diff --git a/src/wp-includes/html-api/class-wp-html-tag-processor.php b/src/wp-includes/html-api/class-wp-html-tag-processor.php
index 69e3e5d2c7557..9d1830ad37623 100644
--- a/src/wp-includes/html-api/class-wp-html-tag-processor.php
+++ b/src/wp-includes/html-api/class-wp-html-tag-processor.php
@@ -3851,20 +3851,11 @@ public function set_modifiable_text( string $plaintext_content ): bool {
 				return true;
 
 			case 'STYLE':
-				$plaintext_content = preg_replace_callback(
-					'~</(?P<TAG_NAME>style)~i',
-					static function ( $tag_match ) {
-						return "\\3c\\2f{$tag_match['TAG_NAME']}";
-					},
-					$plaintext_content
-				);
-
 				$this->lexical_updates['modifiable text'] = new WP_HTML_Text_Replacement(
 					$this->text_starts_at,
 					$this->text_length,
-					$plaintext_content
+					self::escape_style_contents( $plaintext_content )
 				);
-
 				return true;
 
 			case 'TEXTAREA':
@@ -4240,6 +4231,60 @@ private static function escape_javascript_script_contents( string $sourcecode ):
 		return $escaped;
 	}
 
+	/**
+	 * Escape style tag contents.
+	 *
+	 * Prevent CSS text from modifying the HTML structure of a document and
+	 * ensure that it's contained within its enclosing STYLE tag as intended.
+	 *
+	 * @since 7.0.0
+	 *
+	 * @param string $text Raw contents intended to be serialized into an HTML STYLE element.
+	 * @return string Escaped form of input contents which will not lead to premature closing of the containing STYLE element.
+	 */
+	private static function escape_style_contents( string $text ): string {
+		$at      = 0;
+		$was_at  = 0;
+		$end     = strlen( $text );
+		$escaped = '';
+
+		/*
+		 * Replace all instances of the ASCII case-insensitive match of "</style"
+		 * when followed by whitespace or "/" or ">", by using a CSS Unicode
+		 * escape sequence for the "s" (or the "S").
+		 *
+		 * CSS Unicode escape sequences will terminate at the first non-hexadecimal,
+		 * so the `t` character in `style` ensures that a Unicode escape sequence
+		 * like `\73t` is correctly interpreted as `st`.
+		 */
+		while ( $at < $end ) {
+			$tag_at = stripos( $text, '</style', $at );
+			if ( false === $tag_at ) {
+				break;
+			}
+
+			if ( 1 !== strspn( $text, " \t\f\r\n/>", $tag_at + 7, 1 ) ) {
+				$at = $tag_at + 7;
+				continue;
+			}
+
+			$escaped .= substr( $text, $was_at, $tag_at - $was_at + 2 );
+			$escaped .= 's' === $text[ $tag_at + 2 ] ? '\73' : '\53';
+			$was_at   = $tag_at + 3;
+			$at       = $tag_at + 8;
+		}
+
+		if ( '' === $escaped ) {
+			return $text;
+		}
+
+		if ( $was_at < $end ) {
+			$escaped .= substr( $text, $was_at );
+		}
+
+		return $escaped;
+	}
+
 	/**
 	 * Updates or creates a new attribute on the currently matched tag with the passed value.
 	 *
diff --git a/tests/phpunit/tests/html-api/wpHtmlTagProcessorModifiableText.php b/tests/phpunit/tests/html-api/wpHtmlTagProcessorModifiableText.php
index 9e0d94aecd17e..a58a905e693d4 100644
--- a/tests/phpunit/tests/html-api/wpHtmlTagProcessorModifiableText.php
+++ b/tests/phpunit/tests/html-api/wpHtmlTagProcessorModifiableText.php
@@ -426,18 +426,22 @@ public function test_updates_basic_modifiable_text_on_supported_nodes( string $h
 	 */
 	public static function data_tokens_with_basic_modifiable_text_updates() {
 		return array(
-			'Text node (start)'       => array( 'Text', 1, 'Blubber', 'Blubber' ),
-			'Text node (middle)'      => array( '<em>Bold move</em>', 2, 'yo', '<em>yo</em>' ),
-			'Text node (end)'         => array( '<img>of a dog', 2, 'of a cat', '<img>of a cat' ),
-			'Encoded text node'       => array( '<figcaption>birds and dogs</figcaption>', 2, '<birds> & <dogs>', '<figcaption>&lt;birds&gt; &amp; &lt;dogs&gt;</figcaption>' ),
-			'SCRIPT tag'              => array( 'before<script></script>after', 2, 'const img = "<img> & <br>";', 'before<script>const img = "<img> & <br>";</script>after' ),
