diff --git a/extensions/git/src/api/git.d.ts b/extensions/git/src/api/git.d.ts
index ae8eb5315bc..14eeff9942c 100644
--- a/extensions/git/src/api/git.d.ts
+++ b/extensions/git/src/api/git.d.ts
@@ -26,6 +26,11 @@ export interface Ref {
 	readonly remote?: string;
 }
 
+export interface TrackingShip {
+	readonly local: string;
+	readonly upstream: string;
+}
+
 export interface UpstreamRef {
 	readonly remote: string;
 	readonly name: string;
@@ -235,4 +240,4 @@ export const enum GitErrorCodes {
 	CantRebaseMultipleBranches = 'CantRebaseMultipleBranches',
 	PatchDoesNotApply = 'PatchDoesNotApply',
 	NoPathFound = 'NoPathFound'
-}
\ No newline at end of file
+}
diff --git a/extensions/git/src/commands.ts b/extensions/git/src/commands.ts
index f6e00e9abdd..a87b7dddfe2 100755
--- a/extensions/git/src/commands.ts
+++ b/extensions/git/src/commands.ts
@@ -52,11 +52,20 @@ class CheckoutRemoteHeadItem extends CheckoutItem {
 	}
 
 	async run(repository: Repository): Promise<void> {
-		if (!this.ref.name) {
+		const ref = this.ref.name;
+		if (!ref) {
 			return;
 		}
 
-		await repository.checkoutTracking(this.ref.name);
+		// Check whether there's a local branch which already has the target branch as an upstream
+		const trackings = await repository.getTracking(ref);
+		if (trackings.length > 0) {
+			//Just checkout the local branch
+			await repository.checkout(trackings[0].local);
+		} else {
+			// Default: checkout a new local branch tracking the upstream
+			await repository.checkoutTracking(ref);
+		}
 	}
 }
 
diff --git a/extensions/git/src/git.ts b/extensions/git/src/git.ts
index 896942d2d3f..ef1d0e8c70f 100644
--- a/extensions/git/src/git.ts
+++ b/extensions/git/src/git.ts
@@ -14,7 +14,7 @@ import * as filetype from 'file-type';
 import { assign, groupBy, denodeify, IDisposable, toDisposable, dispose, mkdirp, readBytes, detectUnicodeEncoding, Encoding, onceEvent } from './util';
 import { CancellationToken, Uri, workspace } from 'vscode';
 import { detectEncoding } from './encoding';
-import { Ref, RefType, Branch, Remote, GitErrorCodes, LogOptions, Change, Status } from './api/git';
+import { Ref, RefType, Branch, Remote, GitErrorCodes, LogOptions, Change, Status, TrackingShip } from './api/git';
 
 const readfile = denodeify<string, string | null, string>(fs.readFile);
 
@@ -1578,6 +1578,21 @@ export class Repository {
 		}
 	}
 
+	async GetTracking(upstreamBranch: string): Promise<TrackingShip[]> {
+		const result = await this.run(['for-each-ref', '--format', '%(if)%(upstream:short)%(then)%(refname:short)->%(upstream:short) %(else)*  %(end)', 'refs/heads']);
+		return result.stdout.trim().split('\n')
+			.map(line => line.trim())
+			.filter(line => line !== '*')
+			.map(line => {
+				const splited = line.split('->');
+				return {
+					local: splited[0],
+					upstream: splited[1]
+				} as TrackingShip;
+			})
+			.filter(trackingShip => trackingShip.upstream === upstreamBranch);
+	}
+
 	async getRefs(): Promise<Ref[]> {
 		const result = await this.run(['for-each-ref', '--format', '%(refname) %(objectname)', '--sort', '-committerdate']);
 
diff --git a/extensions/git/src/repository.ts b/extensions/git/src/repository.ts
index 803c4881fa5..a085336e653 100644
--- a/extensions/git/src/repository.ts
+++ b/extensions/git/src/repository.ts
@@ -13,7 +13,7 @@ import * as path from 'path';
 import * as nls from 'vscode-nls';
 import * as fs from 'fs';
 import { StatusBarCommands } from './statusbar';
-import { Branch, Ref, Remote, RefType, GitErrorCodes, Status, LogOptions, Change } from './api/git';
+import { Branch, Ref, Remote, RefType, GitErrorCodes, Status, LogOptions, Change, TrackingShip } from './api/git';
 
 const timeout = (millis: number) => new Promise(c => setTimeout(c, millis));
 
@@ -299,6 +299,7 @@ export const enum Operation {
 	GetObjectDetails = 'GetObjectDetails',
 	SubmoduleUpdate = 'SubmoduleUpdate',
 	RebaseContinue = 'RebaseContinue',
+	GetTracking = 'GetTracking',
 	Apply = 'Apply',
 	Blame = 'Blame',
 	Log = 'Log',
@@ -909,6 +910,10 @@ export class Repository implements Disposable {
 		await this.run(Operation.CheckoutTracking, () => this.repository.checkout(treeish, [], { track: true }));
 	}
 
+	async getTracking(treeish: string): Promise<TrackingShip[]> {
+		return await this.run(Operation.GetTracking, () => this.repository.GetTracking(treeish));
+	}
+
 	async getCommit(ref: string): Promise<Commit> {
 		return await this.repository.getCommit(ref);
 	}