diff --git a/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala b/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
index 1341fac7d735..695575e68def 100644
--- a/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
+++ b/compiler/src/dotty/tools/dotc/core/OrderingConstraint.scala
@@ -454,7 +454,7 @@ class OrderingConstraint(private val boundsMap: ParamBounds,
    *  of the parameter elsewhere in the constraint by type `tp`.
    */
   def replace(param: TypeParamRef, tp: Type)(using Context): OrderingConstraint =
-    val replacement = tp.dealiasKeepAnnots.stripTypeVar
+    val replacement = tp.withDealiased(_.stripTypeVar)
     if param == replacement then this.checkNonCyclic()
     else
       assert(replacement.isValueTypeOrLambda)
diff --git a/compiler/src/dotty/tools/dotc/core/TypeOps.scala b/compiler/src/dotty/tools/dotc/core/TypeOps.scala
index 332129e72850..4d0e37e88a4a 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeOps.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeOps.scala
@@ -451,8 +451,8 @@ object TypeOps:
       try
         tp match
           case tp: TermRef if toAvoid(tp) =>
-            tp.info.widenExpr.dealias match {
-              case info: SingletonType => apply(info)
+            tp.info.widenExpr.withDealiased {
+              case singleton: SingletonType => apply(singleton)
               case info => range(defn.NothingType, apply(info))
             }
           case tp: TypeRef if toAvoid(tp) =>
diff --git a/compiler/src/dotty/tools/dotc/core/Types.scala b/compiler/src/dotty/tools/dotc/core/Types.scala
index 483745928f25..1cfd144358c5 100644
--- a/compiler/src/dotty/tools/dotc/core/Types.scala
+++ b/compiler/src/dotty/tools/dotc/core/Types.scala
@@ -1430,6 +1430,14 @@ object Types {
      */
     final def dealiasKeepOpaques(using Context): Type = dealias1(keepNever, keepOpaques = true)
 
+    /** Apply `f` to this type dealiased. If the type changes, keep the change,
+     *  otherwise return the original (not dealiased) type.
+     */
+    final def withDealiased(f: Type => Type)(using Context): Type =
+      val tpd = dealias
+      val result = f(tpd)
+      if result eq tpd then this else result
+
     /** Approximate this type with a type that does not contain skolem types. */
     final def deskolemized(using Context): Type =
       val deskolemizer = new ApproximatingTypeMap {
@@ -1478,10 +1486,9 @@ object Types {
     }
 
     /** Dealias, and if result is a dependent function type, drop the `apply` refinement. */
-    final def dropDependentRefinement(using Context): Type = dealias match {
+    final def dropDependentRefinement(using Context): Type = dealias match
       case RefinedType(parent, nme.apply, _) => parent
-      case tp => tp
-    }
+      case _ => this
 
     /** The type constructor of an applied type, otherwise the type itself */
     final def typeConstructor(using Context): Type = this match {
diff --git a/tests/neg/i14171.scala b/tests/neg/i14171.scala
new file mode 100644
index 000000000000..005746c0aaf3
--- /dev/null
+++ b/tests/neg/i14171.scala
@@ -0,0 +1,13 @@
+object Test:
+  trait MyTypeclass[F[_]]
+  def f[F[_]: MyTypeclass, U](t: F[U]) = ()
+
+  // using a non-singleton type makes it compile because `widenSingletons` dealiases
+  type MyType[T] = Nil.type
+  given MyTypeclass[MyType] = null
+
+  val stream: Option[MyType[Int]] = null
+  for
+    keyStream <- stream
+    x = 17 // commenting this line makes it compile
+  yield f(keyStream) // error
\ No newline at end of file
diff --git a/tests/pos/i14171.scala b/tests/pos/i14171.scala
new file mode 100644
index 000000000000..d2ab70179d02
--- /dev/null
+++ b/tests/pos/i14171.scala
@@ -0,0 +1,12 @@
+object Test:
+  trait MyTypeclass[F[_]]
+  def f[F[_]: MyTypeclass, U](t: F[U]) = ()
+
+  type MyType[T] = String
+  given MyTypeclass[MyType] = null
+
+  val stream: Option[MyType[Int]] = null
+  for
+    keyStream <- stream
+    x = 17
+  yield f(keyStream)
\ No newline at end of file