diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index b8a8be57ca05..56914108b7a8 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -25,6 +25,7 @@ import annotation.constructorOnly
 import cc.*
 import NameKinds.WildcardParamName
 import MatchTypes.isConcrete
+import scala.util.boundary, boundary.break
 
 /** Provides methods to compare types.
  */
@@ -2054,6 +2055,45 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
     else op2
   end necessaryEither
 
+  /** Finds the necessary (the weakest) GADT constraint among a list of them.
+   * It returns the one being subsumed by all others if exists, and `None` otherwise.
+   *
+   * This is used when typechecking pattern alternatives, for instance:
+   *
+   *   enum Expr[+T]:
+   *     case I1(x: Int) extends Expr[Int]
+   *     case I2(x: Int) extends Expr[Int]
+   *     case B(x: Boolean) extends Expr[Boolean]
+   *   import Expr.*
+   *
+   * The following function should compile:
+   *
+   *   def foo[T](e: Expr[T]): T = e match
+   *     case I1(_) | I2(_) => 42
+   *
+   * since `T >: Int` is subsumed by both alternatives in the first match clause.
+   *
+   * However, the following should not:
+   * 
+   *   def foo[T](e: Expr[T]): T = e match
+   *     case I1(_) | B(_) => 42
+   *
+   * since the `I1(_)` case gives the constraint `T >: Int` while `B(_)` gives `T >: Boolean`.
+   * Neither of the constraints is subsumed by the other.
+   */
+  def necessaryGadtConstraint(constrs: List[GadtConstraint], preGadt: GadtConstraint)(using Context): Option[GadtConstraint] = boundary:
+    constrs match
+      case Nil => break(None)
+      case c0 :: constrs =>
+        var weakest = c0
+        for c <- constrs do
+          if subsumes(weakest.constraint, c.constraint, preGadt.constraint) then
+            weakest = c
+          else if !subsumes(c.constraint, weakest.constraint, preGadt.constraint) then
+            // this two constraints are disjoint
+            break(None)
+        break(Some(weakest))
+
   inline def rollbackConstraintsUnless(inline op: Boolean): Boolean =
     val saved = constraint
     var result = false
@@ -3376,6 +3416,9 @@ object TypeComparer {
   def constrainPatternType(pat: Type, scrut: Type, forceInvariantRefinement: Boolean = false)(using Context): Boolean =
     comparing(_.constrainPatternType(pat, scrut, forceInvariantRefinement))
 
+  def necessaryGadtConstraint(constrs: List[GadtConstraint], preGadt: GadtConstraint)(using Context): Option[GadtConstraint] =
+    comparing(_.necessaryGadtConstraint(constrs, preGadt))
+
   def explained[T](op: ExplainingTypeComparer => T, header: String = "Subtype trace:", short: Boolean = false)(using Context): String =
     comparing(_.explained(op, header, short))
 
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index b69873e2b49f..40e30aed582b 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -2826,10 +2826,20 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
       else
         assert(ctx.reporter.errorsReported)
         tree.withType(defn.AnyType)
-    val savedGadt = nestedCtx.gadt
-    val trees1 = tree.trees.mapconserve(typed(_, pt)(using nestedCtx))
+    val preGadt = nestedCtx.gadt
+    var gadtConstrs: mutable.ArrayBuffer[GadtConstraint] = mutable.ArrayBuffer.empty
+    val trees1 = tree.trees.mapconserve: t =>
+        nestedCtx.gadtState.restore(preGadt)
+        val res = typed(t, pt)(using nestedCtx)
+        gadtConstrs += ctx.gadt
+        res
       .mapconserve(ensureValueTypeOrWildcard)
-    nestedCtx.gadtState.restore(savedGadt)  // Disable GADT reasoning for pattern alternatives
+    // Look for the necessary constraint that is subsumed by all alternatives.
+    // Use that constraint as the outcome if possible, otherwise fallback to not using
+    // GADT reasoning for soundness.
+    TypeComparer.necessaryGadtConstraint(gadtConstrs.toList, preGadt) match
+      case Some(constr) => nestedCtx.gadtState.restore(constr)
+      case None => nestedCtx.gadtState.restore(preGadt)
     assignType(cpy.Alternative(tree)(trees1), trees1)
   }
 
