diff --git a/compiler/src/dotty/tools/dotc/tastyreflect/QuotedOpsImpl.scala b/compiler/src/dotty/tools/dotc/tastyreflect/QuotedOpsImpl.scala
index 8d7eb49c808d..ac6a0ddb033b 100644
--- a/compiler/src/dotty/tools/dotc/tastyreflect/QuotedOpsImpl.scala
+++ b/compiler/src/dotty/tools/dotc/tastyreflect/QuotedOpsImpl.scala
@@ -1,9 +1,6 @@
 package dotty.tools.dotc.tastyreflect
 
-import dotty.tools.dotc.core.Contexts.FreshContext
 import dotty.tools.dotc.core.quoted.PickledQuotes
-import dotty.tools.dotc.reporting.Reporter
-import dotty.tools.dotc.reporting.diagnostic.MessageContainer
 
 trait QuotedOpsImpl extends scala.tasty.reflect.QuotedOps with CoreImpl {
 
@@ -18,30 +15,17 @@ trait QuotedOpsImpl extends scala.tasty.reflect.QuotedOps with CoreImpl {
   def TermToQuoteDeco(term: Term): TermToQuotedAPI = new TermToQuotedAPI {
 
     def seal[T: scala.quoted.Type](implicit ctx: Context): scala.quoted.Expr[T] = {
-      typecheck(ctx)
+      typecheck()
       new scala.quoted.Exprs.TastyTreeExpr(term).asInstanceOf[scala.quoted.Expr[T]]
     }
 
-    private def typecheck[T: scala.quoted.Type](ctx: Context): Unit = {
-      implicit val ctx0: FreshContext = ctx.fresh
-      ctx0.setTyperState(ctx0.typerState.fresh())
-      ctx0.typerState.setReporter(new Reporter {
-        def doReport(m: MessageContainer)(implicit ctx: Context): Unit = ()
-      })
-      val tp = QuotedTypeDeco(implicitly[scala.quoted.Type[T]]).unseal
-      ctx0.typer.typed(term, tp.tpe)
-      if (ctx0.reporter.hasErrors) {
-        val stack = new Exception().getStackTrace
-        def filter(elem: StackTraceElement) =
-          elem.getClassName.startsWith("dotty.tools.dotc.tasty.ReflectionImpl") ||
-            !elem.getClassName.startsWith("dotty.tools.dotc")
+    private def typecheck[T: scala.quoted.Type]()(implicit ctx: Context): Unit = {
+      val tpt = QuotedTypeDeco(implicitly[scala.quoted.Type[T]]).unseal
+      if (!(term.tpe <:< tpt.tpe)) {
         throw new scala.tasty.TastyTypecheckError(
-          s"""Error during tasty reflection while typing term
-             |term: ${term.show}
-             |with expected type: ${tp.tpe.show}
-             |
-               |  ${stack.takeWhile(filter).mkString("\n  ")}
-             """.stripMargin
+          s"""Term: ${term.show}
+             |did not conform to type: ${tpt.tpe.show}
+             |""".stripMargin
         )
       }
     }
diff --git a/library/src/scala/tasty/TastyTypecheckError.scala b/library/src/scala/tasty/TastyTypecheckError.scala
index fc506c1ddecb..3fdeac37ae37 100644
--- a/library/src/scala/tasty/TastyTypecheckError.scala
+++ b/library/src/scala/tasty/TastyTypecheckError.scala
@@ -1,3 +1,3 @@
 package scala.tasty
 
