diff --git a/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.test.ts b/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.test.ts
index 037a4906ab0..70a4c9d02f7 100644
--- a/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.test.ts
+++ b/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.test.ts
@@ -2,19 +2,76 @@ import { modifyListLines } from './useCursorUtils';
 
 describe('useCursorUtils', () => {
 
-	const listWithDashes = `- item1
-- item2
-- item3`;
+	const listWithDashes = [
+		'- item1',
+		'- item2',
+		'- item3',
+	];
 
-	const listNoDashes = `item1
-item2
-item3`;
+	const listWithNoPrefixes = [
+		'item1',
+		'item2',
+		'item3',
+	];
 
-	test('should remove "- " from beggining of each line of input string', () => {
-		expect(JSON.stringify(modifyListLines(listWithDashes.split('\n'), 0, '- '))).toBe(JSON.stringify(listNoDashes.split('\n')));
+	const listWithNumbers = [
+		'1. item1',
+		'2. item2',
+		'3. item3',
+	];
+
+	const listWithOnes = [
+		'1. item1',
+		'1. item2',
+		'1. item3',
+	];
+
+	const listWithSomeNumbers = [
+		'1. item1',
+		'item2',
+		'2. item3',
+	];
+
+	const numberedListWithEmptyLines = [
+		'1. item1',
+		'2. item2',
+		'3. ' ,
+		'4. item3',
+	];
+
+	const noPrefixListWithEmptyLines = [
+		'item1',
+		'item2',
+		'' ,
+		'item3',
+	];
+
+	test('should remove "- " from beginning of each line of input string', () => {
+		expect(modifyListLines([...listWithDashes], NaN, '- ')).toStrictEqual(listWithNoPrefixes);
+	});
+
+	test('should add "- " at the beginning of each line of the input string', () => {
+		expect(modifyListLines([...listWithNoPrefixes], NaN, '- ')).toStrictEqual(listWithDashes);
+	});
+
+	test('should remove "n. " at the beginning of each line of the input string', () => {
+		expect(modifyListLines([...listWithNumbers], 4, '1. ')).toStrictEqual(listWithNoPrefixes);
+	});
+
+	test('should add "n. " at the beginning of each line of the input string', () => {
+		expect(modifyListLines([...listWithNoPrefixes], 1, '1. ')).toStrictEqual(listWithNumbers);
+	});
+
+	test('should remove "1. " at the beginning of each line of the input string', () => {
+		expect(modifyListLines([...listWithOnes], 2, '1. ')).toStrictEqual(listWithNoPrefixes);
+	});
+
+	test('should remove "n. " from each line that has it, and ignore' +
+        ' lines which do not', () => {
+		expect(modifyListLines([...listWithSomeNumbers], 2, '2. ')).toStrictEqual(listWithNoPrefixes);
 	});
 
-	test('should add "- " at the beggining of each line of the input string', () => {
-		expect(JSON.stringify(modifyListLines(listNoDashes.split('\n'), 0, '- '))).toBe(JSON.stringify(listWithDashes.split('\n')));
+	test('should add numbers to each line including empty one', () => {
+		expect(modifyListLines(noPrefixListWithEmptyLines, 1, '1. ')).toStrictEqual(numberedListWithEmptyLines);
 	});
 });
diff --git a/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.ts b/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.ts
index ad2c2c8a093..f55636325f4 100644
--- a/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.ts
+++ b/packages/app-desktop/gui/NoteEditor/NoteBody/CodeMirror/utils/useCursorUtils.ts
@@ -1,20 +1,27 @@
 import markdownUtils from '@joplin/lib/markdownUtils';
 import Setting from '@joplin/lib/models/Setting';
-export function modifyListLines(lines: string[],num: number,listSymbol: string) {
+export function modifyListLines(lines: string[], num: number, listSymbol: string) {
+	const isNotNumbered = num === 1;
 	for (let j = 0; j < lines.length; j++) {
 		const line = lines[j];
 		if (!line && j === lines.length - 1) continue;
 		// Only add the list token if it's not already there
 		// if it is, remove it
-		if (!line.startsWith(listSymbol)) {
-			if (num) {
+		if (num) {
+			const lineNum = markdownUtils.olLineNumber(line);
+			if (!lineNum && isNotNumbered) {
 				lines[j] = `${num.toString()}. ${line}`;
 				num++;
 			} else {
-				lines[j] = listSymbol + line;
+				const listToken = markdownUtils.extractListToken(line);
+				lines[j] = line.substr(listToken.length, line.length - listToken.length);
 			}
 		} else {
-			lines[j] = line.substr(listSymbol.length, line.length - listSymbol.length);
+			if (!line.startsWith(listSymbol)) {
+				lines[j] = listSymbol + line;
+			} else {
+				lines[j] = line.substr(listSymbol.length, line.length - listSymbol.length);
+			}
 		}
 	}
 	return lines;