diff --git a/pkg/core/interop/runtime/engine.go b/pkg/core/interop/runtime/engine.go
index 8bb3f8e19..fe25c8b77 100644
--- a/pkg/core/interop/runtime/engine.go
+++ b/pkg/core/interop/runtime/engine.go
@@ -61,7 +61,7 @@ func Notify(ic *interop.Context) error {
 	// But it has to be serializable, otherwise we either have some broken
 	// (recursive) structure inside or an interop item that can't be used
 	// outside of the interop subsystem anyway.
-	bytes, err := stackitem.SerializeItem(elem.Item())
+	bytes, err := stackitem.Serialize(elem.Item())
 	if err != nil {
 		return fmt.Errorf("bad notification: %w", err)
 	}
diff --git a/pkg/core/interop/storage/find.go b/pkg/core/interop/storage/find.go
index a969e1077..045c9290f 100644
--- a/pkg/core/interop/storage/find.go
+++ b/pkg/core/interop/storage/find.go
@@ -57,7 +57,7 @@ func (s *Iterator) Value() stackitem.Item {
 	if s.opts&FindDeserialize != 0 {
 		bs := s.m[s.index].Value.Value().([]byte)
 		var err error
-		value, err = stackitem.DeserializeItem(bs)
+		value, err = stackitem.Deserialize(bs)
 		if err != nil {
 			panic(err)
 		}
diff --git a/pkg/core/interop_system_test.go b/pkg/core/interop_system_test.go
index 298bf29e9..a64b45aa1 100644
--- a/pkg/core/interop_system_test.go
+++ b/pkg/core/interop_system_test.go
@@ -266,11 +266,11 @@ func TestStorageFind(t *testing.T) {
 		stackitem.NewByteArray([]byte("second")),
 		stackitem.Null{},
 	}
-	rawArr, err := stackitem.SerializeItem(stackitem.NewArray(arr))
+	rawArr, err := stackitem.Serialize(stackitem.NewArray(arr))
 	require.NoError(t, err)
-	rawArr0, err := stackitem.SerializeItem(stackitem.NewArray(arr[:0]))
+	rawArr0, err := stackitem.Serialize(stackitem.NewArray(arr[:0]))
 	require.NoError(t, err)
-	rawArr1, err := stackitem.SerializeItem(stackitem.NewArray(arr[:1]))
+	rawArr1, err := stackitem.Serialize(stackitem.NewArray(arr[:1]))
 	require.NoError(t, err)
 
 	skeys := [][]byte{{0x01, 0x02}, {0x02, 0x01}, {0x01, 0x01},
diff --git a/pkg/core/native/native_neo.go b/pkg/core/native/native_neo.go
index b3ae87b85..dadeaee35 100644
--- a/pkg/core/native/native_neo.go
+++ b/pkg/core/native/native_neo.go
@@ -904,7 +904,7 @@ func (n *NEO) getAccountState(ic *interop.Context, args []stackitem.Item) stacki
 	}
 
 	r := io.NewBinReaderFromBuf(si)
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		panic(r.Err) // no errors are expected but we better be sure
 	}
diff --git a/pkg/core/native/native_neo_candidate.go b/pkg/core/native/native_neo_candidate.go
index 0fa014eb6..a1a7bb44f 100644
--- a/pkg/core/native/native_neo_candidate.go
+++ b/pkg/core/native/native_neo_candidate.go
@@ -15,14 +15,14 @@ type candidate struct {
 // Bytes marshals c to byte array.
 func (c *candidate) Bytes() []byte {
 	w := io.NewBufBinWriter()
-	stackitem.EncodeBinaryStackItem(c.toStackItem(), w.BinWriter)
+	stackitem.EncodeBinary(c.toStackItem(), w.BinWriter)
 	return w.Bytes()
 }
 
 // FromBytes unmarshals candidate from byte array.
 func (c *candidate) FromBytes(data []byte) *candidate {
 	r := io.NewBinReaderFromBuf(data)
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		panic(r.Err)
 	}
diff --git a/pkg/core/native/neo_types.go b/pkg/core/native/neo_types.go
index aeefda5b9..15dcf1e97 100644
--- a/pkg/core/native/neo_types.go
+++ b/pkg/core/native/neo_types.go
@@ -86,7 +86,7 @@ func (k *keysWithVotes) fromStackItem(item stackitem.Item) error {
 func (k keysWithVotes) Bytes() []byte {
 	var it = k.toStackItem()
 	var w = io.NewBufBinWriter()
-	stackitem.EncodeBinaryStackItem(it, w.BinWriter)
+	stackitem.EncodeBinary(it, w.BinWriter)
 	if w.Err != nil {
 		panic(w.Err)
 	}
@@ -96,7 +96,7 @@ func (k keysWithVotes) Bytes() []byte {
 // DecodeBytes deserializes keys and votes slice.
 func (k *keysWithVotes) DecodeBytes(data []byte) error {
 	var r = io.NewBinReaderFromBuf(data)
-	var it = stackitem.DecodeBinaryStackItem(r)
+	var it = stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		return r.Err
 	}
diff --git a/pkg/core/native/oracle.go b/pkg/core/native/oracle.go
index b6deb469c..7c500f6cf 100644
--- a/pkg/core/native/oracle.go
+++ b/pkg/core/native/oracle.go
@@ -278,7 +278,7 @@ func (o *Oracle) FinishInternal(ic *interop.Context) error {
 	})
 
 	r := io.NewBinReaderFromBuf(req.UserData)
-	userData := stackitem.DecodeBinaryStackItem(r)
+	userData := stackitem.DecodeBinary(r)
 	args := []stackitem.Item{
 		stackitem.Make(req.URL),
 		stackitem.Make(userData),
@@ -358,7 +358,7 @@ func (o *Oracle) RequestInternal(ic *interop.Context, url string, filter *string
 	}
 
 	w := io.NewBufBinWriter()
-	stackitem.EncodeBinaryStackItem(userData, w.BinWriter)
+	stackitem.EncodeBinary(userData, w.BinWriter)
 	if w.Err != nil {
 		return w.Err
 	}
diff --git a/pkg/core/native/oracle_types.go b/pkg/core/native/oracle_types.go
index fc6c90145..985897e72 100644
--- a/pkg/core/native/oracle_types.go
+++ b/pkg/core/native/oracle_types.go
@@ -25,12 +25,12 @@ func (l IDList) Bytes() []byte {
 
