diff --git a/src/vs/workbench/contrib/url/common/trustedDomainsFileSystemProvider.ts b/src/vs/workbench/contrib/url/common/trustedDomainsFileSystemProvider.ts
index f38fa6ed5836d49252d32b6af2501cdd35cdcebc..763f038e087c82b1c9c4cf7882697b9ca18fdeb2 100644
--- a/src/vs/workbench/contrib/url/common/trustedDomainsFileSystemProvider.ts
+++ b/src/vs/workbench/contrib/url/common/trustedDomainsFileSystemProvider.ts
@@ -26,6 +26,8 @@ const TRUSTED_DOMAINS_STAT: IStat = {
 const CONFIG_HELP_TEXT_PRE = `// Links matching one or more entries in the list below can be opened without link protection.
 // The following examples show what entries can look like:
 // - "https://microsoft.com": Matches this specific domain 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
diff --git a/src/vs/workbench/contrib/url/common/trustedDomainsValidator.ts b/src/vs/workbench/contrib/url/common/trustedDomainsValidator.ts
index ebe36feb710de6b1eda1a935d7ce535defeb14a4..afef62fa5e110c00178da79f82586042fc0478bd 100644
--- a/src/vs/workbench/contrib/url/common/trustedDomainsValidator.ts
+++ b/src/vs/workbench/contrib/url/common/trustedDomainsValidator.ts
@@ -5,7 +5,7 @@
 
 import { Schemas } from 'vs/base/common/network';
 import Severity from 'vs/base/common/severity';
-import { equalsIgnoreCase } from 'vs/base/common/strings';
+import { equalsIgnoreCase, startsWith } from 'vs/base/common/strings';
 import { URI } from 'vs/base/common/uri';
 import { localize } from 'vs/nls';
 import { IDialogService } from 'vs/platform/dialogs/common/dialogs';
@@ -14,7 +14,10 @@ import { IProductService } from 'vs/platform/product/common/productService';
 import { IQuickInputService } from 'vs/platform/quickinput/common/quickInput';
 import { IStorageService } from 'vs/platform/storage/common/storage';
 import { IWorkbenchContribution } from 'vs/workbench/common/contributions';
-import { configureOpenerTrustedDomainsHandler, readTrustedDomains } from 'vs/workbench/contrib/url/common/trustedDomains';
+import {
+	configureOpenerTrustedDomainsHandler,
+	readTrustedDomains
+} from 'vs/workbench/contrib/url/common/trustedDomains';
 import { IEditorService } from 'vs/workbench/services/editor/common/editorService';
 
 export class OpenerValidatorContributions implements IWorkbenchContribution {
@@ -132,10 +135,11 @@ export function isURLDomainTrusted(url: URI, trustedDomains: string[]) {
 		}
 
 		if (url.authority === parsedTrustedDomain.authority) {
-			return true;
+			return pathMatches(url.path, parsedTrustedDomain.path);
 		}
 
 		if (trustedDomains[i].indexOf('*') !== -1) {
+
 			let reversedAuthoritySegments = url.authority.split('.').reverse();
 			const reversedTrustedDomainAuthoritySegments = parsedTrustedDomain.authority.split('.').reverse();
 
@@ -146,11 +150,11 @@ export function isURLDomainTrusted(url: URI, trustedDomains: string[]) {
 				reversedAuthoritySegments = reversedAuthoritySegments.slice(0, reversedTrustedDomainAuthoritySegments.length);
 			}
 
-			if (
-				reversedAuthoritySegments.every((val, i) => {
-					return reversedTrustedDomainAuthoritySegments[i] === '*' || val === reversedTrustedDomainAuthoritySegments[i];
-				})
-			) {
+			const authorityMatches = reversedAuthoritySegments.every((val, i) => {
+				return reversedTrustedDomainAuthoritySegments[i] === '*' || val === reversedTrustedDomainAuthoritySegments[i];
+			});
+
+			if (authorityMatches && pathMatches(url.path, parsedTrustedDomain.path)) {
 				return true;
 			}
 		}
@@ -158,3 +162,19 @@ export function isURLDomainTrusted(url: URI, trustedDomains: string[]) {
 
 	return false;
 }
+
+function pathMatches(open: string, rule: string) {
+	if (rule === '/') {
+		return true;
+	}
+
+	const openSegments = open.split('/');
+	const ruleSegments = rule.split('/');
+	for (let i = 0; i < ruleSegments.length; i++) {
+		if (ruleSegments[i] !== openSegments[i]) {
+			return false;
+		}
+	}
+
+	return true;
+}
diff --git a/src/vs/workbench/test/contrib/linkProtection.test.ts b/src/vs/workbench/test/contrib/linkProtection.test.ts
index f027009a14131dc323481db3e6d55c75d456d6f0..43c443119a7d7d06b5e30e7266c08e4f911c29ef 100644
--- a/src/vs/workbench/test/contrib/linkProtection.test.ts
+++ b/src/vs/workbench/test/contrib/linkProtection.test.ts
@@ -8,49 +8,67 @@ import * as assert from 'assert';
 import { isURLDomainTrusted } from 'vs/workbench/contrib/url/common/trustedDomainsValidator';
 import { URI } from 'vs/base/common/uri';
 
