diff --git a/stubs/PyMySQL/pymysql/constants/CLIENT.pyi b/stubs/PyMySQL/pymysql/constants/CLIENT.pyi
index ac8fb5514..21019e028 100644
--- a/stubs/PyMySQL/pymysql/constants/CLIENT.pyi
+++ b/stubs/PyMySQL/pymysql/constants/CLIENT.pyi
@@ -15,4 +15,11 @@ TRANSACTIONS: int
 SECURE_CONNECTION: int
 MULTI_STATEMENTS: int
 MULTI_RESULTS: int
+PS_MULTI_RESULTS: int
+PLUGIN_AUTH: int
+CONNECT_ATTRS: int
+PLUGIN_AUTH_LENENC_CLIENT_DATA: int
 CAPABILITIES: int
+HANDLE_EXPIRED_PASSWORDS: int
+SESSION_TRACK: int
+DEPRECATE_EOF: int
diff --git a/stubs/PyMySQL/pymysql/constants/COMMAND.pyi b/stubs/PyMySQL/pymysql/constants/COMMAND.pyi
index 1163e6b4b..fe74c540b 100644
--- a/stubs/PyMySQL/pymysql/constants/COMMAND.pyi
+++ b/stubs/PyMySQL/pymysql/constants/COMMAND.pyi
@@ -20,3 +20,13 @@ COM_BINLOG_DUMP: int
 COM_TABLE_DUMP: int
 COM_CONNECT_OUT: int
 COM_REGISTER_SLAVE: int
+COM_STMT_PREPARE: int
+COM_STMT_EXECUTE: int
+COM_STMT_SEND_LONG_DATA: int
+COM_STMT_CLOSE: int
+COM_STMT_RESET: int
+COM_SET_OPTION: int
+COM_STMT_FETCH: int
+COM_DAEMON: int
+COM_BINLOG_DUMP_GTID: int
+COM_END: int
diff --git a/stubs/PyMySQL/pymysql/constants/CR.pyi b/stubs/PyMySQL/pymysql/constants/CR.pyi
new file mode 100644
index 000000000..010373963
--- /dev/null
+++ b/stubs/PyMySQL/pymysql/constants/CR.pyi
@@ -0,0 +1,64 @@
+CR_ERROR_FIRST: int
+CR_UNKNOWN_ERROR: int
+CR_SOCKET_CREATE_ERROR: int
+CR_CONNECTION_ERROR: int
+CR_CONN_HOST_ERROR: int
+CR_IPSOCK_ERROR: int
+CR_UNKNOWN_HOST: int
+CR_SERVER_GONE_ERROR: int
+CR_VERSION_ERROR: int
+CR_OUT_OF_MEMORY: int
+CR_WRONG_HOST_INFO: int
+CR_LOCALHOST_CONNECTION: int
+CR_TCP_CONNECTION: int
+CR_SERVER_HANDSHAKE_ERR: int
+CR_SERVER_LOST: int
+CR_COMMANDS_OUT_OF_SYNC: int
+CR_NAMEDPIPE_CONNECTION: int
+CR_NAMEDPIPEWAIT_ERROR: int
+CR_NAMEDPIPEOPEN_ERROR: int
+CR_NAMEDPIPESETSTATE_ERROR: int
+CR_CANT_READ_CHARSET: int
+CR_NET_PACKET_TOO_LARGE: int
+CR_EMBEDDED_CONNECTION: int
+CR_PROBE_SLAVE_STATUS: int
+CR_PROBE_SLAVE_HOSTS: int
+CR_PROBE_SLAVE_CONNECT: int
+CR_PROBE_MASTER_CONNECT: int
+CR_SSL_CONNECTION_ERROR: int
+CR_MALFORMED_PACKET: int
+CR_WRONG_LICENSE: int
+CR_NULL_POINTER: int
+CR_NO_PREPARE_STMT: int
+CR_PARAMS_NOT_BOUND: int
+CR_DATA_TRUNCATED: int
+CR_NO_PARAMETERS_EXISTS: int
+CR_INVALID_PARAMETER_NO: int