 // EncodeBinary implements io.Serializable.
 func (l IDList) EncodeBinary(w *io.BinWriter) {
-	stackitem.EncodeBinaryStackItem(l.toStackItem(), w)
+	stackitem.EncodeBinary(l.toStackItem(), w)
 }
 
 // DecodeBinary implements io.Serializable.
 func (l *IDList) DecodeBinary(r *io.BinReader) {
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil || item == nil {
 		return
 	}
@@ -84,12 +84,12 @@ func (l NodeList) Bytes() []byte {
 
 // EncodeBinary implements io.Serializable.
 func (l NodeList) EncodeBinary(w *io.BinWriter) {
-	stackitem.EncodeBinaryStackItem(l.toStackItem(), w)
+	stackitem.EncodeBinary(l.toStackItem(), w)
 }
 
 // DecodeBinary implements io.Serializable.
 func (l *NodeList) DecodeBinary(r *io.BinReader) {
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil || item == nil {
 		return
 	}
diff --git a/pkg/core/native/oracle_types_test.go b/pkg/core/native/oracle_types_test.go
index 78acf7bf2..c58323dd9 100644
--- a/pkg/core/native/oracle_types_test.go
+++ b/pkg/core/native/oracle_types_test.go
@@ -14,7 +14,7 @@ func getInvalidTestFunc(actual io.Serializable, value interface{}) func(t *testi
 	return func(t *testing.T) {
 		w := io.NewBufBinWriter()
 		it := stackitem.Make(value)
-		stackitem.EncodeBinaryStackItem(it, w.BinWriter)
+		stackitem.EncodeBinary(it, w.BinWriter)
 		require.NoError(t, w.Err)
 		require.Error(t, testserdes.DecodeBinary(w.Bytes(), actual))
 	}
diff --git a/pkg/core/native/std.go b/pkg/core/native/std.go
index d27be752e..f2e614b0a 100644
--- a/pkg/core/native/std.go
+++ b/pkg/core/native/std.go
@@ -160,7 +160,7 @@ func newStd() *Std {
 }
 
 func (s *Std) serialize(_ *interop.Context, args []stackitem.Item) stackitem.Item {
-	data, err := stackitem.SerializeItem(args[0])
+	data, err := stackitem.Serialize(args[0])
 	if err != nil {
 		panic(err)
 	}
@@ -177,7 +177,7 @@ func (s *Std) deserialize(_ *interop.Context, args []stackitem.Item) stackitem.I
 		panic(err)
 	}
 
-	item, err := stackitem.DeserializeItem(data)
+	item, err := stackitem.Deserialize(data)
 	if err != nil {
 		panic(err)
 	}
diff --git a/pkg/core/native/std_test.go b/pkg/core/native/std_test.go
index ce16eb01d..2558b5f2d 100644
--- a/pkg/core/native/std_test.go
+++ b/pkg/core/native/std_test.go
@@ -276,7 +276,7 @@ func TestStdLibSerialize(t *testing.T) {
 		})
 
 		w := io.NewBufBinWriter()
-		stackitem.EncodeBinaryStackItem(stackitem.Make(42), w.BinWriter)
+		stackitem.EncodeBinary(stackitem.Make(42), w.BinWriter)
 		require.NoError(t, w.Err)
 
 		encoded := w.Bytes()
@@ -368,7 +368,7 @@ func TestStdLibSerializeDeserialize(t *testing.T) {
 		})
 	})
 	t.Run("Deserialize unknown", func(t *testing.T) {
-		data, err := stackitem.SerializeItem(stackitem.NewBigInteger(big.NewInt(123)))
+		data, err := stackitem.Serialize(stackitem.NewBigInteger(big.NewInt(123)))
 		require.NoError(t, err)
 
 		data[0] = 0xFF
diff --git a/pkg/core/native_management_test.go b/pkg/core/native_management_test.go
index 355a57e37..57ec4c54e 100644
--- a/pkg/core/native_management_test.go
+++ b/pkg/core/native_management_test.go
@@ -94,7 +94,7 @@ func TestContractDeployAndUpdateWithParameter(t *testing.T) {
 		res, err := invokeContractMethod(bc, 1_00000000, cs1.Hash, "getValue")
 		require.NoError(t, err)
 		require.Equal(t, 1, len(res.Stack))
-		item, err := stackitem.DeserializeItem(res.Stack[0].Value().([]byte))
+		item, err := stackitem.Deserialize(res.Stack[0].Value().([]byte))
 		require.NoError(t, err)
 		expected := []stackitem.Item{stackitem.Make("create"), stackitem.Make(42)}
 		require.Equal(t, stackitem.NewArray(expected), item)
@@ -114,7 +114,7 @@ func TestContractDeployAndUpdateWithParameter(t *testing.T) {
 		res, err := invokeContractMethod(bc, 1_00000000, cs1.Hash, "getValue")
 		require.NoError(t, err)
 		require.Equal(t, 1, len(res.Stack))
-		item, err := stackitem.DeserializeItem(res.Stack[0].Value().([]byte))
+		item, err := stackitem.Deserialize(res.Stack[0].Value().([]byte))
 		require.NoError(t, err)
 		expected := []stackitem.Item{stackitem.Make("update"), stackitem.Make("new data")}
 		require.Equal(t, stackitem.NewArray(expected), item)
@@ -259,7 +259,7 @@ func TestContractDeploy(t *testing.T) {
 			res, err := invokeContractMethod(bc, 1_00000000, cs1.Hash, "getValue")
 			require.NoError(t, err)
 			require.Equal(t, 1, len(res.Stack))
-			item, err := stackitem.DeserializeItem(res.Stack[0].Value().([]byte))
+			item, err := stackitem.Deserialize(res.Stack[0].Value().([]byte))
 			require.NoError(t, err)
 			expected := []stackitem.Item{stackitem.Make("create"), stackitem.Null{}}
 			require.Equal(t, stackitem.NewArray(expected), item)
@@ -466,7 +466,7 @@ func TestContractUpdate(t *testing.T) {
 			res, err := invokeContractMethod(bc, 1_00000000, cs1.Hash, "getValue")
 			require.NoError(t, err)
 			require.Equal(t, 1, len(res.Stack))
-			item, err := stackitem.DeserializeItem(res.Stack[0].Value().([]byte))
+			item, err := stackitem.Deserialize(res.Stack[0].Value().([]byte))
 			require.NoError(t, err)
 			expected := []stackitem.Item{stackitem.Make("update"), stackitem.Null{}}
 			require.Equal(t, stackitem.NewArray(expected), item)
diff --git a/pkg/core/native_oracle_test.go b/pkg/core/native_oracle_test.go
index 3c56fb00a..660eb1ba7 100644
--- a/pkg/core/native_oracle_test.go
+++ b/pkg/core/native_oracle_test.go
@@ -183,7 +183,7 @@ func TestOracle_Request(t *testing.T) {
 
