diff --git a/compiler/src/dotty/tools/dotc/parsing/Scanners.scala b/compiler/src/dotty/tools/dotc/parsing/Scanners.scala
index 1412b5a04f47..15b3f6e63134 100644
--- a/compiler/src/dotty/tools/dotc/parsing/Scanners.scala
+++ b/compiler/src/dotty/tools/dotc/parsing/Scanners.scala
@@ -369,7 +369,7 @@ object Scanners {
       *     token that can start an expression.
       *  If a leading infix operator is found and the source version is `3.0-migration`, emit a change warning.
       */
-    def isLeadingInfixOperator(inConditional: Boolean = true) =
+    def isLeadingInfixOperator(nextWidth: IndentWidth = indentWidth(offset), inConditional: Boolean = true) =
       allowLeadingInfixOperators
       && isOperator
       && (isWhitespace(ch) || ch == LF)
@@ -397,6 +397,20 @@ object Scanners {
         assumeStartsExpr(lookahead)
         || lookahead.token == NEWLINE && assumeStartsExpr(lookahead.next)
       }
+      && {
+        currentRegion match
+          case r: Indented =>
+            r.width <= nextWidth
+            || {
+              r.outer match
+                case null => true
+                case Indented(outerWidth, others, _, _) =>
+                  outerWidth < nextWidth && !others.contains(nextWidth)
+                case outer =>
+                  outer.indentWidth < nextWidth
+            }
+          case _ => true
+      }
       && {
         if migrateTo3 then
           val (what, previous) =
@@ -512,7 +526,7 @@ object Scanners {
       if newlineIsSeparating
          && canEndStatTokens.contains(lastToken)
          && canStartStatTokens.contains(token)
-         && !isLeadingInfixOperator()
+         && !isLeadingInfixOperator(nextWidth)
          && !(lastWidth < nextWidth && isContinuing(lastToken))
       then
         insert(if (pastBlankLine) NEWLINES else NEWLINE, lineOffset)
@@ -521,7 +535,7 @@ object Scanners {
            || nextWidth == lastWidth && (indentPrefix == MATCH || indentPrefix == CATCH) && token != CASE then
           if currentRegion.isOutermost then
             if nextWidth < lastWidth then currentRegion = topLevelRegion(nextWidth)
-          else if !isLeadingInfixOperator() && !statCtdTokens.contains(lastToken) then
+          else if !isLeadingInfixOperator(nextWidth) && !statCtdTokens.contains(lastToken) then
             currentRegion match
               case r: Indented =>
                 currentRegion = r.enclosing
@@ -1105,7 +1119,7 @@ object Scanners {
           putChar(ch)
           nextRawChar()
         getStringPart(multiLine)
-      } 
+      }
       else if (ch == '$') {
         nextRawChar()
         if (ch == '$' || ch == '"') {
diff --git a/docs/docs/reference/other-new-features/indentation.md b/docs/docs/reference/other-new-features/indentation.md
index 7d28c821cbf3..4b1b78a9bf4e 100644
--- a/docs/docs/reference/other-new-features/indentation.md
+++ b/docs/docs/reference/other-new-features/indentation.md
@@ -80,8 +80,11 @@ There are two rules:
       ```
       then  else  do  catch  finally  yield  match
       ```
-    - the first token on the next line is not a
+    - if the first token on the next line is a
         [leading infix operator](../changed-features/operators.md).
+      then its indentation width is less then the current indentation width,
+      and it either matches a previous indentation width or is also less
+      than the enclosing indentation width.
 
     If an `<outdent>` is inserted, the top element is popped from `IW`.
     If the indentation width of the token on the next line is still less than the new current indentation width, step (2) repeats. Therefore, several `<outdent>` tokens
@@ -105,6 +108,24 @@ if x < 0 then
 Indentation tokens are only inserted in regions where newline statement separators are also inferred:
 at the top-level, inside braces `{...}`, but not inside parentheses `(...)`, patterns or types.
 
+**Note:** The rules for leading infix operators above are there to make sure that
+```scala
+  one
+  + two.match
+      case 1 => b
+      case 2 => c
+  + three
+```
+is parsed as `one + (two.match ...) + three`. Also, that
+```scala
+if x then
+    a
+  + b
+  + c
+else d
+```
+is parsed as `if x then a + b + c else d`.
+
 ### Optional Braces Around Template Bodies
 
 The Scala grammar uses the term _template body_ for the definitions of a class, trait, or object that are normally enclosed in braces. The braces around a template body can also be omitted by means of the following rule.
diff --git a/tests/run/indent.scala b/tests/run/indent.scala
new file mode 100644
index 000000000000..24cb22a5c354
--- /dev/null
+++ b/tests/run/indent.scala
@@ -0,0 +1,12 @@
+@main def Test =
+  val x = false
+  val y = 1
+  val result =
+    x
+    || y.match
+        case 1 => false
+        case 3 => false
+        case _ => true
+    || !x
+  assert(result)
+