diff --git a/compiler/src/dotty/tools/dotc/typer/ConstFold.scala b/compiler/src/dotty/tools/dotc/typer/ConstFold.scala
index 4633c187912f..3e09642d291d 100644
--- a/compiler/src/dotty/tools/dotc/typer/ConstFold.scala
+++ b/compiler/src/dotty/tools/dotc/typer/ConstFold.scala
@@ -29,12 +29,12 @@ object ConstFold:
   def Apply[T <: Apply](tree: T)(using Context): T =
     tree.fun match
       case Select(xt, op) if foldedBinops.contains(op) =>
-        xt.tpe.widenTermRefExpr.normalized match
-          case ConstantType(x) =>
+        xt match
+          case ConstantTree(x) =>
             tree.args match
               case yt :: Nil =>
-                yt.tpe.widenTermRefExpr.normalized match
-                  case ConstantType(y) => tree.withFoldedType(foldBinop(op, x, y))
+                yt match
+                  case ConstantTree(y) => tree.withFoldedType(foldBinop(op, x, y))
                   case _ => tree
               case _ => tree
           case _ => tree
@@ -46,8 +46,8 @@ object ConstFold:
 
   def Select[T <: Select](tree: T)(using Context): T =
     if foldedUnops.contains(tree.name) then
-      tree.qualifier.tpe.widenTermRefExpr.normalized match
-        case ConstantType(x) => tree.withFoldedType(foldUnop(tree.name, x))
+      tree.qualifier match
+        case ConstantTree(x) => tree.withFoldedType(foldUnop(tree.name, x))
         case _ => tree
     else tree
 
@@ -59,6 +59,17 @@ object ConstFold:
       tree.withFoldedType(Constant(targ.tpe))
     case _ => tree
 
+  private object ConstantTree:
+    def unapply(tree: Tree)(using Context): Option[Constant] =
+      tree match
+        case Inlined(_, Nil, expr) => unapply(expr)
+        case Typed(expr, _) => unapply(expr)
+        case Literal(c) if c.tag == Constants.NullTag => Some(c)
+        case _ =>
+          tree.tpe.widenTermRefExpr.normalized.simplified match
+            case ConstantType(c) => Some(c)
+            case _ => None
+
   extension [T <: Tree](tree: T)(using Context)
     private def withFoldedType(c: Constant | Null): T =
       if c == null then tree else tree.withType(ConstantType(c)).asInstanceOf[T]
@@ -164,15 +175,24 @@ object ConstFold:
     case _ => null
   }
   private def foldStringOp(op: Name, x: Constant, y: Constant): Constant = op match {
-    case nme.ADD  => Constant(x.stringValue + y.stringValue)
+    case nme.ADD => Constant(x.stringValue + y.stringValue)
     case nme.EQ  => Constant(x.stringValue == y.stringValue)
+    case nme.NE  => Constant(x.stringValue != y.stringValue)
     case _ => null
   }
 
+  private def foldNullOp(op: Name, x: Constant, y: Constant): Constant =
+    assert(x.tag == NullTag || y.tag == NullTag)
+    op match
+      case nme.EQ => Constant(x.tag == y.tag)
+      case nme.NE => Constant(x.tag != y.tag)
+      case _ => null
+
   private def foldBinop(op: Name, x: Constant, y: Constant): Constant =
     val optag =
       if (x.tag == y.tag) x.tag
       else if (x.isNumeric && y.isNumeric) math.max(x.tag, y.tag)
+      else if (x.tag == NullTag || y.tag == NullTag) NullTag
       else NoTag
 
