diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
index 166cfd6c7b21..5f5cbc5625bc 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/ErrorMessageID.java
@@ -57,6 +57,7 @@ public enum ErrorMessageID {
     CyclicReferenceInvolvingImplicitID,
     SuperQualMustBeParentID,
     AmbiguousImportID,
+    AmbiguousOverloadID,
     ReassignmentToValID,
     ;
 
diff --git a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
index d93f2c7299ec..3d9cde9235ae 100644
--- a/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/diagnostic/messages.scala
@@ -18,6 +18,7 @@ import dotc.parsing.Tokens
 import printing.Highlighting._
 import printing.Formatting
 import ErrorMessageID._
+import Denotations.SingleDenotation
 import dotty.tools.dotc.core.SymDenotations.SymDenotation
 
 object messages {
@@ -1193,7 +1194,6 @@ object messages {
   extends Message(SuperQualMustBeParentID) {
 
     val msg = hl"""|$qual does not name a parent of $cls"""
-
     val kind = "Reference"
 
     private val parents: Seq[String] = (cls.info.parents map (_.name.show)).sorted
@@ -1208,15 +1208,13 @@ object messages {
   }
 
   case class VarArgsParamMustComeLast()(implicit ctx: Context)
-    extends Message(IncorrectRepeatedParameterSyntaxID) {
-    override def msg: String = "varargs parameter must come last"
-
-    override def kind: String = "Syntax"
-
-    override def explanation: String =
+  extends Message(IncorrectRepeatedParameterSyntaxID) {
+    val msg = "varargs parameter must come last"
+    val kind = "Syntax"
+    val explanation =
       hl"""|The varargs field must be the last field in the method signature.
            |Attempting to define a field in a method signature after a varargs field is an error.
-           |""".stripMargin
+           |"""
   }
 
   case class AmbiguousImport(name: Names.Name, newPrec: Int, prevPrec: Int, prevCtx: Context)(implicit ctx: Context)
@@ -1253,6 +1251,25 @@ object messages {
            |"""
   }
 
+  case class AmbiguousOverload(tree: tpd.Tree, alts: List[SingleDenotation], pt: Type)(
+    err: typer.ErrorReporting.Errors)(
+    implicit ctx: Context)
+  extends Message(AmbiguousOverloadID) {
+
+    private val all = if (alts.length == 2) "both" else "all"
+    val msg =
+      s"""|Ambiguous overload. The ${err.overloadedAltsStr(alts)}
+          |$all match ${err.expectedTypeStr(pt)}""".stripMargin
+    val kind = "Reference"
+    val explanation =
+      hl"""|There are ${alts.length} methods that could be referenced as the compiler knows too little
+           |about the expected type.
+           |You may specify the expected type e.g. by
+           |- assigning it to a value with a specified type, or
+           |- adding a type ascription as in `${"instance.myMethod: String => Int"}`
+           |"""
+  }
+                        
   case class ReassignmentToVal(name: Names.Name)(implicit ctx: Context)
     extends Message(ReassignmentToValID) {
     val kind = "Reference"
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 557e9b3e41d8..6c481e5e462e 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -1791,7 +1791,6 @@ class Typer extends Namer with TypeAssigner with Applications with Implicits wit
       typr.println(i"adapt overloaded $ref with alternatives ${altDenots map (_.info)}%, %")
       val alts = altDenots map (alt =>
         TermRef.withSigAndDenot(ref.prefix, ref.name, alt.info.signature, alt))
-      def expectedStr = err.expectedTypeStr(pt)
       resolveOverloaded(alts, pt) match {
         case alt :: Nil =>
           adapt(tree.withType(alt), pt, original)
@@ -1799,7 +1798,7 @@ class Typer extends Namer with TypeAssigner with Applications with Implicits wit
           def noMatches =
             errorTree(tree,
               em"""none of the ${err.overloadedAltsStr(altDenots)}
-                  |match $expectedStr""")
+                  |match ${err.expectedTypeStr(pt)}""")
           def hasEmptyParams(denot: SingleDenotation) = denot.info.paramInfoss == ListOfNil
           pt match {
             case pt: FunProto =>
@@ -1812,10 +1811,7 @@ class Typer extends Namer with TypeAssigner with Applications with Implicits wit
           }
         case alts =>
           val remainingDenots = alts map (_.denot.asInstanceOf[SingleDenotation])
-          def all = if (remainingDenots.length == 2) "both" else "all"
-          errorTree(tree,
-            em"""Ambiguous overload. The ${err.overloadedAltsStr(remainingDenots)}
-                |$all match $expectedStr""")
+          errorTree(tree, AmbiguousOverload(tree, remainingDenots, pt)(err))
       }
     }
 
diff --git a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
index 53043ab57206..20c5e2905f06 100644
--- a/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
+++ b/compiler/test/dotty/tools/dotc/reporting/ErrorMessagesTests.scala
@@ -4,6 +4,7 @@ package reporting
 
 import core.Contexts.Context
 import diagnostic.messages._
+import dotty.tools.dotc.core.Types.WildcardType
 import dotty.tools.dotc.parsing.Tokens
 import org.junit.Assert._
 import org.junit.{Ignore, Test}
@@ -359,6 +360,31 @@ class ErrorMessagesTests extends ErrorMessagesTest {
         assertEquals(namedImport, prevPrec)
       }
 
+  @Test def ambiugousOverloadWithWildcard =
+    checkMessagesAfter("frontend") {
+      """object Context {
+        |  trait A {
+        |    def foo(s: String): String
+        |    def foo: String = foo("foo")
+        |  }
+        |  object B extends A {
+        |    def foo(s: String): String = s
+        |  }
+        |  B.foo
+        |}
+      """.stripMargin
+    }
+    .expect { (ictx, messages) =>
+      implicit val ctx: Context = ictx
+      val defn = ictx.definitions
+
+      assertMessageCount(1, messages)
+      val AmbiguousOverload(tree, List(alt1, alt2), pt: WildcardType) :: Nil = messages
+      assertEquals("method foo", alt1.show)
+      assertEquals("(s: String)String", alt1.info.show)
+      assertEquals("method foo", alt2.show)
+    }
+
   @Test def reassignmentToVal =
     checkMessagesAfter("frontend") {
       """
@@ -368,10 +394,10 @@ class ErrorMessagesTests extends ErrorMessagesTest {
         |}
       """.stripMargin
     }
-      .expect { (ictx, messages) =>
-        implicit val ctx: Context = ictx
-        assertMessageCount(1, messages)
-        val ReassignmentToVal(name) :: Nil = messages
-        assertEquals("value", name.show)
-      }
+    .expect { (ictx, messages) =>
+      implicit val ctx: Context = ictx
+      assertMessageCount(1, messages)
+      val ReassignmentToVal(name) :: Nil = messages
+      assertEquals("value", name.show)
+    }
 }