diff --git a/compiler/src/dotty/tools/dotc/typer/Inliner.scala b/compiler/src/dotty/tools/dotc/typer/Inliner.scala
index d097ed8dcc4e..4a06ee3ce07c 100644
--- a/compiler/src/dotty/tools/dotc/typer/Inliner.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Inliner.scala
@@ -196,7 +196,7 @@ object Inliner {
     // as its right hand side. The call to the wrapper unapply serves as the signpost for pattern matching.
     // After pattern matching, the anonymous class is removed in phase InlinePatterns with a beta reduction step.
     //
-    // An inline unapply `P.unapply` in a plattern `P(x1,x2,...)` is transformed into
+    // An inline unapply `P.unapply` in a pattern `P(x1,x2,...)` is transformed into
     // `{ class $anon { def unapply(t0: T0)(using t1: T1, t2: T2, ...): R = P.unapply(t0)(using t1, t2, ...) }; new $anon }.unapply`
     // and the call `P.unapply(x1, x2, ...)` is inlined.
     // This serves as a placeholder for the inlined body until the `patternMatcher` phase. After pattern matcher
@@ -210,18 +210,24 @@ object Inliner {
 
     val targs = fun match
       case TypeApply(_, targs) => targs
+      case Apply(TypeApply(_, targs), _) => targs
       case _ => Nil
     val unapplyInfo = sym.info match
-      case info: PolyType => info.instantiate(targs.map(_.tpe))
+      case info: PolyType => info.instantiate(targs.map(_.tpe)) match
+        case MethodTpe(_, _, rt: PolyType) => rt.instantiate(targs.map(_.tpe))
+        case MethodTpe(_, _, rt) if sym.flags.is(ExtensionMethod) => rt
+        case info => info
+      case MethodTpe(_, _, rt: PolyType) => rt.instantiate(targs.map(_.tpe))
+      case MethodTpe(_, _, rt) if sym.flags.is(ExtensionMethod) => rt
       case info => info
 
-    val unappplySym = newSymbol(cls, sym.name.toTermName, Synthetic | Method, unapplyInfo, coord = sym.coord).entered
-    val unapply = DefDef(unappplySym, argss =>
-      inlineCall(fun.appliedToArgss(argss).withSpan(unapp.span))(using ctx.withOwner(unappplySym))
+    val unapplySym = newSymbol(cls, sym.name.toTermName, Synthetic | Method, unapplyInfo, coord = sym.coord).entered
+    val unapply = DefDef(unapplySym, argss =>
+      inlineCall(fun.appliedToArgss(argss).withSpan(unapp.span))(using ctx.withOwner(unapplySym))
     )
     val cdef = ClassDef(cls, DefDef(constr), List(unapply))
     val newUnapply = Block(cdef :: Nil, New(cls.typeRef, Nil))
-    val newFun = newUnapply.select(unappplySym).withSpan(unapp.span)
+    val newFun = newUnapply.select(unapplySym).withSpan(unapp.span)
     cpy.UnApply(unapp)(newFun, implicits, patterns)
   }
 
diff --git a/tests/pos/i8577/MacroA_1.scala b/tests/pos/i8577/MacroA_1.scala
new file mode 100644
index 000000000000..1a147038adce
--- /dev/null
+++ b/tests/pos/i8577/MacroA_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroA:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyA(sc: Expr[MacroB.StringContext], input: Expr[Int])
+                   (using Quotes): Expr[Option[Seq[Int]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroB_1.scala b/tests/pos/i8577/MacroB_1.scala
new file mode 100644
index 000000000000..e5b4ee5b5c66
--- /dev/null
+++ b/tests/pos/i8577/MacroB_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroB:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyB[U](sc: Expr[MacroB.StringContext], input: Expr[U])
