diff --git a/pkg/conversion/deep_equal.go b/pkg/conversion/deep_equal.go
index 3ff089a5666..557c6aa3a0f 100644
--- a/pkg/conversion/deep_equal.go
+++ b/pkg/conversion/deep_equal.go
@@ -174,6 +174,8 @@ func (e Equalities) deepValueEqual(v1, v2 reflect.Value, visited map[visit]bool,
 
 	switch v1.Kind() {
 	case reflect.Array:
+		// We don't need to check length here because length is part of
+		// an array's type, which has already been filtered for.
 		for i := 0; i < v1.Len(); i++ {
 			if !e.deepValueEqual(v1.Index(i), v2.Index(i), visited, depth+1) {
 				return false
@@ -187,6 +189,9 @@ func (e Equalities) deepValueEqual(v1, v2 reflect.Value, visited map[visit]bool,
 		if v1.IsNil() || v1.Len() == 0 {
 			return true
 		}
+		if v1.Len() != v2.Len() {
+			return false
+		}
 		if v1.Pointer() == v2.Pointer() {
 			return true
 		}
@@ -217,6 +222,9 @@ func (e Equalities) deepValueEqual(v1, v2 reflect.Value, visited map[visit]bool,
 		if v1.IsNil() || v1.Len() == 0 {
 			return true
 		}
+		if v1.Len() != v2.Len() {
+			return false
+		}
 		if v1.Pointer() == v2.Pointer() {
 			return true
 		}
@@ -309,6 +317,8 @@ func (e Equalities) deepValueDerive(v1, v2 reflect.Value, visited map[visit]bool
 
 	switch v1.Kind() {
 	case reflect.Array:
+		// We don't need to check length here because length is part of
+		// an array's type, which has already been filtered for.
 		for i := 0; i < v1.Len(); i++ {
 			if !e.deepValueDerive(v1.Index(i), v2.Index(i), visited, depth+1) {
 				return false
@@ -316,12 +326,12 @@ func (e Equalities) deepValueDerive(v1, v2 reflect.Value, visited map[visit]bool
 		}
 		return true
 	case reflect.Slice:
-		if (v1.IsNil() || v1.Len() == 0) != (v2.IsNil() || v2.Len() == 0) {
-			return false
-		}
 		if v1.IsNil() || v1.Len() == 0 {
 			return true
 		}
+		if v1.Len() > v2.Len() {
+			return false
+		}
 		if v1.Pointer() == v2.Pointer() {
 			return true
 		}
@@ -335,6 +345,9 @@ func (e Equalities) deepValueDerive(v1, v2 reflect.Value, visited map[visit]bool
 		if v1.Len() == 0 {
 			return true
 		}
+		if v1.Len() > v2.Len() {
+			return false
+		}
 		return v1.String() == v2.String()
 	case reflect.Interface:
 		if v1.IsNil() {
@@ -354,12 +367,12 @@ func (e Equalities) deepValueDerive(v1, v2 reflect.Value, visited map[visit]bool
 		}
 		return true
 	case reflect.Map:
-		if (v1.IsNil() || v1.Len() == 0) != (v2.IsNil() || v2.Len() == 0) {
-			return false
-		}
 		if v1.IsNil() || v1.Len() == 0 {
 			return true
 		}
+		if v1.Len() > v2.Len() {
+			return false
+		}
 		if v1.Pointer() == v2.Pointer() {
 			return true
 		}
diff --git a/pkg/conversion/deep_equal_test.go b/pkg/conversion/deep_equal_test.go
index d89ab53e5cf..3feb13e3cec 100644
--- a/pkg/conversion/deep_equal_test.go
+++ b/pkg/conversion/deep_equal_test.go
@@ -50,14 +50,31 @@ func TestEqualities(t *testing.T) {
 	}{
 		{1, 2, true},
 		{2, 1, false},
+		{"foo", "fo", false},
 		{"foo", "foo", true},
+		{"foo", "foobar", false},
 		{Foo{1}, Foo{2}, true},
+		{Foo{2}, Foo{1}, false},
 		{Bar{1}, Bar{10}, true},
 		{&Bar{1}, &Bar{10}, true},
 		{Baz{Bar{1}}, Baz{Bar{10}}, true},
+		{[...]string{}, [...]string{"1", "2", "3"}, false},
+		{[...]string{"1"}, [...]string{"1", "2", "3"}, false},
+		{[...]string{"1", "2", "3"}, [...]string{}, false},
+		{[...]string{"1", "2", "3"}, [...]string{"1", "2", "3"}, true},
+		{map[string]int{"foo": 1}, map[string]int{}, false},
 		{map[string]int{"foo": 1}, map[string]int{"foo": 2}, true},
+		{map[string]int{"foo": 2}, map[string]int{"foo": 1}, false},
+		{map[string]int{"foo": 1}, map[string]int{"foo": 2, "bar": 6}, false},
+		{map[string]int{"foo": 1, "bar": 6}, map[string]int{"foo": 2}, false},
 		{map[string]int{}, map[string]int(nil), true},
-		{[]int{}, []int(nil), true},
+		{[]string(nil), []string(nil), true},
+		{[]string{}, []string(nil), true},
+		{[]string(nil), []string{}, true},
+		{[]string{"1"}, []string(nil), false},
+		{[]string{}, []string{"1", "2", "3"}, false},
+		{[]string{"1"}, []string{"1", "2", "3"}, false},
+		{[]string{"1", "2", "3"}, []string{}, false},
 	}
 
