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How to Remotely Connect to a Windows Server

Recommended Article : 【Operating System】 Operating System Table of Contents


1. Step 1. (Preparation) Opening Ports

2. Step 2. (Preparation) Closed Port Method

3. Step 3. (Intermediate Process) VPN Configuration

4. Step 4. (Required Application Installation) RDP (Remote Desktop Protocol)

5. Step 5. (Required Application Installation) SSH (Secure Shell)

6. Step 6. (Other Application Installation) WOL (Wake on LAN)

7. Step 7. Server Computer Management



1. Step 1. (Preparation) Opening Ports

⑴ Port

① A channel through which requests are sent from a lower node

Inbound Traffic : Traffic coming into the server

○ Example: In the case of a client uploading a file to the server, there is inbound traffic from the server’s perspective

○ Inbound traffic is mostly blocked by routers, so ports need to be opened

○ When opening ports, the source is the client, and the destination is the server (router), ultimately opened on the server side

Outbound Traffic- : Traffic going out from the server

○ Example: In the case of the server sending a file to the client, there is outbound traffic from the server’s perspective

○ Outbound traffic is almost always open on routers

○ For example, when a client downloads a file from the server, it’s a typical outbound traffic scenario

④ Both the server and the router have port numbers

⑵ Port Opening Method

① When sending traffic from one node to another, the receiving node needs to have its port opened as it becomes inbound traffic

Step 1. Port Forwarding

① Changing port numbers on the router for each server : Sometimes referred to as port opening

○ Example: If a user connects on port 1234 and the Linux computer only allows connections on port 22 (default port), the port number can be changed to allow connection

○ Some routers allow setting for all IP addresses, while others do not

Step 2. Opening Ports in the Computer Room

① For security reasons, certain predefined ports (e.g., RDP port, 3389) are closed in the computer room

② In such cases, inquire with the computer room to open the required port

③ If a different port is opened instead, use regedit to change the remote access port number of the server computer

④ If a different port is opened instead, the port needs to be opened in Step 1



2. Step 2. (Preparation) Closed Port Method

⑴ Closed Port Method

① After setting up a relay server in the middle, only outbound traffic is received from users, so port opening is not required

Example 1. TeamViewer

① Login-based remote access program

② Works similarly to VPN, but it is not using VPN

③ Might use a different protocol than RDP

④ However, TeamViewer, which uses a 6-letter password, has poor security to the extent that it can be hacked using brute-force methods

Example 2. Google Chrome Remote Desktop

Example 3. Zoom

Example 4. Google Meet

Example 5. Duo

Example 6. AnyDesk



3. Step 3. (Intermediate Process) VPN Configuration

⑴ VPN (Virtual Private Network)

① Private network established with security to allow specific authorized users to enter the network

② VPN may need to be turned on and off, and internet speed might slightly decrease

③ Even with a VPN, port opening is generally required

④ Using a VPN can bypass connection blocks by the server on blocked IP addresses

⑤ Example: Mareel VPN

Example 1. WireGuard

Example 2. Tailscale : UI overlay on top of WireGuard protocol

① Overview

Advantage 1. Free accounts can register up to 20 devices

Advantage 2. Low security concerns

Step 1. Install Tailscale on the server and log in

Step 2. Install Tailscale on personal computer and log in with the same account

Step 3. Go to the Tailscale website and log in to check the VPN internal IP for each device

Step 4. Connect my computer to the server

Case 1. Server RDP connection

Case 2. SSH connection from my computer

Example 3. wg-easy : Open-source project with included UI

Example 4. Implementation through Windows-provided VPN

① Can be done using IPTIME

② The server computer should have Windows password lock



4. Step 4. (Required Application Installation) RDP (Remote Desktop Protocol)

⑴ Overview

① Remote connection with GUI support

② Concurrent connections are limited

③ RDP does not work on Windows Home Edition

Step 1. Installing RDP (Linux-specific, Required)

① RDP server and client are both built-in Windows features, no separate installation required, simple configuration needed

② Since RDP is a Microsoft protocol, it requires separate installation of server and client on Linux

Step 2. Connecting the Client and Windows Server (Required)

① Windows-to-Windows server connection is well supported natively due to RDP being Windows-based

② Mac-to-Windows server connection is done through Microsoft Remote Desktop

③ RDP default port number is 3389



5. Step 5. (Required Application Installation) SSH (Secure Shell)

⑴ Overview

① Terminal-based remote connection

Step 1. Installing Windows SSH server : Compare with Step 2 and Step 3 for selection

① Many Linux OS like Ubuntu come with SSH server and client pre-installed and configured

② Unlike Ubuntu, installing SSH on Windows is difficult

③ SSH server and SSH client need to be considered separately

Step 2. Installing WSL (Windows Subsystem for Linux) : Compare with Step 1 and Step 3 for selection

① WSL is like virtualization within Windows, different from dual OS setup

② WSL is advantageous for managing environment variables and paths in Python development

Installation Tutorial

Step 3. Dual OS Installation : Compare with Step 1 and Step 2 for selection

Step 4. Checking if SSH is open on the remote server

Step 5. Installing VScode Remote-SSH on personal computer (client) (Link 1, Link 2) : Required

① Remote-SSH is Microsoft’s official software with guaranteed performance

② By entering the server address and connecting, you can develop on your personal computer remotely with server resources and development environment intact

Step 6. Disabling password login and setting up RSA key login only : Optional for enhanced security

① To enhance security

Step 7. SSH can be made easier to use through software like Mobaxterm (free), PuTTY, etc.



6. Step 6. (Other Application Installation) Wake on LAN (WOL)

⑴ Software to turn on and off remotely : Provides power function in LAN, making it possible

⑵ Many routers support WOL, so it’s easy to turn on using a smartphone app when configured correctly

⑶ Servers on VPN without physical connection cannot be turned on or off using WOL

⑷ Generally, server lifespan is several years if overheating issues are absent, so WOL might not be necessary



7. Step 7. Server Computer Management

⑴ Turning off the monitor is recommended to avoid burn-in

⑵ Windows Desktop Protocol allows concurrent connections, but since it shares a single GUI, it is realistically possible for only one person to use it at a time.



Input: 2022.08.05 00:28

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