diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
index c20fc27f9d1a..889f32e9d06e 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
@@ -125,6 +125,7 @@ public enum ErrorMessageID {
     UnableToEmitSwitchID,
     MissingCompanionForStaticID,
     PolymorphicMethodMissingTypeInParentID,
+    NotAValidResultTypeOfUnapplyID
     ;
 
     public int errorNumber() {
diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
index fb8b5705b604..5f93fa21ba03 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
@@ -2074,4 +2074,21 @@ object messages {
           |$rsym does not override any method in $parentSym. Structural refinement does not allow for
           |polymorphic methods."""
   }
+
+  case class NotAValidResultTypeOfUnapply(sym: Symbol, resultType: Type, args: List[untpd.Tree])(implicit ctx: Context) extends Message(NotAValidResultTypeOfUnapplyID) {
+    val kind = "Reference"
+    val resultClassName = resultType.classSymbol.name
+    val msg = hl"Cannot extract (${sym.name}) from ${sym.owner}. $resultClassName is not a valid extractor return type"
+    val explanation =
+      hl"""${sym.name} method of ${sym.owner} has been tried as a candidate to extract ${args.map(_.show).mkString("[", ", ", "]")}
+          |Its return type: ${s"$resultClassName"} is not a valid return type for an extractor.
+          |
+          |The return type of an extractor should be chosen as follows:
+          | - If it is just a test, return a ${"Boolean"}. For instance ${"case even()"}
+          | - If it returns a single sub-value of type ${s"$resultClassName"}, return an ${s"Option[$resultClassName]"}
+          | - If you want to return several sub-values ${"T1,...,Tn"}, group them in an optional tuple ${"Option[(T1,...,Tn)]"}.
+        """.stripMargin
+
+  }
+
 }
diff --git a/compiler/src/dotty/tools/dotc/typer/Applications.scala b/compiler/src/dotty/tools/dotc/typer/Applications.scala
index a49e0f73bea9..f95a6849c32d 100644
--- a/compiler/src/dotty/tools/dotc/typer/Applications.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Applications.scala
@@ -33,7 +33,7 @@ import language.implicitConversions
 import reporting.diagnostic.Message
 import reporting.trace
 import Constants.{Constant, IntTag, LongTag}
-import dotty.tools.dotc.reporting.diagnostic.messages.UnapplyInvalidNumberOfArguments
+import dotty.tools.dotc.reporting.diagnostic.messages.{NotAValidResultTypeOfUnapply, UnapplyInvalidNumberOfArguments}
 
 import scala.collection.mutable.ListBuffer
 
@@ -93,7 +93,8 @@ object Applications {
     def getTp = extractorMemberType(unapplyResult, nme.get, pos)
 
     def fail = {
-      ctx.error(i"$unapplyResult is not a valid result type of an $unapplyName method of an extractor", pos)
+      // ctx.error(i"$unapplyResult is not a valid result type of an $unapplyName method of an extractor", pos)
+      ctx.error(NotAValidResultTypeOfUnapply(unapplyFn.symbol, unapplyResult, args), pos)
       Nil
     }
 
diff --git a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
index c94af01eb3cd..6f246eb5282e 100644
--- a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
+++ b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
@@ -2,12 +2,10 @@ package dotty.tools
 package dotc
 package reporting
 
-import core.Contexts.Context
-import diagnostic.messages._
-import dotty.tools.dotc.core.Flags
-import dotty.tools.dotc.core.Flags.FlagSet
+import dotty.tools.dotc.core.Contexts.Context
 import dotty.tools.dotc.core.Types.WildcardType
 import dotty.tools.dotc.parsing.Tokens
+import dotty.tools.dotc.reporting.diagnostic.messages._
 import org.junit.Assert._
 import org.junit.Test
 
@@ -1294,4 +1292,26 @@ class ErrorMessagesTests extends ErrorMessagesTest {
       assertEquals("method get", rsym.show)
       assertEquals("class Object", parentSym.show)
     }
+
+    @Test def notAValidReturnTypeOfUnapply =
+      checkMessagesAfter("frontend") {
+        """
+           |object Test {
+           | object Foo {
+           |  def unapply(arg: String): String = arg.toUpperCase
+           | }
+           | val Foo(unextractedValue) = "test"
+           |}
+        """.stripMargin
+      }.expect { (ictx, messages) =>
+        implicit val ctx: Context = ictx
+
+        assertMessageCount(1, messages)
+        val NotAValidResultTypeOfUnapply(sym, resultType, args) = messages.head
+        assertEquals("method unapply", sym.show)
+        assertEquals("String", resultType.show)
+        assertEquals(1, args.length)
+        assertEquals("unextractedValue", args.head.show)
+      }
+
 }