diff --git a/src/vs/editor/common/cursor/cursorWordOperations.ts b/src/vs/editor/common/cursor/cursorWordOperations.ts
index b16172cc89a..a43538215b2 100644
--- a/src/vs/editor/common/cursor/cursorWordOperations.ts
+++ b/src/vs/editor/common/cursor/cursorWordOperations.ts
@@ -208,7 +208,7 @@ export class WordOperations {
 		return 0;
 	}
 
-	public static moveWordLeft(wordSeparators: WordCharacterClassifier, model: ICursorSimpleModel, position: Position, wordNavigationType: WordNavigationType): Position {
+	public static moveWordLeft(wordSeparators: WordCharacterClassifier, model: ICursorSimpleModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
 		let lineNumber = position.lineNumber;
 		let column = position.column;
 
@@ -227,7 +227,8 @@ export class WordOperations {
 
 		if (wordNavigationType === WordNavigationType.WordStartFast) {
 			if (
-				prevWordOnLine
+				!hasMulticursor // avoid having multiple cursors stop at different locations when doing word start
+				&& prevWordOnLine
 				&& prevWordOnLine.wordType === WordType.Separator
 				&& prevWordOnLine.end - prevWordOnLine.start === 1
 				&& prevWordOnLine.nextCharClass === WordCharacterClass.Regular
@@ -830,10 +831,10 @@ export class WordPartOperations extends WordOperations {
 		return candidates[0];
 	}
 
-	public static moveWordPartLeft(wordSeparators: WordCharacterClassifier, model: ICursorSimpleModel, position: Position): Position {
+	public static moveWordPartLeft(wordSeparators: WordCharacterClassifier, model: ICursorSimpleModel, position: Position, hasMulticursor: boolean): Position {
 		const candidates = enforceDefined([
-			WordOperations.moveWordLeft(wordSeparators, model, position, WordNavigationType.WordStart),
-			WordOperations.moveWordLeft(wordSeparators, model, position, WordNavigationType.WordEnd),
+			WordOperations.moveWordLeft(wordSeparators, model, position, WordNavigationType.WordStart, hasMulticursor),
+			WordOperations.moveWordLeft(wordSeparators, model, position, WordNavigationType.WordEnd, hasMulticursor),
 			WordOperations._moveWordPartLeft(model, position)
 		]);
 		candidates.sort(Position.compare);
diff --git a/src/vs/editor/contrib/wordOperations/browser/wordOperations.ts b/src/vs/editor/contrib/wordOperations/browser/wordOperations.ts
index 388d42021d2..29381ecf63f 100644
--- a/src/vs/editor/contrib/wordOperations/browser/wordOperations.ts
+++ b/src/vs/editor/contrib/wordOperations/browser/wordOperations.ts
@@ -48,10 +48,10 @@ export abstract class MoveWordCommand extends EditorCommand {
 		const wordSeparators = getMapForWordSeparators(editor.getOption(EditorOption.wordSeparators), editor.getOption(EditorOption.wordSegmenterLocales));
 		const model = editor.getModel();
 		const selections = editor.getSelections();
-
+		const hasMulticursor = selections.length > 1;
 		const result = selections.map((sel) => {
 			const inPosition = new Position(sel.positionLineNumber, sel.positionColumn);
-			const outPosition = this._move(wordSeparators, model, inPosition, this._wordNavigationType);
+			const outPosition = this._move(wordSeparators, model, inPosition, this._wordNavigationType, hasMulticursor);
 			return this._moveTo(sel, outPosition, this._inSelectionMode);
 		});
 
@@ -83,17 +83,17 @@ export abstract class MoveWordCommand extends EditorCommand {
 		}
 	}
 
-	protected abstract _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position;
+	protected abstract _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position;
 }
 
 export class WordLeftCommand extends MoveWordCommand {
-	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return WordOperations.moveWordLeft(wordSeparators, model, position, wordNavigationType);
+	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return WordOperations.moveWordLeft(wordSeparators, model, position, wordNavigationType, hasMulticursor);
 	}
 }
 
 export class WordRightCommand extends MoveWordCommand {
-	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
+	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
 		return WordOperations.moveWordRight(wordSeparators, model, position, wordNavigationType);
 	}
 }
@@ -187,8 +187,8 @@ export class CursorWordAccessibilityLeft extends WordLeftCommand {
 		});
 	}
 
-	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType);
+	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType, hasMulticursor);
 	}
 }
 
