diff --git a/extensions/simple-browser/src/extension.ts b/extensions/simple-browser/src/extension.ts
index 8ee1f0faaf2..7274a7343b7 100644
--- a/extensions/simple-browser/src/extension.ts
+++ b/extensions/simple-browser/src/extension.ts
@@ -49,15 +49,17 @@ export function activate(context: vscode.ExtensionContext) {
 		canOpenExternalUri(uri: vscode.Uri) {
 			const configuration = vscode.workspace.getConfiguration('simpleBrowser');
 			if (!configuration.get('opener.enabled', false)) {
-				return false;
+				return vscode.ExternalUriOpenerEnablement.Disabled;
 			}
 
 			const originalUri = new URL(uri.toString());
 			if (enabledHosts.has(originalUri.hostname)) {
-				return true;
+				return isWeb()
+					? vscode.ExternalUriOpenerEnablement.Preferred
+					: vscode.ExternalUriOpenerEnablement.Enabled;
 			}
 
-			return false;
+			return vscode.ExternalUriOpenerEnablement.Disabled;
 		},
 		openExternalUri(resolveUri: vscode.Uri) {
 			return manager.show(resolveUri.toString());
@@ -67,3 +69,8 @@ export function activate(context: vscode.ExtensionContext) {
 		label: localize('openTitle', "Open in simple browser"),
 	}));
 }
+
+function isWeb(): boolean {
+	// @ts-expect-error
+	return typeof navigator !== 'undefined' && vscode.env.uiKind === vscode.UIKind.Web;
+}
diff --git a/src/vs/editor/browser/services/openerService.ts b/src/vs/editor/browser/services/openerService.ts
index a968cfad07e..5479ec29bd6 100644
--- a/src/vs/editor/browser/services/openerService.ts
+++ b/src/vs/editor/browser/services/openerService.ts
@@ -4,6 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as dom from 'vs/base/browser/dom';
+import { CancellationToken } from 'vs/base/common/cancellation';
 import { IDisposable } from 'vs/base/common/lifecycle';
 import { LinkedList } from 'vs/base/common/linkedList';
 import { ResourceMap } from 'vs/base/common/map';
@@ -211,13 +212,13 @@ export class OpenerService implements IOpenerService {
 		}
 
 		for (const opener of this._externalOpeners) {
-			const didOpen = await opener.openExternal(href);
+			const didOpen = await opener.openExternal(href, { sourceUri: uri }, CancellationToken.None);
 			if (didOpen) {
 				return true;
 			}
 		}
 
-		return this._defaultExternalOpener.openExternal(href);
+		return this._defaultExternalOpener.openExternal(href, { sourceUri: uri }, CancellationToken.None);
 	}
 
 	dispose() {
diff --git a/src/vs/editor/common/modes.ts b/src/vs/editor/common/modes.ts
index 6a51e49b9f1..35b306d602f 100644
--- a/src/vs/editor/common/modes.ts
+++ b/src/vs/editor/common/modes.ts
@@ -1876,3 +1876,13 @@ export interface ITokenizationRegistry {
  * @internal
  */
 export const TokenizationRegistry = new TokenizationRegistryImpl();
+
+
+/**
+ * @internal
+ */
+export enum ExternalUriOpenerEnablement {
+	Disabled,
+	Enabled,
+	Preferred
+}
diff --git a/src/vs/platform/opener/common/opener.ts b/src/vs/platform/opener/common/opener.ts
index c1ea8a6b349..3f96fc90032 100644
--- a/src/vs/platform/opener/common/opener.ts
+++ b/src/vs/platform/opener/common/opener.ts
@@ -3,11 +3,12 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { URI } from 'vs/base/common/uri';
-import { createDecorator } from 'vs/platform/instantiation/common/instantiation';
-import { IDisposable, Disposable } from 'vs/base/common/lifecycle';
+import { CancellationToken } from 'vs/base/common/cancellation';
+import { Disposable, IDisposable } from 'vs/base/common/lifecycle';
 import { equalsIgnoreCase, startsWithIgnoreCase } from 'vs/base/common/strings';
+import { URI } from 'vs/base/common/uri';
 import { IEditorOptions } from 'vs/platform/editor/common/editor';
+import { createDecorator } from 'vs/platform/instantiation/common/instantiation';
 
 export const IOpenerService = createDecorator<IOpenerService>('openerService');
 
@@ -46,7 +47,7 @@ export interface IOpener {
 }
 
 export interface IExternalOpener {
-	openExternal(href: string): Promise<boolean>;
+	openExternal(href: string, ctx: { sourceUri: URI }, token: CancellationToken): Promise<boolean>;
 	dispose?(): void;
 }
 
diff --git a/src/vs/vscode.proposed.d.ts b/src/vs/vscode.proposed.d.ts
index a9849d1eae4..d4f775ccc45 100644
--- a/src/vs/vscode.proposed.d.ts
+++ b/src/vs/vscode.proposed.d.ts
@@ -2288,6 +2288,23 @@ declare module 'vscode' {
 
 	//#region Opener service (https://github.com/microsoft/vscode/issues/109277)
 
