diff --git a/compiler/src/dotty/tools/MainGenericRunner.scala b/compiler/src/dotty/tools/MainGenericRunner.scala
index fa6faa7d570e..dfc56a8c11d2 100644
--- a/compiler/src/dotty/tools/MainGenericRunner.scala
+++ b/compiler/src/dotty/tools/MainGenericRunner.scala
@@ -105,17 +105,20 @@ object MainGenericRunner {
     case "-run" :: fqName :: tail =>
       process(tail, settings.withExecuteMode(ExecuteMode.Run).withTargetToRun(fqName))
     case ("-cp" | "-classpath" | "--class-path") :: cp :: tail =>
-      val globdir = cp.replaceAll("[\\/][^\\/]*$", "") // slash/backslash agnostic
-      val (tailargs, cpstr) = if globdir.nonEmpty && classpathSeparator != ";" || cp.contains(classpathSeparator) then
-        (tail, cp)
+      val cpEntries = cp.split(classpathSeparator).toList
+      val singleEntryClasspath: Boolean = cpEntries.take(2).size == 1
+      val globdir: String = if singleEntryClasspath then cp.replaceAll("[\\\\/][^\\\\/]*$", "") else "" // slash/backslash agnostic
+      def validGlobbedJar(s: String): Boolean = s.startsWith(globdir) && ((s.toLowerCase.endsWith(".jar") || s.toLowerCase.endsWith(".zip")))
+      val (tailargs, newEntries) = if singleEntryClasspath && validGlobbedJar(cpEntries.head) then
+        // reassemble globbed wildcard classpath
+        // globdir is wildcard directory for globbed jar files, reconstruct the intended classpath
+        val cpJars = tail.takeWhile( f => validGlobbedJar(f) )
+        val remainingArgs = tail.drop(cpJars.size)
+        (remainingArgs, cpEntries ++ cpJars)
       else
-        // combine globbed classpath entries into a classpath
-        val jarfiles = cp :: tail
-        val cpfiles = jarfiles.takeWhile( f => f.startsWith(globdir) && ((f.toLowerCase.endsWith(".jar") || f.endsWith(".zip"))) )
-        val tailargs = jarfiles.drop(cpfiles.size)
-        (tailargs, cpfiles.mkString(classpathSeparator))
-        
-      process(tailargs, settings.copy(classPath = settings.classPath ++ cpstr.split(classpathSeparator).filter(_.nonEmpty)))
+        (tail, cpEntries)
+
+      process(tailargs, settings.copy(classPath = settings.classPath ++ newEntries.filter(_.nonEmpty)))
 
     case ("-version" | "--version") :: _ =>
       settings.copy(
@@ -204,16 +207,15 @@ object MainGenericRunner {
         val targetScript = Paths.get(settings.targetScript).toFile
         val targetJar = settings.targetScript.replaceAll("[.][^\\/]*$", "")+".jar"
         val precompiledJar = Paths.get(targetJar).toFile
-        def mainClass = Jar(targetJar).mainClass.getOrElse("") // throws exception if file not found
-        val jarIsValid = precompiledJar.isFile && mainClass.nonEmpty && precompiledJar.lastModified >= targetScript.lastModified
+        val mainClass = if !precompiledJar.isFile then "" else Jar(targetJar).mainClass.getOrElse("")
+        val jarIsValid = mainClass.nonEmpty && precompiledJar.lastModified >= targetScript.lastModified
         if jarIsValid then
           // precompiledJar exists, is newer than targetScript, and manifest defines a mainClass
           sys.props("script.path") = targetScript.toPath.toAbsolutePath.normalize.toString
           val scalaClasspath = ClasspathFromClassloader(Thread.currentThread().getContextClassLoader).split(classpathSeparator)
           val newClasspath = (settings.classPath.flatMap(_.split(classpathSeparator).filter(_.nonEmpty)) ++ removeCompiler(scalaClasspath) :+ ".").map(File(_).toURI.toURL)
-          val mc = mainClass
-          if mc.nonEmpty then
-            ObjectRunner.runAndCatch(newClasspath :+ File(targetJar).toURI.toURL, mc, settings.scriptArgs)
+          if mainClass.nonEmpty then
+            ObjectRunner.runAndCatch(newClasspath :+ File(targetJar).toURI.toURL, mainClass, settings.scriptArgs)
           else
             Some(IllegalArgumentException(s"No main class defined in manifest in jar: $precompiledJar"))
         else
diff --git a/compiler/test-resources/scripting/unglobClasspath.sc b/compiler/test-resources/scripting/unglobClasspath.sc
new file mode 100755
index 000000000000..796697cdedf2
--- /dev/null
+++ b/compiler/test-resources/scripting/unglobClasspath.sc
@@ -0,0 +1,8 @@
+#!bin/scala -classpath 'dist/target/pack/lib/*'
+
+// won't compile unless the hashbang line sets classpath
+import org.jline.terminal.Terminal
+
+def main(args: Array[String]) =
+  val cp = sys.props("java.class.path")
+  printf("unglobbed classpath: %s\n", cp)
diff --git a/compiler/test/dotty/tools/scripting/BashScriptsTests.scala b/compiler/test/dotty/tools/scripting/BashScriptsTests.scala
index 8a6c6aad1ec1..061350e86e33 100644
--- a/compiler/test/dotty/tools/scripting/BashScriptsTests.scala
+++ b/compiler/test/dotty/tools/scripting/BashScriptsTests.scala
@@ -97,11 +97,13 @@ class BashScriptsTests:
     printf("===> verify SCALA_OPTS='@argsfile' is properly handled by `dist/bin/scala`\n")
     val envPairs = List(("SCALA_OPTS", s"@$argsfile"))
     val (validTest, exitCode, stdout, stderr) = bashCommand(scriptFile.absPath, envPairs)
+    printf("stdout: %s\n", stdout.mkString("\n","\n",""))
     if validTest then
-      val expected = s"${workingDirectory.toString}"
-      val List(line1: String, line2: String) = stdout.take(2)
-      printf("line1 [%s]\n", line1)
-      val valid = line2.dropWhile( _ != ' ').trim.startsWith(expected)
+      val expected = s"${workingDirectory.norm}"
+      val output = stdout.find( _.trim.startsWith("cwd") ).getOrElse("").dropWhile(_!=' ').trim
+      printf("output  [%s]\n", output)
+      printf("expected[%s]\n", expected)
+      val valid = output.startsWith(expected)
       if valid then printf(s"\n===> success: classpath begins with %s, as reported by [%s]\n", workingDirectory, scriptFile.getName)
       assert(valid, s"script ${scriptFile.absPath} did not report valid java.class.path first entry")
 