 	si := ic.DAO.GetStorageItem(cs.ID, []byte("lastOracleResponse"))
 	require.NotNil(t, si)
-	item, err := stackitem.DeserializeItem(si)
+	item, err := stackitem.Deserialize(si)
 	require.NoError(t, err)
 	arr, ok := item.Value().([]stackitem.Item)
 	require.True(t, ok)
diff --git a/pkg/core/state/contract.go b/pkg/core/state/contract.go
index 3c6da196b..e6ee4e873 100644
--- a/pkg/core/state/contract.go
+++ b/pkg/core/state/contract.go
@@ -37,7 +37,7 @@ type NativeContract struct {
 
 // DecodeBinary implements Serializable interface.
 func (c *Contract) DecodeBinary(r *io.BinReader) {
-	si := stackitem.DecodeBinaryStackItem(r)
+	si := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		return
 	}
@@ -51,7 +51,7 @@ func (c *Contract) EncodeBinary(w *io.BinWriter) {
 		w.Err = err
 		return
 	}
-	stackitem.EncodeBinaryStackItem(si, w)
+	stackitem.EncodeBinary(si, w)
 }
 
 // ToStackItem converts state.Contract to stackitem.Item.
diff --git a/pkg/core/state/native_state.go b/pkg/core/state/native_state.go
index 4b45239ab..75baee89d 100644
--- a/pkg/core/state/native_state.go
+++ b/pkg/core/state/native_state.go
@@ -58,12 +58,12 @@ func (s *NEP17BalanceState) fromStackItem(item stackitem.Item) {
 // EncodeBinary implements io.Serializable interface.
 func (s *NEP17BalanceState) EncodeBinary(w *io.BinWriter) {
 	si := s.toStackItem()
-	stackitem.EncodeBinaryStackItem(si, w)
+	stackitem.EncodeBinary(si, w)
 }
 
 // DecodeBinary implements io.Serializable interface.
 func (s *NEP17BalanceState) DecodeBinary(r *io.BinReader) {
-	si := stackitem.DecodeBinaryStackItem(r)
+	si := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		return
 	}
@@ -98,12 +98,12 @@ func (s *NEOBalanceState) Bytes() []byte {
 // EncodeBinary implements io.Serializable interface.
 func (s *NEOBalanceState) EncodeBinary(w *io.BinWriter) {
 	si := s.toStackItem()
-	stackitem.EncodeBinaryStackItem(si, w)
+	stackitem.EncodeBinary(si, w)
 }
 
 // DecodeBinary implements io.Serializable interface.
 func (s *NEOBalanceState) DecodeBinary(r *io.BinReader) {
-	si := stackitem.DecodeBinaryStackItem(r)
+	si := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		return
 	}
diff --git a/pkg/core/state/notification_event.go b/pkg/core/state/notification_event.go
index a7c032b76..87ea9dbb1 100644
--- a/pkg/core/state/notification_event.go
+++ b/pkg/core/state/notification_event.go
@@ -31,14 +31,14 @@ type AppExecResult struct {
 func (ne *NotificationEvent) EncodeBinary(w *io.BinWriter) {
 	ne.ScriptHash.EncodeBinary(w)
 	w.WriteString(ne.Name)
-	stackitem.EncodeBinaryStackItem(ne.Item, w)
+	stackitem.EncodeBinary(ne.Item, w)
 }
 
 // DecodeBinary implements the Serializable interface.
 func (ne *NotificationEvent) DecodeBinary(r *io.BinReader) {
 	ne.ScriptHash.DecodeBinary(r)
 	ne.Name = r.ReadString()
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil {
 		return
 	}
@@ -59,7 +59,7 @@ func (aer *AppExecResult) EncodeBinary(w *io.BinWriter) {
 	// Stack items are expected to be marshaled one by one.
 	w.WriteVarUint(uint64(len(aer.Stack)))
 	for _, it := range aer.Stack {
-		stackitem.EncodeBinaryStackItemAppExec(it, w)
+		stackitem.EncodeBinaryProtected(it, w)
 	}
 	w.WriteArray(aer.Events)
 	w.WriteVarBytes([]byte(aer.FaultException))
@@ -80,7 +80,7 @@ func (aer *AppExecResult) DecodeBinary(r *io.BinReader) {
 	}
 	arr := make([]stackitem.Item, sz)
 	for i := 0; i < int(sz); i++ {
-		arr[i] = stackitem.DecodeBinaryStackItemAppExec(r)
+		arr[i] = stackitem.DecodeBinaryProtected(r)
 		if r.Err != nil {
 			return
 		}
@@ -101,7 +101,7 @@ type notificationEventAux struct {
 func (ne NotificationEvent) MarshalJSON() ([]byte, error) {
 	item, err := stackitem.ToJSONWithTypes(ne.Item)
 	if err != nil {
-		item = []byte(`"error: recursive reference"`)
+		item = []byte(fmt.Sprintf(`"error: %v"`, err))
 	}
 	return json.Marshal(&notificationEventAux{
 		ScriptHash: ne.ScriptHash,
@@ -191,16 +191,11 @@ type executionAux struct {
 
 // MarshalJSON implements implements json.Marshaler interface.
 func (e Execution) MarshalJSON() ([]byte, error) {
-	var errRecursive = []byte(`"error: recursive reference"`)
 	arr := make([]json.RawMessage, len(e.Stack))
 	for i := range arr {
-		if e.Stack[i] == nil {
-			arr[i] = errRecursive
-			continue
-		}
 		data, err := stackitem.ToJSONWithTypes(e.Stack[i])
 		if err != nil {
-			data = errRecursive
+			data = []byte(fmt.Sprintf(`"error: %v"`, err))
 		}
 		arr[i] = data
 	}
diff --git a/pkg/core/state/notification_event_test.go b/pkg/core/state/notification_event_test.go
index 2429b7c81..2f6667f61 100644
--- a/pkg/core/state/notification_event_test.go
+++ b/pkg/core/state/notification_event_test.go
@@ -77,7 +77,7 @@ func TestEncodeDecodeAppExecResult(t *testing.T) {
 		w.WriteB(byte(aer.Trigger))
 		w.WriteB(byte(aer.VMState))
 		w.WriteU64LE(uint64(aer.GasConsumed))
-		stackitem.EncodeBinaryStackItem(stackitem.NewBool(true), w.BinWriter)
+		stackitem.EncodeBinary(stackitem.NewBool(true), w.BinWriter)
 		require.NoError(t, w.Err)
 		require.Error(t, testserdes.DecodeBinary(w.Bytes(), new(AppExecResult)))
 	})
@@ -184,7 +184,13 @@ func TestMarshalUnmarshalJSONAppExecResult(t *testing.T) {
 
