diff --git a/src/vs/code/electron-main/app.ts b/src/vs/code/electron-main/app.ts
index 390317f4391..9fdb90b0295 100644
--- a/src/vs/code/electron-main/app.ts
+++ b/src/vs/code/electron-main/app.ts
@@ -9,7 +9,7 @@ import { WindowsMainService } from 'vs/platform/windows/electron-main/windowsMai
 import { IWindowOpenable } from 'vs/platform/windows/common/windows';
 import { OpenContext } from 'vs/platform/windows/node/window';
 import { ILifecycleMainService, LifecycleMainPhase } from 'vs/platform/lifecycle/electron-main/lifecycleMainService';
-import { getShellEnvironment } from 'vs/code/node/shellEnv';
+import { resolveShellEnv } from 'vs/code/node/shellEnv';
 import { IUpdateService } from 'vs/platform/update/common/update';
 import { UpdateChannel } from 'vs/platform/update/electron-main/updateIpc';
 import { Server as ElectronIPCServer } from 'vs/base/parts/ipc/electron-main/ipc.electron-main';
@@ -84,6 +84,7 @@ import { EncryptionMainService, IEncryptionMainService } from 'vs/platform/encry
 import { ActiveWindowManager } from 'vs/platform/windows/common/windowTracker';
 import { IKeyboardLayoutMainService, KeyboardLayoutMainService } from 'vs/platform/keyboardLayout/electron-main/keyboardLayoutMainService';
 import { toErrorMessage } from 'vs/base/common/errorMessage';
+import { NativeParsedArgs } from 'vs/platform/environment/common/argv';
 
 export class CodeApplication extends Disposable {
 	private windowsMainService: IWindowsMainService | undefined;
@@ -283,7 +284,24 @@ export class CodeApplication extends Disposable {
 			}, 10000);
 
 			try {
-				const shellEnv = await getShellEnvironment(this.logService, this.environmentService);
+
+				// Prefer to use the args and env from the target window
+				// when resolving the shell env. It is possible that
+				// a first window was opened from the UI but a second
+				// from the CLI and that has implications for wether to
+				// resolve the shell environment or not.
+				let args: NativeParsedArgs;
+				let env: NodeJS.ProcessEnv;
+				if (window?.config) {
+					args = window.config;
+					env = { ...process.env, ...window.config.userEnv };
+				} else {
+					args = this.environmentService.args;
+					env = process.env;
+				}
+
+				// Resolve shell env
+				const shellEnv = await resolveShellEnv(this.logService, args, env);
 				acceptShellEnv(shellEnv);
 			} catch (error) {
 				window?.sendWhenReady('vscode:showShellEnvError', toErrorMessage(error)); // notify inside window if we have one
@@ -368,7 +386,7 @@ export class CodeApplication extends Disposable {
 		});
 		this.lifecycleMainService.when(LifecycleMainPhase.AfterWindowOpen).then(() => {
 			this._register(new RunOnceScheduler(async () => {
-				sharedProcess.spawn(await getShellEnvironment(this.logService, this.environmentService));
+				sharedProcess.spawn(await resolveShellEnv(this.logService, this.environmentService.args, process.env));
 			}, 3000)).schedule();
 		});
 
@@ -825,8 +843,8 @@ export class CodeApplication extends Disposable {
 			updateService.initialize();
 		}
 
-		// Start to fetch shell environment after window has opened
-		getShellEnvironment(this.logService, this.environmentService);
+		// Start to fetch shell environment (if needed) after window has opened
+		resolveShellEnv(this.logService, this.environmentService.args, process.env);
 
