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 7b2d3e9b82..59116636ea 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
@@ -374,8 +374,8 @@ class FormatOps(
       if (afterInfix ne Newlines.AfterInfix.keep)
         if (isBeforeOp) Seq(Split(spaceMod, 0))
         else {
-          val (fullInfix, isEnclosed) = InfixSplits.findMaybeEnclosingInfix(app)
-          val ok = isEnclosed || fullInfix.parent.forall {
+          val (fullInfix, enclosedIn) = InfixSplits.findMaybeEnclosingInfix(app)
+          val ok = enclosedIn.isDefined || fullInfix.parent.forall {
             case t: Defn.Val => t.rhs eq fullInfix
             case t: Defn.Var => t.body eq fullInfix
             case _ => true
@@ -387,9 +387,10 @@ class FormatOps(
       else {
         // we don't modify line breaks generally around infix expressions
         // TODO: if that ever changes, modify how rewrite rules handle infix
-        val (fullInfix, isFullInfixEnclosed) = InfixSplits
+        val (fullInfix, fullInfixEnclosedIn) = InfixSplits
           .findMaybeEnclosingInfix(app)
-        def okToBreak: Boolean = !isBeforeOp || isFullInfixEnclosed ||
+        val fullInfixEnclosedInParens = fullInfixEnclosedIn.exists(_.isRight)
+        def okToBreak: Boolean = !isBeforeOp || fullInfixEnclosedInParens ||
           initStyle.dialect.allowInfixOperatorAfterNL ||
           (fullInfix.parent match {
             case Some(p: Case) => p.cond.contains(fullInfix)
@@ -401,7 +402,7 @@ class FormatOps(
           }
         val mod =
           if (ft.noBreak || !okToBreak) spaceMod
-          else Newline2x(isFullInfixEnclosed && ft.hasBlankLine)
+          else Newline2x(fullInfixEnclosedInParens && ft.hasBlankLine)
         def split(implicit fl: FileLine) = Split(mod, 0)
         if (isBeforeOp && isFewerBracesRhs(app.arg)) Seq(split)
         else Seq(InfixSplits.withNLIndent(split, app, fullInfix))
@@ -452,8 +453,9 @@ class FormatOps(
     private def findMaybeEnclosingInfix(
         child: Member.Infix,
         childTree: Tree,
-    ): (Member.Infix, Boolean) =
-      if (isEnclosedWithinParensOrBraces(childTree)) (child, true)
+    ): (Member.Infix, Option[Either[FT, FT]]) = {
+      val inParensOrBraces = getClosingIfWithinParensOrBraces(childTree)
+      if (inParensOrBraces.isDefined) (child, inParensOrBraces)
       else childTree.parent match {
         case Some(p: Member.Infix) if !p.isAssignment =>
           findMaybeEnclosingInfix(p, p)
@@ -461,12 +463,13 @@ class FormatOps(
           findMaybeEnclosingInfix(child, p)
         case Some(p @ Tree.Block(`childTree` :: Nil)) =>
           findMaybeEnclosingInfix(child, p)
-        case _ => (child, false)
+        case _ => (child, None)
       }
+    }
 
     private[FormatOps] def findMaybeEnclosingInfix(
         app: Member.Infix,
-    ): (Member.Infix, Boolean) = findMaybeEnclosingInfix(app, app)
+    ): (Member.Infix, Option[Either[FT, FT]]) = findMaybeEnclosingInfix(app, app)
 
     private[FormatOps] def findEnclosingInfix(app: Member.Infix): Member.Infix =
       findMaybeEnclosingInfix(app)._1
@@ -1745,7 +1748,7 @@ class FormatOps(
           val op = t.op.value
           op == "->" || op == "→"
         } => None
-    case _ => getClosingIfWithinParens(body).toOption
+    case _ => getClosingIfWithinParens(body)
   }
 
