diff --git a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatOps.scala b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatOps.scala
index d523067bc7..4fcb426418 100644
--- a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatOps.scala
+++ b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatOps.scala
@@ -650,7 +650,8 @@ class FormatOps(val tree: Tree, baseStyle: ScalafmtConfig) {
       ft: FormatToken,
       newStmtModOrBody: Either[Modification, Tree]
   )(implicit style: ScalafmtConfig): Seq[Split] = {
-    val fullInfixTreeOpt = findTreeWithParentSimple(lhsApp.all)(!isInfixApp(_))
+    val fullInfixTreeOpt =
+      findTreeWithParentSimple(lhsApp.all, false)(isInfixApp)
     val fullInfix = fullInfixTreeOpt.flatMap(asInfixApp).getOrElse(lhsApp)
     val app = findLeftInfix(fullInfix)
     newStmtModOrBody.fold(
diff --git a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/State.scala b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/State.scala
index 1ca0142e99..ef696cff98 100644
--- a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/State.scala
+++ b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/State.scala
@@ -217,9 +217,10 @@ final case class State(
           if (startsWithLeft(lo)) Some(lo) else None
         }
       owner.map { x =>
-        val y =
-          if (!x.parent.exists(startsWithLeft)) None
-          else TreeOps.findTreeWithParentSimple(x)(!startsWithLeft(_))
+        val y = x.parent.flatMap { p =>
+          if (!startsWithLeft(p)) None
+          else TreeOps.findTreeWithParentSimple(p, false)(startsWithLeft)
+        }
         (ft, y.getOrElse(x))
       }
     }
@@ -235,13 +236,13 @@ final case class State(
     getLineStartOwner(isComment).flatMap {
       case (lineFt, lineOwner) =>
         val ft = fops.tokens(depth)
-        val ok = (ft.meta.leftOwner eq lineOwner) || {
+        val ok = {
           // comment could be preceded by a comma
           isComment && ft.left.is[Token.Comma] &&
           (fops.prev(ft).meta.leftOwner eq lineOwner)
         } ||
           TreeOps
-            .findTreeWithParentSimple(ft.meta.leftOwner)(_ eq lineOwner)
+            .findTreeOrParentSimple(ft.meta.leftOwner)(_ eq lineOwner)
             .isDefined
         if (ok) Some(lineFt) else None
     }
@@ -389,7 +390,6 @@ object State {
 
   @inline
   private def isWithinInterpolation(tree: meta.Tree): Boolean =
-    isInterpolation(tree) ||
-      TreeOps.findTreeWithParentSimple(tree)(isInterpolation).isDefined
+    TreeOps.findTreeOrParentSimple(tree)(isInterpolation).isDefined
 
 }
diff --git a/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TokenOps.scala b/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TokenOps.scala
index a4a7380e6c..a261a68614 100644
--- a/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TokenOps.scala
+++ b/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TokenOps.scala
@@ -1,7 +1,7 @@
 package org.scalafmt.util
 
 import scala.meta.classifiers.Classifier
-import scala.meta.{Defn, Pkg, Template, Tree}
+import scala.meta.{Defn, Pkg, Source, Template, Term, Tree}
 import scala.meta.tokens.Token
 import scala.meta.tokens.Token._
 import scala.meta.tokens.Tokens
@@ -54,8 +54,13 @@ object TokenOps {
     style.optIn.forceNewlineBeforeDocstringSummary &&
       ft.right.is[Token.Comment] && !ft.left.is[Token.Comment] &&
       ft.meta.right.text.startsWith("/**") &&
-      !ft.meta.leftOwner.is[meta.Mod] &&
-      !TreeOps.existsParentOfType[meta.Mod](ft.meta.leftOwner)
+      TreeOps
+        .findTreeOrParent(ft.meta.leftOwner) {
+          case _: Pkg | _: Source | _: Template | _: Term.Block => Some(false)
+          case t if t.pos.end > ft.right.start => Some(true)
+          case _ => None
+        }
+        .isEmpty
 
   // 2.13 implements SeqOps.findLast
   def findLast[A](seq: Seq[A])(cond: A => Boolean): Option[A] =
diff --git a/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TreeOps.scala b/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TreeOps.scala
index 9fff244bee..b8abad822b 100644
--- a/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TreeOps.scala
+++ b/scalafmt-core/shared/src/main/scala/org/scalafmt/util/TreeOps.scala
@@ -229,6 +229,28 @@ object TreeOps {
       case _ => cnt
     }
 
+  /**
+    * Returns first ancestor which matches the given predicate.
+    */
+  @tailrec
+  def findTreeOrParent(
+      tree: Tree
+  )(pred: Tree => Option[Boolean]): Option[Tree] =
+    pred(tree) match {
+      case Some(true) => Some(tree)
+      case Some(false) => None
+      case None =>
+        tree.parent match {
+          case None => None
+          case Some(p) => findTreeOrParent(p)(pred)
+        }
+    }
+  def findTreeOrParentSimple(
+      tree: Tree,
+      flag: Boolean = true
+  )(pred: Tree => Boolean): Option[Tree] =
+    findTreeOrParent(tree)(x => if (pred(x) == flag) Some(true) else None)
+
   /**
     * Returns first ancestor whose parent matches the given predicate.
     */
@@ -246,9 +268,10 @@ object TreeOps {
         }
     }
   def findTreeWithParentSimple(
-      tree: Tree
+      tree: Tree,
+      flag: Boolean = true
   )(pred: Tree => Boolean): Option[Tree] =
-    findTreeWithParent(tree)(x => if (pred(x)) Some(true) else None)
+    findTreeWithParent(tree)(x => if (pred(x) == flag) Some(true) else None)
 
   /**
     * Returns first ancestor with a parent of a given type.
diff --git a/scalafmt-tests/src/test/resources/test/JavaDoc.stat b/scalafmt-tests/src/test/resources/test/JavaDoc.stat
index 1bd3260036..e4e1543656 100644
--- a/scalafmt-tests/src/test/resources/test/JavaDoc.stat
+++ b/scalafmt-tests/src/test/resources/test/JavaDoc.stat
@@ -1259,3 +1259,19 @@ object a {
   /** alias for [[literal]] */
   /** alias for [[literal]] */
 }
+<<< #2043
+object Day extends Enumeration {
+  type Day = Value
+
+  val
+  /** Monday */
+  MON = Value
+}
+>>>
+object Day extends Enumeration {
+  type Day = Value
+
+  val
+  /** Monday */
+  MON = Value
+}