diff --git a/src/utils/PhutilProseDiff.php b/src/utils/PhutilProseDiff.php
--- a/src/utils/PhutilProseDiff.php
+++ b/src/utils/PhutilProseDiff.php
@@ -164,6 +164,12 @@
       '!' => true,
       ',' => true,
       '?' => true,
+      ']' => true,
+      '[' => true,
+      '(' => true,
+      ')' => true,
+      '<' => true,
+      '>' => true,
     );
 
     $o_text = $o_merge['text'];
diff --git a/src/utils/__tests__/PhutilProseDiffTestCase.php b/src/utils/__tests__/PhutilProseDiffTestCase.php
--- a/src/utils/__tests__/PhutilProseDiffTestCase.php
+++ b/src/utils/__tests__/PhutilProseDiffTestCase.php
@@ -152,6 +152,27 @@
       ),
       pht('Diff with a removed comma and new trailing content.'));
 
+    $this->assertProseParts(
+      '[ ] Walnuts',
+      '[X] Walnuts',
+      array(
+        '= [',
+        '-  ',
+        '+ X',
+        '= ] Walnuts',
+      ),
+      pht('Diff adding a tickmark to a checkbox list.'));
+
+    $this->assertProseParts(
+      '[[ ./week49 ]]',
+      '[[ ./week50 ]]',
+      array(
+        '= [[ ./week',
+        '- 49',
+        '+ 50',
+        '=  ]]',
+      ),
+      pht('Diff changing a remarkup wiki link target.'));
   }
 
   private function assertProseParts($old, $new, array $expect_parts, $label) {