diff --git a/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala b/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
index d8f7dd32c9bd..2e49e7ffce72 100644
--- a/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
+++ b/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
@@ -125,6 +125,18 @@ trait TypeAssigner {
     else
       qualType
 
+  def maybeSkolemizePrefix(tree: untpd.Tree, qualType: Type, name: Name)(using Context): Type =
+    if name.isTermName && !TypeOps.isLegalPrefix(qualType) then
+      tree.getAttachment(QualSkolem) match
+        case Some(skolem) if skolem.info == qualType =>
+          skolem
+        case _ =>
+          val skolem = QualSkolemType(qualType)
+          tree.putAttachment(QualSkolem, skolem)
+          skolem
+    else
+      qualType
+
   /** The type of the selection `tree`, where `qual1` is the typed qualifier part. */
   def selectionType(tree: untpd.RefTree, qual1: Tree)(using Context): Type =
     val qualType =
@@ -155,7 +167,7 @@ trait TypeAssigner {
       // is casted to T[] by javac. Since the return type of Array[T]#clone() is Array[T],
       // this is exactly what Erasure will do.
       case _ =>
-        val pre = maybeSkolemizePrefix(qualType, name)
+        val pre = maybeSkolemizePrefix(tree, qualType, name)
         val mbr =
           if ctx.isJava then
             // don't look in the companion class here if qual is a module,
@@ -621,6 +633,11 @@ object TypeAssigner extends TypeAssigner:
    */
   private[dotc] val SkolemizedArgs = new Property.StickyKey[Map[tpd.Tree, SkolemType]]
 
+  /** An attachment on a selection holding the `QualSkolemType` used to type it.
+   *  Sticky so that copies of the tree (e.g. while inlining) keep the same skolem.
+   */
+  private[dotc] val QualSkolem = new Property.StickyKey[QualSkolemType]
+
   def seqLitType(tree: untpd.SeqLiteral, elemType: Type)(using Context) = tree match
     case tree: untpd.JavaSeqLiteral => defn.ArrayOf(elemType)
     case _ => if ctx.erasedTypes then defn.SeqType else defn.SeqType.appliedTo(elemType)
diff --git a/compiler/test/dotc/run-test-pickling.excludelist b/compiler/test/dotc/run-test-pickling.excludelist
index 6aa8a67982b3..05f772a17cc2 100644
--- a/compiler/test/dotc/run-test-pickling.excludelist
+++ b/compiler/test/dotc/run-test-pickling.excludelist
@@ -52,5 +52,9 @@ typeCheckErrors.scala
 i18150.scala
 i22968.scala
 
+# Unstable-prefix selection: typer skolemizes, unpickling recomputes without skolem
+# so info goes from Box[(Owner#w : Int)] to Box[? <: (Owner#w : Int)]. Separate fix later.
+i26681.scala
+
 # Pickling differences with local parameters export forwarders of methods with into parameters. But their external type is the same
 Parser.scala
diff --git a/tests/neg/i26681b.scala b/tests/neg/i26681b.scala
new file mode 100644
index 000000000000..2e3aa19f22f5
--- /dev/null
+++ b/tests/neg/i26681b.scala
@@ -0,0 +1,16 @@
+// https://github.com/scala/scala3/issues/26681
+class Box[T](val x: T)
+
+class Owner:
+  val w: Int = 8
+  val b: Box[w.type] = new Box(w)
+  def get: Box[w.type] = new Box(w)
+  def set(bb: Box[w.type]): Unit = ()
+
+def unstable: Owner = new Owner
+
+def same[T](a: Box[T], b: Box[T]): Unit = ()
+
+def t1 = same(unstable.b, unstable.b) // error
+def t2 = same(unstable.get, unstable.get) // error
+def t3 = unstable.set(unstable.get) // error
diff --git a/tests/run/i26681.check b/tests/run/i26681.check
new file mode 100644
index 000000000000..79ebd0860f49
--- /dev/null
+++ b/tests/run/i26681.check
@@ -0,0 +1,2 @@
+ok
+ok
diff --git a/tests/run/i26681.scala b/tests/run/i26681.scala
new file mode 100644
index 000000000000..5f299659f94b
--- /dev/null
+++ b/tests/run/i26681.scala
@@ -0,0 +1,19 @@
+// https://github.com/scala/scala3/issues/26681
+class Box[T]
+
+class Owner:
+  val w: Int = 8
+  val b: Box[w.type] = new Box[w.type]
+
+def use[T](b: Box[T]): String = "ok"
+
+def unstable: Owner = new Owner
+
+transparent inline def f(inline rhs: Any): Any =
+  inline rhs match
+    case r: Box[t] => use[t](r)
+
+@main def Test =
+  println(f(unstable.b))
+  val o = unstable
+  println(f(o.b))