+                   (using Type[U])(using Quotes): Expr[Option[Seq[U]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroC_1.scala b/tests/pos/i8577/MacroC_1.scala
new file mode 100644
index 000000000000..be7047cb3527
--- /dev/null
+++ b/tests/pos/i8577/MacroC_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroC:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyC[T](sc: Expr[MacroC.StringContext], input: Expr[T])
+                   (using Type[T])(using Quotes): Expr[Option[Seq[T]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroD_1.scala b/tests/pos/i8577/MacroD_1.scala
new file mode 100644
index 000000000000..3e8d6df54484
--- /dev/null
+++ b/tests/pos/i8577/MacroD_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroD:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyD[T](sc: Expr[MacroD.StringContext], input: Expr[T])
+                   (using Type[T])(using Quotes): Expr[Option[Seq[T]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroE_1.scala b/tests/pos/i8577/MacroE_1.scala
new file mode 100644
index 000000000000..3351e3329c65
--- /dev/null
+++ b/tests/pos/i8577/MacroE_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroE:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyE[T, U](sc: Expr[MacroE.StringContext], input: Expr[U])
+                      (using Type[U])(using Quotes): Expr[Option[Seq[U]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroF_1.scala b/tests/pos/i8577/MacroF_1.scala
new file mode 100644
index 000000000000..ebe01cbbacd7
--- /dev/null
+++ b/tests/pos/i8577/MacroF_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroF:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyF[T, U](sc: Expr[MacroF.StringContext], input: Expr[(T, U)])
+                      (using Type[T], Type[U])(using Quotes): Expr[Option[Seq[(T, U)]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/MacroG_1.scala b/tests/pos/i8577/MacroG_1.scala
new file mode 100644
index 000000000000..4324b553a7c1
--- /dev/null
+++ b/tests/pos/i8577/MacroG_1.scala
@@ -0,0 +1,12 @@
+package i8577
+
+import scala.quoted._
+
+object MacroG:
+  opaque type StringContext = scala.StringContext
+  def apply(ctx: scala.StringContext): StringContext = ctx
+  def unapply(ctx: StringContext): Option[scala.StringContext] = Some(ctx)
+
+def implUnapplyG[T, U](sc: Expr[MacroG.StringContext], input: Expr[T | U])
+                      (using Type[T], Type[U])(using Quotes): Expr[Option[Seq[T | U]]] =
+  '{ Some(Seq(${input})) }
diff --git a/tests/pos/i8577/Main_2.scala b/tests/pos/i8577/Main_2.scala
new file mode 100644
index 000000000000..43c818237689
--- /dev/null
+++ b/tests/pos/i8577/Main_2.scala
@@ -0,0 +1,164 @@
+package i8577
+
+def main: Unit = {
+  {
+    extension (ctx: StringContext) def macroA: MacroB.StringContext = MacroB(ctx)
+    extension (inline ctx: MacroB.StringContext) inline def unapplySeq(inline input: Int): Option[Seq[Int]] =
+      ${implUnapplyA('ctx, 'input)}
+
+    val macroA"$xA" = 1
+  }
+
+  {
+    extension (ctx: StringContext) def macroB: MacroB.StringContext = MacroB(ctx)
+    extension (inline ctx: MacroB.StringContext) inline def unapplySeq[U](inline input: U): Option[Seq[U]] =
+      ${ implUnapplyB('ctx, 'input) }
+
+    val macroB"$xB" = 2
+  }
+
+  {
+    extension (ctx: StringContext) def macroC: MacroC.StringContext = MacroC(ctx)
+    extension [T] (inline ctx: MacroC.StringContext) inline def unapplySeq(inline input: T): Option[Seq[T]] =
