diff --git a/compiler/src/dotty/tools/dotc/classpath/ClassPathFactory.scala b/compiler/src/dotty/tools/dotc/classpath/ClassPathFactory.scala
index 0b66f339bf53..bda35386d7b1 100644
--- a/compiler/src/dotty/tools/dotc/classpath/ClassPathFactory.scala
+++ b/compiler/src/dotty/tools/dotc/classpath/ClassPathFactory.scala
@@ -52,14 +52,23 @@ class ClassPathFactory {
 
   // Internal
   protected def classesInPathImpl(path: String, expand: Boolean)(using Context): List[ClassPath] =
-    for {
+    val files = for {
       file <- expandPath(path, expand)
       dir <- {
         def asImage = if (file.endsWith(".jimage")) Some(AbstractFile.getFile(file)) else None
         Option(AbstractFile.getDirectory(file)).orElse(asImage)
       }
     }
-    yield newClassPath(dir)
+    yield dir
+
+    val expanded = for file <- files
+        a <- ClassPath.expandManifestPath(file.absolutePath)
+      yield
+        newClassPath(AbstractFile.getFile(a.getPath().toString()))
+
+    files.map(newClassPath) ++ expanded
+
+  end classesInPathImpl
 
   private def createSourcePath(file: AbstractFile)(using Context): ClassPath =
     if (file.isJarOrZip)
diff --git a/compiler/src/dotty/tools/io/ClassPath.scala b/compiler/src/dotty/tools/io/ClassPath.scala
index f77bc1efca91..01a3f2cc1870 100644
--- a/compiler/src/dotty/tools/io/ClassPath.scala
+++ b/compiler/src/dotty/tools/io/ClassPath.scala
@@ -152,13 +152,18 @@ object ClassPath {
 
     val baseDir = file.parent
     new Jar(file).classPathElements map (elem =>
-      specToURL(elem) getOrElse (baseDir / elem).toURL
+      specToURL(elem, baseDir) getOrElse (baseDir / elem).toURL
     )
   }
 
-  def specToURL(spec: String): Option[URL] =
-    try Some(new URI(spec).toURL)
-    catch case _: MalformedURLException | _: URISyntaxException => None
+  def specToURL(spec: String, basedir: Directory): Option[URL] =
+    try
+      val uri = new URI(spec)
+      if uri.isAbsolute() then Some(uri.toURL())
+      else
+        Some(basedir.resolve(Path(spec)).toURL)
+    catch
+      case _: MalformedURLException | _: URISyntaxException => None
 
   def manifests: List[java.net.URL] = {
     import scala.jdk.CollectionConverters.EnumerationHasAsScala