diff --git a/cli/tests/integration/run_tests.rs b/cli/tests/integration/run_tests.rs
index e4d6709350..d466849057 100644
--- a/cli/tests/integration/run_tests.rs
+++ b/cli/tests/integration/run_tests.rs
@@ -3261,8 +3261,8 @@ itest!(unhandled_rejection_dynamic_import2 {
 });
 
 itest!(nested_error {
-  args: "run run/nested_error.ts",
-  output: "run/nested_error.ts.out",
+  args: "run run/nested_error/main.ts",
+  output: "run/nested_error/main.ts.out",
   exit_code: 1,
 });
 
diff --git a/cli/tests/testdata/run/nested_error.ts.out b/cli/tests/testdata/run/nested_error.ts.out
deleted file mode 100644
index f5ebeec4d8..0000000000
--- a/cli/tests/testdata/run/nested_error.ts.out
+++ /dev/null
@@ -1,4 +0,0 @@
-error: Uncaught {
-  foo: Error
-    at file:///[WILDCARD]testdata/run/nested_error.ts:2:8
-}
diff --git a/cli/tests/testdata/run/nested_error.ts b/cli/tests/testdata/run/nested_error/main.ts
similarity index 100%
rename from cli/tests/testdata/run/nested_error.ts
rename to cli/tests/testdata/run/nested_error/main.ts
diff --git a/cli/tests/testdata/run/nested_error/main.ts.out b/cli/tests/testdata/run/nested_error/main.ts.out
new file mode 100644
index 0000000000..47c818ac12
--- /dev/null
+++ b/cli/tests/testdata/run/nested_error/main.ts.out
@@ -0,0 +1,4 @@
+error: Uncaught {
+  foo: Error
+    at file:///[WILDCARD]/main.ts:2:8
+}
diff --git a/ext/console/02_console.js b/ext/console/02_console.js
index 295fef4c31..e93272de11 100644
--- a/ext/console/02_console.js
+++ b/ext/console/02_console.js
@@ -1291,12 +1291,17 @@ function inspectRawObject(
   inspectOptions.indentLevel--;
 
   // Making sure color codes are ignored when calculating the total length
+  const entriesText = colors.stripColor(ArrayPrototypeJoin(entries, ""));
   const totalLength = entries.length + inspectOptions.indentLevel +
-    colors.stripColor(ArrayPrototypeJoin(entries, "")).length;
+    entriesText.length;
 
   if (entries.length === 0) {
     baseString = "{}";
-  } else if (totalLength > LINE_BREAKING_LENGTH || !inspectOptions.compact) {
+  } else if (
+    totalLength > LINE_BREAKING_LENGTH ||
+    !inspectOptions.compact ||
+    StringPrototypeIncludes(entriesText, "\n")
+  ) {
     const entryIndent = StringPrototypeRepeat(
       DEFAULT_INDENT,
       inspectOptions.indentLevel + 1,