diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 9b60fb63c409..2942b3a92930 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -431,10 +431,17 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
           case Some(b) => return b
           case None =>
 
+        /** `recur` shouldn't normally be used with approximated types, according to its
+          * documentation. In the specific examples where this function is
+          * called, it is sound to do so as long as we freeze GADTs.
+          */
+        def recurInFrozenGadt(tp1: Type, tp2: Type) =
+          inFrozenGadt { recur(tp1, tp2) }
+
         def widenOK =
           (tp2.widenSingletons eq tp2)
           && (tp1.widenSingletons ne tp1)
-          && recur(tp1.widenSingletons, tp2)
+          && recurInFrozenGadt(tp1.widenSingletons, tp2)
 
         def joinOK = tp2.dealiasKeepRefiningAnnots match {
           case tp2: AppliedType if !tp2.tycon.typeSymbol.isClass =>
@@ -442,7 +449,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
             // type parameter, we will instantiate `C` to `A` and then fail when comparing
             // with `B[Y]`. To do the right thing, we need to instantiate `C` to the
             // common superclass of `A` and `B`.
-            recur(tp1.join, tp2)
+            recurInFrozenGadt(tp1.join, tp2)
           case _ =>
             false
         }
@@ -469,7 +476,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
         widenOK
         || joinOK
         || (tp1.isSoft || constrainRHSVars(tp2)) && recur(tp11, tp2) && recur(tp12, tp2)
-        || containsAnd(tp1) && recur(tp1.join, tp2)
+        || containsAnd(tp1) && recurInFrozenGadt(tp1.join, tp2)
      case tp1: MatchType =>
         val reduced = tp1.reduced
         if (reduced.exists) recur(reduced, tp2) else thirdTry
diff --git a/tests/neg/gadt-lhs-union.scala b/tests/neg/gadt-lhs-union.scala
new file mode 100644
index 000000000000..af34524c1f3f
--- /dev/null
+++ b/tests/neg/gadt-lhs-union.scala
@@ -0,0 +1,33 @@
+object A {
+  sealed trait Expr[+T]
+  final case class FooExpr() extends Expr[1 | 2]
+
+  object Test {
+    def foo[T](x: Expr[T]): T = x match {
+      case x: FooExpr =>
+        3 // error
+    }
+
+    val x: 1 | 2 = foo(FooExpr())
+  }
+}
+
+object B {
+  trait C
+  trait D extends C
+  trait E extends C
+  trait F extends C
+  trait G extends C
+
+  sealed trait Expr[+T]
+  final case class FooExpr[+S >: (D & E) | F]() extends Expr[S]
+
+  object Test {
+    def foo[T](x: Expr[T]): T = x match {
+      case x: FooExpr[(D & E) | F] =>
+        new D with E
+    }
+
+    val x: (D & E) | F = foo(FooExpr[(D & E) | F]())
+  }
+}