diff --git a/lib/internal/url.js b/lib/internal/url.js
index 3cb186182947a1..702caf8788ddb3 100644
--- a/lib/internal/url.js
+++ b/lib/internal/url.js
@@ -1518,11 +1518,20 @@ const carriageReturnRegEx = /\r/g;
 const tabRegEx = /\t/g;
 const questionRegex = /\?/g;
 const hashRegex = /#/g;
+const leftBracketRegEx = /\[/g;
+const rightBracketRegEx = /\]/g;
+const caretRegEx = /\^/g;
 
 function encodePathChars(filepath, options = kEmptyObject) {
   const windows = options?.windows;
   if (StringPrototypeIndexOf(filepath, '%') !== -1)
     filepath = RegExpPrototypeSymbolReplace(percentRegEx, filepath, '%25');
+  if (StringPrototypeIndexOf(filepath, '[') !== -1)
+    filepath = RegExpPrototypeSymbolReplace(leftBracketRegEx, filepath, '%5B');
+  if (StringPrototypeIndexOf(filepath, ']') !== -1)
+    filepath = RegExpPrototypeSymbolReplace(rightBracketRegEx, filepath, '%5D');
+  if (StringPrototypeIndexOf(filepath, '^') !== -1)
+    filepath = RegExpPrototypeSymbolReplace(caretRegEx, filepath, '%5E');
   // In posix, backslash is a valid character in paths:
   if (!(windows ?? isWindows) && StringPrototypeIndexOf(filepath, '\\') !== -1)
     filepath = RegExpPrototypeSymbolReplace(backslashRegEx, filepath, '%5C');
diff --git a/test/parallel/test-url-pathtofileurl.js b/test/parallel/test-url-pathtofileurl.js
index 20609eb0ff5c9f..9e3d0497194dfe 100644
--- a/test/parallel/test-url-pathtofileurl.js
+++ b/test/parallel/test-url-pathtofileurl.js
@@ -88,6 +88,12 @@ const windowsTestCases = [
   { path: 'C:\\foo;bar', expected: 'file:///C:/foo;bar' },
   // percent
   { path: 'C:\\foo%bar', expected: 'file:///C:/foo%25bar' },
+  // caret
+  { path: 'C:\\foo^bar', expected: 'file:///C:/foo%5Ebar' },
+  // left bracket
+  { path: 'C:\\foo[bar', expected: 'file:///C:/foo%5Bbar' },
+  // right bracket
+  { path: 'C:\\foo]bar', expected: 'file:///C:/foo%5Dbar' },
   // backslash
   { path: 'C:\\foo\\bar', expected: 'file:///C:/foo/bar' },
   // backspace
@@ -138,6 +144,12 @@ const posixTestCases = [
   { path: '/foo;bar', expected: 'file:///foo;bar' },
   // percent
   { path: '/foo%bar', expected: 'file:///foo%25bar' },
+  // caret
+  { path: '/foo^bar', expected: 'file:///foo%5Ebar' },
+  // left bracket
+  { path: '/foo[bar', expected: 'file:///foo%5Bbar' },
+  // right bracket
+  { path: '/foo]bar', expected: 'file:///foo%5Dbar' },
   // backslash
   { path: '/foo\\bar', expected: 'file:///foo%5Cbar' },
   // backspace