diff --git a/README.md b/README.md
index 368b098..03996db 100644
--- a/README.md
+++ b/README.md
@@ -444,7 +444,7 @@ Tag                    | Description
 `format:"X"`           | Format for parsing input, if supported.
 `sep:"X"`              | Separator for sequences (defaults to ","). May be `none` to disable splitting.
 `mapsep:"X"`           | Separator for maps (defaults to ";"). May be `none` to disable splitting.
-`enum:"X,Y,..."`       | Set of valid values allowed for this flag.
+`enum:"X,Y,..."`       | Set of valid values allowed for this flag. An enum field must be `required` or have a valid `default`.
 `group:"X"`            | Logical group for a flag or command.
 `xor:"X,Y,..."`        | Exclusive OR groups for flags. Only one flag in the group can be used which is restricted within the same command. When combined with `required`, at least one of the `xor` group will be required.
 `prefix:"X"`           | Prefix for all sub-flags.
diff --git a/build.go b/build.go
index d2ca41c..22f9839 100644
--- a/build.go
+++ b/build.go
@@ -51,7 +51,7 @@ func flattenedFields(v reflect.Value) (out []flattenedField) {
 	for i := 0; i < v.NumField(); i++ {
 		ft := v.Type().Field(i)
 		fv := v.Field(i)
-		tag := parseTag(fv, ft)
+		tag := parseTag(v, fv, ft)
 		if tag.Ignored {
 			continue
 		}
@@ -156,8 +156,7 @@ func buildChild(k *Kong, node *Node, typ NodeType, v reflect.Value, ft reflect.S
 	// a positional argument is provided to the child, and move it to the branching argument field.
 	if tag.Arg {
 		if len(child.Positional) == 0 {
-			fail("positional branch %s.%s must have at least one child positional argument named %q",
-				v.Type().Name(), ft.Name, name)
+			failField(v, ft, "positional branch must have at least one child positional argument named %q", name)
 		}
 
 		value := child.Positional[0]
@@ -168,8 +167,7 @@ func buildChild(k *Kong, node *Node, typ NodeType, v reflect.Value, ft reflect.S
 
 		child.Name = value.Name
 		if child.Name != name {
-			fail("first field in positional branch %s.%s must have the same name as the parent field (%s).",
-				v.Type().Name(), ft.Name, child.Name)
+			failField(v, ft, "first field in positional branch must have the same name as the parent field (%s).", child.Name)
 		}
 
 		child.Argument = value
@@ -179,14 +177,14 @@ func buildChild(k *Kong, node *Node, typ NodeType, v reflect.Value, ft reflect.S
 	node.Children = append(node.Children, child)
 
 	if len(child.Positional) > 0 && len(child.Children) > 0 {
-		fail("can't mix positional arguments and branching arguments on %s.%s", v.Type().Name(), ft.Name)
+		failField(v, ft, "can't mix positional arguments and branching arguments")
 	}
 }
 
 func buildField(k *Kong, node *Node, v reflect.Value, ft reflect.StructField, fv reflect.Value, tag *Tag, name string, seenFlags map[string]bool) {
 	mapper := k.registry.ForNamedValue(tag.Type, fv)
 	if mapper == nil {
-		fail("unsupported field type %s.%s (of type %s), perhaps missing a cmd:\"\" tag?", v.Type(), ft.Name, ft.Type)
+		failField(v, ft, "unsupported field type %s, perhaps missing a cmd:\"\" tag?", ft.Type)
 	}
 
 	value := &Value{
@@ -209,13 +207,13 @@ func buildField(k *Kong, node *Node, v reflect.Value, ft reflect.StructField, fv
 		node.Positional = append(node.Positional, value)
 	} else {
 		if seenFlags["--"+value.Name] {
-			fail("duplicate flag --%s", value.Name)
+			failField(v, ft, "duplicate flag --%s", value.Name)
 		} else {
 			seenFlags["--"+value.Name] = true
 		}
 		if tag.Short != 0 {
 			if seenFlags["-"+string(tag.Short)] {
-				fail("duplicate short flag -%c", tag.Short)
+				failField(v, ft, "duplicate short flag -%c", tag.Short)
 			} else {
 				seenFlags["-"+string(tag.Short)] = true
 			}
diff --git a/config_test.go b/config_test.go
index 69e279d..a63205b 100644
--- a/config_test.go
+++ b/config_test.go
@@ -32,7 +32,7 @@ func TestMultipleConfigLoading(t *testing.T) {
 
 func TestConfigValidation(t *testing.T) {
 	var cli struct {
-		Flag string `json:"flag,omitempty" enum:"valid"`
+		Flag string `json:"flag,omitempty" enum:"valid" required:""`
 	}
 
 	cli.Flag = "invalid"
diff --git a/kong.go b/kong.go
index f02b867..3edfc3b 100644
--- a/kong.go
+++ b/kong.go
@@ -22,6 +22,15 @@ func fail(format string, args ...interface{}) {
 	panic(Error{msg: fmt.Sprintf(format, args...)})
 }
 
