diff --git a/src/vs/code/electron-main/app.ts b/src/vs/code/electron-main/app.ts
index 33db58c922f98e78b931cea1945b354dd57a4f4c..597c45bad0240860afd4aea7e3c887d7b187fbe8 100644
--- a/src/vs/code/electron-main/app.ts
+++ b/src/vs/code/electron-main/app.ts
@@ -86,6 +86,7 @@ import { IKeyboardLayoutMainService, KeyboardLayoutMainService } from 'vs/platfo
 import { toErrorMessage } from 'vs/base/common/errorMessage';
 import { NativeParsedArgs } from 'vs/platform/environment/common/argv';
 import { DisplayMainService, IDisplayMainService } from 'vs/platform/display/electron-main/displayMainService';
+import { isLaunchedFromCli } from 'vs/platform/environment/node/argvHelper';
 
 export class CodeApplication extends Disposable {
 	private windowsMainService: IWindowsMainService | undefined;
@@ -703,7 +704,7 @@ export class CodeApplication extends Disposable {
 		// Open our first window
 		const args = this.environmentService.args;
 		const macOpenFiles: string[] = (<any>global).macOpenFiles;
-		const context = !!process.env['VSCODE_CLI'] ? OpenContext.CLI : OpenContext.DESKTOP;
+		const context = isLaunchedFromCli(process.env) ? OpenContext.CLI : OpenContext.DESKTOP;
 		const hasCliArgs = args._.length;
 		const hasFolderURIs = !!args['folder-uri'];
 		const hasFileURIs = !!args['file-uri'];
diff --git a/src/vs/code/electron-main/window.ts b/src/vs/code/electron-main/window.ts
index f8fe899ca4b4ef8e5020cb11087cc458ed234051..6019f2d2062dd9591408e4c6987a5916763c90c9 100644
--- a/src/vs/code/electron-main/window.ts
+++ b/src/vs/code/electron-main/window.ts
@@ -35,6 +35,7 @@ import { ILifecycleMainService } from 'vs/platform/lifecycle/electron-main/lifec
 import { IStorageMainService } from 'vs/platform/storage/node/storageMainService';
 import { ByteSize, IFileService } from 'vs/platform/files/common/files';
 import { FileAccess, Schemas } from 'vs/base/common/network';
+import { isLaunchedFromCli } from 'vs/platform/environment/node/argvHelper';
 
 export interface IWindowCreationOptions {
 	state: IWindowState;
@@ -677,6 +678,16 @@ export class CodeWindow extends Disposable implements ICodeWindow {
 
 	load(config: INativeWindowConfiguration, isReload?: boolean, disableExtensions?: boolean): void {
 
+		// If this window was loaded before from the command line
+		// (as indicated by VSCODE_CLI environment), make sure to
+		// preserve that user environment in subsequent loads,
+		// unless the new configuration context was also a CLI
+		// (for https://github.com/microsoft/vscode/issues/108571)
+		const currentUserEnv = (this.currentConfig ?? this.pendingLoadConfig)?.userEnv;
+		if (currentUserEnv && isLaunchedFromCli(currentUserEnv) && !isLaunchedFromCli(config.userEnv)) {
+			config.userEnv = currentUserEnv;
+		}
+
 		// If this is the first time the window is loaded, we associate the paths
 		// directly with the window because we assume the loading will just work
 		if (this._readyState === ReadyState.NONE) {
diff --git a/src/vs/code/node/shellEnv.ts b/src/vs/code/node/shellEnv.ts
index a7422f5357a895b533ac5ea6e4f4f6786f859447..79ba3d252fe74dcfd5caa4ec77a50dded42b0465 100644
--- a/src/vs/code/node/shellEnv.ts
+++ b/src/vs/code/node/shellEnv.ts
@@ -8,6 +8,7 @@ import { generateUuid } from 'vs/base/common/uuid';
 import { isWindows } from 'vs/base/common/platform';
 import { ILogService } from 'vs/platform/log/common/log';
 import { NativeParsedArgs } from 'vs/platform/environment/common/argv';
+import { isLaunchedFromCli } from 'vs/platform/environment/node/argvHelper';
 
 /**
  * We need to get the environment from a user's shell.
@@ -31,7 +32,7 @@ export async function resolveShellEnv(logService: ILogService, args: NativeParse
 	}
 
 	// Skip if running from CLI already
-	else if (env['VSCODE_CLI'] === '1' && !args['force-user-env']) {
+	else if (isLaunchedFromCli(env) && !args['force-user-env']) {
 		logService.trace('resolveShellEnv(): skipped (VSCODE_CLI is set)');
 
 		return {};
@@ -39,7 +40,7 @@ export async function resolveShellEnv(logService: ILogService, args: NativeParse
 
