How I Connected to My EC2 Windows Instance Using AWS Session Manager — Without Opening RDP

Today, I successfully connected to a Windows EC2 instance without using RDP or SSH — all thanks to AWS Systems Manager Session Manager (SSM). Here’s how I did it step-by-step, including setup, troubleshooting, and the moment it finally worked.

Why Use Session Manager?

• No need to open port 3389 (RDP) or use SSH keys
• Secure and auditable via AWS CloudTrail/CloudWatch
• Works even in private subnets

Step-by-Step Setup

1. Launched an EC2 Instance

• AMI: Windows Server 2019
• Instance Type: t3.micro
• Region: eu-north-1
• Attached a key pair: Demo Key (for fallback RDP if needed)

2. Created IAM Role

I created a role with this policy:

AmazonSSMManagedInstanceCore

Then I attached it to the running instance via EC2 > Actions > Security > Modify IAM Role.

3. Verified Networking

• The instance had a public IP
• Security group had outbound access to port 443 (HTTPS)
• Inbound port 3389 was open for fallback RDP

4. Started the SSM Agent (Windows)

I connected via RDP using the key pair, then ran this in PowerShell:

Start-Service AmazonSSMAgent

5. Connected via Session Manager

Once the agent was running and IAM role in place, I went to:

EC2 > Instances > Connect > Session Manager

And boom — I was in!

Test Commands I Ran:

systeminfo | Select-String "^OS"
Get-Service AmazonSSMAgent
Invoke-WebRequest https://www.google.com
whoami

Results

Connected securely via AWS Session Manager — no RDP, no SSH, and no exposed ports. Clean, secure, and auditable.

Conclusion

SSM is a must-use tool for secure AWS access — especially in enterprise environments or boot camps where minimizing exposure matters.

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