+	export enum ExternalUriOpenerEnablement {
+		/**
+		 * The opener cannot handle the uri.
+		 */
+		Disabled = 0,
+
+		/**
+		 * The opener can handle the uri.
+		 */
+		Enabled = 1,
+
+		/**
+		 * The opener can handle the uri and should be automatically selected if possible.
+		 */
+		Preferred = 2
+	}
+
 	/**
 	 * Handles opening uris to external resources, such as http(s) links.
 	 *
@@ -2305,9 +2322,9 @@ declare module 'vscode' {
 		 * not yet gone through port forwarding.
 		 * @param token Cancellation token indicating that the result is no longer needed.
 		 *
-		 * @return True if the opener can open the external uri.
+		 * @return If the opener can open the external uri.
 		 */
-		canOpenExternalUri(uri: Uri, token: CancellationToken): ProviderResult<boolean>;
+		canOpenExternalUri(uri: Uri, token: CancellationToken): ProviderResult<ExternalUriOpenerEnablement>;
 
 		/**
 		 * Open the given uri.
diff --git a/src/vs/workbench/api/browser/mainThreadUriOpeners.ts b/src/vs/workbench/api/browser/mainThreadUriOpeners.ts
index f521610aa0d..99e26769eb0 100644
--- a/src/vs/workbench/api/browser/mainThreadUriOpeners.ts
+++ b/src/vs/workbench/api/browser/mainThreadUriOpeners.ts
@@ -3,7 +3,6 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { CancellationToken } from 'vs/base/common/cancellation';
 import { isPromiseCanceledError } from 'vs/base/common/errors';
 import { Disposable } from 'vs/base/common/lifecycle';
 import { Schemas } from 'vs/base/common/network';
@@ -13,7 +12,7 @@ import { ExtensionIdentifier } from 'vs/platform/extensions/common/extensions';
 import { INotificationService } from 'vs/platform/notification/common/notification';
 import { ExtHostContext, ExtHostUriOpenersShape, IExtHostContext, MainContext, MainThreadUriOpenersShape } from 'vs/workbench/api/common/extHost.protocol';
 import { externalUriOpenerIdSchemaAddition } from 'vs/workbench/contrib/externalUriOpener/common/configuration';
-import { ExternalOpenerEntry, IExternalOpenerProvider, IExternalUriOpenerService } from 'vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService';
+import { IExternalOpenerProvider, IExternalUriOpener, IExternalUriOpenerService } from 'vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService';
 import { IExtensionService } from 'vs/workbench/services/extensions/common/extensions';
 import { extHostNamedCustomer } from '../common/extHostCustomers';
 
@@ -31,45 +30,42 @@ export class MainThreadUriOpeners extends Disposable implements MainThreadUriOpe
 
 	constructor(
 		context: IExtHostContext,
-		@IExternalUriOpenerService private readonly externalUriOpenerService: IExternalUriOpenerService,
+		@IExternalUriOpenerService externalUriOpenerService: IExternalUriOpenerService,
 		@IExtensionService private readonly extensionService: IExtensionService,
 		@INotificationService private readonly notificationService: INotificationService,
 	) {
 		super();
 		this.proxy = context.getProxy(ExtHostContext.ExtHostUriOpeners);
 
-		this._register(this.externalUriOpenerService.registerExternalOpenerProvider(this));
+		this._register(externalUriOpenerService.registerExternalOpenerProvider(this));
 	}
 
-	public async provideExternalOpeners(href: string | URI): Promise<readonly ExternalOpenerEntry[]> {
-		const targetUri = typeof href === 'string' ? URI.parse(href) : href;
+	public async *getOpeners(targetUri: URI): AsyncIterable<IExternalUriOpener> {
 
 		// Currently we only allow openers for http and https urls
 		if (targetUri.scheme !== Schemas.http && targetUri.scheme !== Schemas.https) {
-			return [];
+			return;
 		}
 
 		await this.extensionService.activateByEvent(`onUriOpen:${targetUri.scheme}`);
 
-		// If there are no handlers there is no point in making a round trip
-		const hasHandler = Array.from(this._registeredOpeners.values()).some(x => x.schemes.has(targetUri.scheme));
-		if (!hasHandler) {
-			return [];
+		for (const [id, openerMetadata] of this._registeredOpeners) {
+			if (openerMetadata.schemes.has(targetUri.scheme)) {
+				yield this.createOpener(id, openerMetadata);
+			}
 		}
-
-		const openerIds = await this.proxy.$getOpenersForUri(targetUri, CancellationToken.None);
-		return openerIds.map(id => this.createOpener(id, targetUri));
 	}
 
