diff --git a/src/vs/platform/request/common/request.ts b/src/vs/platform/request/common/request.ts
index 64818e0598598..af71380553aef 100644
--- a/src/vs/platform/request/common/request.ts
+++ b/src/vs/platform/request/common/request.ts
@@ -138,6 +138,18 @@ export function updateProxyConfigurationsScope(useHostProxy: boolean, useHostPro
 	registerProxyConfigurations(useHostProxy, useHostProxyDefault);
 }
 
+export const USER_LOCAL_AND_REMOTE_SETTINGS = [
+	'http.proxy',
+	'http.proxyStrictSSL',
+	'http.proxyKerberosServicePrincipal',
+	'http.noProxy',
+	'http.proxyAuthorization',
+	'http.proxySupport',
+	'http.systemCertificates',
+	'http.experimental.systemCertificatesV2',
+	'http.fetchAdditionalSupport',
+];
+
 let proxyConfiguration: IConfigurationNode[] = [];
 function registerProxyConfigurations(useHostProxy = true, useHostProxyDefault = true): void {
 	const configurationRegistry = Registry.as<IConfigurationRegistry>(Extensions.Configuration);
diff --git a/src/vs/workbench/contrib/preferences/browser/settingsTreeModels.ts b/src/vs/workbench/contrib/preferences/browser/settingsTreeModels.ts
index 87ec480c25a24..646164d1c8415 100644
--- a/src/vs/workbench/contrib/preferences/browser/settingsTreeModels.ts
+++ b/src/vs/workbench/contrib/preferences/browser/settingsTreeModels.ts
@@ -22,6 +22,7 @@ import { ILanguageService } from '../../../../editor/common/languages/language.j
 import { Registry } from '../../../../platform/registry/common/platform.js';
 import { IUserDataProfileService } from '../../../services/userDataProfile/common/userDataProfile.js';
 import { IProductService } from '../../../../platform/product/common/productService.js';
+import { USER_LOCAL_AND_REMOTE_SETTINGS } from '../../../../platform/request/common/request.js';
 
 export const ONLINE_SERVICES_SETTING_TAG = 'usesOnlineServices';
 
@@ -425,12 +426,12 @@ export class SettingsTreeSettingElement extends SettingsTreeElement {
 		}
 
 		if (configTarget === ConfigurationTarget.USER_REMOTE) {
-			return REMOTE_MACHINE_SCOPES.includes(this.setting.scope);
+			return REMOTE_MACHINE_SCOPES.includes(this.setting.scope) || USER_LOCAL_AND_REMOTE_SETTINGS.includes(this.setting.key);
 		}
 
 		if (configTarget === ConfigurationTarget.USER_LOCAL) {
 			if (isRemote) {
-				return LOCAL_MACHINE_SCOPES.includes(this.setting.scope);
+				return LOCAL_MACHINE_SCOPES.includes(this.setting.scope) || USER_LOCAL_AND_REMOTE_SETTINGS.includes(this.setting.key);
 			}
 		}