diff --git a/CHANGELOG.md b/CHANGELOG.md
index 316cdb0..711af83 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,6 +11,12 @@
   - For this major update a `ssh2.ts` replacing `@types/ssh2` is added to the `common` module
   - This does pull in a lot of new fixes/features added since `ssh2@1.0.0` though
   - Some feature requests are now easier/possible to implement with these new features
+- Add initial support for Windows OpenSSH servers (fixes #338)
+  - This adds initial support for Command Prompt, and theoretically PowerShell (untested)
+  - The `REMOTE_COMMANDS` is not yet supported, as it uses the pty's `tty` for cross-terminal communication
+  - Future `REMOTE_COMMANDS` support for PowerShell (since it can interact with named pipes) is planned
+  - Future `REMOTE_COMMANDS` support for Command Prompt is currently not yet planned, but might be possible
+  - Mind that some (future) features won't work (maybe just for now, maybe forever) on Windows
 
 ### New features
 - Added `FS_NOTIFY_ERRORS` flag to display notifications for FS errors (#282)
diff --git a/src/connection.ts b/src/connection.ts
index 365391c..f68ccc5 100644
--- a/src/connection.ts
+++ b/src/connection.ts
@@ -6,7 +6,7 @@ import * as vscode from 'vscode';
 import { configMatches, getFlagBoolean, loadConfigs } from './config';
 import { Logging, LOGGING_NO_STACKTRACE } from './logging';
 import type { SSHPseudoTerminal } from './pseudoTerminal';
-import { calculateShellConfig, ShellConfig, tryEcho } from './shellConfig';
+import { calculateShellConfig, ShellConfig, tryCommand, tryEcho } from './shellConfig';
 import type { SSHFileSystem } from './sshFileSystem';
 import { mergeEnvironment, toPromise } from './utils';
 