-	private createOpener(openerId: string, sourceUri: URI): ExternalOpenerEntry {
-		const metadata = this._registeredOpeners.get(openerId)!;
+	private createOpener(id: string, metadata: RegisteredOpenerMetadata): IExternalUriOpener {
 		return {
-			id: openerId,
+			id: id,
 			label: metadata.label,
-			openExternal: async (href) => {
-				const resolveUri = URI.parse(href);
+			canOpen: (uri, token) => {
+				return this.proxy.$canOpenUri(id, uri, token);
+			},
+			openExternalUri: async (uri, ctx, token) => {
 				try {
-					await this.proxy.$openUri(openerId, { resolveUri, sourceUri }, CancellationToken.None);
+					await this.proxy.$openUri(id, { resolvedUri: uri, sourceUri: ctx.sourceUri }, token);
 				} catch (e) {
 					if (!isPromiseCanceledError(e)) {
 						this.notificationService.error(localize('openerFailedMessage', "Could not open uri: {0}", e.toString()));
diff --git a/src/vs/workbench/api/common/extHost.api.impl.ts b/src/vs/workbench/api/common/extHost.api.impl.ts
index 27c8d06fb5c..232d2734fd9 100644
--- a/src/vs/workbench/api/common/extHost.api.impl.ts
+++ b/src/vs/workbench/api/common/extHost.api.impl.ts
@@ -1133,6 +1133,7 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 			EventEmitter: Emitter,
 			ExtensionKind: extHostTypes.ExtensionKind,
 			ExtensionMode: extHostTypes.ExtensionMode,
+			ExternalUriOpenerEnablement: extHostTypes.ExternalUriOpenerEnablement,
 			FileChangeType: extHostTypes.FileChangeType,
 			FileDecoration: extHostTypes.FileDecoration,
 			FileSystemError: extHostTypes.FileSystemError,
diff --git a/src/vs/workbench/api/common/extHost.protocol.ts b/src/vs/workbench/api/common/extHost.protocol.ts
index c2a8614457f..a5f6d3ed535 100644
--- a/src/vs/workbench/api/common/extHost.protocol.ts
+++ b/src/vs/workbench/api/common/extHost.protocol.ts
@@ -807,8 +807,8 @@ export interface MainThreadUriOpenersShape extends IDisposable {
 }
 
 export interface ExtHostUriOpenersShape {
-	$getOpenersForUri(uri: UriComponents, token: CancellationToken): Promise<readonly string[]>;
-	$openUri(id: string, context: { resolveUri: UriComponents, sourceUri: UriComponents }, token: CancellationToken): Promise<void>;
+	$canOpenUri(id: string, uri: UriComponents, token: CancellationToken): Promise<modes.ExternalUriOpenerEnablement>;
+	$openUri(id: string, context: { resolvedUri: UriComponents, sourceUri: UriComponents }, token: CancellationToken): Promise<void>;
 }
 
 export interface ITextSearchComplete {
diff --git a/src/vs/workbench/api/common/extHostTypes.ts b/src/vs/workbench/api/common/extHostTypes.ts
index a4cd5a326f6..e153af8aa46 100644
--- a/src/vs/workbench/api/common/extHostTypes.ts
+++ b/src/vs/workbench/api/common/extHostTypes.ts
@@ -2976,3 +2976,9 @@ export type RequiredTestItem = {
 
 
 //#endregion
+
+export enum ExternalUriOpenerEnablement {
+	Disabled = 0,
+	Enabled = 1,
+	Preferred = 2
+}
diff --git a/src/vs/workbench/api/common/extHostUriOpener.ts b/src/vs/workbench/api/common/extHostUriOpener.ts
index 7d8115d41e2..eaaaca2088d 100644
--- a/src/vs/workbench/api/common/extHostUriOpener.ts
+++ b/src/vs/workbench/api/common/extHostUriOpener.ts
@@ -6,6 +6,7 @@
 import { CancellationToken } from 'vs/base/common/cancellation';
 import { toDisposable } from 'vs/base/common/lifecycle';
 import { URI, UriComponents } from 'vs/base/common/uri';
+import * as modes from 'vs/editor/common/modes';
 import { ExtensionIdentifier } from 'vs/platform/extensions/common/extensions';
 import type * as vscode from 'vscode';
 import { ExtHostUriOpenersShape, IMainContext, MainContext, MainThreadUriOpenersShape } from './extHost.protocol';
@@ -54,35 +55,23 @@ export class ExtHostUriOpeners implements ExtHostUriOpenersShape {
 		});
 	}
 
-	async $getOpenersForUri(uriComponents: UriComponents, token: CancellationToken): Promise<readonly string[]> {
+	async $canOpenUri(id: string, uriComponents: UriComponents, token: CancellationToken): Promise<modes.ExternalUriOpenerEnablement> {
+		const entry = this._openers.get(id);
+		if (!entry) {
+			throw new Error(`Unknown opener with id: ${id}`);
+		}
+
 		const uri = URI.revive(uriComponents);
-
-		const promises = Array.from(this._openers.entries())
-			.map(async ([id, { schemes, opener, }]): Promise<string | undefined> => {
-				if (!schemes.has(uri.scheme)) {
-					return undefined;
-				}
-
-				try {
-					if (await opener.canOpenExternalUri(uri, token)) {
-						return id;
-					}
-				} catch (e) {
-					console.log(e);
-					// noop
-				}
-				return undefined;
-			});
-
-		return (await Promise.all(promises)).filter(handle => typeof handle === 'string') as string[];
+		const result = await entry.opener.canOpenExternalUri(uri, token);
+		return result ? result : modes.ExternalUriOpenerEnablement.Disabled;
 	}
 
