diff --git a/extensions/git/package.json b/extensions/git/package.json
index 56055194944..cddee92cf55 100644
--- a/extensions/git/package.json
+++ b/extensions/git/package.json
@@ -1662,10 +1662,27 @@
           "scope": "resource"
         },
         "git.checkoutType": {
-          "type": "string",
-
+          "type": "array",
+          "items": {
+            "type": "string",
+            "enum": [
+              "local",
+              "tags",
+              "remote"
+            ],
+            "enumDescriptions": [
+              "%config.checkoutType.local%",
+              "%config.checkoutType.tags%",
+              "%config.checkoutType.remote%"
+            ]
+          },
+          "uniqueItems": true,
           "markdownDescription": "%config.checkoutType%",
-          "default": "local,remote,tags"
+          "default": [
+            "local",
+            "remote",
+            "tags"
+          ]
         },
         "git.ignoreLegacyWarning": {
           "type": "boolean",
diff --git a/extensions/git/package.nls.json b/extensions/git/package.nls.json
index bc09de34c05..1f37952eeaa 100644
--- a/extensions/git/package.nls.json
+++ b/extensions/git/package.nls.json
@@ -101,7 +101,10 @@
 	"config.countBadge.all": "Count all changes.",
 	"config.countBadge.tracked": "Count only tracked changes.",
 	"config.countBadge.off": "Turn off counter.",
-	"config.checkoutType": "Controls what type of branches (local, remote or tags, split with ',') are listed when running `Checkout to...`.",
+	"config.checkoutType": "Controls what type of git refs are listed when running `Checkout to...`.",
+	"config.checkoutType.local": "Local branches",
+	"config.checkoutType.tags": "Tags",
+	"config.checkoutType.remote": "Remote branches",
 	"config.branchValidationRegex": "A regular expression to validate new branch names.",
 	"config.branchWhitespaceChar": "The character to replace whitespace in new branch names.",
 	"config.ignoreLegacyWarning": "Ignores the legacy Git warning.",
diff --git a/extensions/git/src/commands.ts b/extensions/git/src/commands.ts
index 1be44336f2d..90d5d6401c0 100644
--- a/extensions/git/src/commands.ts
+++ b/extensions/git/src/commands.ts
@@ -70,11 +70,6 @@ class CheckoutRemoteHeadItem extends CheckoutItem {
 	}
 }
 
-interface RefTypeAndCheckoutItem {
-	refType: RefType;
-	checkoutItemCtor: { new(ref: Ref): CheckoutItem; };
-}
-
 class BranchDeleteItem implements QuickPickItem {
 
 	private get shortCommit(): string { return (this.ref.commit || '').substr(0, 8); }
@@ -212,37 +207,53 @@ async function categorizeResourceByResolution(resources: Resource[]): Promise<{
 
 function createCheckoutItems(repository: Repository): CheckoutItem[] {
 	const config = workspace.getConfiguration('git');
-	const checkoutTypeString = config.get<string>('checkoutType');
+	const checkoutTypeConfig = config.get<string | string[]>('checkoutType');
+	let checkoutTypes: string[];
 
-	const checkoutTypeOptions = ['local', 'remote', 'tags'];
-	const checkoutTypes = checkoutTypeString?.trim().split(',').map(type => type.trim()).filter(type => checkoutTypeOptions.includes(type));
+	if (checkoutTypeConfig === 'all' || !checkoutTypeConfig || checkoutTypeConfig.length === 0) {
+		checkoutTypes = ['local', 'remote', 'tags'];
+	} else if (typeof checkoutTypeConfig === 'string') {
+		checkoutTypes = [checkoutTypeConfig];
+	} else {
+		checkoutTypes = checkoutTypeConfig;
+	}
 
-	const results: CheckoutItem[] = [];
-	const seens = new Set<string>();
-	(checkoutTypes && checkoutTypes.length ? checkoutTypes : checkoutTypeOptions).forEach(type => {
-		if (seens.has(type)) {
-			return;
+	const processors = checkoutTypes.map(getCheckoutProcessor)
+		.filter(p => !!p) as CheckoutProcessor[];
+
+	for (const ref of repository.refs) {
+		for (const processor of processors) {
+			processor.onRef(ref);
 		}
-		seens.add(type);
+	}
 
-		const { refType, checkoutItemCtor } = getRefTypeAndCheckoutItem(type);
-		results.push(...repository.refs.filter(ref => ref.type === refType).map(ref => new checkoutItemCtor(ref)));
-	});
-
-	return results;
+	return processors.reduce<CheckoutItem[]>((r, p) => r.concat(...p.items), []);
 }
 
-function getRefTypeAndCheckoutItem(type: string): RefTypeAndCheckoutItem {
+class CheckoutProcessor {
+
+	private refs: Ref[] = [];
+	get items(): CheckoutItem[] { return this.refs.map(r => new this.ctor(r)); }
+	constructor(private type: RefType, private ctor: { new(ref: Ref): CheckoutItem }) { }
+
+	onRef(ref: Ref): void {
+		if (ref.type === this.type) {
+			this.refs.push(ref);
+		}
+	}
+}
+
+function getCheckoutProcessor(type: string): CheckoutProcessor | undefined {
 	switch (type) {
 		case 'local':
-			return { refType: RefType.Head, checkoutItemCtor: CheckoutItem };
+			return new CheckoutProcessor(RefType.Head, CheckoutItem);
 		case 'remote':
-			return { refType: RefType.RemoteHead, checkoutItemCtor: CheckoutRemoteHeadItem };
+			return new CheckoutProcessor(RefType.RemoteHead, CheckoutRemoteHeadItem);
 		case 'tags':
-			return { refType: RefType.Tag, checkoutItemCtor: CheckoutTagItem };
-		default:
-			throw new Error(`Unexpected type: ${type}`);
+			return new CheckoutProcessor(RefType.Tag, CheckoutTagItem);
 	}
+
+	return undefined;
 }
 
 function sanitizeRemoteName(name: string) {