 		bs1, err := json.Marshal(actual)
 		require.NoError(t, err)
-		require.Equal(t, bs, bs1)
+		require.NotEqual(t, bs, bs1) // recursive ref error vs. unserializable nil
+
+		actual2 := new(AppExecResult)
+		require.NoError(t, json.Unmarshal(bs, actual2))
+		bs2, err := json.Marshal(actual2)
+		require.NoError(t, err)
+		require.Equal(t, bs1, bs2) // unserializable nil in both cases
 	})
 
 	t.Run("UnmarshalJSON error", func(t *testing.T) {
diff --git a/pkg/core/state/oracle.go b/pkg/core/state/oracle.go
index ac8fa114d..96efde901 100644
--- a/pkg/core/state/oracle.go
+++ b/pkg/core/state/oracle.go
@@ -30,12 +30,12 @@ func (o *OracleRequest) Bytes() []byte {
 
 // EncodeBinary implements io.Serializable.
 func (o *OracleRequest) EncodeBinary(w *io.BinWriter) {
-	stackitem.EncodeBinaryStackItem(o.toStackItem(), w)
+	stackitem.EncodeBinary(o.toStackItem(), w)
 }
 
 // DecodeBinary implements io.Serializable.
 func (o *OracleRequest) DecodeBinary(r *io.BinReader) {
-	item := stackitem.DecodeBinaryStackItem(r)
+	item := stackitem.DecodeBinary(r)
 	if r.Err != nil || item == nil {
 		return
 	}
diff --git a/pkg/core/state/oracle_test.go b/pkg/core/state/oracle_test.go
index dc0a9ed12..bb17ee6bc 100644
--- a/pkg/core/state/oracle_test.go
+++ b/pkg/core/state/oracle_test.go
@@ -34,7 +34,7 @@ func TestOracleRequest_EncodeBinary(t *testing.T) {
 		t.Run("NotArray", func(t *testing.T) {
 			w.Reset()
 			it := stackitem.NewByteArray([]byte{})
-			stackitem.EncodeBinaryStackItem(it, w.BinWriter)
+			stackitem.EncodeBinary(it, w.BinWriter)
 			require.Error(t, testserdes.DecodeBinary(w.Bytes(), new(OracleRequest)))
 		})
 		t.Run("NotStackItem", func(t *testing.T) {
@@ -57,7 +57,7 @@ func TestOracleRequest_EncodeBinary(t *testing.T) {
 				w.Reset()
 				before := items[i]
 				items[i] = elem
-				stackitem.EncodeBinaryStackItem(arrItem, w.BinWriter)
+				stackitem.EncodeBinary(arrItem, w.BinWriter)
 				items[i] = before
 				require.Error(t, testserdes.DecodeBinary(w.Bytes(), new(OracleRequest)))
 			}
diff --git a/pkg/rpc/response/result/invoke.go b/pkg/rpc/response/result/invoke.go
index cbd2740f0..83685a7ac 100644
--- a/pkg/rpc/response/result/invoke.go
+++ b/pkg/rpc/response/result/invoke.go
@@ -70,7 +70,7 @@ func (r Invoke) MarshalJSON() ([]byte, error) {
 			for j := range iteratorValues {
 				value[j], err = stackitem.ToJSONWithTypes(iteratorValues[j])
 				if err != nil {
-					st = []byte(`"error: recursive reference"`)
+					st = []byte(fmt.Sprintf(`"error: %v"`, err))
 					break
 				}
 			}
@@ -85,7 +85,7 @@ func (r Invoke) MarshalJSON() ([]byte, error) {
 		} else {
 			data, err = stackitem.ToJSONWithTypes(r.Stack[i])
 			if err != nil {
-				st = []byte(`"error: recursive reference"`)
+				st = []byte(fmt.Sprintf(`"error: %v"`, err))
 				break
 			}
 		}
diff --git a/pkg/vm/stackitem/item.go b/pkg/vm/stackitem/item.go
index a8af99573..db2c1cac4 100644
--- a/pkg/vm/stackitem/item.go
+++ b/pkg/vm/stackitem/item.go
@@ -53,10 +53,28 @@ type Item interface {
 }
 
 var (
-	errInvalidConversion          = errors.New("invalid conversion type")
-	errExceedingMaxComparableSize = errors.New("the operand exceeds the maximum comparable size")
+	// ErrInvalidConversion is returned on attempt to make an incorrect
+	// conversion between item types.
+	ErrInvalidConversion = errors.New("invalid conversion")
+
+	// ErrTooBig is returned when item exceeds some size constraints like
+	// maximum allowed integer value of number of elements in array. It
+	// can also be returned by serialization functions if resulting
+	// value exceeds MaxSize.
+	ErrTooBig = errors.New("too big")
+
+	errTooBigComparable = fmt.Errorf("%w: uncomparable", ErrTooBig)
+	errTooBigInteger    = fmt.Errorf("%w: integer", ErrTooBig)
+	errTooBigKey        = fmt.Errorf("%w: map key", ErrTooBig)
+	errTooBigSize       = fmt.Errorf("%w: size", ErrTooBig)
 )
 
+// mkInvConversion creates conversion error with additional metadata (from and
+// to types).
+func mkInvConversion(from Item, to Type) error {
+	return fmt.Errorf("%w: %s/%s", ErrInvalidConversion, from, to)
+}
+
 // Make tries to make appropriate stack item from provided value.
 // It will panic if it's not possible.
 func Make(v interface{}) Item {
@@ -138,7 +156,7 @@ func ToString(item Item) (string, error) {
 		return "", err
 	}
 	if !utf8.Valid(bs) {
-		return "", errors.New("not a valid UTF-8")
+		return "", fmt.Errorf("%w: not UTF-8", ErrInvalidValue)
 	}
 	return string(bs), nil
 }
@@ -174,7 +192,7 @@ func convertPrimitive(item Item, typ Type) (Item, error) {
 		}
 		return NewBool(b), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(item, typ)
 	}
 }
 
