diff --git a/src/vs/workbench/parts/preferences/browser/keybindingsEditorContribution.ts b/src/vs/workbench/parts/preferences/browser/keybindingsEditorContribution.ts
index e5e9b2392be67798f92e8ce3406e6ba92c7af53d..c5b4851bbd11f93001d70b11f5c7df60531e7051 100644
--- a/src/vs/workbench/parts/preferences/browser/keybindingsEditorContribution.ts
+++ b/src/vs/workbench/parts/preferences/browser/keybindingsEditorContribution.ts
@@ -9,7 +9,7 @@ import * as nls from 'vs/nls';
 import * as dom from 'vs/base/browser/dom';
 import { RunOnceScheduler } from 'vs/base/common/async';
 import { MarkedString } from 'vs/base/common/htmlContent';
-import { KeyCode, KeyMod, KeyChord } from 'vs/base/common/keyCodes';
+import { KeyCode, KeyMod, KeyChord, SimpleKeybinding } from 'vs/base/common/keyCodes';
 import { IDisposable, dispose } from 'vs/base/common/lifecycle';
 import { IKeybindingService } from 'vs/platform/keybinding/common/keybinding';
 import { IInstantiationService } from 'vs/platform/instantiation/common/instantiation';
@@ -24,6 +24,8 @@ import { SnippetController } from 'vs/editor/contrib/snippet/common/snippetContr
 import { SmartSnippetInserter } from 'vs/workbench/parts/preferences/common/smartSnippetInserter';
 import { DefineKeybindingOverlayWidget } from 'vs/workbench/parts/preferences/browser/keybindingWidgets';
 import { parseTree, Node } from 'vs/base/common/json';
+import { KeybindingIO } from 'vs/workbench/services/keybinding/common/keybindingIO';
+import { ScanCodeBinding } from 'vs/workbench/services/keybinding/common/scanCode';
 
 import EditorContextKeys = editorCommon.EditorContextKeys;
 
@@ -200,7 +202,7 @@ export class DefineKeybindingController implements editorCommon.IEditorContribut
 				return this._createDecoration(false, resolvedKeybinding.getLabel(), model, value);
 			}
 			const expectedUserSettingsLabel = resolvedKeybinding.getUserSettingsLabel();
-			if (value.value.trim().toLowerCase() !== expectedUserSettingsLabel.trim().toLowerCase()) {
+			if (!DefineKeybindingController._userSettingsFuzzyEquals(value.value, expectedUserSettingsLabel)) {
 				return this._createDecoration(false, resolvedKeybinding.getLabel(), model, value);
 			}
 			return null;
@@ -208,6 +210,42 @@ export class DefineKeybindingController implements editorCommon.IEditorContribut
 		return null;
 	}
 
+	static _userSettingsFuzzyEquals(a: string, b: string): boolean {
+		a = a.trim().toLowerCase();
+		b = b.trim().toLowerCase();
+
+		if (a === b) {
+			return true;
+		}
+
+		const [parsedA1, parsedA2] = KeybindingIO._readUserBinding(a);
+		const [parsedB1, parsedB2] = KeybindingIO._readUserBinding(b);
+
+		return (
+			this._userBindingEquals(parsedA1, parsedB1)
+			&& this._userBindingEquals(parsedA2, parsedB2)
+		);
+	}
+
+	private static _userBindingEquals(a: SimpleKeybinding | ScanCodeBinding, b: SimpleKeybinding | ScanCodeBinding): boolean {
+		if (a === null && b === null) {
+			return true;
+		}
+		if (!a || !b) {
+			return false;
+		}
+
+		if (a instanceof SimpleKeybinding && b instanceof SimpleKeybinding) {
+			return a.equals(b);
+		}
+
+		if (a instanceof ScanCodeBinding && b instanceof ScanCodeBinding) {
+			return a.equals(b);
+		}
+
+		return false;
+	}
+
 	private _createDecoration(isError: boolean, message: string, model: editorCommon.IModel, keyNode: Node): editorCommon.IModelDeltaDecoration {
 		let msg: MarkedString[];
 		let className: string;
diff --git a/src/vs/workbench/parts/preferences/test/browser/keybindingsEditorContribution.test.ts b/src/vs/workbench/parts/preferences/test/browser/keybindingsEditorContribution.test.ts
new file mode 100644
index 0000000000000000000000000000000000000000..fe187cbe3ff619c45188da478a04c0382352fac5
--- /dev/null
+++ b/src/vs/workbench/parts/preferences/test/browser/keybindingsEditorContribution.test.ts
@@ -0,0 +1,42 @@
+/*---------------------------------------------------------------------------------------------
+ *  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 * as assert from 'assert';
+import { DefineKeybindingController } from 'vs/workbench/parts/preferences/browser/keybindingsEditorContribution';
+
+suite('KeybindingsEditorContribution', () => {
+
+	function assertUserSettingsFuzzyEquals(a: string, b: string, expected: boolean): void {
+		const actual = DefineKeybindingController._userSettingsFuzzyEquals(a, b);
+		const message = expected ? `${a} == ${b}` : `${a} != ${b}`;
+		assert.equal(actual, expected, 'fuzzy: ' + message);
+	}
+
+	function assertEqual(a: string, b: string): void {
+		assertUserSettingsFuzzyEquals(a, b, true);
+	}
+
+	function assertDifferent(a: string, b: string): void {
+		assertUserSettingsFuzzyEquals(a, b, false);
+	}
+
+	test('_userSettingsFuzzyEquals', () => {
+		assertEqual('a', 'a');
+		assertEqual('a', 'A');
+		assertEqual('ctrl+a', 'CTRL+A');
+		assertEqual('ctrl+a', ' CTRL+A ');
+
+		assertEqual('ctrl+shift+a', 'shift+ctrl+a');
+		assertEqual('ctrl+shift+a ctrl+alt+b', 'shift+ctrl+a alt+ctrl+b');
+
+		assertDifferent('ctrl+[KeyA]', 'ctrl+a');
+
+		// issue #23335
+		assertEqual('cmd+shift+p', 'shift+cmd+p');
+		assertEqual('cmd+shift+p', 'shift-cmd-p');
+	});
+});
diff --git a/src/vs/workbench/services/keybinding/common/scanCode.ts b/src/vs/workbench/services/keybinding/common/scanCode.ts
index 52c84c82f15627e1c5a7a7ea3305401b149d5b2d..bc4545febce198dfef9806a1319f626b8422b73d 100644
--- a/src/vs/workbench/services/keybinding/common/scanCode.ts
+++ b/src/vs/workbench/services/keybinding/common/scanCode.ts
@@ -239,6 +239,16 @@ export class ScanCodeBinding {
 		this.scanCode = scanCode;
 	}
 
+	public equals(other: ScanCodeBinding): boolean {
+		return (
+			this.ctrlKey === other.ctrlKey
+			&& this.shiftKey === other.shiftKey
+			&& this.altKey === other.altKey
+			&& this.metaKey === other.metaKey
+			&& this.scanCode === other.scanCode
+		);
+	}
+
 	/**
 	 * Does this keybinding refer to the key code of a modifier and it also has the modifier flag?
 	 */