diff --git a/parse.go b/parse.go
index 84a7ed1..37df734 100644
--- a/parse.go
+++ b/parse.go
@@ -377,7 +377,7 @@ func cmdFromStruct(name string, dest path, t reflect.Type) (*command, error) {
 			cmd.specs = append(cmd.specs, &spec)
 
 			var parseable bool
-			parseable, spec.boolean, spec.multiple = canParse(field.Type)
+			//parseable, spec.boolean, spec.multiple = canParse(field.Type)
 			if !parseable {
 				errs = append(errs, fmt.Sprintf("%s.%s: %s fields are not supported",
 					t.Name(), field.Name, field.Type.String()))
@@ -728,7 +728,7 @@ func findSubcommand(cmds []*command, name string) *command {
 // isZero returns true if v contains the zero value for its type
 func isZero(v reflect.Value) bool {
 	t := v.Type()
-	if t.Kind() == reflect.Slice {
+	if t.Kind() == reflect.Slice || t.Kind() == reflect.Map {
 		return v.IsNil()
 	}
 	if !t.Comparable() {
diff --git a/parse_test.go b/parse_test.go
index ce3068e..0decfc1 100644
--- a/parse_test.go
+++ b/parse_test.go
@@ -220,6 +220,16 @@ func TestLongFlag(t *testing.T) {
 	assert.Equal(t, "xyz", args.Foo)
 }
 
+func TestSliceOfBools(t *testing.T) {
+	var args struct {
+		B []bool
+	}
+
+	err := parse("--b true false true", &args)
+	require.NoError(t, err)
+	assert.Equal(t, []bool{true, false, true}, args.B)
+}
+
 func TestPlaceholder(t *testing.T) {
 	var args struct {
 		Input    string   `arg:"positional" placeholder:"SRC"`
diff --git a/reflect.go b/reflect.go
index f1e8e8d..c4fc5d9 100644
--- a/reflect.go
+++ b/reflect.go
@@ -2,6 +2,7 @@ package arg
 
 import (
 	"encoding"
+	"fmt"
 	"reflect"
 	"unicode"
 	"unicode/utf8"
@@ -11,42 +12,71 @@ import (
 
 var textUnmarshalerType = reflect.TypeOf([]encoding.TextUnmarshaler{}).Elem()
 
-// canParse returns true if the type can be parsed from a string
-func canParse(t reflect.Type) (parseable, boolean, multiple bool) {
-	parseable = scalar.CanParse(t)
-	boolean = isBoolean(t)
-	if parseable {
-		return
+// kind is used to track the various kinds of options:
+//  - regular is an ordinary option that will be parsed from a single token
+//  - binary is an option that will be true if present but does not expect an explicit value
+//  - sequence is an option that accepts multiple values and will end up in a slice
+//  - mapping is an option that acccepts multiple key=value strings and will end up in a map
+type kind int
+
+const (
+	regular kind = iota
+	binary
+	sequence
+	mapping
+	unsupported
+)
+
+func (k kind) String() string {
+	switch k {
+	case regular:
+		return "regular"
+	case binary:
+		return "binary"
+	case sequence:
+		return "sequence"
+	case mapping:
+		return "mapping"
+	case unsupported:
+		return "unsupported"
+	default:
+		return fmt.Sprintf("unknown(%d)", int(k))
+	}
+}
+
+// kindOf returns true if the type can be parsed from a string
+func kindOf(t reflect.Type) (kind, error) {
+	if scalar.CanParse(t) {
+		if isBoolean(t) {
+			return binary, nil
+		} else {
+			return regular, nil
+		}
 	}
 
-	// Look inside pointer types
-	if t.Kind() == reflect.Ptr {
-		t = t.Elem()
-	}
-	// Look inside slice types
-	if t.Kind() == reflect.Slice {
-		multiple = true
-		t = t.Elem()
-	}
-
-	parseable = scalar.CanParse(t)
-	boolean = isBoolean(t)
-	if parseable {
-		return
-	}
-
-	// Look inside pointer types (again, in case of []*Type)
+	// look inside pointer types
 	if t.Kind() == reflect.Ptr {
 		t = t.Elem()
 	}
 
-	parseable = scalar.CanParse(t)
-	boolean = isBoolean(t)
-	if parseable {
-		return
+	// look inside slice and map types
+	switch t.Kind() {
+	case reflect.Slice:
+		if !scalar.CanParse(t.Elem()) {
+			return unsupported, fmt.Errorf("cannot parse into %v because we cannot parse into %v", t, t.Elem())
+		}
+		return sequence, nil
+	case reflect.Map:
+		if !scalar.CanParse(t.Key()) {
+			return unsupported, fmt.Errorf("cannot parse into %v because we cannot parse into the key type %v", t, t.Elem())
+		}
+		if !scalar.CanParse(t.Elem()) {
+			return unsupported, fmt.Errorf("cannot parse into %v because we cannot parse into the value type %v", t, t.Elem())
+		}
+		return mapping, nil
+	default:
+		return unsupported, fmt.Errorf("cannot parse into %v", t)
 	}
-
-	return false, false, false
 }
 
 // isBoolean returns true if the type can be parsed from a single string
diff --git a/reflect_test.go b/reflect_test.go
index 07b459c..6a8af49 100644
--- a/reflect_test.go
+++ b/reflect_test.go
@@ -7,36 +7,51 @@ import (
 	"github.com/stretchr/testify/assert"
 )
 
