diff --git a/compiler/src/dotty/tools/dotc/ast/NavigateAST.scala b/compiler/src/dotty/tools/dotc/ast/NavigateAST.scala
index 61561d5eaa24..730149381487 100644
--- a/compiler/src/dotty/tools/dotc/ast/NavigateAST.scala
+++ b/compiler/src/dotty/tools/dotc/ast/NavigateAST.scala
@@ -60,19 +60,19 @@ object NavigateAST {
    *  the given `span`.
    */
   def untypedPath(span: Span)(using Context): List[Positioned] =
-    pathTo(span, ctx.compilationUnit.untpdTree)
+    pathTo(span, List(ctx.compilationUnit.untpdTree))
 
 
-  /** The reverse path from node `from` to the node that closest encloses `span`,
+  /** The reverse path from any node in `from` to the node that closest encloses `span`,
    *  or `Nil` if no such path exists. If a non-empty path is returned it starts with
-   *  the node closest enclosing `span` and ends with `from`.
+   *  the node closest enclosing `span` and ends with one of the nodes in `from`.
    *
    *  @param skipZeroExtent  If true, skip over zero-extent nodes in the search. These nodes
    *                         do not correspond to code the user wrote since their start and
    *                         end point are the same, so this is useful when trying to reconcile
    *                         nodes with source code.
    */
-  def pathTo(span: Span, from: Positioned, skipZeroExtent: Boolean = false)(using Context): List[Positioned] = {
+  def pathTo(span: Span, from: List[Positioned], skipZeroExtent: Boolean = false)(using Context): List[Positioned] = {
     def childPath(it: Iterator[Any], path: List[Positioned]): List[Positioned] = {
       var bestFit: List[Positioned] = path
       while (it.hasNext) {
@@ -120,6 +120,6 @@ object NavigateAST {
           case _ => path
         }
       }
-    singlePath(from, Nil)
+    childPath(from.iterator, Nil)
   }
 }
diff --git a/compiler/src/dotty/tools/dotc/interactive/Interactive.scala b/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
index 20a746ceb5ac..cb41650c0b57 100644
--- a/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
+++ b/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
@@ -252,14 +252,14 @@ object Interactive {
    *  the tree closest enclosing `pos` and ends with an element of `trees`.
    */
   def pathTo(trees: List[SourceTree], pos: SourcePosition)(using Context): List[Tree] =
-    trees.find(_.pos.contains(pos)) match {
-      case Some(tree) => pathTo(tree.tree, pos.span)
-      case None => Nil
-    }
+    pathTo(trees.map(_.tree), pos.span)
 
   def pathTo(tree: Tree, span: Span)(using Context): List[Tree] =
-    if (tree.span.contains(span))
-      NavigateAST.pathTo(span, tree, skipZeroExtent = true)
+    pathTo(List(tree), span)
+
+  private def pathTo(trees: List[Tree], span: Span)(using Context): List[Tree] =
+    if (trees.exists(_.span.contains(span)))
+      NavigateAST.pathTo(span, trees, skipZeroExtent = true)
         .collect { case t: untpd.Tree => t }
         .dropWhile(!_.hasType).asInstanceOf[List[tpd.Tree]]
     else Nil
diff --git a/language-server/test/dotty/tools/languageserver/HoverTest.scala b/language-server/test/dotty/tools/languageserver/HoverTest.scala
index 868134d6ea21..b396f1a15044 100644
--- a/language-server/test/dotty/tools/languageserver/HoverTest.scala
+++ b/language-server/test/dotty/tools/languageserver/HoverTest.scala
@@ -222,4 +222,13 @@ class HoverTest {
            |""".withSource
       .hover(m1 to m2, hoverContent("example.SimpleEnum.Color"))
   }
+  
+  @Test def enums: Unit = {
+    code"""|package example
+           |enum TestEnum3:
+           | case ${m1}A${m2} // no tooltip
+           |
+           |""".withSource
+      .hover(m1 to m2, hoverContent("example.TestEnum3"))
+  }
 }