-	async $openUri(id: string, context: { resolveUri: UriComponents, sourceUri: UriComponents }, token: CancellationToken): Promise<void> {
+	async $openUri(id: string, context: { resolvedUri: UriComponents, sourceUri: UriComponents }, token: CancellationToken): Promise<void> {
 		const entry = this._openers.get(id);
 		if (!entry) {
 			throw new Error(`Unknown opener id: '${id}'`);
 		}
-		return entry.opener.openExternalUri(URI.revive(context.resolveUri), {
+		return entry.opener.openExternalUri(URI.revive(context.resolvedUri), {
 			sourceUri: URI.revive(context.sourceUri)
 		}, token);
 	}
diff --git a/src/vs/workbench/contrib/externalUriOpener/common/configuration.ts b/src/vs/workbench/contrib/externalUriOpener/common/configuration.ts
index b61f29d6937..fcd27ca5263 100644
--- a/src/vs/workbench/contrib/externalUriOpener/common/configuration.ts
+++ b/src/vs/workbench/contrib/externalUriOpener/common/configuration.ts
@@ -11,7 +11,7 @@ import { IJSONSchema } from 'vs/base/common/jsonSchema';
 export const externalUriOpenersSettingId = 'workbench.externalUriOpeners';
 
 export interface ExternalUriOpenerConfiguration {
-	readonly hostname: string;
+	readonly uri: string;
 	readonly id: string;
 }
 
@@ -20,6 +20,18 @@ export const externalUriOpenerIdSchemaAddition: IJSONSchema = {
 	enum: []
 };
 
+const exampleUriPatterns = `
+- \`https://microsoft.com\`: Matches this specific domain using https
+- \`https://microsoft.com:8080\`: Matches this specific domain on this port using https
+- \`https://microsoft.com:*\`: Matches this specific domain on any port using https
+- \`https://microsoft.com/foo\`: Matches \`https://microsoft.com/foo\` and \`https://microsoft.com/foo/bar\`, but not \`https://microsoft.com/foobar\` or \`https://microsoft.com/bar\`
+- \`https://*.microsoft.com\`: Match all domains ending in \`microsoft.com\` using https
+- \`microsoft.com\`: Match this specific domain using either http or https
+- \`*.microsoft.com\`: Match all domains ending in \`microsoft.com\` using either http or https
+- \`http://192.168.0.1\`: Matches this specific IP using http
+- \`http://192.168.0.*\`: Matches all IP's with this prefix using http
+- \`*\`: Match all domains using either http or https`;
+
 export const externalUriOpenersConfigurationNode: IConfigurationNode = {
 	...workbenchConfigurationNodeBase,
 	properties: {
@@ -30,15 +42,15 @@ export const externalUriOpenersConfigurationNode: IConfigurationNode = {
 				type: 'object',
 				defaultSnippets: [{
 					body: {
-						'hostname': '$1',
+						'uri': '$1',
 						'id': '$2'
 					}
 				}],
-				required: ['hostname', 'id'],
+				required: ['uri', 'id'],
 				properties: {
-					'hostname': {
+					'uri': {
 						type: 'string',
-						description: nls.localize('externalUriOpeners.hostname', "The hostname of sites the opener applies to."),
+						markdownDescription: nls.localize('externalUriOpeners.uri', "Uri pattern that the opener applies to. Example patterns: \n{0}", exampleUriPatterns),
 					},
 					'id': {
 						anyOf: [
diff --git a/src/vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService.ts b/src/vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService.ts
index 056e43eef95..75fa9995d8d 100644
--- a/src/vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService.ts
+++ b/src/vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService.ts
@@ -3,28 +3,35 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { firstOrDefault } from 'vs/base/common/arrays';
+import { CancellationToken } from 'vs/base/common/cancellation';
+import { Iterable } from 'vs/base/common/iterator';
 import { Disposable, IDisposable } from 'vs/base/common/lifecycle';
 import { LinkedList } from 'vs/base/common/linkedList';
 import { URI } from 'vs/base/common/uri';
+import * as modes from 'vs/editor/common/modes';
 import * as nls from 'vs/nls';
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
 import { createDecorator } from 'vs/platform/instantiation/common/instantiation';
 import { IExternalOpener, IOpenerService } from 'vs/platform/opener/common/opener';
 import { IQuickInputService, IQuickPickItem, IQuickPickSeparator } from 'vs/platform/quickinput/common/quickInput';
 import { ExternalUriOpenerConfiguration, externalUriOpenersSettingId } from 'vs/workbench/contrib/externalUriOpener/common/configuration';
+import { testUrlMatchesGlob } from 'vs/workbench/contrib/url/common/urlGlob';
 import { IPreferencesService } from 'vs/workbench/services/preferences/common/preferences';
 
 export const IExternalUriOpenerService = createDecorator<IExternalUriOpenerService>('externalUriOpenerService');
 
