diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
index cc67c76c33b9..e580288316b5 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
@@ -116,6 +116,7 @@ public enum ErrorMessageID {
     TraitRedefinedFinalMethodFromAnyRefID,
     PackageNameAlreadyDefinedID,
     UnapplyInvalidNumberOfArgumentsID,
+    UnapplyInvalidReturnTypeID,
     StaticFieldsOnlyAllowedInObjectsID,
     CyclicInheritanceID,
     BadSymbolicReferenceID,
diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
index 6cbc0526b9d6..aea289b4e1b3 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
@@ -25,6 +25,7 @@ import dotty.tools.dotc.core.Flags._
 import dotty.tools.dotc.core.SymDenotations.SymDenotation
 import dotty.tools.dotc.typer.ErrorReporting.Errors
 import scala.util.control.NonFatal
+import StdNames.nme
 
 object messages {
 
@@ -1919,6 +1920,61 @@ object messages {
         |""".stripMargin
   }
 
+  case class UnapplyInvalidReturnType(unapplyResult: Type, unapplyName: Symbol#ThisName)(implicit ctx: Context)
+    extends Message(UnapplyInvalidReturnTypeID) {
+    val kind = "Type Mismatch"
+    val addendum =
+      if (ctx.scala2Mode && unapplyName == nme.unapplySeq)
+        "\nYou might want to try to rewrite the extractor to use `unapply` instead."
+      else ""
+    val msg = hl"""| ${Red(i"$unapplyResult")} is not a valid result type of an $unapplyName method of an ${Magenta("extractor")}.$addendum"""
+    val explanation = if (unapplyName.show == "unapply")
+      hl"""
+          |To be used as an extractor, an unapply method has to return a type that either:
+          | - has members ${Magenta("isEmpty: Boolean")} and ${Magenta("get: S")} (usually an ${Green("Option[S]")})
+          | - is a ${Green("Boolean")}
+          | - is a ${Green("Product")} (like a ${Magenta("Tuple2[T1, T2]")})
+          |
+          |class A(val i: Int)
+          |
+          |object B {
+          |  def unapply(a: A): ${Green("Option[Int]")} = Some(a.i)
+          |}
+          |
+          |object C {
+          |  def unapply(a: A): ${Green("Boolean")} = a.i == 2
+          |}
+          |
+          |object D {
+          |  def unapply(a: A): ${Green("(Int, Int)")} = (a.i, a.i)
+          |}
+          |
+          |object Test {
+          |  def test(a: A) = a match {
+          |    ${Magenta("case B(1)")} => 1
+          |    ${Magenta("case a @ C()")} => 2
+          |    ${Magenta("case D(3, 3)")} => 3
+          |  }
+          |}
+        """.stripMargin
+    else
+      hl"""
+          |To be used as an extractor, an unapplySeq method has to return a type which has members
+          |${Magenta("isEmpty: Boolean")} and ${Magenta("get: S")} where ${Magenta("S <: Seq[V]")} (usually an ${Green("Option[Seq[V]]")}):
+          |
+          |object CharList {
+          |  def unapplySeq(s: String): ${Green("Option[Seq[Char]")} = Some(s.toList)
+          |
+          |  "example" match {
+          |    ${Magenta("case CharList(c1, c2, c3, c4, _, _, _)")} =>
+          |      println(s"$$c1,$$c2,$$c3,$$c4")
+          |    case _ =>
+          |      println("Expected *exactly* 7 characters!")
+          |  }
+          |}
+        """.stripMargin
+  }
+
   case class StaticFieldsOnlyAllowedInObjects(member: Symbol)(implicit ctx: Context) extends Message(StaticFieldsOnlyAllowedInObjectsID) {
     val msg: String = hl"${"@static"} $member in ${member.owner} must be defined inside an ${"object"}."
     val kind: String = "Syntax"
diff --git a/compiler/src/dotty/tools/dotc/typer/Applications.scala b/compiler/src/dotty/tools/dotc/typer/Applications.scala
index e9ffaeddb404..96b5edd0bfdb 100644
--- a/compiler/src/dotty/tools/dotc/typer/Applications.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Applications.scala
@@ -28,7 +28,7 @@ import TypeApplications._
 import reporting.diagnostic.Message
 import reporting.trace
 import Constants.{Constant, IntTag, LongTag}
-import dotty.tools.dotc.reporting.diagnostic.messages.{NotAnExtractor, UnapplyInvalidNumberOfArguments}
+import dotty.tools.dotc.reporting.diagnostic.messages.{UnapplyInvalidReturnType, NotAnExtractor, UnapplyInvalidNumberOfArguments}
 import Denotations.SingleDenotation
 import annotation.constructorOnly
 
@@ -99,11 +99,7 @@ object Applications {
     def getTp = extractorMemberType(unapplyResult, nme.get, pos)
 
     def fail = {
-      val addendum =
-        if (ctx.scala2Mode && unapplyName == nme.unapplySeq)
-          "\nYou might want to try to rewrite the extractor to use `unapply` instead."
-        else ""
-      ctx.error(em"$unapplyResult is not a valid result type of an $unapplyName method of an extractor$addendum", pos)
+      ctx.error(UnapplyInvalidReturnType(unapplyResult, unapplyName), pos)
       Nil
     }
 
diff --git a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
index fdec58fa1933..cf6460f207d1 100644
--- a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
+++ b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
@@ -1380,6 +1380,46 @@ class ErrorMessagesTests extends ErrorMessagesTest {
         assertEquals("(class Int, class String)", argTypes.map(_.typeSymbol).mkString("(", ", ", ")"))
       }
 
+  @Test def unapplyInvalidReturnType =
+    checkMessagesAfter("frontend") {
+      """
+        |class A(val i: Int)
+        |
+        |object A {
+        |  def unapply(a: A): Int = a.i
+        |  def test(a: A) = a match {
+        |    case A() => 1
+        |  }
+        |}
+      """.stripMargin
+    }.expect { (ictx, messages) =>
+      implicit val ctx: Context = ictx
+      assertMessageCount(1, messages)
+      val UnapplyInvalidReturnType(unapplyResult, unapplyName) :: Nil = messages
+      assertEquals("Int", unapplyResult.show)
+      assertEquals("unapply", unapplyName.show)
+    }
+
+  @Test def unapplySeqInvalidReturnType =
+    checkMessagesAfter("frontend") {
+      """
+        |class A(val i: Int)
+        |
+        |object A {
+        |  def unapplySeq(a: A): Int = a.i
+        |  def test(a: A) = a match {
+        |    case A() => 1
+        |  }
+        |}
+      """.stripMargin
+    }.expect { (ictx, messages) =>
+      implicit val ctx: Context = ictx
+      assertMessageCount(1, messages)
+      val UnapplyInvalidReturnType(unapplyResult, unapplyName) :: Nil = messages
+      assertEquals("Int", unapplyResult.show)
+      assertEquals("unapplySeq", unapplyName.show)
+    }
+
   @Test def staticOnlyAllowedInsideObjects =
     checkMessagesAfter(CheckStatic.name) {
       """