@@ -51,6 +51,7 @@ export class ConnectionManager {
     }
     protected async _createCommandTerminal(client: Client, shellConfig: ShellConfig, authority: string, debugLogging: boolean): Promise<string> {
         const logging = Logging.scope(`CmdTerm(${authority})`);
+        if (!shellConfig.embedSubstitutions) throw new Error(`Shell '${shellConfig.shell}' does not support embedding substitutions`);
         const shell = await toPromise<ClientChannel>(cb => client.shell({}, cb));
         logging.debug(`TTY COMMAND: ${`echo ${shellConfig.embedSubstitutions`::sshfs:${'echo TTY'}:${'tty'}`}\n`}`);
         shell.write(`echo ${shellConfig.embedSubstitutions`::sshfs:${'echo TTY'}:${'tty'}`}\n`);
@@ -128,7 +129,15 @@ export class ConnectionManager {
         // Calculate shell config
         const shellConfig = await calculateShellConfig(client, logging);
         // Query home directory
-        let home = await tryEcho(client, shellConfig, '~').catch((e: Error) => e);
+        let home: string | Error | null;
+        if (shellConfig.isWindows) {
+            home = await tryCommand(client, "echo %USERPROFILE%").catch((e: Error) => e);
+            if (home === null) home = new Error(`No output for "echo %USERPROFILE%"`);
+            if (typeof home === 'string') home = home.trim();
+            if (home === "%USERPROFILE%") home = new Error(`Non-substituted output for "echo %USERPROFILE%"`);
+        } else {
+            home = await tryEcho(client, shellConfig, '~').catch((e: Error) => e);
+        }
         if (typeof home !== 'string') {
             const [flagCH] = getFlagBoolean('CHECK_HOME', true, config.flags);
             logging.error('Could not detect home directory', LOGGING_NO_STACKTRACE);
@@ -153,8 +162,12 @@ export class ConnectionManager {
             const [flagRCDV, flagRCDR] = getFlagBoolean('DEBUG_REMOTE_COMMANDS', false, actualConfig.flags);
             const withDebugStr = flagRCDV ? ` with debug logging enabled by '${flagRCDR}'` : '';
             logging.info`Flag REMOTE_COMMANDS provided in '${flagRCR}', setting up command terminal${withDebugStr}`;
-            const cmdPath = await this._createCommandTerminal(client, shellConfig, name, flagRCDV);
-            environment.push({ key: 'KELVIN_SSHFS_CMD_PATH', value: cmdPath });
+            if (shellConfig.isWindows) {
+                logging.error(`Windows detected, command terminal is not yet supported`, LOGGING_NO_STACKTRACE);
+            } else {
+                const cmdPath = await this._createCommandTerminal(client, shellConfig, name, flagRCDV);
+                environment.push({ key: 'KELVIN_SSHFS_CMD_PATH', value: cmdPath });
+            }
         }
         logging.debug`Environment: ${environment}`;
         // Set up the Connection object
diff --git a/src/manager.ts b/src/manager.ts
index f394413..f2b1697 100644
--- a/src/manager.ts
+++ b/src/manager.ts
@@ -156,7 +156,7 @@ export class Manager implements vscode.TaskProvider, vscode.TerminalLinkProvider
           const connection = await this.connectionManager.createConnection(resolved.host);
           resolved = await replaceVariablesRecursive(resolved, value => replaceVariables(value, connection.actualConfig));
           let { command, workingDirectory } = resolved;
-          const [useWinCmdSep] = getFlagBoolean('WINDOWS_COMMAND_SEPARATOR', false, connection.actualConfig.flags);
+          const [useWinCmdSep] = getFlagBoolean('WINDOWS_COMMAND_SEPARATOR', connection.shellConfig.isWindows, connection.actualConfig.flags);
           const separator = useWinCmdSep ? ' && ' : '; ';
           let { taskCommand = '$COMMAND' } = connection.actualConfig;
           taskCommand = joinCommands(taskCommand, separator)!;
diff --git a/src/pseudoTerminal.ts b/src/pseudoTerminal.ts
index e360505..93f0e47 100644
--- a/src/pseudoTerminal.ts
+++ b/src/pseudoTerminal.ts
@@ -170,15 +170,16 @@ export async function createTerminal(options: TerminalOptions): Promise<SSHPseud
         async open(dims) {
             onDidWrite.fire(`Connecting to ${actualConfig.label || actualConfig.name}...\r\n`);
             try {
-                const [useWinCmdSep] = getFlagBoolean('WINDOWS_COMMAND_SEPARATOR', false, actualConfig.flags);
+                const [useWinCmdSep] = getFlagBoolean('WINDOWS_COMMAND_SEPARATOR', shellConfig.isWindows, actualConfig.flags);
                 const separator = useWinCmdSep ? ' && ' : '; ';
                 let commands: string[] = [];
                 let SHELL = '$SHELL';
+                if (shellConfig.isWindows) SHELL = shellConfig.shell;
                 // Add exports for environment variables if needed
                 const env = mergeEnvironment(connection.environment, options.environment);
                 commands.push(environmentToExportString(env, shellConfig.setEnv));
                 // Beta feature to add a "code <file>" command in terminals to open the file locally
-                if (getFlagBoolean('REMOTE_COMMANDS', false, actualConfig.flags)[0]) {
+                if (getFlagBoolean('REMOTE_COMMANDS', false, actualConfig.flags)[0] && shellConfig.setupRemoteCommands) {
                     const rcCmds = await shellConfig.setupRemoteCommands(connection);
                     if (rcCmds?.length) commands.push(joinCommands(rcCmds, separator)!);
                 }
@@ -198,12 +199,16 @@ export async function createTerminal(options: TerminalOptions): Promise<SSHPseud
                     if (cmd.includes('${workingDirectory}')) {
                         cmd = cmd.replace(/\${workingDirectory}/g, workingDirectory);
                     } else {
-                        // TODO: Maybe replace with `connection.home`?
+                        // TODO: Maybe replace with `connection.home`? Especially with Windows not supporting ~
                         if (workingDirectory.startsWith('~')) {
+                            if (shellConfig.isWindows)
+                                throw new Error(`Working directory '${workingDirectory}' starts with ~ for a Windows shell`);
                             // So `cd "~/a/b/..." apparently doesn't work, but `~/"a/b/..."` does
                             // `"~"` would also fail but `~/""` works fine it seems
-                            workingDirectory = `~/"${workingDirectory.substr(2)}"`;
+                            workingDirectory = `~/"${workingDirectory.slice(2)}"`;
                         } else {
+                            if (shellConfig.isWindows && workingDirectory.match(/^\/[a-zA-Z]:/))
+                                workingDirectory = workingDirectory.slice(1);
                             workingDirectory = `"${workingDirectory}"`;
                         }
                         cmd = joinCommands([`cd ${workingDirectory}`, ...commands], separator)!;
diff --git a/src/shellConfig.ts b/src/shellConfig.ts
index 68716a2..8315522 100644
--- a/src/shellConfig.ts
+++ b/src/shellConfig.ts
@@ -1,7 +1,7 @@
 import { posix as path } from 'path';
 import type { Client, ClientChannel, SFTP } from "ssh2";
 import type { Connection } from './connection';
-import { Logger, Logging } from "./logging";
+import { Logger, Logging, LOGGING_NO_STACKTRACE } from "./logging";
 import { toPromise } from "./utils";
 