-class TastyTypecheckError(msg: String) extends Throwable
+class TastyTypecheckError(msg: String) extends Throwable(msg)
diff --git a/tests/run-separate-compilation/i5533.check b/tests/run-separate-compilation/i5533.check
new file mode 100644
index 000000000000..27ba77ddaf61
--- /dev/null
+++ b/tests/run-separate-compilation/i5533.check
@@ -0,0 +1 @@
+true
diff --git a/tests/run-separate-compilation/i5533/Macro_1.scala b/tests/run-separate-compilation/i5533/Macro_1.scala
new file mode 100644
index 000000000000..05552fcc7513
--- /dev/null
+++ b/tests/run-separate-compilation/i5533/Macro_1.scala
@@ -0,0 +1,20 @@
+import scala.quoted._
+import scala.tasty._
+
+object scalatest {
+
+  def f(x: Int): Boolean = false
+  def f(x: String): Boolean = true
+
+  inline def assert(condition: => Boolean): Unit = ~assertImpl('(condition))
+
+  def assertImpl(condition: Expr[Boolean])(implicit refl: Reflection): Expr[Unit] = {
+    import refl._
+
+    val tree = condition.unseal
+
+    val expr = tree.seal[Boolean]
+
+    '(println(~expr))
+  }
+}
diff --git a/tests/run-separate-compilation/i5533/Test_2.scala b/tests/run-separate-compilation/i5533/Test_2.scala
new file mode 100644
index 000000000000..e982bb0fa7e9
--- /dev/null
+++ b/tests/run-separate-compilation/i5533/Test_2.scala
@@ -0,0 +1,9 @@
+object Test {
+
+  def main(args: Array[String]): Unit = {
+    import scalatest._
+    val x = "String"
+    assert(f("abc"))
+  }
+
+}
diff --git a/tests/run-separate-compilation/i5533b.check b/tests/run-separate-compilation/i5533b.check
new file mode 100644
index 000000000000..e33d1368f00f
--- /dev/null
+++ b/tests/run-separate-compilation/i5533b.check
@@ -0,0 +1,3 @@
+String
+String
+()
diff --git a/tests/run-separate-compilation/i5533b/Macro_1.scala b/tests/run-separate-compilation/i5533b/Macro_1.scala
new file mode 100644
index 000000000000..5a5443619fb8
--- /dev/null
+++ b/tests/run-separate-compilation/i5533b/Macro_1.scala
@@ -0,0 +1,34 @@
+import scala.quoted._
+import scala.tasty._
+
+object scalatest {
+  def f(x: Int): Int = x
+  def f(x: String): String = x
+
+  inline def assert(condition: => Boolean): Unit = ~assertImpl('(condition))
+
+  def assertImpl(condition: Expr[Boolean])(implicit refl: Reflection): Expr[Unit] = {
+    import refl._
+    import quoted.Toolbox.Default._
+
+    val tree = condition.unseal
+    def exprStr: String = condition.show
+
+    tree.underlyingArgument match {
+      case Term.Apply(Term.Select(lhs, op, _), rhs :: Nil) =>
+        val left = lhs.seal[Any]
+        val right = rhs.seal[Any]
+        op match {
+          case "==" =>
+        '{
+          val _left   = ~left
+          val _right  = ~right
+          val _result = _left == _right
+          println(_left)
+          println(_right)
+          scala.Predef.assert(_result)
+        }
+      }
+    }
+  }
+}
\ No newline at end of file
diff --git a/tests/run-separate-compilation/i5533b/Test_2.scala b/tests/run-separate-compilation/i5533b/Test_2.scala
new file mode 100644
index 000000000000..3d07d155ad23
--- /dev/null
+++ b/tests/run-separate-compilation/i5533b/Test_2.scala
@@ -0,0 +1,9 @@
+object Test {
+
+  def main(args: Array[String]): Unit = {
+    import scalatest._
+    val x = "String"
+    println(assert(f(x) == "String"))
+  }
+
+}
diff --git a/tests/run-separate-compilation/i5536/Macro_1.scala b/tests/run-separate-compilation/i5536/Macro_1.scala
new file mode 100644
index 000000000000..3de01d6d445f
--- /dev/null
+++ b/tests/run-separate-compilation/i5536/Macro_1.scala
@@ -0,0 +1,29 @@
+import scala.quoted._
+import scala.tasty._
+
+object scalatest {
+  inline def assert(condition: => Boolean): Unit = ~assertImpl('(condition))
+
+  def assertImpl(condition: Expr[Boolean])(implicit refl: Reflection): Expr[Unit] = {
+    import refl._
+    import quoted.Toolbox.Default._
+
+    val tree = condition.unseal
+    def exprStr: String = condition.show
+
+    tree.underlyingArgument match {
+      case Term.Apply(Term.Select(lhs, op, _), rhs :: Nil) =>
+        val left = lhs.seal[Any]
+        val right = rhs.seal[Any]
+        op match {
+          case "===" =>
+            '{
+              val _left   = ~left
+              val _right  = ~right
+              val _result = _left == _right
+              scala.Predef.assert(_result)
+            }
+        }
+    }
+  }
+}
diff --git a/tests/run-separate-compilation/i5536/Test_2.scala b/tests/run-separate-compilation/i5536/Test_2.scala
new file mode 100644
index 000000000000..671ff6044f28
--- /dev/null
+++ b/tests/run-separate-compilation/i5536/Test_2.scala
@@ -0,0 +1,22 @@
+
+class Equalizer[L](val leftSide: L) {
+  def ===(literalNull: Null): Boolean = leftSide == null
+}
+
+object Equality {
+  implicit def toEqualizer[T](x: T): Equalizer[T] = new Equalizer(x)
+}
+
+
+object Test {
+  import scalatest._
+  import Equality._
+
+  def main(args: Array[String]): Unit = {
+    val x = "String"
+    try assert(x === null)
+    catch {
+      case _: AssertionError => // OK
+    }
+  }
+}