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How to set up server 2019 on amazon web services

Published: December 1, 2025 (Updated: Dec 1, 2025)

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Quick Start Guide: Deploying Windows Server 2019 on AWS EC2 in Minutes

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

Working with cloud infrastructure is essential in the modern IT landscape, and few platforms are as important as Amazon Web Services (AWS). Today, we’re tackling one of the most practical setups: launching a Windows Server 2019 instance on AWS EC2.

Whether you need a dedicated testing environment, a domain controller, or a powerful remote desktop, running Server 2019 in the cloud is fast and surprisingly easy. By the end of this tutorial, you’ll have your new server running and be logged in via Remote Desktop Protocol (RDP).

Let’s dive in and get that server spinning!

Step 1: Accessing the AWS Console and EC2 Dashboard

Before we begin, you need to ensure you are logged into your AWS management console.

  1. Once logged in, navigate to the main dashboard.
  2. Click on Services at the top of the screen.
  3. Under the Compute section, select EC2 (Elastic Compute Cloud).
  4. On the EC2 dashboard, look for the prominent blue button labeled Launch Instance. Click it to begin the setup wizard.

Step 2: Selecting the Windows Server 2019 AMI

The first step in launching your instance is selecting the proper Amazon Machine Image (AMI).

  1. In the search bar provided, type 2019 and press Enter.
  2. Locate and select the image titled Microsoft Windows Server 2019 Base.

Important Note on Free Tier Eligibility

We strongly recommend leaving the instance type set to t2.micro. This instance type is included under the AWS Free Tier, meaning you won’t incur charges for basic usage. If you select a larger instance type, you may be billed instantly!

  1. Ensure t2.micro is selected, and then click Next: Configure Instance Details.

Step 3: Configuring Instance Details

For this quick start guide, we can leave most of the configuration details at their default settings.

  • Network: Leave the default VPC selected.
  • We won’t be changing subnet, IAM role, or placement group settings for this simple deployment.
  1. Once confirmed, click Next: Add Storage.

Step 4: Storage, Tagging, and Security Group Setup

Adding Storage and Tags

We will stick to the default storage settings, which typically allocate 30GB of GP2 storage—plenty for a base installation and testing.

  1. Click Next: Add Tags.
  2. Add one tag for easy identification. Click Add Tag and set the Key to Name (capital N) and the Value to something descriptive, like Windows Server 2019 Server.
  3. Click Next: Configure Security Group.

Setting Up the Security Group (CRITICAL WARNING)

The Security Group acts as a firewall for your instance. Since we are running a Windows Server, we must ensure RDP (Remote Desktop Protocol) is allowed. The default port for RDP is 3389.

  1. The wizard should automatically include an RDP rule on port 3389.
  2. By default, the source may be set to 0.0.0.0/0. This means RDP access is open to the entire world.

For Production Use: You must lock this down to only your own static IP address (or a specific IP range) for security. Leaving it open to the world means anyone can try to brute-force the administrator password.

For Testing/Tutorial: Leaving it as 0.0.0.0/0 is acceptable, as long as you understand the risk.

  1. Once the Security Group is configured, click Review and Launch.

Step 5: Launching the Instance and Creating the Key Pair

Review all your settings one last time (especially confirming you selected the t2.micro instance type).

  1. Click the blue Launch button.
  2. A pop-up will appear prompting you for a Key Pair. This key pair is absolutely essential for decrypting the Windows Administrator password later.
    • Select Create a new key pair.
    • Give it a memorable name (e.g., MyWindowsServerKey).
    • Click Download Key Pair. Save the generated .pem file to a secure location on your local machine (like your Downloads folder). You cannot connect without this file!
  3. After downloading the key, click Launch Instance.

Your instance is now launching! Click on the instance ID link to view its status. The instance status will transition from Pending to Running. This typically takes 2–4 minutes.

Step 6: Connecting to Your Server via RDP

Once your instance status is Running, it’s time to retrieve the password and connect.

  1. Right-click on your running instance and select Get Windows Password.
  2. If you get a warning that you must wait 4 minutes, simply wait a minute or two and try again.
  3. Click the Browse button and locate the Key Pair file (.pem) you downloaded in Step 5.
  4. Once the key is loaded, click Decrypt Password.
  5. AWS will generate and display a complex password. Copy this password to your clipboard.

Establishing the RDP Connection

  1. Open your local Remote Desktop Connection application (RDP client).
  2. In the RDP application, enter the Public IPv4 Address of your running EC2 instance (found on the instance details screen).
  3. Click Connect.
  4. When prompted for credentials, use the following:
    • Username: Administrator
    • Password: Paste the complex password you copied from the decryption step.
  5. Click OK. You will receive a standard certificate warning; click Yes to continue.

Congratulations! After a brief setup time while Windows initializes, you will be logged into your new Windows Server 2019 instance running live on AWS. You can confirm the environment by seeing the Server Manager dashboard load up.

Conclusion

And there you have it—a brand new Windows Server 2019 instance, set up and secured (with our security group caveats!) on the Amazon Web Services cloud platform.

If this quick guide helped you launch your server successfully, please drop a comment below and let me know what you plan to use your new cloud machine for!

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