diff --git a/spring-web/src/main/java/org/springframework/http/HttpHeaders.java b/spring-web/src/main/java/org/springframework/http/HttpHeaders.java
index 5e742ee9f99..0c7e1d42607 100644
--- a/spring-web/src/main/java/org/springframework/http/HttpHeaders.java
+++ b/spring-web/src/main/java/org/springframework/http/HttpHeaders.java
@@ -1872,7 +1872,10 @@ public class HttpHeaders implements MultiValueMap<String, String>, Serializable
 		if (headers == EMPTY) {
 			return new HttpHeaders();
 		}
-		return (headers instanceof ReadOnlyHttpHeaders ? new HttpHeaders(headers.headers) : headers);
+		while (headers.headers instanceof HttpHeaders wrapped) {
+			headers = wrapped;
+		}
+		return new HttpHeaders(headers.headers);
 	}
 
 	/**
diff --git a/spring-web/src/test/java/org/springframework/http/HttpHeadersTests.java b/spring-web/src/test/java/org/springframework/http/HttpHeadersTests.java
index 80d62a344ac..5725b0b4324 100644
--- a/spring-web/src/test/java/org/springframework/http/HttpHeadersTests.java
+++ b/spring-web/src/test/java/org/springframework/http/HttpHeadersTests.java
@@ -57,6 +57,14 @@ class HttpHeadersTests {
 	private final HttpHeaders headers = new HttpHeaders();
 
 
+	@Test
+	void writableHttpHeadersUnwrapsMultiple() {
+		HttpHeaders originalExchangeHeaders = HttpHeaders.readOnlyHttpHeaders(new HttpHeaders());
+		HttpHeaders firewallHeaders = new HttpHeaders(originalExchangeHeaders);
+		HttpHeaders writeable = HttpHeaders.writableHttpHeaders(firewallHeaders);
+		writeable.setContentType(MediaType.APPLICATION_JSON);
+	}
+
 	@Test
 	void getOrEmpty() {
 		String key = "FOO";