-export interface ExternalOpenerEntry extends IExternalOpener {
-	readonly id: string;
-	readonly label: string;
-}
-
-
 
 export interface IExternalOpenerProvider {
-	provideExternalOpeners(resource: URI | string): Promise<readonly ExternalOpenerEntry[]>;
+	getOpeners(targetUri: URI): AsyncIterable<IExternalUriOpener>;
+}
+
+export interface IExternalUriOpener {
+	readonly id: string;
+	readonly label: string;
+
+	canOpen(uri: URI, token: CancellationToken): Promise<modes.ExternalUriOpenerEnablement>;
+	openExternalUri(uri: URI, ctx: { sourceUri: URI }, token: CancellationToken): Promise<boolean>;
 }
 
 export interface IExternalUriOpenerService {
@@ -40,7 +47,7 @@ export class ExternalUriOpenerService extends Disposable implements IExternalUri
 
 	public readonly _serviceBrand: undefined;
 
-	private readonly _externalOpenerProviders = new LinkedList<IExternalOpenerProvider>();
+	private readonly _providers = new LinkedList<IExternalOpenerProvider>();
 
 	constructor(
 		@IOpenerService openerService: IOpenerService,
@@ -53,44 +60,89 @@ export class ExternalUriOpenerService extends Disposable implements IExternalUri
 	}
 
 	registerExternalOpenerProvider(provider: IExternalOpenerProvider): IDisposable {
-		const remove = this._externalOpenerProviders.push(provider);
+		const remove = this._providers.push(provider);
 		return { dispose: remove };
 	}
 
-	async openExternal(href: string): Promise<boolean> {
+	async openExternal(href: string, ctx: { sourceUri: URI }, token: CancellationToken): Promise<boolean> {
 
 		const targetUri = typeof href === 'string' ? URI.parse(href) : href;
 
-		const openers: ExternalOpenerEntry[] = [];
-		for (const provider of this._externalOpenerProviders) {
-			openers.push(...(await provider.provideExternalOpeners(targetUri)));
-		}
+		const allOpeners = new Map<string, IExternalUriOpener>();
+		await Promise.all(Iterable.map(this._providers, async (provider) => {
+			for await (const opener of provider.getOpeners(targetUri)) {
+				allOpeners.set(opener.id, opener);
+			}
+		}));
 
-		if (openers.length === 0) {
+		if (allOpeners.size === 0) {
 			return false;
 		}
 
-		const authority = targetUri.authority;
+		// First check to see if we have a configured opener
+		const configuredOpener = this.getConfiguredOpenerForUri(allOpeners, targetUri);
+		if (configuredOpener) {
+			return configuredOpener.openExternalUri(targetUri, ctx, token);
+		}
+
+		// Then check to see if there is a valid opener
+		const validOpeners: Array<{ opener: IExternalUriOpener, preferred: boolean }> = [];
+		await Promise.all(Array.from(allOpeners.values()).map(async opener => {
+			switch (await opener.canOpen(targetUri, token)) {
+				case modes.ExternalUriOpenerEnablement.Enabled:
+					validOpeners.push({ opener, preferred: false });
+					break;
+
+				case modes.ExternalUriOpenerEnablement.Preferred:
+					validOpeners.push({ opener, preferred: true });
+					break;
+			}
+		}));
+		if (validOpeners.length === 0) {
+			return false;
+		}
+
+		// See if we have a preferred opener first
+		const preferred = firstOrDefault(validOpeners.filter(x => x.preferred));
+		if (preferred) {
+			return preferred.opener.openExternalUri(targetUri, ctx, token);
+		}
+
+		// Otherwise prompt
+		return this.showOpenerPrompt(validOpeners, targetUri, ctx, token);
+	}
+
+	private getConfiguredOpenerForUri(openers: Map<string, IExternalUriOpener>, targetUri: URI): IExternalUriOpener | undefined {
 		const config = this.configurationService.getValue<readonly ExternalUriOpenerConfiguration[]>(externalUriOpenersSettingId) || [];
-		for (const entry of config) {
-			if (entry.hostname === authority) {
-				const opener = openers.find(opener => opener.id === entry.id);
-				if (opener) {
-					return opener.openExternal(href);
+		for (const { id, uri } of config) {
+			const entry = openers.get(id);
+			if (entry) {
+				if (testUrlMatchesGlob(targetUri.toString(), uri)) {
+					// Skip the `canOpen` check here since the opener was specifically requested.
+					return entry;
 				}
 			}
 		}
+		return undefined;
+	}
 
