diff --git a/CHANGELOG.md b/CHANGELOG.md
index 67ab6974..0afe8963 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,7 +13,7 @@ Versioning].
 - Add support for `bsd-csh` as a C shell (`csh`) identifier. ([#2388])
 - Improve rejecting non-array inputs to `escapeAll` & `quoteAll`. ([#2363],
   [#2382])
-- Expand support for `--enable-experimental-regexp-engine`. ([#2358])
+- Expand support for `--enable-experimental-regexp-engine`. ([#2358], [#2383])
 
 ## [2.1.8] - 2026-01-25
 
@@ -387,6 +387,7 @@ Versioning].
 [#2358]: https://github.com/ericcornelissen/shescape/pull/2358
 [#2363]: https://github.com/ericcornelissen/shescape/pull/2363
 [#2382]: https://github.com/ericcornelissen/shescape/pull/2382
+[#2383]: https://github.com/ericcornelissen/shescape/pull/2383
 [#2388]: https://github.com/ericcornelissen/shescape/pull/2388
 [552e8ea]: https://github.com/ericcornelissen/shescape/commit/552e8eab56861720b1d4e5474fb65741643358f9
 [keep a changelog]: https://keepachangelog.com/en/1.0.0/
diff --git a/src/internal/win/cmd.js b/src/internal/win/cmd.js
index bd16dfb0..e6f0c34b 100644
--- a/src/internal/win/cmd.js
+++ b/src/internal/win/cmd.js
@@ -3,19 +3,7 @@
  * @license MPL-2.0
  */
 
-/**
- * Escape an argument for use in CMD.
- *
- * @param {string} arg The argument to escape.
- * @returns {string} The escaped argument.
- */
-function escapeArg(arg) {
-  return arg
-    .replace(/[\0\u0008\r\u001B\u009B]/gu, "")
-    .replace(/\n/gu, " ")
-    .replace(/(?<!\\)(\\*)"/gu, '$1$1\\"')
-    .replace(/(["%&<>^|])/gu, "^$1");
-}
+import RegExp from "@ericcornelissen/lregexp";
 
 /**
  * Returns a function to escape arguments for use in CMD for the given use case.
@@ -23,22 +11,38 @@ function escapeArg(arg) {
  * @returns {function(string): string} A function to escape arguments.
  */
 export function getEscapeFunction() {
-  return escapeArg;
+  const controls = new RegExp("[\0\u0008\r\u001B\u009B]", "g");
+  const newlines = new RegExp("\n", "g");
+  const specials = new RegExp("([%&<>^|])", "g");
+  const quotes = new RegExp('"', "g");
+  const backslashes = new RegExp("(^|[^\\\\])(\\\\*)\0", "g");
+  return (arg) =>
+    arg
+      .replace(controls, "")
+      .replace(newlines, " ")
+      .replace(specials, "^$1")
+      .replace(quotes, '\0\\^"')
+      .replace(backslashes, "$1$2$2");
 }
 
 /**
  * Escape an argument for use in CMD when the argument is being quoted.
  *
- * @param {string} arg The argument to escape.
- * @returns {string} The escaped argument.
+ * @returns {function(string): string} A function to escape arguments.
  */
-function escapeArgForQuoted(arg) {
-  return arg
-    .replace(/[\0\u0008\r\u001B\u009B]/gu, "")
-    .replace(/\n/gu, " ")
-    .replace(/"/gu, '""')
-    .replace(/([%&<>^|])/gu, '"^$1"')
-    .replace(/(?<!\\)(\\*)(?="|$)/gu, "$1$1");
+function getQuoteEscapeFunction() {
+  const controls = new RegExp("[\0\u0008\r\u001B\u009B]", "g");
+  const newlines = new RegExp("\n", "g");
+  const quotes = new RegExp('"', "g");
+  const specials = new RegExp("([%&<>^|])", "g");
+  const backslashes = new RegExp('(^|[^\\\\])(\\\\+)("|$)', "g");
+  return (arg) =>
+    arg
+      .replace(controls, "")
+      .replace(newlines, " ")
+      .replace(quotes, '""')
+      .replace(specials, '"^$1"')
+      .replace(backslashes, "$1$2$2$3");
 }
 
