diff --git a/packages/editor/CodeMirror/markdown/markdownCommands.toggleList.test.ts b/packages/editor/CodeMirror/markdown/markdownCommands.toggleList.test.ts
index c96bcfd59..a8e57bd90 100644
--- a/packages/editor/CodeMirror/markdown/markdownCommands.toggleList.test.ts
+++ b/packages/editor/CodeMirror/markdown/markdownCommands.toggleList.test.ts
@@ -232,4 +232,19 @@ describe('markdownCommands.toggleList', () => {
 		);
 		expect(editor.state.selection.main.from).toBe(preSubListText.length);
 	});
+
+	it('should not treat a list of IP addresses as a numbered list', async () => {
+		const initialDocText = '192.168.1.1. This\n127.0.0.1. is\n0.0.0.0. a list';
+
+		const editor = await createTestEditor(
+			initialDocText,
+			EditorSelection.range(0, initialDocText.length),
+			[],
+		);
+
+		toggleList(ListType.UnorderedList)(editor);
+		expect(editor.state.doc.toString()).toBe(
+			'- 192.168.1.1. This\n- 127.0.0.1. is\n- 0.0.0.0. a list',
+		);
+	});
 });
diff --git a/packages/editor/CodeMirror/markdown/markdownCommands.ts b/packages/editor/CodeMirror/markdown/markdownCommands.ts
index 490a8faf1..a230d50c3 100644
--- a/packages/editor/CodeMirror/markdown/markdownCommands.ts
+++ b/packages/editor/CodeMirror/markdown/markdownCommands.ts
@@ -132,9 +132,9 @@ export const toggleList = (listType: ListType): Command => {
 		// RegExps for different list types. The regular expressions MUST
 		// be mutually exclusive.
 		// `(?!\[[ xX]+\])` means "not followed by [x] or [ ]".
-		const bulletedRegex = /^\s*([-*])\s(?!\[[ xX]+\])/;
-		const checklistRegex = /^\s*[-*]\s\[[ xX]+\]\s?/;
-		const numberedRegex = /^\s*\d+\.\s?/;
+		const bulletedRegex = /^\s*([-*])\s(?!\[[ xX]+\]\s)/;
+		const checklistRegex = /^\s*[-*]\s\[[ xX]+\]\s/;
+		const numberedRegex = /^\s*\d+\.\s/;
 
 		const listRegexes: Record<ListType, RegExp> = {
 			[ListType.OrderedList]: numberedRegex,