diff --git a/src/wp-includes/formatting.php b/src/wp-includes/formatting.php
index 46922c752a..55321a15c5 100644
--- a/src/wp-includes/formatting.php
+++ b/src/wp-includes/formatting.php
@@ -127,10 +127,10 @@ function wptexturize( $text, $reset = false ) {
 
 		// '99' and '99" are ambiguous among other patterns; assume it's an abbreviated year at the end of a quotation.
 		if ( "'" !== $apos || "'" !== $closing_single_quote ) {
-			$dynamic[ '/\'(\d\d)\'(?=\Z|[.,)}\-\]]|>|' . $spaces . ')/' ] = $apos . '$1' . $closing_single_quote;
+			$dynamic[ '/\'(\d\d)\'(?=\Z|[.,:;!?)}\-\]]|>|' . $spaces . ')/' ] = $apos . '$1' . $closing_single_quote;
 		}
 		if ( "'" !== $apos || '"' !== $closing_quote ) {
-			$dynamic[ '/\'(\d\d)"(?=\Z|[.,)}\-\]]|>|' . $spaces . ')/' ] = $apos . '$1' . $closing_quote;
+			$dynamic[ '/\'(\d\d)"(?=\Z|[.,:;!?)}\-\]]|>|' . $spaces . ')/' ] = $apos . '$1' . $closing_quote;
 		}
 
 		// '99 '99s '99's (apostrophe)  But never '9 or '99% or '999 or '99.0.
@@ -150,7 +150,7 @@ function wptexturize( $text, $reset = false ) {
 
 		// Apostrophe in a word.  No spaces, double apostrophes, or other punctuation.
 		if ( "'" !== $apos ) {
-			$dynamic[ '/(?<!' . $spaces . ')\'(?!\Z|[.,:;"\'(){}[\]\-]|&[lg]t;|' . $spaces . ')/' ] = $apos;
+			$dynamic[ '/(?<!' . $spaces . ')\'(?!\Z|[.,:;!?"\'(){}[\]\-]|&[lg]t;|' . $spaces . ')/' ] = $apos;
 		}
 
 		// 9' (prime)
@@ -160,7 +160,7 @@ function wptexturize( $text, $reset = false ) {
 
 		// Single quotes followed by spaces or ending punctuation.
 		if ( "'" !== $closing_single_quote ) {
-			$dynamic[ '/\'(?=\Z|[.,)}\-\]]|&gt;|' . $spaces . ')/' ] = $closing_single_quote;
+			$dynamic[ '/\'(?=\Z|[.,:;!?)}\-\]]|&gt;|' . $spaces . ')/' ] = $closing_single_quote;
 		}
 
 		$dynamic_characters['apos'] = array_keys( $dynamic );
diff --git a/tests/phpunit/tests/formatting/WPTexturize.php b/tests/phpunit/tests/formatting/WPTexturize.php
index dea7684edf..326a91e52c 100644
--- a/tests/phpunit/tests/formatting/WPTexturize.php
+++ b/tests/phpunit/tests/formatting/WPTexturize.php
@@ -112,12 +112,25 @@ class Tests_Formatting_WPTexturize extends WP_UnitTestCase {
 		$this->assertEquals('Class of &#8217;99', wptexturize("Class of '99"));
 		$this->assertEquals('Class of &#8217;99&#8217;s', wptexturize("Class of '99's"));
 		$this->assertEquals('&#8216;Class of &#8217;99&#8217;', wptexturize("'Class of '99'"));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217; ', wptexturize("'Class of '99' "));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;.', wptexturize("'Class of '99'."));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;, she said', wptexturize("'Class of '99', she said"));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;:', wptexturize("'Class of '99':"));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;;', wptexturize("'Class of '99';"));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;!', wptexturize("'Class of '99'!"));
+		$this->assertEquals('&#8216;Class of &#8217;99&#8217;?', wptexturize("'Class of '99'?"));
 		$this->assertEquals('&#8216;Class of &#8217;99&#8217;s&#8217;', wptexturize("'Class of '99's'"));
 		$this->assertEquals('&#8216;Class of &#8217;99&#8217;s&#8217;', wptexturize("'Class of '99&#8217;s'"));
 		//$this->assertEquals('&#8220;Class of 99&#8221;', wptexturize("\"Class of 99\""));
 		$this->assertEquals('&#8220;Class of &#8217;99&#8221;', wptexturize("\"Class of '99\""));
 		$this->assertEquals('{&#8220;Class of &#8217;99&#8221;}', wptexturize("{\"Class of '99\"}"));
 		$this->assertEquals(' &#8220;Class of &#8217;99&#8221; ', wptexturize(" \"Class of '99\" "));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;.', wptexturize(" \"Class of '99\"."));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;, she said', wptexturize(" \"Class of '99\", she said"));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;:', wptexturize(" \"Class of '99\":"));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;;', wptexturize(" \"Class of '99\";"));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;!', wptexturize(" \"Class of '99\"!"));
+		$this->assertEquals(' &#8220;Class of &#8217;99&#8221;?', wptexturize(" \"Class of '99\"?"));
 		$this->assertEquals('}&#8221;Class of &#8217;99&#8243;{', wptexturize("}\"Class of '99\"{")); // Not a quotation, may be between two other quotations.
 	}
 
@@ -701,6 +714,26 @@ class Tests_Formatting_WPTexturize extends WP_UnitTestCase {
 				'test sentence".',
 				'test sentence&#8221;.',
 			),
+			array(
+				'test sentence",',
+				'test sentence&#8221;,',
+			),
+			array(
+				'test sentence":',
+				'test sentence&#8221;:',
+			),
+			array(
+				'test sentence";',
+				'test sentence&#8221;;',
+			),
+			array(
+				'test sentence"!',
+				'test sentence&#8221;!',
+			),
+			array(
+				'test sentence"?',
+				'test sentence&#8221;?',
+			),
 			array(
 				'test sentence."',
 				'test sentence.&#8221;',
@@ -746,6 +779,22 @@ class Tests_Formatting_WPTexturize extends WP_UnitTestCase {
 				"word word', she said",
 				"word word&#8217;, she said",
 			),
+			array(
+				"word word': word",
+				"word word&#8217;: word",
+			),
+			array(
+				"word word'; word",
+				"word word&#8217;; word",
+			),
+			array(
+				"word word'! word",
+				"word word&#8217;! word",
+			),
+			array(
+				"word word'? word",
+				"word word&#8217;? word",
+			),
 			array(
 				"word word'- word",
 				"word word&#8217;- word",