 	// Otherwise resolve (macOS, Linux)
 	else {
-		if (env['VSCODE_CLI'] === '1') {
+		if (isLaunchedFromCli(env)) {
 			logService.trace('resolveShellEnv(): running (--force-user-env)');
 		} else {
 			logService.trace('resolveShellEnv(): running (macOS/Linux)');
diff --git a/src/vs/platform/environment/node/argvHelper.ts b/src/vs/platform/environment/node/argvHelper.ts
index a3c16f98de7e888b407ee4560fafb6bcf6c98e11..3ace20cfc456455006f26b652e01a3883bcd5782 100644
--- a/src/vs/platform/environment/node/argvHelper.ts
+++ b/src/vs/platform/environment/node/argvHelper.ts
@@ -52,7 +52,7 @@ export function parseMainProcessArgv(processArgv: string[]): NativeParsedArgs {
 	}
 
 	// If called from CLI, don't report warnings as they are already reported.
-	let reportWarnings = !process.env['VSCODE_CLI'];
+	const reportWarnings = !isLaunchedFromCli(process.env);
 	return parseAndValidate(args, reportWarnings);
 }
 
@@ -60,7 +60,7 @@ export function parseMainProcessArgv(processArgv: string[]): NativeParsedArgs {
  * Use this to parse raw code CLI process.argv such as: `Electron cli.js . --verbose --wait`
  */
 export function parseCLIProcessArgv(processArgv: string[]): NativeParsedArgs {
-	let [, , ...args] = processArgv; // remove the first non-option argument: it's always the app location
+	const [, , ...args] = processArgv; // remove the first non-option argument: it's always the app location
 
 	return parseAndValidate(args, true);
 }
@@ -78,3 +78,7 @@ export function addArg(argv: string[], ...args: string[]): string[] {
 
 	return argv;
 }
+
+export function isLaunchedFromCli(env: NodeJS.ProcessEnv): boolean {
+	return env['VSCODE_CLI'] === '1';
+}
diff --git a/src/vs/platform/environment/node/environmentService.ts b/src/vs/platform/environment/node/environmentService.ts
index 76e81a13ce7ac21e36d5e74e37f0cb3d631182e7..cef263622d4f8c7b757d35a1cd82effe7186dbd8 100644
--- a/src/vs/platform/environment/node/environmentService.ts
+++ b/src/vs/platform/environment/node/environmentService.ts
@@ -3,10 +3,10 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import * as os from 'os';
 import { IDebugParams, IExtensionHostDebugParams, INativeEnvironmentService } from 'vs/platform/environment/common/environment';
 import { NativeParsedArgs } from 'vs/platform/environment/common/argv';
 import * as paths from 'vs/base/node/paths';
-import * as os from 'os';
 import * as path from 'vs/base/common/path';
 import * as resources from 'vs/base/common/resources';
 import { memoize } from 'vs/base/common/decorators';
diff --git a/src/vs/platform/launch/electron-main/launchMainService.ts b/src/vs/platform/launch/electron-main/launchMainService.ts
index ac0c66cf60013917292e8329e8792e558bfa4907..069bb585c19ed5d52e0965d4d5b7a43daa0efaf6 100644
--- a/src/vs/platform/launch/electron-main/launchMainService.ts
+++ b/src/vs/platform/launch/electron-main/launchMainService.ts
@@ -19,6 +19,7 @@ import { BrowserWindow, ipcMain, Event as IpcEvent, app } from 'electron';
 import { coalesce } from 'vs/base/common/arrays';
 import { IDiagnosticInfoOptions, IDiagnosticInfo, IRemoteDiagnosticInfo, IRemoteDiagnosticError } from 'vs/platform/diagnostics/common/diagnostics';
 import { IMainProcessInfo, IWindowInfo } from 'vs/platform/launch/node/launch';
+import { isLaunchedFromCli } from 'vs/platform/environment/node/argvHelper';
 
 export const ID = 'launchMainService';
 export const ILaunchMainService = createDecorator<ILaunchMainService>(ID);
@@ -112,7 +113,7 @@ export class LaunchMainService implements ILaunchMainService {
 	}
 
 	private startOpenWindow(args: NativeParsedArgs, userEnv: IProcessEnvironment): Promise<void> {
-		const context = !!userEnv['VSCODE_CLI'] ? OpenContext.CLI : OpenContext.DESKTOP;
+		const context = isLaunchedFromCli(userEnv) ? OpenContext.CLI : OpenContext.DESKTOP;
 		let usedWindows: ICodeWindow[] = [];
 
 		const waitMarkerFileURI = args.wait && args.waitMarkerFilePath ? URI.file(args.waitMarkerFilePath) : undefined;