diff --git a/src/vs/platform/userDataSync/common/keybindingsSync.ts b/src/vs/platform/userDataSync/common/keybindingsSync.ts
index ff3b25fe604eedc8886e48eed0135d3df8fb90d8..cfafec8c3aecc63cbab9d7a007f7192a2e2c67f1 100644
--- a/src/vs/platform/userDataSync/common/keybindingsSync.ts
+++ b/src/vs/platform/userDataSync/common/keybindingsSync.ts
@@ -73,8 +73,9 @@ export class KeybindingsSynchroniser extends AbstractJsonFileSynchroniser implem
 		let hasConflicts: boolean = false;
 
 		if (remoteContent) {
-			const localContent: string = fileContent ? fileContent.value.toString() : '[]';
-			if (!localContent.trim() || this.hasErrors(localContent)) {
+			let localContent: string = fileContent ? fileContent.value.toString() : '[]';
+			localContent = localContent || '[]';
+			if (this.hasErrors(localContent)) {
 				throw new UserDataSyncError(localize('errorInvalidSettings', "Unable to sync keybindings because the content in the file is not valid. Please open the file and correct it."), UserDataSyncErrorCode.LocalInvalidContent, this.resource);
 			}
 
@@ -177,8 +178,12 @@ export class KeybindingsSynchroniser extends AbstractJsonFileSynchroniser implem
 			this.logService.info(`${this.syncResourceLogLabel}: No changes found during synchronizing keybindings.`);
 		}
 
-		if (content !== null && this.hasErrors(content)) {
-			throw new UserDataSyncError(localize('errorInvalidSettings', "Unable to sync keybindings because the content in the file is not valid. Please open the file and correct it."), UserDataSyncErrorCode.LocalInvalidContent, this.resource);
+		if (content !== null) {
+			content = content.trim();
+			content = content || '[]';
+			if (this.hasErrors(content)) {
+				throw new UserDataSyncError(localize('errorInvalidSettings', "Unable to sync keybindings because the content in the file is not valid. Please open the file and correct it."), UserDataSyncErrorCode.LocalInvalidContent, this.resource);
+			}
 		}
 
 		if (localChange !== Change.None) {
diff --git a/src/vs/platform/userDataSync/common/settingsSync.ts b/src/vs/platform/userDataSync/common/settingsSync.ts
index 44e2941b04ca703542d6b8691a9ff42be019c180..cbba5c25c3dc5d7fb553cc9cdc7af8ffc13e81a7 100644
--- a/src/vs/platform/userDataSync/common/settingsSync.ts
+++ b/src/vs/platform/userDataSync/common/settingsSync.ts
@@ -78,7 +78,8 @@ export class SettingsSynchroniser extends AbstractJsonFileSynchroniser implement
 		let hasConflicts: boolean = false;
 
 		if (remoteSettingsSyncContent) {
-			const localContent: string = fileContent ? fileContent.value.toString() : '{}';
+			let localContent: string = fileContent ? fileContent.value.toString().trim() : '{}';
+			localContent = localContent || '{}';
 			this.validateContent(localContent);
 			this.logService.trace(`${this.syncResourceLogLabel}: Merging remote settings with local settings...`);
 			const result = merge(localContent, remoteSettingsSyncContent.settings, lastSettingsSyncContent ? lastSettingsSyncContent.settings : null, ignoredSettings, [], formattingOptions);
@@ -183,7 +184,8 @@ export class SettingsSynchroniser extends AbstractJsonFileSynchroniser implement
 			this.logService.info(`${this.syncResourceLogLabel}: No changes found during synchronizing settings.`);
 		}
 
-		content = content !== null ? content : '{}';
+		content = content ? content.trim() : '{}';
+		content = content || '{}';
 		this.validateContent(content);
 
 		if (localChange !== Change.None) {
diff --git a/src/vs/platform/userDataSync/test/common/keybindingsSync.test.ts b/src/vs/platform/userDataSync/test/common/keybindingsSync.test.ts
index 49d439bfd608b97b67487378232b1a73a56e97f2..02b0154b62769980ec075ee05b9260f5d168bc74 100644
--- a/src/vs/platform/userDataSync/test/common/keybindingsSync.test.ts
+++ b/src/vs/platform/userDataSync/test/common/keybindingsSync.test.ts
@@ -61,6 +61,45 @@ suite('KeybindingsSync', () => {
 		assert.deepEqual(server.requests, []);
 	});
 