 /**
@@ -57,18 +61,7 @@ function quoteArg(arg) {
  * @returns {(function(string): string)[]} A function pair to escape & quote arguments.
  */
 export function getQuoteFunction() {
-  return [escapeArgForQuoted, quoteArg];
-}
-
-/**
- * Remove any prefix from the provided argument that might be interpreted as a
- * flag on Windows systems for CMD.
- *
- * @param {string} arg The argument to update.
- * @returns {string} The updated argument.
- */
-function stripFlagPrefix(arg) {
-  return arg.replace(/^(?:-+|\/+)/gu, "");
+  return [getQuoteEscapeFunction(), quoteArg];
 }
 
 /**
@@ -77,5 +70,6 @@ function stripFlagPrefix(arg) {
  * @returns {function(string): string} A function to protect against flag injection.
  */
 export function getFlagProtectionFunction() {
-  return stripFlagPrefix;
+  const leadingHyphensAndSlashes = new RegExp("^(?:-+|/+)");
+  return (arg) => arg.replace(leadingHyphensAndSlashes, "");
 }
diff --git a/test/fixtures/win.js b/test/fixtures/win.js
index 17199ac1..93938c30 100644
--- a/test/fixtures/win.js
+++ b/test/fixtures/win.js
@@ -1766,6 +1766,10 @@ export const escape = {
         input: '"a',
         expected: '\\^"a',
       },
+      {
+        input: 'a""b',
+        expected: 'a\\^"\\^"b',
+      },
     ],
     "double quotes ('\"') + backslashes ('\\')": [
       {
@@ -4550,6 +4554,14 @@ export const quote = {
       },
     ],
     "double quotes ('\"') + backslashes ('\\')": [
+      {
+        input: '\\"a',
+        expected: '"\\\\""a"',
+      },
+      {
+        input: 'a\\"',
+        expected: '"a\\\\"""',
+      },
       {
         input: 'a\\"b',
         expected: '"a\\\\""b"',
@@ -4558,6 +4570,10 @@ export const quote = {
         input: 'a\\\\"b',
         expected: '"a\\\\\\\\""b"',
       },
+      {
+        input: 'a\\\\"b\\\\"c',
+        expected: '"a\\\\\\\\""b\\\\\\\\""c"',
+      },
     ],
     "backticks ('`')": [
       {
@@ -4594,6 +4610,14 @@ export const quote = {
         input: "^a",
         expected: '""^^"a"',
       },
+      {
+        input: "a\\^b",
+        expected: '"a\\\\"^^"b"',
+      },
+      {
+        input: "^\\",
+        expected: '""^^"\\\\"',
+      },
     ],
     "carets ('^') + double quotes ('\"')": [
       {
@@ -4644,6 +4668,14 @@ export const quote = {
         input: "%a",
         expected: '""^%"a"',
       },
+      {
+        input: "a\\%b",
+        expected: '"a\\\\"^%"b"',
+      },
+      {
+        input: "%\\",
+        expected: '""^%"\\\\"',
+      },
     ],
     "percentage signs ('%') + double quotes ('\"')": [
       {
@@ -4676,6 +4708,14 @@ export const quote = {
         input: "&a",
         expected: '""^&"a"',
       },
+      {
+        input: "a\\&b",
+        expected: '"a\\\\"^&"b"',
+      },
+      {
+        input: "&\\",
+        expected: '""^&"\\\\"',
+      },
     ],
     "ampersands ('&') + double quotes ('\"')": [
       {
@@ -4744,6 +4784,14 @@ export const quote = {
         input: "|a",
         expected: '""^|"a"',
       },
+      {
+        input: "a\\|b",
+        expected: '"a\\\\"^|"b"',
+      },
+      {
+        input: "|\\",
+        expected: '""^|"\\\\"',
+      },
     ],
     "pipes ('|') + double quotes ('\"')": [
       {
@@ -4796,6 +4844,22 @@ export const quote = {
         input: "a<b>c",
         expected: '"a"^<"b"^>"c"',
       },
+      {
+        input: "a\\<b",
+        expected: '"a\\\\"^<"b"',
+      },
+      {
+        input: "a\\>b",
+        expected: '"a\\\\"^>"b"',
+      },
+      {
+        input: "<\\",
+        expected: '""^<"\\\\"',
+      },
+      {
+        input: ">\\",
+        expected: '""^>"\\\\"',
+      },
     ],
     "angle brackets ('<', '>') + double quotes ('\"')": [
       {