diff --git a/src/vs/code/electron-browser/issue/issueReporterMain.ts b/src/vs/code/electron-browser/issue/issueReporterMain.ts
index 83392e33bd6..c0539a469d7 100644
--- a/src/vs/code/electron-browser/issue/issueReporterMain.ts
+++ b/src/vs/code/electron-browser/issue/issueReporterMain.ts
@@ -40,6 +40,7 @@ import { createSpdLogService } from 'vs/platform/log/node/spdlogService';
 import { LogLevelSetterChannelClient, FollowerLogService } from 'vs/platform/log/common/logIpc';
 import { ILogService, getLogLevel } from 'vs/platform/log/common/log';
 import { OcticonLabel } from 'vs/base/browser/ui/octiconLabel/octiconLabel';
+import { normalizeGitHubIssuesUrl } from 'vs/code/electron-browser/issue/issueReporterUtil';
 
 const MAX_URL_LENGTH = platform.isWindows ? 2081 : 5400;
 
@@ -440,6 +441,11 @@ export class IssueReporter extends Disposable {
 		return selectedExtension && selectedExtension.manifest && selectedExtension.manifest.repository && selectedExtension.manifest.repository.url;
 	}
 
+	private getExtensionBugsUrl(): string {
+		const selectedExtension = this.issueReporterModel.getData().selectedExtension;
+		return selectedExtension && selectedExtension.manifest && selectedExtension.manifest.bugs && selectedExtension.manifest.bugs.url;
+	}
+
 	private searchVSCodeIssues(title: string, issueDescription: string): void {
 		if (title || issueDescription) {
 			this.searchDuplicates(title, issueDescription);
@@ -746,10 +752,13 @@ export class IssueReporter extends Disposable {
 	private getIssueUrlWithTitle(issueTitle: string): string {
 		let repositoryUrl = product.reportIssueUrl;
 		if (this.issueReporterModel.getData().fileOnExtension) {
+			const bugsUrl = this.getExtensionBugsUrl();
 			const extensionUrl = this.getExtensionRepositoryUrl();
-			if (extensionUrl) {
-				// Remove '.git' suffix
-				repositoryUrl = `${extensionUrl.indexOf('.git') !== -1 ? extensionUrl.substr(0, extensionUrl.length - 4) : extensionUrl}/issues/new/`;
+			// If given, try to match the extension's bug url
+			if (bugsUrl && bugsUrl.match(/^https?:\/\/github\.com\/(.*)/)) {
+				repositoryUrl = normalizeGitHubIssuesUrl(bugsUrl);
+			} else if (extensionUrl && extensionUrl.match(/^https?:\/\/github\.com\/(.*)/)) {
+				repositoryUrl = normalizeGitHubIssuesUrl(extensionUrl);
 			}
 		}
 
diff --git a/src/vs/code/electron-browser/issue/issueReporterUtil.ts b/src/vs/code/electron-browser/issue/issueReporterUtil.ts
new file mode 100644
index 00000000000..2212eaf002c
--- /dev/null
+++ b/src/vs/code/electron-browser/issue/issueReporterUtil.ts
@@ -0,0 +1,30 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+'use strict';
+
+import { endsWith, rtrim } from 'vs/base/common/strings';
+
+export function normalizeGitHubIssuesUrl(url: string): string {
+	// If the url has a .git suffix, remove it
+	if (endsWith(url, '.git')) {
+		url = url.substr(0, url.length - 4);
+	}
+
+	// Remove trailing slash
+	url = rtrim(url, '/');
+
+	// If the url already ends with issues/new, it's beautiful, return it
+	if (endsWith(url, 'issues/new')) {
+		return url;
+	}
+
+	// Add new segment if it does not exist
+	if (endsWith(url, 'issues')) {
+		return url + '/new';
+	}
+
+	return url + '/issues/new';
+}
\ No newline at end of file
diff --git a/src/vs/code/electron-browser/issue/test/testReporterModel.test.ts b/src/vs/code/electron-browser/issue/test/testReporterModel.test.ts
index 24cc0c7731e..34c7c07e8a5 100644
--- a/src/vs/code/electron-browser/issue/test/testReporterModel.test.ts
+++ b/src/vs/code/electron-browser/issue/test/testReporterModel.test.ts
@@ -7,6 +7,7 @@
 
 import * as assert from 'assert';
 import { IssueReporterModel } from 'vs/code/electron-browser/issue/issueReporterModel';
+import { normalizeGitHubIssuesUrl } from 'vs/code/electron-browser/issue/issueReporterUtil';
 
 suite('IssueReporter', () => {
 
@@ -36,4 +37,18 @@ OS version: undefined
 
 <!-- generated by issue reporter -->`);
 	});
+
+	test('should normalize GitHub urls', () => {
+		[
+			'https://github.com/repo',
+			'https://github.com/repo/',
+			'https://github.com/repo.git',
+			'https://github.com/repo/issues',
+			'https://github.com/repo/issues/',
+			'https://github.com/repo/issues/new',
+			'https://github.com/repo/issues/new/'
+		].forEach(url => {
+			assert.equal('https://github.com/repo/issues/new', normalizeGitHubIssuesUrl(url));
+		});
+	});
 });
diff --git a/src/vs/platform/extensionManagement/common/extensionManagement.ts b/src/vs/platform/extensionManagement/common/extensionManagement.ts
index 82d0cc35551..973f0262d75 100644
--- a/src/vs/platform/extensionManagement/common/extensionManagement.ts
+++ b/src/vs/platform/extensionManagement/common/extensionManagement.ts
@@ -120,6 +120,9 @@ export interface IExtensionManifest {
 	repository?: {
 		url: string;
 	};
+	bugs?: {
+		url: string;
+	};
 }
 
 export interface IGalleryExtensionProperties {