@@ -202,8 +202,8 @@ export class CursorWordAccessibilityLeftSelect extends WordLeftCommand {
 		});
 	}
 
-	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType);
+	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType, hasMulticursor);
 	}
 }
 
@@ -295,8 +295,8 @@ export class CursorWordAccessibilityRight extends WordRightCommand {
 		});
 	}
 
-	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType);
+	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType, hasMulticursor);
 	}
 }
 
@@ -310,8 +310,8 @@ export class CursorWordAccessibilityRightSelect extends WordRightCommand {
 		});
 	}
 
-	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType);
+	protected override _move(wordCharacterClassifier: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return super._move(getMapForWordSeparators(EditorOptions.wordSeparators.defaultValue, wordCharacterClassifier.intlSegmenterLocales), model, position, wordNavigationType, hasMulticursor);
 	}
 }
 
diff --git a/src/vs/editor/contrib/wordOperations/test/browser/wordOperations.test.ts b/src/vs/editor/contrib/wordOperations/test/browser/wordOperations.test.ts
index e65c88eeae3..51cdccc4fd3 100644
--- a/src/vs/editor/contrib/wordOperations/test/browser/wordOperations.test.ts
+++ b/src/vs/editor/contrib/wordOperations/test/browser/wordOperations.test.ts
@@ -217,6 +217,40 @@ suite('WordOperations', () => {
 		assert.deepStrictEqual(actual, EXPECTED);
 	});
 
+	test('cursorWordLeft - issue #169904: cursors out of sync', () => {
+		const text = [
+			'.grid1 {',
+			'  display: grid;',
+			'  grid-template-columns:',
+			'    [full-start] minmax(1em, 1fr)',
+			'    [main-start] minmax(0, 40em) [main-end]',
+			'    minmax(1em, 1fr) [full-end];',
+			'}',
+			'.grid2 {',
+			'  display: grid;',
+			'  grid-template-columns:',
+			'    [full-start] minmax(1em, 1fr)',
+			'    [main-start] minmax(0, 40em) [main-end] minmax(1em, 1fr) [full-end];',
+			'}',
+		];
+		withTestCodeEditor(text, {}, (editor) => {
+			editor.setSelections([
+				new Selection(5, 44, 5, 44),
+				new Selection(6, 32, 6, 32),
+				new Selection(12, 44, 12, 44),
+				new Selection(12, 72, 12, 72),
+			]);
+			cursorWordLeft(editor, false);
+			assert.deepStrictEqual(editor.getSelections(), [
+				new Selection(5, 43, 5, 43),
+				new Selection(6, 31, 6, 31),
+				new Selection(12, 43, 12, 43),
+				new Selection(12, 71, 12, 71),
+			]);
+
+		});
+	});
+
 	test('cursorWordLeftSelect - issue #74369: cursorWordLeft and cursorWordLeftSelect do not behave consistently', () => {
 		const EXPECTED = [
 			'|this.|is.|a.|test',
diff --git a/src/vs/editor/contrib/wordPartOperations/browser/wordPartOperations.ts b/src/vs/editor/contrib/wordPartOperations/browser/wordPartOperations.ts
index ebcabc415a4..5ed4d310941 100644
--- a/src/vs/editor/contrib/wordPartOperations/browser/wordPartOperations.ts
+++ b/src/vs/editor/contrib/wordPartOperations/browser/wordPartOperations.ts
@@ -68,8 +68,8 @@ export class DeleteWordPartRight extends DeleteWordCommand {
 }
 
 export class WordPartLeftCommand extends MoveWordCommand {
-	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
-		return WordPartOperations.moveWordPartLeft(wordSeparators, model, position);
+	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
+		return WordPartOperations.moveWordPartLeft(wordSeparators, model, position, hasMulticursor);
 	}
 }
 export class CursorWordPartLeft extends WordPartLeftCommand {
@@ -111,7 +111,7 @@ export class CursorWordPartLeftSelect extends WordPartLeftCommand {
 CommandsRegistry.registerCommandAlias('cursorWordPartStartLeftSelect', 'cursorWordPartLeftSelect');
 
 export class WordPartRightCommand extends MoveWordCommand {
-	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType): Position {
+	protected _move(wordSeparators: WordCharacterClassifier, model: ITextModel, position: Position, wordNavigationType: WordNavigationType, hasMulticursor: boolean): Position {
 		return WordPartOperations.moveWordPartRight(wordSeparators, model, position);
 	}
 }