diff --git a/tests/neg/gadt-alt-expr1.scala b/tests/neg/gadt-alt-expr1.scala
new file mode 100644
index 000000000000..dc3296e781c8
--- /dev/null
+++ b/tests/neg/gadt-alt-expr1.scala
@@ -0,0 +1,13 @@
+enum Expr[+T]:
+  case I1() extends Expr[Int]
+  case I2() extends Expr[Int]
+  case B() extends Expr[Boolean]
+import Expr.*
+def foo[T](e: Expr[T]): T =
+  e match
+    case I1() | I2() => 42  // ok
+    case B() => true
+def bar[T](e: Expr[T]): T =
+  e match
+    case I1() | B() => 42  // error
+    case I2() => 0
diff --git a/tests/neg/gadt-alt-expr2.scala b/tests/neg/gadt-alt-expr2.scala
new file mode 100644
index 000000000000..a7e05cbe0870
--- /dev/null
+++ b/tests/neg/gadt-alt-expr2.scala
@@ -0,0 +1,15 @@
+enum Expr[+T]:
+  case I1() extends Expr[Int]
+  case I2() extends Expr[Int]
+  case I3() extends Expr[Int]
+  case I4() extends Expr[Int]
+  case I5() extends Expr[Int]
+  case B() extends Expr[Boolean]
+import Expr.*
+def test1[T](e: Expr[T]): T =
+  e match
+    case I1() | I2() | I3() | I4() | I5() => 42  // ok
+    case B() => true
+def test2[T](e: Expr[T]): T =
+  e match
+    case I1() | I2() | I3() | I4() | I5() | B() => 42  // error
diff --git a/tests/neg/gadt-alt-expr3.scala b/tests/neg/gadt-alt-expr3.scala
new file mode 100644
index 000000000000..a6ebf69ba8d1
--- /dev/null
+++ b/tests/neg/gadt-alt-expr3.scala
@@ -0,0 +1,34 @@
+trait A
+trait B extends A
+trait C extends B
+trait D
+enum Expr[+T]:
+  case IsA() extends Expr[A]
+  case IsB() extends Expr[B]
+  case IsC() extends Expr[C]
+  case IsD() extends Expr[D]
+import Expr.*
+def test1[T](e: Expr[T]): T = e match
+  case IsA() => new A {}
+  case IsB() => new B {}
+  case IsC() => new C {}
+def test2[T](e: Expr[T]): T = e match
+  case IsA() | IsB() =>
+    // IsA() implies T >: A
+    // IsB() implies T >: B
+    // So T >: B is chosen
+    new B {}
+  case IsC() => new C {}
+def test3[T](e: Expr[T]): T = e match
+  case IsA() | IsB() | IsC() =>
+    // T >: C is chosen
+    new C {}
+def test4[T](e: Expr[T]): T = e match
+  case IsA() | IsB() | IsC() =>
+    new B {}  // error
+def test5[T](e: Expr[T]): T = e match
+  case IsA() | IsB() =>
+    new A {}  // error
+def test6[T](e: Expr[T]): T = e match
+  case IsA() | IsC() | IsD() =>
+    new C {}  // error
diff --git a/tests/neg/gadt-alt-expr4.scala b/tests/neg/gadt-alt-expr4.scala
new file mode 100644
index 000000000000..6b85655c40c1
--- /dev/null
+++ b/tests/neg/gadt-alt-expr4.scala
@@ -0,0 +1,19 @@
+trait A
+trait B extends A
+trait C extends B
+enum Expr[T]:
+  case IsA() extends Expr[A]
+  case IsB() extends Expr[B]
+  case IsC() extends Expr[C]
+import Expr.*
+def test1[T](e: Expr[T]): T = e match
+  case IsA() => new A {}
+  case IsB() => new B {}
+  case IsC() => new C {}
+def test2[T](e: Expr[T]): T = e match
+  case IsA() | IsB() =>
+    // IsA() implies T =:= A
+    // IsB() implies T =:= B
+    // No necessary constraint can be found
+    new B {}  // error
+  case IsC() => new C {}
diff --git a/tests/neg/gadt-alt-expr5.scala b/tests/neg/gadt-alt-expr5.scala
new file mode 100644
index 000000000000..19993a6f34ab
--- /dev/null
+++ b/tests/neg/gadt-alt-expr5.scala
@@ -0,0 +1,14 @@
+trait A
+trait B extends A
+trait C extends B
+enum Expr[-T]:
+  case IsA() extends Expr[A]
+  case IsB() extends Expr[B]
+  case IsC() extends Expr[C]
+import Expr.*
+def test1[T](e: Expr[T]): Unit = e match
+  case IsA() | IsB() =>
+    val t1: T = ???
+    val t2: A = t1
+    val t3: B = t1  // error
+  case IsC() =>
diff --git a/tests/neg/gadt-alternatives.scala b/tests/neg/gadt-alternatives.scala
index 034f88ea5f24..e105e1f1d0fd 100644
--- a/tests/neg/gadt-alternatives.scala
+++ b/tests/neg/gadt-alternatives.scala
@@ -6,4 +6,4 @@ import Expr.*
 def eval[T](e: Expr[T]): T = e match
   case StringVal(_) | IntVal(_) => "42"  // error
 def eval1[T](e: Expr[T]): T = e match
-  case IntValAlt(_) | IntVal(_) => 42  // error // limitation
+  case IntValAlt(_) | IntVal(_) => 42  // previously error, now ok
diff --git a/tests/pos/gadt-alt-doc1.scala b/tests/pos/gadt-alt-doc1.scala
new file mode 100644
index 000000000000..f6457b4660e0
--- /dev/null
+++ b/tests/pos/gadt-alt-doc1.scala
@@ -0,0 +1,8 @@
+trait Document[Doc <: Document[Doc]]
+sealed trait Conversion[Doc, V]
+
+case class C[Doc <: Document[Doc]]() extends Conversion[Doc, Doc]
+
+def Test[Doc <: Document[Doc], V](conversion: Conversion[Doc, V]) =
+  conversion match
+    case C() | C() => ??? // error