diff --git a/compiler/test/dotty/tools/scripting/ClasspathTests.scala b/compiler/test/dotty/tools/scripting/ClasspathTests.scala
index 159605cd967c..82b6affe0c02 100755
--- a/compiler/test/dotty/tools/scripting/ClasspathTests.scala
+++ b/compiler/test/dotty/tools/scripting/ClasspathTests.scala
@@ -18,12 +18,6 @@ class ClasspathTests:
   val packBinDir = "dist/target/pack/bin"
   val packLibDir = "dist/target/pack/lib"
 
-  // only interested in classpath test scripts
-  val testScriptName = "classpathReport.sc"
-  val testScript = scripts("/scripting").find { _.getName.matches(testScriptName) } match
-    case None => sys.error(s"test script not found: ${testScriptName}")
-    case Some(file) => file
-
   def exists(scriptPath: Path): Boolean = Files.exists(scriptPath)
   def packBinScalaExists:Boolean = exists(Paths.get(s"$packBinDir/scala"))
 
@@ -31,6 +25,12 @@ class ClasspathTests:
    * verify classpath reported by called script.
    */
   @Test def hashbangClasspathVerifyTest = {
+    // only interested in classpath test scripts
+    val testScriptName = "classpathReport.sc"
+    val testScript = scripts("/scripting").find { _.getName.matches(testScriptName) } match
+      case None => sys.error(s"test script not found: ${testScriptName}")
+      case Some(file) => file
+
     val relpath = testScript.toPath.relpath.norm
     printf("===> hashbangClasspathVerifyTest for script [%s]\n", relpath)
     printf("bash is [%s]\n", bashExe)
@@ -50,13 +50,41 @@ class ClasspathTests:
       val hashbangClasspathJars = scriptCp.split(psep).map { _.getName }.sorted.distinct
       val packlibJars = listJars(s"$scriptCwd/$packLibDir").sorted.distinct
      
+      printf("%d jar files in dist/target/pack/lib\n", packlibJars.size)
+      printf("%d test script jars in classpath\n", hashbangClasspathJars.size)
+
       // verify that the classpath set in the hashbang line is effective
       if hashbangClasspathJars.size != packlibJars.size then
-        printf("%d test script jars in classpath\n", hashbangClasspathJars.size)
-        printf("%d jar files in dist/target/pack/lib\n", packlibJars.size)
+        printf("hashbangClasspathJars: %s\n", hashbangClasspathJars.mkString("\n ", "\n ", ""))
 
       assert(hashbangClasspathJars.size == packlibJars.size)
   }
+  /*
+   * verify classpath is unglobbed by MainGenericRunner.
+   */
+  @Test def unglobClasspathVerifyTest = {
+    val testScriptName = "unglobClasspath.sc"
+    val testScript = scripts("/scripting").find { _.getName.matches(testScriptName) } match
+      case None => sys.error(s"test script not found: ${testScriptName}")
+      case Some(file) => file
+
+    val relpath = testScript.toPath.relpath.norm
+    printf("===> unglobClasspathVerifyTest for script [%s]\n", relpath)
+    printf("bash is [%s]\n", bashExe)
+
+    if packBinScalaExists then
+      val bashCmdline = s"SCALA_OPTS= $relpath"
+      val cmd = Array(bashExe, "-c", bashCmdline)
+
+      cmd.foreach { printf("[%s]\n", _) }
+
+      // test script reports the classpath it sees 
+      val scriptOutput = exec(cmd:_*)
+      val scriptCp = findTaggedLine("unglobbed classpath", scriptOutput)
+      val classpathJars = scriptCp.split(psep).map { _.getName }.sorted.distinct
+      //classpathJars.foreach { printf("%s\n", _) }
+      assert(classpathJars.size > 1)
+  }
 
 
 //////////////// end of tests ////////////////
diff --git a/compiler/test/dotty/tools/scripting/ScriptingTests.scala b/compiler/test/dotty/tools/scripting/ScriptingTests.scala
index 25fdfe14f5c7..922564d4ff58 100644
--- a/compiler/test/dotty/tools/scripting/ScriptingTests.scala
+++ b/compiler/test/dotty/tools/scripting/ScriptingTests.scala
@@ -19,7 +19,7 @@ class ScriptingTests:
     f.getAbsolutePath.replace('\\', '/')
 
   // classpath tests managed by scripting.ClasspathTests.scala
-  def testFiles = scripts("/scripting").filter { ! _.getName.startsWith("classpath") }
+  def testFiles = scripts("/scripting").filter { ! _.getName.toLowerCase.contains("classpath") }
 
   def script2jar(scriptFile: File) = 
     val jarName = s"${scriptFile.getName.dropExtension}.jar"