next: Configure Security Group.

Configuring the Security Group (RDP Access)

The security group acts as a firewall, controlling inbound and outbound traffic. Since we need to access the Windows Server, we must allow Remote Desktop Protocol (RDP) connections.

  1. RDP Port: Ensure that RDP (Port 3389) is selected.
  2. Source Configuration (Warning!): The default setting will often set the source to 0.0.0.0/0.
    • For Testing: Leaving the source as 0.0.0.0/0 means anyone in the world can attempt to connect to your RDP port. This is fine for quick testing, but be warned!
    • For Production: NEVER use 0.0.0.0/0 for a production environment. You must lock this down to only your specific IP address or a trusted network range.
  3. Click Review and Launch.

4. Launching the Instance and Creating the Key Pair

This is the final step before the server goes live. Review your settings one last time (confirming that t2.micro is selected).

  1. Click Launch.
  2. Create Key Pair: A prompt will appear asking for a Key Pair. You must create one to decrypt the Administrator password later.
    • Select Create a new key pair.
    • Name it: e.g., My Windows Server Key
  3. Download the Key Pair: Click Download Key Pair. Save the resulting .pem file to a secure location on your local machine (you will need this file soon!).
  4. Once the download is confirmed, click Launch Instance.

Your instance will now begin the launch process. Click on the instance ID link to view its status. You must wait until the Instance State changes from “Pending” to “Running.” This usually takes a few minutes.

5. Connecting to Windows Server 2019 via RDP

Once your instance is running, the final step is obtaining the password and connecting via Remote Desktop.

Step A: Retrieving the Password

AWS encrypts the default Administrator password, which is why we needed the Key Pair file.

  1. Right-Click your running instance.
  2. Select Security > Get Windows Password.
  3. Note: If you get a warning that you need to wait 4 minutes, wait a minute or two and try again.
  4. Decrypt Password: In the prompt, click Browse and upload the .pem file you downloaded earlier (My Windows Server Key.pem).
  5. Click Decrypt Password. AWS will reveal the plaintext Administrator password. Copy this password immediately.

Step B: Logging In

  1. Open RDP: Open your local machine’s Remote Desktop Connection application (RDP client).
  2. Enter IP: Find the Public IPv4 Address of your running instance on the EC2 dashboard and enter it into your RDP client. Click Connect.
  3. Credentials:
    • When prompted for credentials, click “More choices” if necessary.
    • Username: Administrator
    • Password: Paste the decrypted password you copied in the previous step.
  4. Click OK. You may receive a certificate warning; click Yes to continue.

Congratulations! You are now logged into your brand new Windows Server 2019 instance running successfully on AWS EC2!

Conclusion

That’s all there is to it! We successfully navigated the AWS console, launched a Free Tier eligible Windows Server 2019 instance, handled the security requirements, and logged in securely using the decrypted password. You now have a powerful Windows server environment ready for development, testing, or learning cloud administration.

If this guide helped you get up and running, please let us know! Give this post a share, and don’t forget to Like and Subscribe to Darren’s Tech Tutorials for more clear and practical guides. If you have any questions about configuration or security, drop a comment below—I’m happy to help!

Happy configuring!