@@ -232,12 +250,12 @@ func (i *Struct) TryBool() (bool, error) { return true, nil }
 
 // TryBytes implements Item interface.
 func (i *Struct) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Struct to ByteString")
+	return nil, mkInvConversion(i, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (i *Struct) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Struct to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -274,7 +292,7 @@ func (i *Struct) Convert(typ Type) (Item, error) {
 	case BooleanT:
 		return NewBool(true), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 }
 
@@ -318,12 +336,12 @@ func (i Null) TryBool() (bool, error) { return false, nil }
 
 // TryBytes implements Item interface.
 func (i Null) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Null to ByteString")
+	return nil, mkInvConversion(i, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (i Null) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Null to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -338,7 +356,7 @@ func (i Null) Type() Type { return AnyT }
 // Convert implements Item interface.
 func (i Null) Convert(typ Type) (Item, error) {
 	if typ == AnyT || !typ.IsValid() {
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 	return i, nil
 }
@@ -350,18 +368,16 @@ type BigInteger struct {
 
 // NewBigInteger returns an new BigInteger object.
 func NewBigInteger(value *big.Int) *BigInteger {
-	const tooBigErrMsg = "integer is too big"
-
 	// There are 2 cases, when `BitLen` differs from actual size:
 	// 1. Positive integer with highest bit on byte boundary = 1.
 	// 2. Negative integer with highest bit on byte boundary = 1
 	//    minus some value. (-0x80 -> 0x80, -0x7F -> 0x81, -0x81 -> 0x7FFF).
 	sz := value.BitLen()
 	if sz > MaxBigIntegerSizeBits {
-		panic(tooBigErrMsg)
+		panic(errTooBigInteger)
 	} else if sz == MaxBigIntegerSizeBits {
 		if value.Sign() == 1 || value.TrailingZeroBits() != MaxBigIntegerSizeBits-1 {
-			panic(tooBigErrMsg)
+			panic(errTooBigInteger)
 		}
 	}
 	return &BigInteger{
@@ -531,7 +547,7 @@ func (i *ByteArray) String() string {
 // TryBool implements Item interface.
 func (i *ByteArray) TryBool() (bool, error) {
 	if len(i.value) > MaxBigIntegerSizeBits/8 {
-		return false, errors.New("too big byte string")
+		return false, errTooBigInteger
 	}
 	for _, b := range i.value {
 		if b != 0 {
@@ -549,7 +565,7 @@ func (i *ByteArray) TryBytes() ([]byte, error) {
 // TryInteger implements Item interface.
 func (i *ByteArray) TryInteger() (*big.Int, error) {
 	if len(i.value) > MaxBigIntegerSizeBits/8 {
-		return nil, errors.New("integer is too big")
+		return nil, errTooBigInteger
 	}
 	return bigint.FromBytes(i.value), nil
 }
@@ -557,7 +573,7 @@ func (i *ByteArray) TryInteger() (*big.Int, error) {
 // Equals implements Item interface.
 func (i *ByteArray) Equals(s Item) bool {
 	if len(i.value) > MaxByteArrayComparableSize {
-		panic(errExceedingMaxComparableSize)
+		panic(errTooBigComparable)
 	}
 	if i == s {
 		return true
@@ -569,7 +585,7 @@ func (i *ByteArray) Equals(s Item) bool {
 		return false
 	}
 	if len(val.value) > MaxByteArrayComparableSize {
-		panic(errExceedingMaxComparableSize)
+		panic(errTooBigComparable)
 	}
 	return bytes.Equal(i.value, val.value)
 }
@@ -641,12 +657,12 @@ func (i *Array) TryBool() (bool, error) { return true, nil }
 
 // TryBytes implements Item interface.
 func (i *Array) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Array to ByteString")
+	return nil, mkInvConversion(i, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (i *Array) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Array to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -675,7 +691,7 @@ func (i *Array) Convert(typ Type) (Item, error) {
 	case BooleanT:
 		return NewBool(true), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 }
 
@@ -731,12 +747,12 @@ func (i *Map) TryBool() (bool, error) { return true, nil }
 
 // TryBytes implements Item interface.
 func (i *Map) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Map to ByteString")
+	return nil, mkInvConversion(i, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (i *Map) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Map to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -780,7 +796,7 @@ func (i *Map) Convert(typ Type) (Item, error) {
 	case BooleanT:
 		return NewBool(true), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 }
 
@@ -812,11 +828,11 @@ func IsValidMapKey(key Item) error {
 	case *ByteArray:
 		size := len(key.Value().([]byte))
 		if size > MaxKeySize {
-			return fmt.Errorf("invalid map key size: %d", size)
+			return errTooBigKey
 		}
 		return nil
 	default:
-		return fmt.Errorf("invalid map key of type %s", key.Type())
+		return fmt.Errorf("%w: %s map key", ErrInvalidType, key.Type())
 	}
 }
 
@@ -853,12 +869,12 @@ func (i *Interop) TryBool() (bool, error) { return true, nil }
 
 // TryBytes implements Item interface.
 func (i *Interop) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Interop to ByteString")
+	return nil, mkInvConversion(i, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (i *Interop) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Interop to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -883,7 +899,7 @@ func (i *Interop) Convert(typ Type) (Item, error) {
 	case BooleanT:
 		return NewBool(true), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 }
 
@@ -946,12 +962,12 @@ func (p *Pointer) TryBool() (bool, error) {
 
 // TryBytes implements Item interface.
 func (p *Pointer) TryBytes() ([]byte, error) {
-	return nil, errors.New("can't convert Pointer to ByteString")
+	return nil, mkInvConversion(p, ByteArrayT)
 }
 
 // TryInteger implements Item interface.
 func (p *Pointer) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Pointer to Integer")
+	return nil, mkInvConversion(p, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -976,7 +992,7 @@ func (p *Pointer) Convert(typ Type) (Item, error) {
 	case BooleanT:
 		return NewBool(true), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(p, typ)
 	}
 }
 
@@ -1024,7 +1040,7 @@ func (i *Buffer) TryBytes() ([]byte, error) {
 
 // TryInteger implements Item interface.
 func (i *Buffer) TryInteger() (*big.Int, error) {
-	return nil, errors.New("can't convert Buffer to Integer")
+	return nil, mkInvConversion(i, IntegerT)
 }
 