   def isBodyEnclosedAsBlock(body: Tree): Boolean =
@@ -1887,7 +1890,7 @@ class FormatOps(
         case _: Member.Tuple => None
         case Term.Block((_: Member.Tuple) :: Nil)
             if !head.left.is[T.LeftBrace] => None
-        case _ => tokens.getClosingIfWithinParens(nonTrivialEnd)(head).toOption
+        case _ => tokens.getClosingIfWithinParens(nonTrivialEnd)(head)
             .map(prevNonCommentSameLine)
       }).getOrElse(nextNonCommentSameLine(end))
       def nlPolicy(implicit fileLine: FileLine) = Policy ? danglingKeyword && {
@@ -2504,7 +2507,7 @@ class FormatOps(
 
       val beg = getOnOrBeforeOwned(hft, tree)
       val end = getLastNonTrivial(treeTokens, tree)
-      val kw = next(getClosingIfWithinParens(end)(beg).toOption.fold(end)(next))
+      val kw = next(getClosingIfWithinParens(end)(beg).fold(end)(next))
       if (!kw.left.is[A]) return None
 
       val indent = style.indent.ctrlSite.getOrElse(style.indent.getSignificant)
diff --git a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatTokens.scala b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatTokens.scala
index 63e4a87e10..823d8cf587 100644
--- a/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatTokens.scala
+++ b/scalafmt-core/shared/src/main/scala/org/scalafmt/internal/FormatTokens.scala
@@ -133,28 +133,37 @@ class FormatTokens(leftTok2tok: Map[TokenHash, Int])(val arr: Array[FT])
     .exists(_._1.left.is[T.LeftBrace])
 
   def isEnclosedWithinParens(tree: Tree): Boolean =
-    getClosingIfWithinParens(tree).isRight
+    getClosingIfWithinParens(tree).isDefined
+
+  def getClosingIfWithinParens(tree: Tree): Option[FT] =
+    getClosingIfWithinParensOrBraces(tree).flatMap(_.toOption)
+
+  def getClosingIfWithinParens(last: FT)(head: FT): Option[FT] =
+    getClosingIfWithinParensOrBraces(last)(head).flatMap(_.toOption)
 
   def isEnclosedWithinParensOrBraces(tree: Tree): Boolean =
-    getClosingIfWithinParens(tree) != Left(false)
+    getClosingIfWithinParensOrBraces(tree).isDefined
 
-  def getClosingIfWithinParens(last: FT)(head: FT): Either[Boolean, FT] = {
+  def getClosingIfWithinParensOrBraces(
+      last: FT,
+  )(head: FT): Option[Either[FT, FT]] = {
     val innerMatched = matchingOptLeft(last).contains(head)
-    if (innerMatched && last.left.is[T.RightParen]) Right(prev(last))
+    if (innerMatched && last.left.is[T.RightParen]) Some(Right(prev(last)))
     else {
       val afterLast = nextNonComment(last)
-      if (matchingOptRight(afterLast).exists(_ eq prevNonCommentBefore(head)))
-        if (afterLast.right.is[T.RightParen]) Right(afterLast) else Left(true)
-      else Left(innerMatched)
+      if (!matchingOptRight(afterLast).exists(_ eq prevNonCommentBefore(head)))
+        if (innerMatched) Some(Left(prev(last))) else None
+      else
+        Some(Either.cond(afterLast.right.is[T.RightParen], afterLast, afterLast))
     }
   }
 
-  def getClosingIfWithinParens(tree: Tree): Either[Boolean, FT] = {
+  def getClosingIfWithinParensOrBraces(tree: Tree): Option[Either[FT, FT]] = {
     val tokens = tree.tokens
     getHeadOpt(tokens, tree) match {
       case Some(head) =>
-        getClosingIfWithinParens(getLastNonTrivial(tokens, tree))(head)
-      case None => Left(false)
+        getClosingIfWithinParensOrBraces(getLastNonTrivial(tokens, tree))(head)
+      case None => None
     }
   }