diff --git a/src/infrastructure/diff/prose/PhutilProseDifferenceEngine.php b/src/infrastructure/diff/prose/PhutilProseDifferenceEngine.php
--- a/src/infrastructure/diff/prose/PhutilProseDifferenceEngine.php
+++ b/src/infrastructure/diff/prose/PhutilProseDifferenceEngine.php
@@ -142,22 +142,9 @@
       }
 
       if ($level < 2) {
-        // Split pieces into separate text and whitespace sections: make one
-        // piece out of all the whitespace at the beginning, one piece out of
-        // all the actual text in the middle, and one piece out of all the
-        // whitespace at the end.
-
-        $matches = null;
-        preg_match('/^(\s*)(.*?)(\s*)\z/s', $result, $matches);
-
-        if (strlen($matches[1])) {
-          $results[] = $matches[1];
-        }
-        if (strlen($matches[2])) {
-          $results[] = $matches[2];
-        }
-        if (strlen($matches[3])) {
-          $results[] = $matches[3];
+        $trimmed_pieces = $this->trimApart($result);
+        foreach ($trimmed_pieces as $trimmed_piece) {
+          $results[] = $trimmed_piece;
         }
       } else {
         $results[] = $result;
@@ -272,4 +259,36 @@
     return $blocks;
   }
 
+  public static function trimApart($input) {
+    // Split pieces into separate text and whitespace sections: make one
+    // piece out of all the whitespace at the beginning, one piece out of
+    // all the actual text in the middle, and one piece out of all the
+    // whitespace at the end.
+
+    $parts = array();
+
+    $length = strlen($input);
+
+    $corpus = ltrim($input);
+    $l_length = strlen($corpus);
+    if ($l_length !== $length) {
+      $parts[] = substr($input, 0, $length - $l_length);
+    }
+
+    $corpus = rtrim($corpus);
+    $lr_length = strlen($corpus);
+
+    if ($lr_length) {
+      $parts[] = $corpus;
+    }
+
+    if ($lr_length !== $l_length) {
+      // NOTE: This will be a negative value; we're slicing from the end of
+      // the input string.
+      $parts[] = substr($input, $lr_length - $l_length);
+    }
+
+    return $parts;
+  }
+
 }
diff --git a/src/infrastructure/diff/prose/__tests__/PhutilProseDiffTestCase.php b/src/infrastructure/diff/prose/__tests__/PhutilProseDiffTestCase.php
--- a/src/infrastructure/diff/prose/__tests__/PhutilProseDiffTestCase.php
+++ b/src/infrastructure/diff/prose/__tests__/PhutilProseDiffTestCase.php
@@ -3,6 +3,39 @@
 final class PhutilProseDiffTestCase
   extends PhabricatorTestCase {
 
+  public function testTrimApart() {
+    $map = array(
+      '' => array(),
+      'a' => array('a'),
+      ' a ' => array(
+        ' ',
+        'a',
+        ' ',
+      ),
+      ' a' => array(
+        ' ',
+        'a',
+      ),
+      'a ' => array(
+        'a',
+        ' ',
+      ),
+      ' a b ' => array(
+        ' ',
+        'a b',
+        ' ',
+      ),
+    );
+
+    foreach ($map as $input => $expect) {
+      $actual = PhutilProseDifferenceEngine::trimApart($input);
+      $this->assertEqual(
+        $expect,
+        $actual,
+        pht('Trim Apart: %s', $input));
+    }
+  }
+
   public function testProseDiffsDistance() {
     $this->assertProseParts(
       '',