 // Equals implements Item interface.
@@ -1058,11 +1074,11 @@ func (i *Buffer) Convert(typ Type) (Item, error) {
 		return NewByteArray(val), nil
 	case IntegerT:
 		if len(i.value) > MaxBigIntegerSizeBits/8 {
-			return nil, errInvalidConversion
+			return nil, errTooBigInteger
 		}
 		return NewBigInteger(bigint.FromBytes(i.value)), nil
 	default:
-		return nil, errInvalidConversion
+		return nil, mkInvConversion(i, typ)
 	}
 }
 
diff --git a/pkg/vm/stackitem/json.go b/pkg/vm/stackitem/json.go
index ae934ba0e..b930344ba 100644
--- a/pkg/vm/stackitem/json.go
+++ b/pkg/vm/stackitem/json.go
@@ -23,8 +23,16 @@ type decoder struct {
 // MaxAllowedInteger is the maximum integer allowed to be encoded.
 const MaxAllowedInteger = 2<<53 - 1
 
-// maxJSONDepth is a maximum allowed depth-level of decoded JSON.
-const maxJSONDepth = 10
+// MaxJSONDepth is the maximum allowed nesting level of encoded/decoded JSON.
+const MaxJSONDepth = 10
+
+// ErrInvalidValue is returned when item value doesn't fit some constraints
+// during serialization or deserialization.
+var ErrInvalidValue = errors.New("invalid value")
+
+// ErrTooDeep is returned when JSON encoder/decoder goes beyond MaxJSONDepth in
+// its processing.
+var ErrTooDeep = errors.New("too deep")
 
 // ToJSON encodes Item to JSON.
 // It behaves as following:
@@ -48,7 +56,7 @@ func toJSON(buf *io.BufBinWriter, item Item) {
 	if w.Err != nil {
 		return
 	} else if buf.Len() > MaxSize {
-		w.Err = errors.New("item is too big")
+		w.Err = errTooBigSize
 	}
 	switch it := item.(type) {
 	case *Array, *Struct:
@@ -76,7 +84,7 @@ func toJSON(buf *io.BufBinWriter, item Item) {
 		w.WriteB('}')
 	case *BigInteger:
 		if it.value.CmpAbs(big.NewInt(MaxAllowedInteger)) == 1 {
-			w.Err = errors.New("too big integer")
+			w.Err = fmt.Errorf("%w (MaxAllowedInteger)", ErrInvalidValue)
 			return
 		}
 		w.WriteBytes([]byte(it.value.String()))
@@ -91,11 +99,11 @@ func toJSON(buf *io.BufBinWriter, item Item) {
 	case Null:
 		w.WriteBytes([]byte("null"))
 	default:
-		w.Err = fmt.Errorf("invalid item: %s", it.String())
+		w.Err = fmt.Errorf("%w: %s", ErrUnserializable, it.String())
 		return
 	}
 	if w.Err == nil && buf.Len() > MaxSize {
-		w.Err = errors.New("item is too big")
+		w.Err = errTooBigSize
 	}
 }
 
@@ -131,7 +139,7 @@ func FromJSON(data []byte) (Item, error) {
 	if item, err := d.decode(); err != nil {
 		return nil, err
 	} else if _, err := d.Token(); err != gio.EOF {
-		return nil, errors.New("unexpected items")
+		return nil, fmt.Errorf("%w: unexpected items", ErrInvalidValue)
 	} else {
 		return item, nil
 	}
@@ -146,8 +154,8 @@ func (d *decoder) decode() (Item, error) {
 	case json.Delim:
 		switch t {
 		case json.Delim('{'), json.Delim('['):
-			if d.depth == maxJSONDepth {
-				return nil, errors.New("JSON depth limit exceeded")
+			if d.depth == MaxJSONDepth {
+				return nil, ErrTooDeep
 			}
 			d.depth++
 			var item Item
@@ -167,7 +175,7 @@ func (d *decoder) decode() (Item, error) {
 		return NewByteArray([]byte(t)), nil
 	case float64:
 		if math.Floor(t) != t {
-			return nil, fmt.Errorf("real value is not allowed: %v", t)
+			return nil, fmt.Errorf("%w (real value for int)", ErrInvalidValue)
 		}
 		return NewBigInteger(big.NewInt(int64(t))), nil
 	case bool:
@@ -221,15 +229,14 @@ func ToJSONWithTypes(item Item) ([]byte, error) {
 }
 
 func toJSONWithTypes(item Item, seen map[Item]bool) (interface{}, error) {
-	typ := item.Type()
-	result := map[string]interface{}{
-		"type": typ.String(),
+	if len(seen) > MaxJSONDepth {
+		return "", ErrTooDeep
 	}
 	var value interface{}
 	switch it := item.(type) {
 	case *Array, *Struct:
 		if seen[item] {
-			return "", errors.New("recursive structures can't be serialized to json")
+			return "", ErrRecursive
 		}
 		seen[item] = true
 		arr := []interface{}{}
@@ -241,6 +248,7 @@ func toJSONWithTypes(item Item, seen map[Item]bool) (interface{}, error) {
 			arr = append(arr, s)
 		}
 		value = arr
+		delete(seen, item)
 	case *Bool:
 		value = it.value
 	case *Buffer, *ByteArray:
@@ -249,7 +257,7 @@ func toJSONWithTypes(item Item, seen map[Item]bool) (interface{}, error) {
 		value = it.value.String()
 	case *Map:
 		if seen[item] {
-			return "", errors.New("recursive structures can't be serialized to json")
+			return "", ErrRecursive
 		}
 		seen[item] = true
 		arr := []interface{}{}
@@ -266,8 +274,14 @@ func toJSONWithTypes(item Item, seen map[Item]bool) (interface{}, error) {
 			})
 		}
 		value = arr
+		delete(seen, item)
 	case *Pointer:
 		value = it.pos
+	case nil:
+		return "", fmt.Errorf("%w: nil", ErrUnserializable)
+	}
+	result := map[string]interface{}{
+		"type": item.Type().String(),
 	}
 	if value != nil {
 		result["value"] = value
@@ -287,6 +301,10 @@ type (
 	}
 )
 