+CR_INVALID_BUFFER_USE: int
+CR_UNSUPPORTED_PARAM_TYPE: int
+CR_SHARED_MEMORY_CONNECTION: int
+CR_SHARED_MEMORY_CONNECT_REQUEST_ERROR: int
+CR_SHARED_MEMORY_CONNECT_ANSWER_ERROR: int
+CR_SHARED_MEMORY_CONNECT_FILE_MAP_ERROR: int
+CR_SHARED_MEMORY_CONNECT_MAP_ERROR: int
+CR_SHARED_MEMORY_FILE_MAP_ERROR: int
+CR_SHARED_MEMORY_MAP_ERROR: int
+CR_SHARED_MEMORY_EVENT_ERROR: int
+CR_SHARED_MEMORY_CONNECT_ABANDONED_ERROR: int
+CR_SHARED_MEMORY_CONNECT_SET_ERROR: int
+CR_CONN_UNKNOW_PROTOCOL: int
+CR_INVALID_CONN_HANDLE: int
+CR_SECURE_AUTH: int
+CR_FETCH_CANCELED: int
+CR_NO_DATA: int
+CR_NO_STMT_METADATA: int
+CR_NO_RESULT_SET: int
+CR_NOT_IMPLEMENTED: int
+CR_SERVER_LOST_EXTENDED: int
+CR_STMT_CLOSED: int
+CR_NEW_STMT_METADATA: int
+CR_ALREADY_CONNECTED: int
+CR_AUTH_PLUGIN_CANNOT_LOAD: int
+CR_DUPLICATE_CONNECTION_ATTR: int
+CR_AUTH_PLUGIN_ERR: int
+CR_ERROR_LAST: int
diff --git a/stubs/PyMySQL/pymysql/constants/ER.pyi b/stubs/PyMySQL/pymysql/constants/ER.pyi
index 5f0a432ee..0f4c17f04 100644
--- a/stubs/PyMySQL/pymysql/constants/ER.pyi
+++ b/stubs/PyMySQL/pymysql/constants/ER.pyi
@@ -469,3 +469,4 @@ USERNAME: int
 HOSTNAME: int
 WRONG_STRING_LENGTH: int
 ERROR_LAST: int
+CONSTRAINT_FAILED: int
diff --git a/stubs/PyMySQL/pymysql/constants/FIELD_TYPE.pyi b/stubs/PyMySQL/pymysql/constants/FIELD_TYPE.pyi
index f1938b001..4790d922e 100644
--- a/stubs/PyMySQL/pymysql/constants/FIELD_TYPE.pyi
+++ b/stubs/PyMySQL/pymysql/constants/FIELD_TYPE.pyi
@@ -15,6 +15,7 @@ YEAR: int
 NEWDATE: int
 VARCHAR: int
 BIT: int
+JSON: int
 NEWDECIMAL: int
 ENUM: int
 SET: int
diff --git a/stubs/PyMySQL/pymysql/constants/FLAG.pyi b/stubs/PyMySQL/pymysql/constants/FLAG.pyi
index 04b99fadc..421f23156 100644
--- a/stubs/PyMySQL/pymysql/constants/FLAG.pyi
+++ b/stubs/PyMySQL/pymysql/constants/FLAG.pyi
@@ -1,17 +1,15 @@
-from typing import Any
-
-NOT_NULL: Any
-PRI_KEY: Any
-UNIQUE_KEY: Any
-MULTIPLE_KEY: Any
-BLOB: Any
-UNSIGNED: Any
-ZEROFILL: Any
-BINARY: Any
-ENUM: Any
-AUTO_INCREMENT: Any
-TIMESTAMP: Any
-SET: Any
-PART_KEY: Any
-GROUP: Any
-UNIQUE: Any
+NOT_NULL: int
+PRI_KEY: int
+UNIQUE_KEY: int
+MULTIPLE_KEY: int
+BLOB: int
+UNSIGNED: int
+ZEROFILL: int
+BINARY: int
+ENUM: int
+AUTO_INCREMENT: int
+TIMESTAMP: int
+SET: int
+PART_KEY: int
+GROUP: int
+UNIQUE: int