-		type PickItem = IQuickPickItem & { opener?: IExternalOpener | 'configureDefault' };
-		const items: Array<PickItem | IQuickPickSeparator> = openers.map((opener, i): PickItem => {
+	private async showOpenerPrompt(
+		openers: ReadonlyArray<{ opener: IExternalUriOpener, preferred: boolean }>,
+		targetUri: URI,
+		ctx: { sourceUri: URI },
+		token: CancellationToken
+	): Promise<boolean> {
+		type PickItem = IQuickPickItem & { opener?: IExternalUriOpener | 'configureDefault' };
+
+		const items: Array<PickItem | IQuickPickSeparator> = openers.map((entry): PickItem => {
 			return {
-				label: opener.label,
-				opener: opener
+				label: entry.opener.label,
+				opener: entry.opener
 			};
 		});
 		items.push(
 			{
-				label: 'Default',
+				label: nls.localize('selectOpenerDefaultLabel', 'Default external uri opener'),
 				opener: undefined
 			},
 			{ type: 'separator' },
@@ -116,7 +168,7 @@ export class ExternalUriOpenerService extends Disposable implements IExternalUri
 			});
 			return true;
 		} else {
-			return picked.opener.openExternal(href);
+			return picked.opener.openExternalUri(targetUri, ctx, token);
 		}
 	}
 }
diff --git a/src/vs/workbench/contrib/externalUriOpener/test/common/externalUriOpenerService.test.ts b/src/vs/workbench/contrib/externalUriOpener/test/common/externalUriOpenerService.test.ts
new file mode 100644
index 00000000000..ab8fc8d7a8a
--- /dev/null
+++ b/src/vs/workbench/contrib/externalUriOpener/test/common/externalUriOpenerService.test.ts
@@ -0,0 +1,128 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as assert from 'assert';
+import { CancellationToken } from 'vs/base/common/cancellation';
+import { Disposable } from 'vs/base/common/lifecycle';
+import { URI } from 'vs/base/common/uri';
+import { ExternalUriOpenerEnablement } from 'vs/editor/common/modes';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { TestConfigurationService } from 'vs/platform/configuration/test/common/testConfigurationService';
+import { TestInstantiationService } from 'vs/platform/instantiation/test/common/instantiationServiceMock';
+import { IOpenerService } from 'vs/platform/opener/common/opener';
+import { IPickOptions, IQuickInputService, IQuickPickItem, QuickPickInput } from 'vs/platform/quickinput/common/quickInput';
+import { ExternalUriOpenerService, IExternalOpenerProvider, IExternalUriOpener } from 'vs/workbench/contrib/externalUriOpener/common/externalUriOpenerService';
+
+
+class MockQuickInputService implements Partial<IQuickInputService>{
+
+	constructor(
+		private readonly pickIndex: number
+	) { }
+
+	public pick<T extends IQuickPickItem>(picks: Promise<QuickPickInput<T>[]> | QuickPickInput<T>[], options?: IPickOptions<T> & { canPickMany: true }, token?: CancellationToken): Promise<T[]>;
+	public pick<T extends IQuickPickItem>(picks: Promise<QuickPickInput<T>[]> | QuickPickInput<T>[], options?: IPickOptions<T> & { canPickMany: false }, token?: CancellationToken): Promise<T>;
+	public async pick<T extends IQuickPickItem>(picks: Promise<QuickPickInput<T>[]> | QuickPickInput<T>[], options?: Omit<IPickOptions<T>, 'canPickMany'>, token?: CancellationToken): Promise<T | undefined> {
+		const resolvedPicks = await picks;
+		const item = resolvedPicks[this.pickIndex];
+		if (item.type === 'separator') {
+			return undefined;
+		}
+		return item;
+	}
+
+}
+
+suite('ExternalUriOpenerService', () => {
+
+	let instantiationService: TestInstantiationService;
+
+	setup(() => {
+		instantiationService = new TestInstantiationService();
+
+		instantiationService.stub(IConfigurationService, new TestConfigurationService());
+		instantiationService.stub(IOpenerService, {
+			registerExternalOpener: () => { return Disposable.None; }