 		// If enable-crash-reporter argv is undefined then this is a fresh start,
 		// based on telemetry.enableCrashreporter settings, generate a UUID which
diff --git a/src/vs/code/node/shellEnv.ts b/src/vs/code/node/shellEnv.ts
index d1dd0bc6dfb..a7422f5357a 100644
--- a/src/vs/code/node/shellEnv.ts
+++ b/src/vs/code/node/shellEnv.ts
@@ -7,9 +7,55 @@ import { spawn } from 'child_process';
 import { generateUuid } from 'vs/base/common/uuid';
 import { isWindows } from 'vs/base/common/platform';
 import { ILogService } from 'vs/platform/log/common/log';
-import { INativeEnvironmentService } from 'vs/platform/environment/common/environment';
+import { NativeParsedArgs } from 'vs/platform/environment/common/argv';
 
-function getUnixShellEnvironment(logService: ILogService): Promise<typeof process.env> {
+/**
+ * We need to get the environment from a user's shell.
+ * This should only be done when Code itself is not launched
+ * from within a shell.
+ */
+export async function resolveShellEnv(logService: ILogService, args: NativeParsedArgs, env: NodeJS.ProcessEnv): Promise<typeof process.env> {
+
+	// Skip if --force-disable-user-env
+	if (args['force-disable-user-env']) {
+		logService.trace('resolveShellEnv(): skipped (--force-disable-user-env)');
+
+		return {};
+	}
+
+	// Skip on windows
+	else if (isWindows) {
+		logService.trace('resolveShellEnv(): skipped (Windows)');
+
+		return {};
+	}
+
+	// Skip if running from CLI already
+	else if (env['VSCODE_CLI'] === '1' && !args['force-user-env']) {
+		logService.trace('resolveShellEnv(): skipped (VSCODE_CLI is set)');
+
+		return {};
+	}
+
+	// Otherwise resolve (macOS, Linux)
+	else {
+		if (env['VSCODE_CLI'] === '1') {
+			logService.trace('resolveShellEnv(): running (--force-user-env)');
+		} else {
+			logService.trace('resolveShellEnv(): running (macOS/Linux)');
+		}
+
+		if (!unixShellEnvPromise) {
+			unixShellEnvPromise = doResolveUnixShellEnv(logService);
+		}
+
+		return unixShellEnvPromise;
+	}
+}
+
+let unixShellEnvPromise: Promise<typeof process.env> | undefined = undefined;
+
+function doResolveUnixShellEnv(logService: ILogService): Promise<typeof process.env> {
 	const promise = new Promise<typeof process.env>((resolve, reject) => {
 		const runAsNode = process.env['ELECTRON_RUN_AS_NODE'];
 		logService.trace('getUnixShellEnvironment#runAsNode', runAsNode);
@@ -81,34 +127,3 @@ function getUnixShellEnvironment(logService: ILogService): Promise<typeof proces
 	// swallow errors
 	return promise.catch(() => ({}));
 }
-
-let shellEnvPromise: Promise<typeof process.env> | undefined = undefined;
-
-/**
- * We need to get the environment from a user's shell.
- * This should only be done when Code itself is not launched
- * from within a shell.
- */
-export function getShellEnvironment(logService: ILogService, environmentService: INativeEnvironmentService): Promise<typeof process.env> {
-	if (!shellEnvPromise) {
-		if (environmentService.args['force-disable-user-env']) {
-			logService.trace('getShellEnvironment(): skipped (--force-disable-user-env)');
-			shellEnvPromise = Promise.resolve({});
-		} else if (isWindows) {
-			logService.trace('getShellEnvironment(): skipped (Windows)');
-			shellEnvPromise = Promise.resolve({});
-		} else if (process.env['VSCODE_CLI'] === '1' && !environmentService.args['force-user-env']) {
-			logService.trace('getShellEnvironment(): skipped (VSCODE_CLI is set)');
-			shellEnvPromise = Promise.resolve({});
-		} else {
-			if (process.env['VSCODE_CLI'] === '1') {
-				logService.trace('getShellEnvironment(): running (--force-user-env)');
-			} else {
-				logService.trace('getShellEnvironment(): running (macOS/Linux)');
-			}
-			shellEnvPromise = getUnixShellEnvironment(logService);
-		}
-	}
-
-	return shellEnvPromise;
-}