diff --git a/modules/cli/src/main/scala/scala/cli/packaging/NativeImage.scala b/modules/cli/src/main/scala/scala/cli/packaging/NativeImage.scala
index 2e886401b6..819f0fe01c 100644
--- a/modules/cli/src/main/scala/scala/cli/packaging/NativeImage.scala
+++ b/modules/cli/src/main/scala/scala/cli/packaging/NativeImage.scala
@@ -115,12 +115,24 @@ object NativeImage {
     }
     dosDevices.mkString
   }
+
   private def availableDriveLetter(): Char = {
+    // if a drive letter has already been mapped by SUBST, it isn't free
+    val substDrives: Set[Char] =
+      os.proc("cmd", "/c", "subst").call().out.text()
+        .linesIterator
+        .flatMap { line =>
+          // lines look like: "I:\: => C:\path"
+          if (line.length >= 2 && line(1) == ':') Some(line(0))
+          else None
+        }
+        .toSet
 
     @tailrec
     def helper(from: Char): Char =
       if (from > 'Z') sys.error("Cannot find free drive letter")
-      else if (mountedDrives.contains(from)) helper((from + 1).toChar)
+      else if (mountedDrives.contains(from) || substDrives.contains(from))
+        helper((from + 1).toChar)
       else from
 
     helper('D')
@@ -149,33 +161,77 @@ object NativeImage {
       val drivePath = os.Path(s"$driveLetter:" + "\\")
       val newHome   = drivePath / currentHome.last
       logger.debug(s"Aliasing $from to $drivePath")
-      val setupCommand  = s"""subst $driveLetter: "$from""""
-      val disableScript = s"""subst $driveLetter: /d"""
+      val setupCommand          = s"""subst $driveLetter: "$from""""
+      val disableScript         = s"""subst $driveLetter: /d"""
+      val savedCodepage: String = getCodePage(logger) // before visual studio sets code page to 437
 
-      os.proc("cmd", "/c", setupCommand).call(stdin = os.Inherit, stdout = os.Inherit)
-      try f(newHome)
-      finally {
-        val res = os.proc("cmd", "/c", disableScript).call(
-          stdin = os.Inherit,
-          stdout = os.Inherit,
-          check = false
-        )
-        if (res.exitCode == 0)
-          logger.debug(s"Unaliased $drivePath")
-        else if (os.exists(drivePath)) {
-          // ignore errors?
-          logger.debug(s"Unaliasing attempt exited with exit code ${res.exitCode}")
-          throw new os.SubprocessException(res)
+      def atexitCleanup(): Unit = {
+        import java.lang.ProcessBuilder
+        try {
+          restoreCodePage(savedCodepage, logger) // best effort
+
+          // cannot use os.proc() because it also installs a shutdown hook
+          val pb = new ProcessBuilder("cmd.exe", "/c", disableScript)
+          pb.inheritIO()
+          val p    = pb.start()
+          val exit = p.waitFor()
+
+          if (exit == 0)
+            logger.debug(s"Unaliased $drivePath")
+          else if (os.exists(drivePath))
+            logger.error(s"Unaliasing attempt exited with exit code $exit")
+            // no throw in a shutdown hook, it might obscure the real cause of the shutdown
+          else
+            logger.debug(
+              s"Failed to unalias $drivePath which seems not to exist anymore, ignoring it"
+            )
+        }
+        catch {
+          case e: Throwable =>
+            logger.error(s"Cleanup failed: ${e.getMessage}")
         }
-        else
-          logger.debug(
-            s"Failed to unalias $drivePath which seems not to exist anymore, ignoring it"
-          )
       }
+      // Runs on JVM shutdown, including Ctrl-C; more reliable than a `finally` block for cleanup
+      Runtime.getRuntime.addShutdownHook(new Thread(() => atexitCleanup()))
+
+      os.proc("cmd", "/c", setupCommand).call(stdin = os.Inherit, stdout = os.Inherit)
+      f(newHome) // no need for a try block
     }
     else
       f(currentHome)
 
+  def restoreCodePage(cp: String, logger: Logger): Unit =
+    if (Properties.isWin && cp.nonEmpty)
+      exec(Seq("cmd", "/c", "chcp", cp), logger, s"restore code page to $cp")
+
+  // execute a fire-and-forget windows command without using os.proc during shutdown.
+  private def exec(cmd: Seq[String], logger: Logger, desc: String): Unit = {
+    try {
+      val pb = new ProcessBuilder(cmd*)
+      pb.inheritIO()
+      val p    = pb.start()
+      val exit = p.waitFor()
+      if (exit == 0)
+        logger.debug(s"$desc succeeded")
+      else
+        logger.error(s"$desc failed with exit code $exit")
+    }
+    catch {
+      case e: Throwable =>
+        logger.error(s"$desc failed: ${e.getMessage}")
+    }
+  }
+  private def getCodePage(logger: Logger): String =
+    try {
+      val out = os.proc("cmd", "/c", "chcp").call().out.text().trim
+      out.split(":").lastOption.map(_.trim).getOrElse("") // Extract the number
+    }
+    catch {
+      case e: Exception =>
+        logger.debug(s"unable to get initial code page: ${e.getMessage}")
+        ""
+    }
+
   def buildNativeImage(
     builds: Seq[Build.Successful],
     mainClass: String,
diff --git a/modules/integration/src/test/scala/scala/cli/integration/PackageTestDefinitions.scala b/modules/integration/src/test/scala/scala/cli/integration/PackageTestDefinitions.scala
index 4d5346af2a..b5f24f1cc3 100644
--- a/modules/integration/src/test/scala/scala/cli/integration/PackageTestDefinitions.scala
+++ b/modules/integration/src/test/scala/scala/cli/integration/PackageTestDefinitions.scala
@@ -8,7 +8,7 @@ import java.nio.file.Files
 import java.util
 import java.util.zip.ZipFile
 