+		});
+	});
+
+	test('Should not open if there are no openers', async () => {
+		const externalUriOpenerService: ExternalUriOpenerService = instantiationService.createInstance(ExternalUriOpenerService);
+
+		externalUriOpenerService.registerExternalOpenerProvider(new class implements IExternalOpenerProvider {
+			async *getOpeners(_targetUri: URI): AsyncGenerator<IExternalUriOpener> {
+				// noop
+			}
+		});
+
+		const uri = URI.parse('http://contoso.com');
+		const didOpen = await externalUriOpenerService.openExternal(uri.toString(), { sourceUri: uri }, CancellationToken.None);
+		assert.strictEqual(didOpen, false);
+	});
+
+	test('Should prompt if there is at least one enabled opener', async () => {
+		instantiationService.stub(IQuickInputService, new MockQuickInputService(0));
+
+		const externalUriOpenerService: ExternalUriOpenerService = instantiationService.createInstance(ExternalUriOpenerService);
+
+		let openedWithEnabled = false;
+		externalUriOpenerService.registerExternalOpenerProvider(new class implements IExternalOpenerProvider {
+			async *getOpeners(_targetUri: URI): AsyncGenerator<IExternalUriOpener> {
+				yield {
+					id: 'disabled-id',
+					label: 'disabled',
+					canOpen: async () => ExternalUriOpenerEnablement.Disabled,
+					openExternalUri: async () => true,
+				};
+				yield {
+					id: 'enabled-id',
+					label: 'enabled',
+					canOpen: async () => ExternalUriOpenerEnablement.Enabled,
+					openExternalUri: async () => {
+						openedWithEnabled = true;
+						return true;
+					}
+				};
+			}
+		});
+
+		const uri = URI.parse('http://contoso.com');
+		const didOpen = await externalUriOpenerService.openExternal(uri.toString(), { sourceUri: uri }, CancellationToken.None);
+		assert.strictEqual(didOpen, true);
+		assert.strictEqual(openedWithEnabled, true);
+	});
+
+	test('Should automatically pick single preferred opener without prompt', async () => {
+		const externalUriOpenerService: ExternalUriOpenerService = instantiationService.createInstance(ExternalUriOpenerService);
+
+		let openedWithPreferred = false;
+		externalUriOpenerService.registerExternalOpenerProvider(new class implements IExternalOpenerProvider {
+			async *getOpeners(_targetUri: URI): AsyncGenerator<IExternalUriOpener> {
+				yield {
+					id: 'other-id',
+					label: 'other',
+					canOpen: async () => ExternalUriOpenerEnablement.Enabled,
+					openExternalUri: async () => {
+						return true;
+					}
+				};
+				yield {
+					id: 'preferred-id',
+					label: 'preferred',
+					canOpen: async () => ExternalUriOpenerEnablement.Preferred,
+					openExternalUri: async () => {
+						openedWithPreferred = true;
+						return true;
+					}
+				};
+			}
+		});
+
+		const uri = URI.parse('http://contoso.com');
+		const didOpen = await externalUriOpenerService.openExternal(uri.toString(), { sourceUri: uri }, CancellationToken.None);
+		assert.strictEqual(didOpen, true);
+		assert.strictEqual(openedWithPreferred, true);
+	});
+});
diff --git a/src/vs/workbench/contrib/url/browser/trustedDomainsValidator.ts b/src/vs/workbench/contrib/url/browser/trustedDomainsValidator.ts
index c8f144bdaf3..564cf24f9cb 100644
--- a/src/vs/workbench/contrib/url/browser/trustedDomainsValidator.ts
+++ b/src/vs/workbench/contrib/url/browser/trustedDomainsValidator.ts
@@ -22,6 +22,7 @@ import { INotificationService } from 'vs/platform/notification/common/notificati
 import { IdleValue } from 'vs/base/common/async';
 import { IAuthenticationService } from 'vs/workbench/services/authentication/browser/authenticationService';
 import { IWorkspaceContextService } from 'vs/platform/workspace/common/workspace';
+import { testUrlMatchesGlob } from 'vs/workbench/contrib/url/common/urlGlob';
 