+func mkErrValue(err error) error {
+	return fmt.Errorf("%w: %v", ErrInvalidValue, err)
+}
+
 // FromJSONWithTypes deserializes an item from typed-json representation.
 func FromJSONWithTypes(data []byte) (Item, error) {
 	raw := new(rawItem)
@@ -295,7 +313,7 @@ func FromJSONWithTypes(data []byte) (Item, error) {
 	}
 	typ, err := FromString(raw.Type)
 	if err != nil {
-		return nil, errors.New("invalid type")
+		return nil, fmt.Errorf("%w: %v", ErrInvalidType, raw.Type)
 	}
 	switch typ {
 	case AnyT:
@@ -303,33 +321,33 @@ func FromJSONWithTypes(data []byte) (Item, error) {
 	case PointerT:
 		var pos int
 		if err := json.Unmarshal(raw.Value, &pos); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		return NewPointer(pos, nil), nil
 	case BooleanT:
 		var b bool
 		if err := json.Unmarshal(raw.Value, &b); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		return NewBool(b), nil
 	case IntegerT:
 		var s string
 		if err := json.Unmarshal(raw.Value, &s); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		val, ok := new(big.Int).SetString(s, 10)
 		if !ok {
-			return nil, errors.New("invalid integer")
+			return nil, mkErrValue(errors.New("not an integer"))
 		}
 		return NewBigInteger(val), nil
 	case ByteArrayT, BufferT:
 		var s string
 		if err := json.Unmarshal(raw.Value, &s); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		val, err := base64.StdEncoding.DecodeString(s)
 		if err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		if typ == ByteArrayT {
 			return NewByteArray(val), nil
@@ -338,7 +356,7 @@ func FromJSONWithTypes(data []byte) (Item, error) {
 	case ArrayT, StructT:
 		var arr []json.RawMessage
 		if err := json.Unmarshal(raw.Value, &arr); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		items := make([]Item, len(arr))
 		for i := range arr {
@@ -355,7 +373,7 @@ func FromJSONWithTypes(data []byte) (Item, error) {
 	case MapT:
 		var arr []rawMapElement
 		if err := json.Unmarshal(raw.Value, &arr); err != nil {
-			return nil, err
+			return nil, mkErrValue(err)
 		}
 		m := NewMap()
 		for i := range arr {
@@ -375,6 +393,6 @@ func FromJSONWithTypes(data []byte) (Item, error) {
 	case InteropT:
 		return NewInterop(nil), nil
 	default:
-		return nil, errors.New("unexpected type")
+		return nil, fmt.Errorf("%w: %v", ErrInvalidType, typ)
 	}
 }
diff --git a/pkg/vm/stackitem/serialization.go b/pkg/vm/stackitem/serialization.go
index b30cb02c1..cbc54b4b0 100644
--- a/pkg/vm/stackitem/serialization.go
+++ b/pkg/vm/stackitem/serialization.go
@@ -9,28 +9,64 @@ import (
 	"github.com/nspcc-dev/neo-go/pkg/io"
 )
 
-// SerializeItem encodes given Item into the byte slice.
-func SerializeItem(item Item) ([]byte, error) {
+// ErrRecursive is returned on attempts to serialize some recursive stack item
+// (like array including an item with reference to the same array).
+var ErrRecursive = errors.New("recursive item")
+
+// ErrUnserializable is returned on attempt to serialize some item that can't
+// be serialized (like Interop item or Pointer).
+var ErrUnserializable = errors.New("unserializable")
+
+// serContext is an internal serialization context.
+type serContext struct {
+	*io.BinWriter
+	buf          *io.BufBinWriter
+	allowInvalid bool
+	seen         map[Item]bool
+}
+
+// Serialize encodes given Item into the byte slice.
+func Serialize(item Item) ([]byte, error) {
 	w := io.NewBufBinWriter()
-	EncodeBinaryStackItem(item, w.BinWriter)
+	sc := serContext{
+		BinWriter:    w.BinWriter,
+		buf:          w,
+		allowInvalid: false,
+		seen:         make(map[Item]bool),
+	}
+	sc.serialize(item)
 	if w.Err != nil {
 		return nil, w.Err
 	}
 	return w.Bytes(), nil
 }
 
-// EncodeBinaryStackItem encodes given Item into the given BinWriter. It's
+// EncodeBinary encodes given Item into the given BinWriter. It's
 // similar to io.Serializable's EncodeBinary, but works with Item
 // interface.
-func EncodeBinaryStackItem(item Item, w *io.BinWriter) {
-	serializeItemTo(item, w, false, make(map[Item]bool))
+func EncodeBinary(item Item, w *io.BinWriter) {
+	sc := serContext{
+		BinWriter:    w,
+		allowInvalid: false,
+		seen:         make(map[Item]bool),
+	}
+	sc.serialize(item)
 }
 
-// EncodeBinaryStackItemAppExec encodes given Item into the given BinWriter. It's
-// similar to EncodeBinaryStackItem but allows to encode interop (only type, value is lost).
-func EncodeBinaryStackItemAppExec(item Item, w *io.BinWriter) {
+// EncodeBinaryProtected encodes given Item into the given BinWriter. It's
+// similar to EncodeBinary but allows to encode interop items (only type,
+// value is lost) and doesn't return any errors in w, instead if error
+// (like recursive array) is encountered it just writes special InvalidT
+// type of element to w.
+func EncodeBinaryProtected(item Item, w *io.BinWriter) {
 	bw := io.NewBufBinWriter()
-	serializeItemTo(item, bw.BinWriter, true, make(map[Item]bool))
+	sc := serContext{
+		BinWriter:    bw.BinWriter,
+		buf:          bw,
+		allowInvalid: true,
+		seen:         make(map[Item]bool),
+	}
+	sc.serialize(item)
 	if bw.Err != nil {
 		w.WriteBytes([]byte{byte(InvalidT)})
 		return
@@ -38,13 +74,12 @@ func EncodeBinaryStackItemAppExec(item Item, w *io.BinWriter) {
 	w.WriteBytes(bw.Bytes())
 }
 
-func serializeItemTo(item Item, w *io.BinWriter, allowInvalid bool, seen map[Item]bool) {
-	if seen[item] {
-		w.Err = errors.New("recursive structures can't be serialized")
+func (w *serContext) serialize(item Item) {
+	if w.Err != nil {
 		return
 	}
-	if item == nil && allowInvalid {
-		w.WriteBytes([]byte{byte(InvalidT)})
+	if w.seen[item] {
+		w.Err = ErrRecursive
 		return
 	}
 
@@ -62,13 +97,13 @@ func serializeItemTo(item Item, w *io.BinWriter, allowInvalid bool, seen map[Ite
 		w.WriteBytes([]byte{byte(IntegerT)})
 		w.WriteVarBytes(bigint.ToBytes(t.Value().(*big.Int)))
 	case *Interop:
-		if allowInvalid {
+		if w.allowInvalid {
 			w.WriteBytes([]byte{byte(InteropT)})
-			return
+		} else {
+			w.Err = fmt.Errorf("%w: Interop", ErrUnserializable)
 		}
-		w.Err = errors.New("interop item can't be serialized")
 	case *Array, *Struct:
-		seen[item] = true
+		w.seen[item] = true
 