     try optag match
@@ -182,6 +202,7 @@ object ConstFold:
       case  FloatTag                              => foldFloatOp(op, x, y)
       case  DoubleTag                             => foldDoubleOp(op, x, y)
       case  StringTag                             => foldStringOp(op, x, y)
+      case  NullTag                               => foldNullOp(op, x, y)
       case  _                                     => null
       catch case ex: ArithmeticException => null // the code will crash at runtime,
                                                  // but that is better than the
diff --git a/tests/explicit-nulls/run/nn.scala b/tests/explicit-nulls/run/nn.scala
index 3ffff69649cf..12c6c2ddb3c8 100644
--- a/tests/explicit-nulls/run/nn.scala
+++ b/tests/explicit-nulls/run/nn.scala
@@ -15,7 +15,7 @@ object Test {
     val y: String|Null = null
     assertThrowsNPE(y.nn)
     assertThrowsNPE(null.nn)
-    assertThrowsNPE(len(null)) 
+    assertThrowsNPE(len(null))
     assertThrowsNPE(load(null))
   }
 }
diff --git a/tests/pos-macros/i12072/Macro_1.scala b/tests/pos-macros/i12072/Macro_1.scala
new file mode 100644
index 000000000000..d58160d8f00a
--- /dev/null
+++ b/tests/pos-macros/i12072/Macro_1.scala
@@ -0,0 +1,12 @@
+import scala.quoted.*
+
+object M {
+
+  transparent inline def f(inline s: String): String | Null =
+    ${ f('s) }
+
+  def f(s: Expr[String])(using Quotes): Expr[String | Null] = {
+    s.valueOrError // required
+    '{ null }
+  }
+}
diff --git a/tests/pos-macros/i12072/Test_2.scala b/tests/pos-macros/i12072/Test_2.scala
new file mode 100644
index 000000000000..772e21903fc5
--- /dev/null
+++ b/tests/pos-macros/i12072/Test_2.scala
@@ -0,0 +1,18 @@
+object T2 {
+  import M.f
+
+  private inline val V = "V"
+  private inline def D = "D"
+
+  trait Trait { def s: String }
+
+  object MatchFV extends Trait {
+    override transparent inline def s: String =
+      inline f(V) match { case "V" => "o"; case _   => "x" } // error in RC1
+  }
+
+  object MatchFD extends Trait {
+    override transparent inline def s: String =
+      inline f(D) match { case "D" => "o"; case _   => "x" }
+  }
+}
diff --git a/tests/pos/i12072-b.scala b/tests/pos/i12072-b.scala
new file mode 100644
index 000000000000..07bca25b68be
--- /dev/null
+++ b/tests/pos/i12072-b.scala
@@ -0,0 +1,9 @@
+transparent inline def f: Null = null
+
+inline def g: Unit =
+  inline if f == "V" then 1 else 2
+  inline if f != "V" then 3 else 4
+  inline if "v" == f then 5 else 6
+  inline if "v" != f then 7 else 8
+
+def test = g
diff --git a/tests/pos/i12072-c.scala b/tests/pos/i12072-c.scala
new file mode 100644
index 000000000000..f99f0da9049f
--- /dev/null
+++ b/tests/pos/i12072-c.scala
@@ -0,0 +1,86 @@
+object T {
+
+  transparent inline def f(inline s: String): String | Null =
+    null
+
+  inline val V = "V"
+  inline def D = "D"
+
+  trait Trait { def s: String }
+
+  // ===========================================================================
+  // inline {if,match} over inline {val,def}
+
+  transparent inline def if_v: String =
+    inline if V == "V" then "o" else "x"
+
+  transparent inline def if_d: String =
+    inline if D == "D" then "o" else "x"
+
+  transparent inline def match_v: String =
+    inline V match { case "V" => "o"; case _   => "x" }
+
+  transparent inline def match_d: String =
+    inline D match { case "D" => "o"; case _   => "x" }
+
+  // ===========================================================================
+  // inline {if,match} over inline f(inline {val,def})
+
+  transparent inline def if_fv: String =
+    inline if f(V) == "V" then "o" else "x"
+
+  transparent inline def if_fd: String =
+    inline if f(D) == "D" then "o" else "x"
+
+  transparent inline def match_fv: String =
+    inline f(V) match { case "V" => "o"; case _   => "x" }
+
+  transparent inline def match_fd: String =
+    inline f(D) match { case "D" => "o"; case _   => "x" }
+
+  // ===========================================================================
+  // inline {if,match} over inline {val,def} in overridden method
+
+  object IfV extends Trait {
+    override transparent inline def s: String =
+      inline if V == "V" then "o" else "x"
+  }
+
+  object IfD extends Trait {
+    override transparent inline def s: String =
+      inline if D == "D" then "o" else "x" // <--------------------------- error
+  }
+
+  object MatchV extends Trait {
+    override transparent inline def s: String =
+      inline V match { case "V" => "o"; case _   => "x" }
+  }
+
+  object MatchD extends Trait {
+    override transparent inline def s: String =
+      inline D match { case "D" => "o"; case _   => "x" }
+  }
+
+  // ===========================================================================
+  // inline {if,match} over inline f(inline {val,def}) in overridden method
+
+  object IfFV extends Trait {
+    override transparent inline def s: String =
+      inline if f(V) == "V" then "o" else "x" // <------------------------ error
+  }
+
+  object IfFD extends Trait {
+    override transparent inline def s: String =
+      inline if f(D) == "D" then "o" else "x" // <------------------------ error
+  }
+
+  object MatchFV extends Trait {
+    override transparent inline def s: String =
+      inline f(V) match { case "V" => "o"; case _   => "x" }
+  }
+
+  object MatchFD extends Trait {
+    override transparent inline def s: String =
+      inline f(D) match { case "D" => "o"; case _   => "x" }
+  }
+}
diff --git a/tests/pos/i12072-d.scala b/tests/pos/i12072-d.scala
new file mode 100644
index 000000000000..486e9f478771
--- /dev/null
+++ b/tests/pos/i12072-d.scala
@@ -0,0 +1,4 @@
+class Test:
+  def n: Null = null
+  def test1: Boolean = n == null
+  def test2: Boolean = null == n
diff --git a/tests/pos/i12072-e.scala b/tests/pos/i12072-e.scala
new file mode 100644
index 000000000000..713c86fba909
--- /dev/null
+++ b/tests/pos/i12072-e.scala
@@ -0,0 +1,3 @@
+def test: Boolean = nn(42) == 42
+
+def nn(x: Int): x.type & Int = ???
diff --git a/tests/pos/i12072.scala b/tests/pos/i12072.scala
new file mode 100644
index 000000000000..ab85059d676a
--- /dev/null
+++ b/tests/pos/i12072.scala
@@ -0,0 +1,8 @@
+inline def c: Int = 2
+
+trait A:
+  def f: Unit
+
+class B extends A:
+  override inline def f: Unit =
+    inline if c == 2 then () else ()