diff --git a/src/jsc/ConsoleObject.rs b/src/jsc/ConsoleObject.rs
index a9270cf88662..5494ae561148 100644
--- a/src/jsc/ConsoleObject.rs
+++ b/src/jsc/ConsoleObject.rs
@@ -3597,7 +3597,15 @@ pub mod formatter {
             };
             writer.add_for_new_line(str.length());
 
-            if self.quote_strings && js_type != jsc::JSType::RegExpObject {
+            // A String wrapper keeps its `[String: "..."]` rendering below when
+            // nested (like `[Number: 1]`) instead of being quoted like a
+            // primitive string.
+            if self.quote_strings
+                && !matches!(
+                    js_type,
+                    jsc::JSType::StringObject | jsc::JSType::RegExpObject
+                )
+            {
                 if str.is_empty() {
                     writer.write_all(b"\"\"");
                     if writer.failed {
@@ -3634,6 +3642,7 @@ pub mod formatter {
             }
 
             if js_type == jsc::JSType::StringObject {
+                writer.add_for_new_line("[String: \"\"]".len());
                 if C {
                     writer.print(format_args!("{}", pfmt!("<r><green>", C)));
                 }
diff --git a/test/js/bun/util/inspect.test.js b/test/js/bun/util/inspect.test.js
index 5c91f3dbe05f..6b8f02c5eeea 100644
--- a/test/js/bun/util/inspect.test.js
+++ b/test/js/bun/util/inspect.test.js
@@ -393,6 +393,43 @@ it("inspect", () => {
   );
 });
 
+it("String wrapper objects print as [String: ...] at every depth", () => {
+  class MyString extends String {}
+
+  // Top level. Bun.inspect quotes strings even at the top level, which used to
+  // turn the wrapper into a plain quoted string.
+  expect(Bun.inspect(new String("s"))).toBe('[String: "s"]');
+  expect(Bun.inspect(new String(""))).toBe('[String: ""]');
+  expect(Bun.inspect(new MyString("s"))).toBe('[String: "s"]');
+
+  // Nested in every container, alongside the other wrappers which already printed correctly.
+  expect(Bun.inspect({ n: new Number(3), b: new Boolean(true), s: new String("s") })).toBe(
+    '{\n  n: [Number: 3],\n  b: [Boolean: true],\n  s: [String: "s"],\n}',
+  );
+  expect(Bun.inspect([new String("s"), new String(""), new MyString("sub")])).toBe(
+    '[ [String: "s"], [String: ""], [String: "sub"] ]',
+  );
+  expect(Bun.inspect(new Map([[new String("k"), new String("v")]]))).toBe(
+    'Map(1) {\n  [String: "k"]: [String: "v"],\n}',
+  );
+  expect(Bun.inspect(new Set([new String("s")]))).toBe('Set(1) {\n  [String: "s"],\n}');
+
+  // The contents go through the same escaping as a quoted primitive string, for
+  // both the Latin-1 and the UTF-16 string representations.
+  expect(Bun.inspect({ s: new String('a"b\\c\n') })).toBe('{\n  s: [String: "a\\"b\\\\c\\n"],\n}');
+  expect(Bun.inspect({ s: new String("héllo") })).toBe('{\n  s: [String: "héllo"],\n}');
+  expect(Bun.inspect({ s: new String('日"本') })).toBe('{\n  s: [String: "日\\"本"],\n}');
+  expect(Bun.inspect({ s: new String("héllo 🌍") })).toBe('{\n  s: [String: "héllo 🌍"],\n}');
+
+  // Primitive strings and RegExps share the printer and keep their rendering.
+  expect(Bun.inspect({ s: "s", r: /r/g })).toBe('{\n  s: "s",\n  r: /r/g,\n}');
+  expect(Bun.inspect(["s", /r/g])).toBe('[ "s", /r/g ]');
+
+  // The colored printer is a separate instantiation of the same code.
+  expect(Bun.inspect([new String("s")], { colors: true })).toContain('\x1b[32m[String: "s"]\x1b[0m');
+  expect(Bun.inspect([new String("日本語")], { colors: true })).toContain('\x1b[32m[String: "日本語"]\x1b[0m');
+});
+
 describe("latin1 supplemental", () => {
   const fixture = [
     [["äbc"], '[ "äbc" ]'],
diff --git a/test/js/web/console/console-log.expected.txt b/test/js/web/console/console-log.expected.txt
index 9a6cdf569c3c..032c2ed87718 100644
--- a/test/js/web/console/console-log.expected.txt
+++ b/test/js/web/console/console-log.expected.txt
@@ -20,6 +20,12 @@ Symbol(Symbol Description)
 [String: "Hello 👋🏼"]
 [Number: 5]
 [Boolean: true]
+{
+  s: [String: "Hello"],
+  n: [Number: 5],
+  b: [Boolean: true],
+}
+[ [String: "Hello"], [String: "Hello 👋🏼"], "Hello" ]
 [ 123, 456, 789 ]
 {
   name: "foo",
diff --git a/test/js/web/console/console-log.js b/test/js/web/console/console-log.js
index 91c3bddd0278..6cdeb1b06e77 100644
--- a/test/js/web/console/console-log.js
+++ b/test/js/web/console/console-log.js
@@ -18,6 +18,8 @@ console.log(new String("Hello"));
 console.log(new String("Hello 👋🏼"));
 console.log(new Number(5));
 console.log(new Boolean(true));
+console.log({ s: new String("Hello"), n: new Number(5), b: new Boolean(true) });
+console.log([new String("Hello"), new String("Hello 👋🏼"), "Hello"]);
 console.log([123, 456, 789]);
 console.log({ name: "foo" });
 console.log({ a: 123, b: 456, c: 789 });