 type TrustedDomainsDialogActionClassification = {
 	action: { classification: 'SystemMetaData', purpose: 'FeatureInsight' };
@@ -216,94 +217,10 @@ export function isURLDomainTrusted(url: URI, trustedDomains: string[]) {
 			return true;
 		}
 
-		if (isTrusted(url.toString(), trustedDomains[i])) {
+		if (testUrlMatchesGlob(url.toString(), trustedDomains[i])) {
 			return true;
 		}
 	}
 
 	return false;
 }
-
-export const isTrusted = (url: string, trustedURL: string): boolean => {
-	const normalize = (url: string) => url.replace(/\/+$/, '');
-	trustedURL = normalize(trustedURL);
-	url = normalize(url);
-
-	const memo = Array.from({ length: url.length + 1 }).map(() =>
-		Array.from({ length: trustedURL.length + 1 }).map(() => undefined),
-	);
-
-	if (/^[^./:]*:\/\//.test(trustedURL)) {
-		return doURLMatch(memo, url, trustedURL, 0, 0);
-	}
-
-	const scheme = /^(https?):\/\//.exec(url)?.[1];
-	if (scheme) {
-		return doURLMatch(memo, url, `${scheme}://${trustedURL}`, 0, 0);
-	}
-
-	return false;
-};
-
-const doURLMatch = (
-	memo: (boolean | undefined)[][],
-	url: string,
-	trustedURL: string,
-	urlOffset: number,
-	trustedURLOffset: number,
-): boolean => {
-	if (memo[urlOffset]?.[trustedURLOffset] !== undefined) {
-		return memo[urlOffset][trustedURLOffset]!;
-	}
-
-	const options = [];
-
-	// Endgame.
-	// Fully exact match
-	if (urlOffset === url.length) {
-		return trustedURLOffset === trustedURL.length;
-	}
-
-	// Some path remaining in url
-	if (trustedURLOffset === trustedURL.length) {
-		const remaining = url.slice(urlOffset);
-		return remaining[0] === '/';
-	}
-
-	if (url[urlOffset] === trustedURL[trustedURLOffset]) {
-		// Exact match.
-		options.push(doURLMatch(memo, url, trustedURL, urlOffset + 1, trustedURLOffset + 1));
-	}
-
-	if (trustedURL[trustedURLOffset] + trustedURL[trustedURLOffset + 1] === '*.') {
-		// Any subdomain match. Either consume one thing that's not a / or : and don't advance base or consume nothing and do.
-		if (!['/', ':'].includes(url[urlOffset])) {
-			options.push(doURLMatch(memo, url, trustedURL, urlOffset + 1, trustedURLOffset));
-		}
-		options.push(doURLMatch(memo, url, trustedURL, urlOffset, trustedURLOffset + 2));
-	}
-
-	if (trustedURL[trustedURLOffset] === '*') {
-		// Any match. Either consume one thing and don't advance base or consume nothing and do.
-		if (urlOffset + 1 === url.length) {
-			// If we're at the end of the input url consume one from both.
-			options.push(doURLMatch(memo, url, trustedURL, urlOffset + 1, trustedURLOffset + 1));
-		} else {
-			options.push(doURLMatch(memo, url, trustedURL, urlOffset + 1, trustedURLOffset));
-		}
-		options.push(doURLMatch(memo, url, trustedURL, urlOffset, trustedURLOffset + 1));
-	}
-
-	if (trustedURL[trustedURLOffset] + trustedURL[trustedURLOffset + 1] === ':*') {
-		// any port match. Consume a port if it exists otherwise nothing. Always comsume the base.
-		if (url[urlOffset] === ':') {
-			let endPortIndex = urlOffset + 1;
-			do { endPortIndex++; } while (/[0-9]/.test(url[endPortIndex]));
-			options.push(doURLMatch(memo, url, trustedURL, endPortIndex, trustedURLOffset + 2));
-		} else {
-			options.push(doURLMatch(memo, url, trustedURL, urlOffset, trustedURLOffset + 2));
-		}
-	}
-
-	return (memo[urlOffset][trustedURLOffset] = options.some(a => a === true));
-};
diff --git a/src/vs/workbench/contrib/url/common/urlGlob.ts b/src/vs/workbench/contrib/url/common/urlGlob.ts
new file mode 100644
index 00000000000..8893796290c
--- /dev/null
+++ b/src/vs/workbench/contrib/url/common/urlGlob.ts
@@ -0,0 +1,88 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+export const testUrlMatchesGlob = (url: string, globUrl: string): boolean => {
+	const normalize = (url: string) => url.replace(/\/+$/, '');
+	globUrl = normalize(globUrl);
+	url = normalize(url);
+
+	const memo = Array.from({ length: url.length + 1 }).map(() =>
+		Array.from({ length: globUrl.length + 1 }).map(() => undefined),
+	);
+
+	if (/^[^./:]*:\/\//.test(globUrl)) {
+		return doUrlMatch(memo, url, globUrl, 0, 0);
+	}
+
+	const scheme = /^(https?):\/\//.exec(url)?.[1];
+	if (scheme) {
+		return doUrlMatch(memo, url, `${scheme}://${globUrl}`, 0, 0);
+	}
+
+	return false;
+};
+
+const doUrlMatch = (
+	memo: (boolean | undefined)[][],
+	url: string,
+	globUrl: string,
+	urlOffset: number,
+	globUrlOffset: number,
+): boolean => {
+	if (memo[urlOffset]?.[globUrlOffset] !== undefined) {
+		return memo[urlOffset][globUrlOffset]!;
+	}
+
+	const options = [];
+
+	// Endgame.
+	// Fully exact match
+	if (urlOffset === url.length) {
+		return globUrlOffset === globUrl.length;
+	}
+
+	// Some path remaining in url
+	if (globUrlOffset === globUrl.length) {
+		const remaining = url.slice(urlOffset);
+		return remaining[0] === '/';
+	}
+
+	if (url[urlOffset] === globUrl[globUrlOffset]) {
+		// Exact match.
+		options.push(doUrlMatch(memo, url, globUrl, urlOffset + 1, globUrlOffset + 1));
+	}
+
+	if (globUrl[globUrlOffset] + globUrl[globUrlOffset + 1] === '*.') {
+		// Any subdomain match. Either consume one thing that's not a / or : and don't advance base or consume nothing and do.
+		if (!['/', ':'].includes(url[urlOffset])) {
+			options.push(doUrlMatch(memo, url, globUrl, urlOffset + 1, globUrlOffset));
+		}
+		options.push(doUrlMatch(memo, url, globUrl, urlOffset, globUrlOffset + 2));
+	}
+
+	if (globUrl[globUrlOffset] === '*') {
+		// Any match. Either consume one thing and don't advance base or consume nothing and do.
+		if (urlOffset + 1 === url.length) {
+			// If we're at the end of the input url consume one from both.
+			options.push(doUrlMatch(memo, url, globUrl, urlOffset + 1, globUrlOffset + 1));
+		} else {
+			options.push(doUrlMatch(memo, url, globUrl, urlOffset + 1, globUrlOffset));
+		}
+		options.push(doUrlMatch(memo, url, globUrl, urlOffset, globUrlOffset + 1));
+	}
+
+	if (globUrl[globUrlOffset] + globUrl[globUrlOffset + 1] === ':*') {
+		// any port match. Consume a port if it exists otherwise nothing. Always comsume the base.
+		if (url[urlOffset] === ':') {
+			let endPortIndex = urlOffset + 1;
+			do { endPortIndex++; } while (/[0-9]/.test(url[endPortIndex]));
+			options.push(doUrlMatch(memo, url, globUrl, endPortIndex, globUrlOffset + 2));
+		} else {
+			options.push(doUrlMatch(memo, url, globUrl, urlOffset, globUrlOffset + 2));
+		}
+	}
+
+	return (memo[urlOffset][globUrlOffset] = options.some(a => a === true));
+};