diff --git a/compiler/src/dotty/tools/dotc/core/SymDenotations.scala b/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
index bd43578e3d53..c39db64b77cf 100644
--- a/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
+++ b/compiler/src/dotty/tools/dotc/core/SymDenotations.scala
@@ -2720,7 +2720,7 @@ object SymDenotations {
       || owner.isRefinementClass
       || owner.is(Scala2x)
       || owner.unforcedDecls.contains(denot.name, denot.symbol)
-      || (denot.is(Synthetic) && denot.is(ModuleClass) && stillValidInOwner(denot.companionClass))
+      || (denot.is(Synthetic) && denot.is(ModuleClass) && denot.companionClass.exists && stillValidInOwner(denot.companionClass))
       || denot.isSelfSym
       || denot.isLocalDummy)
   catch case ex: StaleSymbol => false
diff --git a/tests/neg/i19351.check b/tests/neg/i19351.check
deleted file mode 100644
index a9ee10510b32..000000000000
--- a/tests/neg/i19351.check
+++ /dev/null
@@ -1,4 +0,0 @@
--- Error: tests/neg/i19351/A.scala:3:35 --------------------------------------------------------------------------------
-3 |  inline def myMacro(): x.type = ${myMacroExpr}  // error
-  |                                   ^
-  |Cyclic macro dependency; macro refers to a toplevel symbol in tests/neg/i19351/A.scala from which the macro is called
diff --git a/tests/neg/i19351/A.scala b/tests/neg/i19351/A.scala
deleted file mode 100644
index f2258631a15a..000000000000
--- a/tests/neg/i19351/A.scala
+++ /dev/null
@@ -1,5 +0,0 @@
-//object A:
-  val x: Int = 1
-  inline def myMacro(): x.type = ${myMacroExpr}  // error
-  def test = myMacro()
-
diff --git a/tests/neg/i19351a.check b/tests/neg/i19351a.check
deleted file mode 100644
index 10789c2db5aa..000000000000
--- a/tests/neg/i19351a.check
+++ /dev/null
@@ -1,4 +0,0 @@
--- Error: tests/neg/i19351a/Test.scala:8:34 ----------------------------------------------------------------------------
-8 |inline def not(b: Bool): Bool = ${notMacro('b)} // error
-  |                                  ^
-  |Cyclic macro dependency; macro refers to a toplevel symbol in tests/neg/i19351a/Test.scala from which the macro is called
diff --git a/tests/pos-macros/i13821-a/Macro.scala b/tests/pos-macros/i13821-a/Macro.scala
new file mode 100644
index 000000000000..3583a44ffddc
--- /dev/null
+++ b/tests/pos-macros/i13821-a/Macro.scala
@@ -0,0 +1,6 @@
+trait Conversions:
+  given conv(using DFBits.Candidate): Conversion[Int, DFVal] = ???
+
+import scala.quoted.*
+transparent inline def f: Short = ${ getWidthMacro }
+private def getWidthMacro(using Quotes): Expr[Short] = '{ ??? }
diff --git a/tests/pos-macros/i13821-a/Test.scala b/tests/pos-macros/i13821-a/Test.scala
new file mode 100644
index 000000000000..86f5a6289a80
--- /dev/null
+++ b/tests/pos-macros/i13821-a/Test.scala
@@ -0,0 +1,12 @@
+type DFBits = Long
+object DFBits:
+  def a: Unit = f // forces suspension of this compilation unit in typer
+  def b: DFVal = 2 // uses implicit conversion `DFVal.conv`
+
+  trait Candidate
+  object Candidate:
+    given candidate: Candidate = ??? // completed in run 3 but created in run 2
+end DFBits
+
+trait DFVal
+object DFVal extends Conversions
diff --git a/tests/pos-macros/i13821-b/Macro.scala b/tests/pos-macros/i13821-b/Macro.scala
new file mode 100644
index 000000000000..c1c9c5e17851
--- /dev/null
+++ b/tests/pos-macros/i13821-b/Macro.scala
@@ -0,0 +1,7 @@
+import outer._
+trait Conversions:
+  given conv(using DFBits.Candidate): Conversion[Int, DFVal] = ???
+
+import scala.quoted.*
+transparent inline def f: Short = ${ getWidthMacro }
+private def getWidthMacro(using Quotes): Expr[Short] = '{ ??? }
diff --git a/tests/pos-macros/i13821-b/Test.scala b/tests/pos-macros/i13821-b/Test.scala
new file mode 100644
index 000000000000..5c9b8755a33c
--- /dev/null
+++ b/tests/pos-macros/i13821-b/Test.scala
@@ -0,0 +1,14 @@
+type outer = Int
+object outer:
+  type DFBits = Long
+  object DFBits:
+    def a: Unit = f // forces suspension of this compilation unit in typer
+    def b: DFVal = 2 // uses implicit conversion `DFVal.conv`
+
+    trait Candidate
+    object Candidate:
+      given candidate: Candidate = ??? // completed in run 3 but created in run 2
+  end DFBits
+
+  trait DFVal
+  object DFVal extends Conversions
diff --git a/tests/pos-macros/i19351/A.scala b/tests/pos-macros/i19351/A.scala
new file mode 100644
index 000000000000..0b2c7acc3797
--- /dev/null
+++ b/tests/pos-macros/i19351/A.scala
@@ -0,0 +1,6 @@
+// object A:
+  val x: Int = 1
+  inline def myMacro(): x.type = ${myMacroExpr}
+  def test = myMacro()
+
+@main def main() = ()
\ No newline at end of file
diff --git a/tests/neg/i19351/B.scala b/tests/pos-macros/i19351/B.scala
similarity index 84%
rename from tests/neg/i19351/B.scala
rename to tests/pos-macros/i19351/B.scala
index 8c8c071f3607..a22b4d5c51b6 100644
--- a/tests/neg/i19351/B.scala
+++ b/tests/pos-macros/i19351/B.scala
@@ -1,3 +1,3 @@
 import scala.quoted.*
-//import A.*
+// import A.*
 def myMacroExpr(using Quotes): Expr[x.type] = '{???}
\ No newline at end of file
diff --git a/tests/neg/i19351a/Macro.scala b/tests/pos-macros/i19351a/Macro.scala
similarity index 100%
rename from tests/neg/i19351a/Macro.scala
rename to tests/pos-macros/i19351a/Macro.scala
diff --git a/tests/neg/i19351a/Test.scala b/tests/pos-macros/i19351a/Test.scala
similarity index 87%
rename from tests/neg/i19351a/Test.scala
rename to tests/pos-macros/i19351a/Test.scala
index 84fb6ca4ae78..7f9e6dbc9786 100644
--- a/tests/neg/i19351a/Test.scala
+++ b/tests/pos-macros/i19351a/Test.scala
@@ -5,7 +5,7 @@ type Bool = [R] => (R, R) => R
 val True: Bool = [R] => (t: R, _: R) => t
 val False: Bool = [R] => (_: R, f: R) => f
 
-inline def not(b: Bool): Bool = ${notMacro('b)} // error
+inline def not(b: Bool): Bool = ${notMacro('b)}
 inline def show(b: Bool): String = ${showMacro('b)}
 //inline def not(b: Bool): Bool = ${foldMacro('b, 'False, 'True)}
 //inline def show(b: Bool): String = ${foldMacro('b, '{"TRUE"}, '{"FALSE"})}