 	for _, item := range table {
@@ -66,3 +83,67 @@ func TestEqualities(t *testing.T) {
 		}
 	}
 }
+
+func TestDerivates(t *testing.T) {
+	e := Equalities{}
+	type Bar struct {
+		X int
+	}
+	type Baz struct {
+		Y Bar
+	}
+	err := e.AddFuncs(
+		func(a, b int) bool {
+			return a+1 == b
+		},
+		func(a, b Bar) bool {
+			return a.X*10 == b.X
+		},
+	)
+	if err != nil {
+		t.Fatalf("Unexpected: %v", err)
+	}
+
+	type Foo struct {
+		X int
+	}
+
+	table := []struct {
+		a, b  interface{}
+		equal bool
+	}{
+		{1, 2, true},
+		{2, 1, false},
+		{"foo", "fo", false},
+		{"foo", "foo", true},
+		{"foo", "foobar", false},
+		{Foo{1}, Foo{2}, true},
+		{Foo{2}, Foo{1}, false},
+		{Bar{1}, Bar{10}, true},
+		{&Bar{1}, &Bar{10}, true},
+		{Baz{Bar{1}}, Baz{Bar{10}}, true},
+		{[...]string{}, [...]string{"1", "2", "3"}, false},
+		{[...]string{"1"}, [...]string{"1", "2", "3"}, false},
+		{[...]string{"1", "2", "3"}, [...]string{}, false},
+		{[...]string{"1", "2", "3"}, [...]string{"1", "2", "3"}, true},
+		{map[string]int{"foo": 1}, map[string]int{}, false},
+		{map[string]int{"foo": 1}, map[string]int{"foo": 2}, true},
+		{map[string]int{"foo": 2}, map[string]int{"foo": 1}, false},
+		{map[string]int{"foo": 1}, map[string]int{"foo": 2, "bar": 6}, true},
+		{map[string]int{"foo": 1, "bar": 6}, map[string]int{"foo": 2}, false},
+		{map[string]int{}, map[string]int(nil), true},
+		{[]string(nil), []string(nil), true},
+		{[]string{}, []string(nil), true},
+		{[]string(nil), []string{}, true},
+		{[]string{"1"}, []string(nil), false},
+		{[]string{}, []string{"1", "2", "3"}, true},
+		{[]string{"1"}, []string{"1", "2", "3"}, true},
+		{[]string{"1", "2", "3"}, []string{}, false},
+	}
+
+	for _, item := range table {
+		if e, a := item.equal, e.DeepDerivative(item.a, item.b); e != a {
+			t.Errorf("Expected (%+v ~ %+v) == %v, but got %v", item.a, item.b, e, a)
+		}
+	}
+}