 const SCRIPT_COMMAND_CODE = `#!/bin/sh
@@ -50,26 +50,32 @@ async function rcInitializePATH(connection: Connection): Promise<string[] | stri
 
 export interface ShellConfig {
     shell: string;
+    isWindows: boolean;
     setEnv(key: string, value: string): string;
-    setupRemoteCommands: RemoteCommandInitializer;
-    embedSubstitutions(command: TemplateStringsArray, ...substitutions: (string | number)[]): string;
+    setupRemoteCommands?: RemoteCommandInitializer;
+    embedSubstitutions?(command: TemplateStringsArray, ...substitutions: (string | number)[]): string;
 }
 const KNOWN_SHELL_CONFIGS: Record<string, ShellConfig> = {}; {
     const add = (shell: string,
         setEnv: (key: string, value: string) => string,
-        setupRemoteCommands: RemoteCommandInitializer,
-        embedSubstitution: (command: TemplateStringsArray, ...substitutions: (string | number)[]) => string) => {
-        KNOWN_SHELL_CONFIGS[shell] = { shell, setEnv, setupRemoteCommands, embedSubstitutions: embedSubstitution };
+        setupRemoteCommands?: RemoteCommandInitializer,
+        embedSubstitutions?: (command: TemplateStringsArray, ...substitutions: (string | number)[]) => string,
+        isWindows = false) => {
+        KNOWN_SHELL_CONFIGS[shell] = { shell, setEnv, setupRemoteCommands, embedSubstitutions, isWindows };
     }
     // Ways to set an environment variable
     const setEnvExport = (key: string, value: string) => `export ${key}=${value}`;
     const setEnvSetGX = (key: string, value: string) => `set -gx ${key} ${value}`;
     const setEnvSetEnv = (key: string, value: string) => `setenv ${key} ${value}`;
+    const setEnvPowerShell = (key: string, value: string) => `$env:${key}="${value}"`;
+    const setEnvSet = (key: string, value: string) => `set ${key}=${value}`;
     // Ways to embed a substitution
     const embedSubstitutionsBackticks = (command: TemplateStringsArray, ...substitutions: (string | number)[]): string =>
         '"' + substitutions.reduce((str, sub, i) => `${str}\`${sub}\`${command[i + 1]}`, command[0]) + '"';
-    const embedSubstitutionsFish = (command: TemplateStringsArray, ...substitutions: (string | number)[]) =>
+    const embedSubstitutionsFish = (command: TemplateStringsArray, ...substitutions: (string | number)[]): string =>
         substitutions.reduce((str, sub, i) => `${str}"(${sub})"${command[i + 1]}`, '"' + command[0]) + '"';
+    const embedSubstitutionsPowershell = (command: TemplateStringsArray, ...substitutions: (string | number)[]): string =>
+        substitutions.reduce((str, sub, i) => `${str}$(${sub})${command[i + 1]}`, '"' + command[0]) + '"';
     // Register the known shells
     add('sh', setEnvExport, rcInitializePATH, embedSubstitutionsBackticks);
     add('bash', setEnvExport, rcInitializePATH, embedSubstitutionsBackticks);
@@ -81,6 +87,8 @@ const KNOWN_SHELL_CONFIGS: Record<string, ShellConfig> = {}; {
     add('fish', setEnvSetGX, rcInitializePATH, embedSubstitutionsFish); // https://fishshell.com/docs/current/tutorial.html#autoloading-functions
     add('csh', setEnvSetEnv, rcInitializePATH, embedSubstitutionsBackticks);
     add('tcsh', setEnvSetEnv, rcInitializePATH, embedSubstitutionsBackticks);
+    add('powershell', setEnvPowerShell, undefined, embedSubstitutionsPowershell, true); // experimental
+    add('cmd.exe', setEnvSet, undefined, undefined, true); // experimental
 }
 