+	test('when keybindings file is empty and remote has no changes', async () => {
+		const fileService = client.instantiationService.get(IFileService);
+		const keybindingsResource = client.instantiationService.get(IEnvironmentService).keybindingsResource;
+		await fileService.writeFile(keybindingsResource, VSBuffer.fromString(''));
+
+		await testObject.sync(await client.manifest());
+
+		const lastSyncUserData = await testObject.getLastSyncUserData();
+		const remoteUserData = await testObject.getRemoteUserData(null);
+		assert.equal(testObject.getKeybindingsContentFromSyncContent(lastSyncUserData!.syncData!.content!), '[]');
+		assert.equal(testObject.getKeybindingsContentFromSyncContent(remoteUserData!.syncData!.content!), '[]');
+		assert.equal((await fileService.readFile(keybindingsResource)).value.toString(), '');
+	});
+
+	test('when keybindings file is empty and remote has changes', async () => {
+		const client2 = disposableStore.add(new UserDataSyncClient(server));
+		await client2.setUp(true);
+		const content = JSON.stringify([
+			{
+				'key': 'shift+cmd+w',
+				'command': 'workbench.action.closeAllEditors',
+			}
+		]);
+		await client2.instantiationService.get(IFileService).writeFile(client2.instantiationService.get(IEnvironmentService).keybindingsResource, VSBuffer.fromString(content));
+		await client2.sync();
+
+		const fileService = client.instantiationService.get(IFileService);
+		const keybindingsResource = client.instantiationService.get(IEnvironmentService).keybindingsResource;
+		await fileService.writeFile(keybindingsResource, VSBuffer.fromString(''));
+
+		await testObject.sync(await client.manifest());
+
+		const lastSyncUserData = await testObject.getLastSyncUserData();
+		const remoteUserData = await testObject.getRemoteUserData(null);
+		assert.equal(testObject.getKeybindingsContentFromSyncContent(lastSyncUserData!.syncData!.content!), content);
+		assert.equal(testObject.getKeybindingsContentFromSyncContent(remoteUserData!.syncData!.content!), content);
+		assert.equal((await fileService.readFile(keybindingsResource)).value.toString(), content);
+	});
+
 	test('when keybindings file is created after first sync', async () => {
 		const fileService = client.instantiationService.get(IFileService);
 		const keybindingsResource = client.instantiationService.get(IEnvironmentService).keybindingsResource;
diff --git a/src/vs/platform/userDataSync/test/common/settingsSync.test.ts b/src/vs/platform/userDataSync/test/common/settingsSync.test.ts
index 3121fb533f8cbe16444532d7ddfa4cfc7510d37f..6117c2b55e269a59a4eaa7452011dcd3e8faa257 100644
--- a/src/vs/platform/userDataSync/test/common/settingsSync.test.ts
+++ b/src/vs/platform/userDataSync/test/common/settingsSync.test.ts
@@ -79,6 +79,61 @@ suite('SettingsSync - Auto', () => {
 		assert.deepEqual(server.requests, []);
 	});
 
+	test('when settings file is empty and remote has no changes', async () => {
+		const fileService = client.instantiationService.get(IFileService);
+		const settingsResource = client.instantiationService.get(IEnvironmentService).settingsResource;
+		await fileService.writeFile(settingsResource, VSBuffer.fromString(''));
+
+		await testObject.sync(await client.manifest());
+
+		const lastSyncUserData = await testObject.getLastSyncUserData();
+		const remoteUserData = await testObject.getRemoteUserData(null);
+		assert.equal(testObject.parseSettingsSyncContent(lastSyncUserData!.syncData!.content!)?.settings, '{}');
+		assert.equal(testObject.parseSettingsSyncContent(remoteUserData!.syncData!.content!)?.settings, '{}');
+		assert.equal((await fileService.readFile(settingsResource)).value.toString(), '');
+	});
+
+	test('when settings file is empty and remote has changes', async () => {
+		const client2 = disposableStore.add(new UserDataSyncClient(server));
+		await client2.setUp(true);
+		const content =
+			`{
+	// Always
+	"files.autoSave": "afterDelay",
+	"files.simpleDialog.enable": true,
+
+	// Workbench
+	"workbench.colorTheme": "GitHub Sharp",
+	"workbench.tree.indent": 20,
+	"workbench.colorCustomizations": {
+		"editorLineNumber.activeForeground": "#ff0000",
+		"[GitHub Sharp]": {
+			"statusBarItem.remoteBackground": "#24292E",
+			"editorPane.background": "#f3f1f11a"
+		}
+	},
+
+	"gitBranch.base": "remote-repo/master",
+
+	// Experimental
+	"workbench.view.experimental.allowMovingToNewContainer": true,
+}`;
+		await client2.instantiationService.get(IFileService).writeFile(client2.instantiationService.get(IEnvironmentService).settingsResource, VSBuffer.fromString(content));
+		await client2.sync();
+
+		const fileService = client.instantiationService.get(IFileService);
+		const settingsResource = client.instantiationService.get(IEnvironmentService).settingsResource;
+		await fileService.writeFile(settingsResource, VSBuffer.fromString(''));
+
+		await testObject.sync(await client.manifest());
+
+		const lastSyncUserData = await testObject.getLastSyncUserData();
+		const remoteUserData = await testObject.getRemoteUserData(null);
+		assert.equal(testObject.parseSettingsSyncContent(lastSyncUserData!.syncData!.content!)?.settings, content);
+		assert.equal(testObject.parseSettingsSyncContent(remoteUserData!.syncData!.content!)?.settings, content);
+		assert.equal((await fileService.readFile(settingsResource)).value.toString(), content);
+	});
+
 	test('when settings file is created after first sync', async () => {
 		const fileService = client.instantiationService.get(IFileService);