-			'STYLE tag'               => array( '<style></style>', 1, 'p::before { content: "<img> & </style>"; }', '<style>p::before { content: "<img> & \3c\2fstyle>"; }</style>' ),
-			'TEXTAREA tag'            => array( 'a<textarea>has no need to escape</textarea>b', 2, "so it <doesn't>", "a<textarea>so it <doesn't></textarea>b" ),
-			'TEXTAREA (escape)'       => array( 'a<textarea>has no need to escape</textarea>b', 2, 'but it does for </textarea>', 'a<textarea>but it does for &lt;/textarea></textarea>b' ),
-			'TEXTAREA (escape+attrs)' => array( 'a<textarea>has no need to escape</textarea>b', 2, 'but it does for </textarea not an="attribute">', 'a<textarea>but it does for &lt;/textarea not an="attribute"></textarea>b' ),
-			'TITLE tag'               => array( 'a<title>has no need to escape</title>b', 2, "so it <doesn't>", "a<title>so it <doesn't></title>b" ),
-			'TITLE (escape)'          => array( 'a<title>has no need to escape</title>b', 2, 'but it does for </title>', 'a<title>but it does for &lt;/title></title>b' ),
-			'TITLE (escape+attrs)'    => array( 'a<title>has no need to escape</title>b', 2, 'but it does for </title not an="attribute">', 'a<title>but it does for &lt;/title not an="attribute"></title>b' ),
+			'Text node (start)'               => array( 'Text', 1, 'Blubber', 'Blubber' ),
+			'Text node (middle)'              => array( '<em>Bold move</em>', 2, 'yo', '<em>yo</em>' ),
+			'Text node (end)'                 => array( '<img>of a dog', 2, 'of a cat', '<img>of a cat' ),
+			'Encoded text node'               => array( '<figcaption>birds and dogs</figcaption>', 2, '<birds> & <dogs>', '<figcaption>&lt;birds&gt; &amp; &lt;dogs&gt;</figcaption>' ),
+			'SCRIPT tag'                      => array( 'before<script></script>after', 2, 'const img = "<img> & <br>";', 'before<script>const img = "<img> & <br>";</script>after' ),
+			'STYLE tag'                       => array( '<style></style>', 1, 'p::before { content: "<img> & </style>"; }', '<style>p::before { content: "<img> & </\73tyle>"; }</style>' ),
+			'STYLE tag (mixed casing)'        => array( '<style></style>', 1, 'p::before { content: "<img> & </StYlE>"; }', '<style>p::before { content: "<img> & </\53tYlE>"; }</style>' ),
+			'STYLE tag (trailing characters)' => array( '<style></style>', 1, "p::before { content: \"<img> & </style\t>\"; }", "<style>p::before { content: \"<img> & </\\73tyle\t>\"; }</style>" ),
+			'STYLE tag (non-closing tag)'     => array( '<style></style>', 1, 'p::before { content: "<img> & </stylesheet>"; }', '<style>p::before { content: "<img> & </stylesheet>"; }</style>' ),
+			'STYLE tag (repeats)'             => array( '<style></style>', 1, '*{ content: "</style></STYLE></style</style>" }', '<style>*{ content: "</\73tyle></\53TYLE></style</\73tyle>" }</style>' ),
+			'TEXTAREA tag'                    => array( 'a<textarea>has no need to escape</textarea>b', 2, "so it <doesn't>", "a<textarea>so it <doesn't></textarea>b" ),
+			'TEXTAREA (escape)'               => array( 'a<textarea>has no need to escape</textarea>b', 2, 'but it does for </textarea>', 'a<textarea>but it does for &lt;/textarea></textarea>b' ),
+			'TEXTAREA (escape+attrs)'         => array( 'a<textarea>has no need to escape</textarea>b', 2, 'but it does for </textarea not an="attribute">', 'a<textarea>but it does for &lt;/textarea not an="attribute"></textarea>b' ),
+			'TITLE tag'                       => array( 'a<title>has no need to escape</title>b', 2, "so it <doesn't>", "a<title>so it <doesn't></title>b" ),
+			'TITLE (escape)'                  => array( 'a<title>has no need to escape</title>b', 2, 'but it does for </title>', 'a<title>but it does for &lt;/title></title>b' ),
+			'TITLE (escape+attrs)'            => array( 'a<title>has no need to escape</title>b', 2, 'but it does for </title not an="attribute">', 'a<title>but it does for &lt;/title not an="attribute"></title>b' ),
 		);
 	}