 export async function tryCommand(ssh: Client, command: string): Promise<string | null> {
@@ -103,17 +111,45 @@ export async function tryCommand(ssh: Client, command: string): Promise<string |
 }
 
 export async function tryEcho(ssh: Client, shellConfig: ShellConfig, variable: string): Promise<string | null> {
+    if (!shellConfig.embedSubstitutions) throw new Error(`Shell '${shellConfig.shell}' does not support embedding substitutions`);
     const uniq = Date.now() % 1e5;
     const output = await tryCommand(ssh, `echo ${shellConfig.embedSubstitutions`::${'echo ' + uniq}:echo_result:${`echo ${variable}`}:${'echo ' + uniq}::`}`);
     return output?.match(`::${uniq}:echo_result:(.*?):${uniq}::`)?.[1] || null;
 }
 
+async function getPowershellVersion(client: Client): Promise<string | null> {
+    const version = await tryCommand(client, 'echo $PSversionTable.PSVersion.ToString()').catch(e => {
+        console.error(e);
+        return null;
+    });
+    return !version?.includes('PSVersion') ? version : null;
+}
+
+async function getWindowsVersion(client: Client): Promise<string | null> {
+    const version = await tryCommand(client, 'systeminfo | findstr /BC:"OS Version"').catch(e => {
+        console.error(e);
+        return null;
+    });
+    const match = version?.trim().match(/^OS Version:[ \t]+(.*)$/);
+    return match?.[1] || null;
+}
+
 export async function calculateShellConfig(client: Client, logging?: Logger): Promise<ShellConfig> {
     try {
         const shellStdout = await tryCommand(client, 'echo :::SHELL:$SHELL:SHELL:::');
         const shell = shellStdout?.match(/:::SHELL:([^$].*?):SHELL:::/)?.[1];
         if (!shell) {
-            if (shellStdout) logging?.error(`Could not get $SHELL from following output:\n${shellStdout}`);
+            const psVersion = await getPowershellVersion(client);
+            if (psVersion) {
+                logging?.debug(`Detected PowerShell version ${psVersion}`);
+                return { ...KNOWN_SHELL_CONFIGS['powershell'], shell: 'PowerShell' };
+            }
+            const windowsVersion = await getWindowsVersion(client);
+            if (windowsVersion) {
+                logging?.debug(`Detected Command Prompt for Windows ${windowsVersion}`);
+                return { ...KNOWN_SHELL_CONFIGS['cmd.exe'], shell: 'cmd.exe' };
+            }
+            if (shellStdout) logging?.error(`Could not get $SHELL from following output:\n${shellStdout}`, LOGGING_NO_STACKTRACE);
             throw new Error('Could not get $SHELL');
         }
         const known = KNOWN_SHELL_CONFIGS[path.basename(shell)];