+func failField(parent reflect.Value, field reflect.StructField, format string, args ...interface{}) {
+	name := parent.Type().Name()
+	if name == "" {
+		name = "<anonymous struct>"
+	}
+	msg := fmt.Sprintf("%s.%s: %s", name, field.Name, fmt.Sprintf(format, args...))
+	panic(Error{msg: msg})
+}
+
 // Must creates a new Parser or panics if there is an error.
 func Must(ast interface{}, options ...Option) *Kong {
 	k, err := New(ast, options...)
diff --git a/kong_test.go b/kong_test.go
index 1a8af52..37f7529 100644
--- a/kong_test.go
+++ b/kong_test.go
@@ -643,7 +643,7 @@ func TestRun(t *testing.T) {
 func TestInterpolationIntoModel(t *testing.T) {
 	var cli struct {
 		Flag    string `default:"${default}" help:"Help, I need ${somebody}" enum:"${enum}"`
-		EnumRef string `enum:"a,b" help:"One of ${enum}"`
+		EnumRef string `enum:"a,b" required:"" help:"One of ${enum}"`
 	}
 	_, err := kong.New(&cli)
 	require.Error(t, err)
@@ -763,7 +763,7 @@ func TestHooksCalledForDefault(t *testing.T) {
 
 func TestEnum(t *testing.T) {
 	var cli struct {
-		Flag string `enum:"a,b,c"`
+		Flag string `enum:"a,b,c" required:""`
 	}
 	_, err := mustNew(t, &cli).Parse([]string{"--flag", "d"})
 	require.EqualError(t, err, "--flag must be one of \"a\",\"b\",\"c\" but got \"d\"")
@@ -978,7 +978,7 @@ func TestIssue153(t *testing.T) {
 func TestEnumArg(t *testing.T) {
 	var cli struct {
 		Nested struct {
-			One string `arg:"" enum:"a,b,c"`
+			One string `arg:"" enum:"a,b,c" required:""`
 			Two string `arg:""`
 		} `cmd:""`
 	}
@@ -1142,7 +1142,7 @@ func TestDuplicateShortflags(t *testing.T) {
 		Flag2 bool `short:"t"`
 	}{}
 	_, err := kong.New(&cli)
-	require.EqualError(t, err, "duplicate short flag -t")
+	require.EqualError(t, err, "<anonymous struct>.Flag2: duplicate short flag -t")
 }
 
 func TestDuplicateNestedShortFlags(t *testing.T) {
@@ -1153,5 +1153,5 @@ func TestDuplicateNestedShortFlags(t *testing.T) {
 		} `cmd:""`
 	}{}
 	_, err := kong.New(&cli)
-	require.EqualError(t, err, "duplicate short flag -t")
+	require.EqualError(t, err, "<anonymous struct>.Flag2: duplicate short flag -t")
 }
diff --git a/tag.go b/tag.go
index 9ecde85..7c9ae99 100644
--- a/tag.go
+++ b/tag.go
@@ -129,7 +129,7 @@ func tagSplitFn(r rune) bool {
 	return r == ',' || r == ' '
 }
 
-func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
+func parseTag(parent, fv reflect.Value, ft reflect.StructField) *Tag {
 	if ft.Tag.Get("kong") == "-" {
 		t := newEmptyTag()
 		t.Ignored = true
@@ -146,7 +146,7 @@ func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
 	required := t.Has("required")
 	optional := t.Has("optional")
 	if required && optional {
-		fail("can't specify both required and optional")
+		failField(parent, ft, "can't specify both required and optional")
 	}
 	t.Required = required
 	t.Optional = optional
@@ -161,7 +161,7 @@ func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
 	t.Env = t.Get("env")
 	t.Short, err = t.GetRune("short")
 	if err != nil && t.Get("short") != "" {
-		fail("invalid short flag name %q: %s", t.Get("short"), err)
+		failField(parent, ft, "invalid short flag name %q: %s", t.Get("short"), err)
 	}
 	t.Hidden = t.Has("hidden")
 	t.Format = t.Get("format")
@@ -175,7 +175,7 @@ func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
 	t.Embed = t.Has("embed")
 	negatable := t.Has("negatable")
 	if negatable && ft.Type.Kind() != reflect.Bool {
-		fail("negatable can only be set on booleans")
+		failField(parent, ft, "negatable can only be set on booleans")
 	}
 	t.Negatable = negatable
 	aliases := t.Get("aliases")
@@ -186,7 +186,7 @@ func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
 	for _, set := range t.GetAll("set") {
 		parts := strings.SplitN(set, "=", 2)
 		if len(parts) == 0 {
-			fail("set should be in the form key=value but got %q", set)
+			failField(parent, ft, "set should be in the form key=value but got %q", set)
 		}
 		t.Vars[parts[0]] = parts[1]
 	}
@@ -195,9 +195,12 @@ func parseTag(fv reflect.Value, ft reflect.StructField) *Tag {
 		t.PlaceHolder = strings.ToUpper(dashedString(fv.Type().Name()))
 	}
 	t.Enum = t.Get("enum")
+	if t.Enum != "" && !(t.Required || t.Default != "") {
+		failField(parent, ft, "enum value is only valid if it is either required or has a valid default value")
+	}
 	passthrough := t.Has("passthrough")
 	if passthrough && !t.Arg {
-		fail("passthrough only makes sense for positional arguments")
+		failField(parent, ft, "passthrough only makes sense for positional arguments")
 	}
 	t.Passthrough = passthrough
 	return t
diff --git a/tag_test.go b/tag_test.go
index ae8c38d..ca9f213 100644
--- a/tag_test.go
+++ b/tag_test.go
@@ -198,5 +198,5 @@ func TestInvalidRuneErrors(t *testing.T) {
 		Flag bool `short:"invalid"`
 	}{}
 	_, err := kong.New(&cli)
-	require.EqualError(t, err, "invalid short flag name \"invalid\": invalid rune")
+	require.EqualError(t, err, "<anonymous struct>.Flag: invalid short flag name \"invalid\": invalid rune")
 }