-import scala.cli.integration.TestUtil.removeAnsiColors
+import scala.cli.integration.TestUtil.*
 import scala.jdk.CollectionConverters.*
 import scala.util.{Properties, Using}
 
@@ -998,6 +998,59 @@ abstract class PackageTestDefinitions extends ScalaCliSuite with TestScalaVersio
     }
   }
 
+  if (Properties.isWin)
+    test("availableDriveLetter") {
+      val message    = "Hello from native-image"
+      val dest       = "hello"
+      val actualDest =
+        if (Properties.isWin) "hello.exe"
+        else "hello"
+      val inputs = TestInputs(
+        os.rel / "Hello.scala" ->
+          s"""object Hello {
+             |  def main(args: Array[String]): Unit =
+             |    println("$message")
+             |}
+             |""".stripMargin
+      )
+      setCodePage("65001")
+      val codePageBefore = getCodePage
+      val driveLetter    = availableDriveLetter()
+      val substedBefore  = substedDrives
+      aliasDriveLetter(driveLetter, "C:\\Windows\\Temp") // trigger for #4005
+
+      inputs.fromRoot { root =>
+        os.proc(
+          TestUtil.cli,
+          "--power",
+          "package",
+          extraOptions,
+          ".",
+          "--native-image",
+          "-o",
+          dest,
+          "--",
+          "--no-fallback"
+        ).call(
+          cwd = root,
+          stdin = os.Inherit,
+          stdout = os.Inherit
+        )
+
+        expect(os.isFile(root / actualDest))
+
+        val res    = os.proc(root / actualDest).call(cwd = root)
+        val output = res.out.trim()
+        expect(output == message)
+
+        unaliasDriveLetter(driveLetter) // undo test condition
+        val substedAfter = substedDrives
+        expect(substedBefore == substedAfter)
+        val codePageAfter = getCodePage
+        expect(codePageBefore == codePageAfter)
+      }
+    }
+
   test("correctly list main classes") {
     val (scalaFile1, scalaFile2, scriptName) = ("ScalaMainClass1", "ScalaMainClass2", "ScalaScript")
     val scriptsDir                           = "scripts"
diff --git a/modules/integration/src/test/scala/scala/cli/integration/TestUtil.scala b/modules/integration/src/test/scala/scala/cli/integration/TestUtil.scala
index 1a3e3c0396..36226dfcb9 100644
--- a/modules/integration/src/test/scala/scala/cli/integration/TestUtil.scala
+++ b/modules/integration/src/test/scala/scala/cli/integration/TestUtil.scala
@@ -465,4 +465,73 @@ object TestUtil {
     System.err.println("Cleaning cached JDKs in Coursier cache…")
     cleanCoursierCache(Seq("zulu", "temurin", "adoptium", "corretto", "liberica", "graalvm"))
   }
+
+  def substedDrives: Set[Char] =
+    if Properties.isWin then
+      os.proc("cmd", "/c", "subst").call().out.text()
+        .linesIterator
+        .flatMap { line =>
+          // lines look like: "I:\: => C:\path"
+          if (line.length >= 2 && line(1) == ':') Some(line(0))
+          else None
+        }
+        .toSet
+    else Set.empty[Char]
+
+  def availableDriveLetter(): Char = {
+    import scala.annotation.tailrec
+    @tailrec
+    def helper(from: Char): Char =
+      if (from > 'Z') sys.error("Cannot find free drive letter")
+      // neither physical drives nor SUBSTed drives are free
+      else if (mountedDrives.contains(from) || substedDrives.contains(from))
+        helper((from + 1).toChar)
+      else
+        from
+
+    helper('D')
+  }
+
+  lazy val mountedDrives: String = {
+    val str         = "HKEY_LOCAL_MACHINE/SYSTEM/MountedDevices".replace('/', '\\')
+    val queryDrives = s"reg query $str"
+    val lines       = os.proc("cmd", "/c", queryDrives).call().out.lines()
+    val dosDevices  = lines.filter { s =>
+      s.contains("DosDevices")
+    }.map { s =>
+      s.replaceAll(".DosDevices.", "").replaceAll(":.*", "")
+    }
+    dosDevices.mkString
+  }
+
+  def aliasDriveLetter(driveLetter: Char, from: String): Unit = {
+    val setupCommand = s"""subst $driveLetter: "$from""""
+    os.proc("cmd", "/c", setupCommand).call(stdin = os.Inherit, stdout = os.Inherit)
+  }
+
+  def unaliasDriveLetter(driveLetter: Char): Int = {
+    val disableScript = s"""subst $driveLetter: /d"""
+    val (exit, _)     = execWindowsCmd(Seq("cmd.exe", "/c", disableScript))
+    exit
+  }
+
+  def setCodePage(cp: String): Int =
+    val (exit, _) = execWindowsCmd(Seq("cmd", "/c", s"chcp $cp"))
+    exit
+
+  def getCodePage: String = {
+    val (_, output) = execWindowsCmd(Seq("cmd", "/c", "chcp"))
+    output
+  }
+
+  private def execWindowsCmd(cmd: Seq[String]): (Int, String) =
+    val pb = new ProcessBuilder(cmd*)
+    pb.redirectInput(ProcessBuilder.Redirect.INHERIT)
+    pb.redirectError(ProcessBuilder.Redirect.INHERIT)
+    pb.redirectOutput(ProcessBuilder.Redirect.PIPE)
+    val p = pb.start()
+    // read stdout fully
+    val output   = scala.io.Source.fromInputStream(p.getInputStream, "UTF-8").mkString
+    val exitCode = p.waitFor()
+    (exitCode, output)
 }