 		_, isArray := t.(*Array)
 		if isArray {
@@ -80,47 +115,59 @@ func serializeItemTo(item Item, w *io.BinWriter, allowInvalid bool, seen map[Ite
 		arr := t.Value().([]Item)
 		w.WriteVarUint(uint64(len(arr)))
 		for i := range arr {
-			serializeItemTo(arr[i], w, allowInvalid, seen)
+			w.serialize(arr[i])
 		}
+		delete(w.seen, item)
 	case *Map:
-		seen[item] = true
+		w.seen[item] = true
 
 		w.WriteBytes([]byte{byte(MapT)})
 		w.WriteVarUint(uint64(len(t.Value().([]MapElement))))
 		for i := range t.Value().([]MapElement) {
-			serializeItemTo(t.Value().([]MapElement)[i].Key, w, allowInvalid, seen)
-			serializeItemTo(t.Value().([]MapElement)[i].Value, w, allowInvalid, seen)
+			w.serialize(t.Value().([]MapElement)[i].Key)
+			w.serialize(t.Value().([]MapElement)[i].Value)
 		}
+		delete(w.seen, item)
 	case Null:
 		w.WriteB(byte(AnyT))
+	case nil:
+		if w.allowInvalid {
+			w.WriteBytes([]byte{byte(InvalidT)})
+		} else {
+			w.Err = fmt.Errorf("%w: nil", ErrUnserializable)
+		}
+	}
+
+	if w.Err == nil && w.buf != nil && w.buf.Len() > MaxSize {
+		w.Err = errTooBigSize
 	}
 }
 
-// DeserializeItem decodes Item from the given byte slice.
-func DeserializeItem(data []byte) (Item, error) {
+// Deserialize decodes Item from the given byte slice.
+func Deserialize(data []byte) (Item, error) {
 	r := io.NewBinReaderFromBuf(data)
-	item := DecodeBinaryStackItem(r)
+	item := DecodeBinary(r)
 	if r.Err != nil {
 		return nil, r.Err
 	}
 	return item, nil
 }
 
-// DecodeBinaryStackItem decodes previously serialized Item from the given
+// DecodeBinary decodes previously serialized Item from the given
 // reader. It's similar to the io.Serializable's DecodeBinary(), but implemented
 // as a function because Item itself is an interface. Caveat: always check
 // reader's error value before using the returned Item.
-func DecodeBinaryStackItem(r *io.BinReader) Item {
-	return decodeBinaryStackItem(r, false)
+func DecodeBinary(r *io.BinReader) Item {
+	return decodeBinary(r, false)
 }
 
-// DecodeBinaryStackItemAppExec is similar to DecodeBinaryStackItem
-// but allows Interop values to be present.
-func DecodeBinaryStackItemAppExec(r *io.BinReader) Item {
-	return decodeBinaryStackItem(r, true)
+// DecodeBinaryProtected is similar to DecodeBinary but allows Interop and
+// Invalid values to be present (making it symmetric to EncodeBinaryProtected).
+func DecodeBinaryProtected(r *io.BinReader) Item {
+	return decodeBinary(r, true)
 }
 
-func decodeBinaryStackItem(r *io.BinReader, allowInvalid bool) Item {
+func decodeBinary(r *io.BinReader, allowInvalid bool) Item {
 	var t = Type(r.ReadB())
 	if r.Err != nil {
 		return nil
@@ -144,7 +191,7 @@ func decodeBinaryStackItem(r *io.BinReader, allowInvalid bool) Item {
 		size := int(r.ReadVarUint())
 		arr := make([]Item, size)
 		for i := 0; i < size; i++ {
-			arr[i] = DecodeBinaryStackItem(r)
+			arr[i] = DecodeBinary(r)
 		}
 
 		if t == ArrayT {
@@ -155,8 +202,8 @@ func decodeBinaryStackItem(r *io.BinReader, allowInvalid bool) Item {
 		size := int(r.ReadVarUint())
 		m := NewMap()
 		for i := 0; i < size; i++ {
-			key := DecodeBinaryStackItem(r)
-			value := DecodeBinaryStackItem(r)
+			key := DecodeBinary(r)
+			value := DecodeBinary(r)
 			if r.Err != nil {
 				break
 			}
@@ -174,7 +221,7 @@ func decodeBinaryStackItem(r *io.BinReader, allowInvalid bool) Item {
 		if t == InvalidT && allowInvalid {
 			return nil
 		}
-		r.Err = fmt.Errorf("unknown type: %v", t)
+		r.Err = fmt.Errorf("%w: %v", ErrInvalidType, t)
 		return nil
 	}
 }
diff --git a/pkg/vm/stackitem/serialization_test.go b/pkg/vm/stackitem/serialization_test.go
new file mode 100644
index 000000000..02b07cb24
--- /dev/null
+++ b/pkg/vm/stackitem/serialization_test.go
@@ -0,0 +1,23 @@
+package stackitem
+
+import (
+	"errors"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestSerializationMaxErr(t *testing.T) {
+	base := make([]byte, MaxSize/2+1)
+	item := Make(base)
+
+	// Pointer is unserializable, but we specifically want to catch ErrTooBig.
+	arr := []Item{item, item.Dup(), NewPointer(0, []byte{})}
+	aitem := Make(arr)
+
+	_, err := Serialize(item)
+	require.NoError(t, err)
+
+	_, err = Serialize(aitem)
+	require.True(t, errors.Is(err, ErrTooBig), err)
+}
diff --git a/pkg/vm/stackitem/type.go b/pkg/vm/stackitem/type.go
index b28df9ebe..30dee93fd 100644
--- a/pkg/vm/stackitem/type.go
+++ b/pkg/vm/stackitem/type.go
@@ -2,6 +2,9 @@ package stackitem
 
 import "errors"
 
+// ErrInvalidType is returned on attempts to deserialize some unknown item type.
+var ErrInvalidType = errors.New("invalid type")
+
 // Type represents type of the stack item.
 type Type byte
 
@@ -82,6 +85,6 @@ func FromString(s string) (Type, error) {
 	case "Interop":
 		return InteropT, nil
 	default:
-		return 0xFF, errors.New("invalid type")
+		return 0xFF, ErrInvalidType
 	}
 }