diff --git a/compiler/src/dotty/tools/dotc/interactive/Interactive.scala b/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
index 8ee950707296..8ec7d52c98f6 100644
--- a/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
+++ b/compiler/src/dotty/tools/dotc/interactive/Interactive.scala
@@ -79,7 +79,7 @@ object Interactive {
   def enclosingTree(trees: List[SourceTree], pos: SourcePosition)(using Context): Tree =
     enclosingTree(pathTo(trees, pos))
 
-  /** The closes enclosing tree with a symbol, or the `EmptyTree`.
+  /** The closest enclosing tree with a symbol, or the `EmptyTree`.
    */
   def enclosingTree(path: List[Tree])(using Context): Tree =
     path.dropWhile(!_.symbol.exists).headOption.getOrElse(tpd.EmptyTree)
diff --git a/compiler/src/dotty/tools/dotc/util/Signatures.scala b/compiler/src/dotty/tools/dotc/util/Signatures.scala
index ead84dc9f7d0..d24b4d8c3bf9 100644
--- a/compiler/src/dotty/tools/dotc/util/Signatures.scala
+++ b/compiler/src/dotty/tools/dotc/util/Signatures.scala
@@ -48,19 +48,21 @@ object Signatures {
    *         being called, the list of overloads of this function).
    */
   def callInfo(path: List[tpd.Tree], span: Span)(using Context): (Int, Int, List[SingleDenotation]) =
-    path match {
-      case UnApply(fun, _, patterns) :: _ =>
-        callInfo(span, patterns, fun, Signatures.countParams(fun))
-      case Apply(fun, params) :: _ =>
-        callInfo(span, params, fun, Signatures.countParams(fun))
-      case _ =>
-        (0, 0, Nil)
+    val enclosingApply = path.find {
+      case Apply(fun, _) => !fun.span.contains(span)
+      case UnApply(fun, _, _) => !fun.span.contains(span)
+      case _ => false
     }
 
+    enclosingApply.map {
+      case UnApply(fun, _, patterns) => callInfo(span, patterns, fun, Signatures.countParams(fun))
+      case Apply(fun, params) => callInfo(span, params, fun, Signatures.countParams(fun))
+    }.getOrElse((0, 0, Nil))
+
   def callInfo(
     span: Span,
-    params: List[Tree[Type]], 
-    fun: Tree[Type], 
+    params: List[Tree[Type]],
+    fun: Tree[Type],
     alreadyAppliedCount : Int
   )(using Context): (Int, Int, List[SingleDenotation]) =
     val paramIndex = params.indexWhere(_.span.contains(span)) match {
diff --git a/language-server/src/dotty/tools/languageserver/DottyLanguageServer.scala b/language-server/src/dotty/tools/languageserver/DottyLanguageServer.scala
index c91d66877c6b..179b8002dfb5 100644
--- a/language-server/src/dotty/tools/languageserver/DottyLanguageServer.scala
+++ b/language-server/src/dotty/tools/languageserver/DottyLanguageServer.scala
@@ -556,7 +556,7 @@ class DottyLanguageServer extends LanguageServer
 
     val pos = sourcePosition(driver, uri, params.getPosition)
     val trees = driver.openedTrees(uri)
-    val path = Interactive.pathTo(trees, pos).dropWhile(t => !t.isInstanceOf[Apply | UnApply])
+    val path = Interactive.pathTo(trees, pos)
     val (paramN, callableN, alternatives) = Signatures.callInfo(path, pos.span)
     val signatureInfos = alternatives.flatMap(Signatures.toSignature)
 
diff --git a/language-server/test/dotty/tools/languageserver/SignatureHelpTest.scala b/language-server/test/dotty/tools/languageserver/SignatureHelpTest.scala
index bc4facd7b88f..171a3ac5615d 100644
--- a/language-server/test/dotty/tools/languageserver/SignatureHelpTest.scala
+++ b/language-server/test/dotty/tools/languageserver/SignatureHelpTest.scala
@@ -433,4 +433,63 @@ class SignatureHelpTest {
           Some("Option[A]"), None)
         ), None, 2)
   }
+
+  @Test def nestedApplySignatures: Unit = {
+    val signatures = (1 to 5).map { i =>
+      S(s"foo$i", Nil, List(List(P("x", "Int"))), Some("Int"))
+    }
+    val booSignature = S(s"boo", Nil, List(List(P("x", "Int"), P("y", "Int"))), Some("Int"))
+    code"""|object O:
+           |  def foo1(x: Int): Int = ???
+           |  def foo2(x: Int): Int = ???
+           |  def foo3(x: Int): Int = ???
+           |  def foo4(x: Int): Int = ???
+           |  def foo5(x: Int): Int = ???
+           |  def boo(x: Int, y: Int): Int = ???
+           |  boo(${m1}, fo${m2}o1(fo${m3}o2(fo${m4}o3(fo${m5}o4(fo${m6}o5(${m7}))))))"""
+      .signatureHelp(m1, List(booSignature), None, 0)
+      .signatureHelp(m2, List(booSignature), None, 1)
+      .signatureHelp(m3, List(signatures(0)), None, 0)
+      .signatureHelp(m4, List(signatures(1)), None, 0)
+      .signatureHelp(m5, List(signatures(2)), None, 0)
+      .signatureHelp(m6, List(signatures(3)), None, 0)
+      .signatureHelp(m7, List(signatures(4)), None, 0)
+  }
+
+  @Test def multipleNestedApplySignatures: Unit = {
+    val simpleSignature = S(s"simpleFoo", Nil, List(List(P("x", "Int"))), Some("Int"))
+    val complicatedSignature = S(s"complicatedFoo", Nil, List(List(P("x", "Int"), P("y", "Int"), P("z", "Int"))), Some("Int"))
+    code"""|object O:
+           |  def simpleFoo(x: Int): Int = ???
+           |  def complicatedFoo(x: Int, y: Int, z: Int): Int = ???
+           |  simpleFoo(
+           |    complicated${m1}Foo(
+           |      simp${m2}leFoo(${m3}),
+           |      complic${m4}atedFoo(
+           |        2,
+           |        ${m5},
+           |        simpleF${m6}oo(${m7})),
+           |      complicated${m8}Foo(5,${m9},7)
+           |    )
+           |  )"""
+      .signatureHelp(m1, List(simpleSignature), None, 0)
+      .signatureHelp(m2, List(complicatedSignature), None, 0)
+      .signatureHelp(m3, List(simpleSignature), None, 0)
+      .signatureHelp(m4, List(complicatedSignature), None, 1)
+      .signatureHelp(m5, List(complicatedSignature), None, 1)
+      .signatureHelp(m6, List(complicatedSignature), None, 2)
+      .signatureHelp(m7, List(simpleSignature), None, 0)
+      .signatureHelp(m8, List(complicatedSignature), None, 2)
+      .signatureHelp(m9, List(complicatedSignature), None, 1)
+  }
+
+  @Test def noHelpSignatureWithPositionedOnName: Unit = {
+    val signature = S(s"foo", Nil, List(List(P("x", "Int"))), Some("Int"))
+    code"""|object O:
+           |  def foo(x: Int): Int = ???
+           |  f${m1}oo(${m2})"""
+     .signatureHelp(m1, Nil, None, 0)
+     .signatureHelp(m2, List(signature), None, 0)
+  }
+
 }