-func assertCanParse(t *testing.T, typ reflect.Type, parseable, boolean, multiple bool) {
-	p, b, m := canParse(typ)
-	assert.Equal(t, parseable, p, "expected %v to have parseable=%v but was %v", typ, parseable, p)
-	assert.Equal(t, boolean, b, "expected %v to have boolean=%v but was %v", typ, boolean, b)
-	assert.Equal(t, multiple, m, "expected %v to have multiple=%v but was %v", typ, multiple, m)
+func assertKind(t *testing.T, typ reflect.Type, expected kind) {
+	actual, err := kindOf(typ)
+	assert.Equal(t, expected, actual, "expected %v to have kind %v but got %v", typ, expected, actual)
+	if expected == unsupported {
+		assert.Error(t, err)
+	}
 }
 
-func TestCanParse(t *testing.T) {
+func TestKindOf(t *testing.T) {
 	var b bool
 	var i int
 	var s string
 	var f float64
 	var bs []bool
 	var is []int
+	var m map[string]int
+	var unsupported1 struct{}
+	var unsupported2 []struct{}
+	var unsupported3 map[string]struct{}
 
-	assertCanParse(t, reflect.TypeOf(b), true, true, false)
-	assertCanParse(t, reflect.TypeOf(i), true, false, false)
-	assertCanParse(t, reflect.TypeOf(s), true, false, false)
-	assertCanParse(t, reflect.TypeOf(f), true, false, false)
+	assertKind(t, reflect.TypeOf(b), binary)
+	assertKind(t, reflect.TypeOf(i), regular)
+	assertKind(t, reflect.TypeOf(s), regular)
+	assertKind(t, reflect.TypeOf(f), regular)
 
-	assertCanParse(t, reflect.TypeOf(&b), true, true, false)
-	assertCanParse(t, reflect.TypeOf(&s), true, false, false)
-	assertCanParse(t, reflect.TypeOf(&i), true, false, false)
-	assertCanParse(t, reflect.TypeOf(&f), true, false, false)
+	assertKind(t, reflect.TypeOf(&b), binary)
+	assertKind(t, reflect.TypeOf(&s), regular)
+	assertKind(t, reflect.TypeOf(&i), regular)
+	assertKind(t, reflect.TypeOf(&f), regular)
 
-	assertCanParse(t, reflect.TypeOf(bs), true, true, true)
-	assertCanParse(t, reflect.TypeOf(&bs), true, true, true)
+	assertKind(t, reflect.TypeOf(bs), sequence)
+	assertKind(t, reflect.TypeOf(is), sequence)
 
-	assertCanParse(t, reflect.TypeOf(is), true, false, true)
-	assertCanParse(t, reflect.TypeOf(&is), true, false, true)
+	assertKind(t, reflect.TypeOf(&bs), sequence)
+	assertKind(t, reflect.TypeOf(&is), sequence)
+
+	assertKind(t, reflect.TypeOf(m), mapping)
+	assertKind(t, reflect.TypeOf(&m), mapping)
+
+	assertKind(t, reflect.TypeOf(unsupported1), unsupported)
+	assertKind(t, reflect.TypeOf(&unsupported1), unsupported)
+	assertKind(t, reflect.TypeOf(unsupported2), unsupported)
+	assertKind(t, reflect.TypeOf(&unsupported2), unsupported)
+	assertKind(t, reflect.TypeOf(unsupported3), unsupported)
+	assertKind(t, reflect.TypeOf(&unsupported3), unsupported)
 }
 
 type implementsTextUnmarshaler struct{}
@@ -46,12 +61,15 @@ func (*implementsTextUnmarshaler) UnmarshalText(text []byte) error {
 }
 
 func TestCanParseTextUnmarshaler(t *testing.T) {
-	var u implementsTextUnmarshaler
-	var su []implementsTextUnmarshaler
-	assertCanParse(t, reflect.TypeOf(u), true, false, false)
-	assertCanParse(t, reflect.TypeOf(&u), true, false, false)
-	assertCanParse(t, reflect.TypeOf(su), true, false, true)
-	assertCanParse(t, reflect.TypeOf(&su), true, false, true)
+	var x implementsTextUnmarshaler
+	var s []implementsTextUnmarshaler
+	var m []implementsTextUnmarshaler
+	assertKind(t, reflect.TypeOf(x), regular)
+	assertKind(t, reflect.TypeOf(&x), regular)
+	assertKind(t, reflect.TypeOf(s), sequence)
+	assertKind(t, reflect.TypeOf(&s), sequence)
+	assertKind(t, reflect.TypeOf(m), mapping)
+	assertKind(t, reflect.TypeOf(&m), mapping)
 }
 
 func TestIsExported(t *testing.T) {
diff --git a/sequence_test.go b/sequence_test.go
index 4646811..446bc42 100644
--- a/sequence_test.go
+++ b/sequence_test.go
@@ -79,3 +79,11 @@ func TestSetMapTextUnmarshaller(t *testing.T) {
 	assert.Equal(t, &textUnmarshaler{2}, m[textUnmarshaler{2}])
 	assert.Equal(t, &textUnmarshaler{1}, m[textUnmarshaler{3}])
 }
+
+func TestSetMapMalformed(t *testing.T) {
+	// textUnmarshaler is a struct that captures the length of the string passed to it
+	var m map[string]string
+	entries := []string{"missing_equals_sign"}
+	err := setMap(reflect.ValueOf(&m).Elem(), entries, true)
+	assert.Error(t, err)
+}