-function linkProtectedByRules(link: string, rules: string[]) {
-	assert.ok(isURLDomainTrusted(URI.parse(link), rules));
+function linkAllowedByRules(link: string, rules: string[]) {
+	assert.ok(isURLDomainTrusted(URI.parse(link), rules), `Link\n${link}\n should be protected by rules\n${JSON.stringify(rules)}`);
 }
-function linkNotProtectedByRules(link: string, rules: string[]) {
-	assert.ok(!isURLDomainTrusted(URI.parse(link), rules));
+function linkNotAllowedByRules(link: string, rules: string[]) {
+	assert.ok(!isURLDomainTrusted(URI.parse(link), rules), `Link\n${link}\n should NOT be protected by rules\n${JSON.stringify(rules)}`);
 }
 
 suite('Link protection domain matching', () => {
 	test('simple', () => {
-		linkNotProtectedByRules('https://x.org', []);
+		linkNotAllowedByRules('https://x.org', []);
 
-		linkProtectedByRules('https://x.org', ['https://x.org']);
-		linkProtectedByRules('https://x.org/foo', ['https://x.org']);
+		linkAllowedByRules('https://x.org', ['https://x.org']);
+		linkAllowedByRules('https://x.org/foo', ['https://x.org']);
 
-		linkNotProtectedByRules('https://x.org', ['http://x.org']);
-		linkNotProtectedByRules('http://x.org', ['https://x.org']);
+		linkNotAllowedByRules('https://x.org', ['http://x.org']);
+		linkNotAllowedByRules('http://x.org', ['https://x.org']);
 
-		linkNotProtectedByRules('https://www.x.org', ['https://x.org']);
+		linkNotAllowedByRules('https://www.x.org', ['https://x.org']);
 
-		linkProtectedByRules('https://www.x.org', ['https://www.x.org', 'https://y.org']);
+		linkAllowedByRules('https://www.x.org', ['https://www.x.org', 'https://y.org']);
 	});
 
 	test('localhost', () => {
-		linkProtectedByRules('https://127.0.0.1', []);
-		linkProtectedByRules('https://127.0.0.1:3000', []);
-		linkProtectedByRules('https://localhost', []);
-		linkProtectedByRules('https://localhost:3000', []);
+		linkAllowedByRules('https://127.0.0.1', []);
+		linkAllowedByRules('https://127.0.0.1:3000', []);
+		linkAllowedByRules('https://localhost', []);
+		linkAllowedByRules('https://localhost:3000', []);
 	});
 
 	test('* star', () => {
-		linkProtectedByRules('https://a.x.org', ['https://*.x.org']);
-		linkProtectedByRules('https://a.b.x.org', ['https://*.x.org']);
-		linkProtectedByRules('https://a.x.org', ['https://a.x.*']);
-		linkProtectedByRules('https://a.x.org', ['https://a.*.org']);
-		linkProtectedByRules('https://a.x.org', ['https://*.*.org']);
-		linkProtectedByRules('https://a.b.x.org', ['https://*.b.*.org']);
-		linkProtectedByRules('https://a.a.b.x.org', ['https://*.b.*.org']);
+		linkAllowedByRules('https://a.x.org', ['https://*.x.org']);
+		linkAllowedByRules('https://a.b.x.org', ['https://*.x.org']);
+		linkAllowedByRules('https://a.x.org', ['https://a.x.*']);
+		linkAllowedByRules('https://a.x.org', ['https://a.*.org']);
+		linkAllowedByRules('https://a.x.org', ['https://*.*.org']);
+		linkAllowedByRules('https://a.b.x.org', ['https://*.b.*.org']);
+		linkAllowedByRules('https://a.a.b.x.org', ['https://*.b.*.org']);
 	});
 
 	test('no scheme', () => {
-		linkProtectedByRules('https://a.x.org', ['a.x.org']);
-		linkProtectedByRules('https://a.x.org', ['*.x.org']);
-		linkProtectedByRules('https://a.b.x.org', ['*.x.org']);
-		linkProtectedByRules('https://x.org', ['*.x.org']);
+		linkAllowedByRules('https://a.x.org', ['a.x.org']);
+		linkAllowedByRules('https://a.x.org', ['*.x.org']);
+		linkAllowedByRules('https://a.b.x.org', ['*.x.org']);
+		linkAllowedByRules('https://x.org', ['*.x.org']);
+	});
+
+	test('sub paths', () => {
+		linkAllowedByRules('https://x.org/foo', ['https://x.org/foo']);
+		linkAllowedByRules('https://x.org/foo', ['x.org/foo']);
+		linkAllowedByRules('https://x.org/foo', ['*.org/foo']);
+
+		linkNotAllowedByRules('https://x.org/bar', ['https://x.org/foo']);
+		linkNotAllowedByRules('https://x.org/bar', ['x.org/foo']);
+		linkNotAllowedByRules('https://x.org/bar', ['*.org/foo']);
+
+		linkAllowedByRules('https://x.org/foo/bar', ['https://x.org/foo']);
+		linkNotAllowedByRules('https://x.org/foo2', ['https://x.org/foo']);
+
+		linkNotAllowedByRules('https://www.x.org/foo', ['https://x.org/foo']);
+
+		linkNotAllowedByRules('https://a.x.org/bar', ['https://*.x.org/foo']);
+		linkNotAllowedByRules('https://a.b.x.org/bar', ['https://*.x.org/foo']);
 	});
 });