+      ${ implUnapplyC('ctx, 'input) }
+
+    val macroC"$xC" = 3
+  }
+
+  {
+    extension (ctx: StringContext) def macroD: MacroD.StringContext = MacroD(ctx)
+    extension [T] (inline ctx: MacroD.StringContext) inline def unapplySeq[U](inline input: T): Option[Seq[T]] =
+      ${ implUnapplyD('ctx, 'input) }
+
+    // miscompilation
+//    val macroD"$xD" = 4
+  }
+
+  {
+    extension (ctx: StringContext) def macroE: MacroE.StringContext = MacroE(ctx)
+    extension [T] (inline ctx: MacroE.StringContext) inline def unapplySeq[U](inline input: U): Option[Seq[U]] =
+      ${ implUnapplyE('ctx, 'input) }
+
+    val macroE"$xE" = 5
+  }
+
+  {
+    extension (ctx: StringContext) def macroF: MacroF.StringContext = MacroF(ctx)
+    extension [T] (inline ctx: MacroF.StringContext) inline def unapplySeq[U](inline input: (T, U)): Option[Seq[(T, U)]] =
+      ${ implUnapplyF('ctx, 'input) }
+
+    val macroF"$xF" = (6, 7)
+
+    // miscompilation
+//    val macroF"$xF" = (6, "7")
+  }
+
+  {
+    extension (ctx: StringContext) def macroG: MacroG.StringContext = MacroG(ctx)
+    extension [T] (inline ctx: MacroG.StringContext) inline def unapplySeq[U](inline input: T | U): Option[Seq[T | U]] =
+      ${ implUnapplyG('ctx, 'input) }
+
+    // compiler error
+//    val macroG"$xG" = 8
+  }
+}
+
+//  {
+//    // B
+//    object F2
+//    extension (o: F2.type) inline def unapplySeq[T](inline x: T) = Some(Seq(x))
+//
+//    val F2(x) = 16
+//    println(s"F2: $x")
+//  }
+//
+//  {
+//    // C
+//    object F1
+//    extension [T] (o: F1.type) inline def unapplySeq(inline x: T) = Some(Seq(x))
+//
+//    val F1(x) = 15
+//    println(s"F1: $x")
+//  }
+//
+//  {
+//    // D
+//    object F4b
+//    extension [T] (o: F4b.type) inline def unapplySeq[U](inline x: T) = Some(Seq(x))
+//
+//    val F4b(x) = 18.2
+//    println(s"F4b: $x")
+//  }
+//
+//  {
+//    // E
+//    object F4b
+//    extension [T] (o: F4b.type) inline def unapplySeq[U](inline x: U) = Some(Seq(x))
+//
+//    val F4b(x) = 18.2
+//    println(s"F4b: $x")
+//  }
+//
+//  {
+//    // F
+//    object F4d
+//    extension [T] (o: F4d.type) inline def unapplySeq[U](inline x: (T, U)) = Some(Seq(x))
+//
+//    val F4d(x) = (18.4, 18.5)
+//    println(s"F4d: $x")
+//  }
+//
+//  {
+//    // G
+//    object H1
+//    extension (inline o: H1.type) inline def unapplySeq(inline x: Int) = Some(Seq(x))
+//
+//    val H1(x) = 23
+//    println(s"H1: $x")
+//  }
+//
+//  {
+//    // H
+//    object H2
+//    extension (inline o: H2.type) inline def unapplySeq[T](inline x: T) = Some(Seq(x))
+//
+//    val H2(x) = 24
+//    println(s"H2: $x")
+//  }
+//
+//  {
+//    // I
+//    object H2
+//    extension [T] (inline o: H2.type) inline def unapplySeq(inline x: T) = Some(Seq(x))
+//
+//    val H2(x) = 24
+//    println(s"H2: $x")
+//  }
+//
+//  {
+//    // J
+//    object H2
+//    extension [T] (inline o: H2.type) inline def unapplySeq[U](inline x: T) = Some(Seq(x))
+//
+//    val H2(x) = 24
+//    println(s"H2: $x")
+//  }
+//
+//  {
+//    // K
+//    object H2
+//    extension [T] (inline o: H2.type) inline def unapplySeq[U](inline x: U) = Some(Seq(x))
+//
+//    val H2(x) = 24
+//    println(s"H2: $x")
+//  }
+//
+//  {
+//    // L
+//    object H2
+//    extension [T] (inline o: H2.type) inline def unapplySeq[U](inline x: (T, U)) = Some(Seq(x))
+//
+//    val H2(x) = (24, "a")
+//    println(s"H2: $x")
+//  }
+//}