diff --git a/docs/library/ssl.rst b/docs/library/ssl.rst
index f9be27745379..e1e738aa9fe9 100644
--- a/docs/library/ssl.rst
+++ b/docs/library/ssl.rst
@@ -117,11 +117,32 @@ Exceptions
 
    This exception does NOT exist. Instead its base class, OSError, is used.
 
+DTLS support
+------------
+
+.. admonition:: Difference to CPython
+   :class: attention
+
+   This is a MicroPython extension.
+
+This module supports DTLS in client and server mode via the `PROTOCOL_DTLS_CLIENT`
+and `PROTOCOL_DTLS_SERVER` constants that can be used as the ``protocol`` argument
+of `SSLContext`.
+
+In this case the underlying socket is expected to behave as a datagram socket (i.e.
+like the socket opened with ``socket.socket`` with ``socket.AF_INET`` as ``af`` and
+``socket.SOCK_DGRAM`` as ``type``).
+
+DTLS is only supported on ports that use mbed TLS, and it is not enabled by default:
+it requires enabling ``MBEDTLS_SSL_PROTO_DTLS`` in the specific port configuration.
+
 Constants
 ---------
 
 .. data:: ssl.PROTOCOL_TLS_CLIENT
           ssl.PROTOCOL_TLS_SERVER
+          ssl.PROTOCOL_DTLS_CLIENT (when DTLS support is enabled)
+          ssl.PROTOCOL_DTLS_SERVER (when DTLS support is enabled)
 
     Supported values for the *protocol* parameter.
 
diff --git a/extmod/modssl_mbedtls.c b/extmod/modssl_mbedtls.c
index 0190c96a9ab1..feb6d04306aa 100644
--- a/extmod/modssl_mbedtls.c
+++ b/extmod/modssl_mbedtls.c
@@ -37,6 +37,8 @@
 #include "py/stream.h"
 #include "py/objstr.h"
 #include "py/reader.h"
+#include "py/smallint.h"
+#include "py/mphal.h"
 #include "extmod/vfs.h"
 
 // mbedtls_time_t
@@ -46,6 +48,9 @@
 #include "mbedtls/pk.h"
 #include "mbedtls/entropy.h"
 #include "mbedtls/ctr_drbg.h"
+#ifdef MBEDTLS_SSL_PROTO_DTLS
+#include "mbedtls/timing.h"
+#endif
 #include "mbedtls/debug.h"
 #include "mbedtls/error.h"
 #if MBEDTLS_VERSION_NUMBER >= 0x03000000
@@ -56,6 +61,14 @@
 
 #define MP_STREAM_POLL_RDWR (MP_STREAM_POLL_RD | MP_STREAM_POLL_WR)
 
+#define MP_ENDPOINT_IS_SERVER (1 << 0)
+#define MP_TRANSPORT_IS_DTLS  (1 << 1)
+
+#define MP_PROTOCOL_TLS_CLIENT  0
+#define MP_PROTOCOL_TLS_SERVER  MP_ENDPOINT_IS_SERVER
+#define MP_PROTOCOL_DTLS_CLIENT MP_TRANSPORT_IS_DTLS
+#define MP_PROTOCOL_DTLS_SERVER MP_ENDPOINT_IS_SERVER | MP_TRANSPORT_IS_DTLS
+
 // This corresponds to an SSLContext object.
 typedef struct _mp_obj_ssl_context_t {
     mp_obj_base_t base;
@@ -78,6 +91,12 @@ typedef struct _mp_obj_ssl_socket_t {
 
     uintptr_t poll_mask; // Indicates which read or write operations the protocol needs next
     int last_error; // The last error code, if any
+
+    #ifdef MBEDTLS_SSL_PROTO_DTLS
+    mp_uint_t timer_start_ms;
+    mp_int_t timer_fin_ms;
+    mp_int_t timer_int_ms;
+    #endif
 } mp_obj_ssl_socket_t;
 
 STATIC const mp_obj_type_t ssl_context_type;
@@ -213,7 +232,10 @@ STATIC mp_obj_t ssl_context_make_new(const mp_obj_type_t *type_in, size_t n_args
     mp_arg_check_num(n_args, n_kw, 1, 1, false);
 
     // This is the "protocol" argument.
-    mp_int_t endpoint = mp_obj_get_int(args[0]);
+    mp_int_t protocol = mp_obj_get_int(args[0]);
+
+    int endpoint = (protocol & MP_ENDPOINT_IS_SERVER) ? MBEDTLS_SSL_IS_SERVER : MBEDTLS_SSL_IS_CLIENT;
+    int transport = (protocol & MP_TRANSPORT_IS_DTLS) ? MBEDTLS_SSL_TRANSPORT_DATAGRAM : MBEDTLS_SSL_TRANSPORT_STREAM;
 
     // Create SSLContext object.
     #if MICROPY_PY_SSL_FINALISER
@@ -250,7 +272,7 @@ STATIC mp_obj_t ssl_context_make_new(const mp_obj_type_t *type_in, size_t n_args
     }
 
     ret = mbedtls_ssl_config_defaults(&self->conf, endpoint,
-        MBEDTLS_SSL_TRANSPORT_STREAM, MBEDTLS_SSL_PRESET_DEFAULT);
+        transport, MBEDTLS_SSL_PRESET_DEFAULT);
     if (ret != 0) {
         mbedtls_raise_error(ret);
     }
@@ -518,6 +540,41 @@ STATIC int _mbedtls_ssl_recv(void *ctx, byte *buf, size_t len) {
     }
 }
 
+#ifdef MBEDTLS_SSL_PROTO_DTLS
+STATIC void _mbedtls_timing_set_delay(void *ctx, uint32_t int_ms, uint32_t fin_ms) {
+    mp_obj_ssl_socket_t *o = (mp_obj_ssl_socket_t *)ctx;
+
+    o->timer_int_ms = int_ms;
+    o->timer_fin_ms = fin_ms;
+
+    if (fin_ms != 0) {
+        o->timer_start_ms = mp_hal_ticks_ms() & (MICROPY_PY_TIME_TICKS_PERIOD - 1);
+    }
+}
+
+STATIC int _mbedtls_timing_get_delay(void *ctx) {
+    mp_obj_ssl_socket_t *o = (mp_obj_ssl_socket_t *)ctx;
+
+    if (o->timer_fin_ms == 0) {
+        return -1;
+    }
+
+    mp_uint_t now = mp_hal_ticks_ms() & (MICROPY_PY_TIME_TICKS_PERIOD - 1);
+    mp_int_t elapsed_ms = ((now - o->timer_start_ms + MICROPY_PY_TIME_TICKS_PERIOD / 2) & (MICROPY_PY_TIME_TICKS_PERIOD - 1))
+        - MICROPY_PY_TIME_TICKS_PERIOD / 2;
+
+    if (elapsed_ms >= o->timer_fin_ms) {
+        return 2;
+    }
+
+    if (elapsed_ms >= o->timer_int_ms) {
+        return 1;
+    }
+
+    return 0;
+}
+#endif
+
 STATIC mp_obj_t ssl_socket_make_new(mp_obj_ssl_context_t *ssl_context, mp_obj_t sock,
     bool server_side, bool do_handshake_on_connect, mp_obj_t server_hostname) {
 
@@ -558,6 +615,12 @@ STATIC mp_obj_t ssl_socket_make_new(mp_obj_ssl_context_t *ssl_context, mp_obj_t
         mp_raise_ValueError(MP_ERROR_TEXT("CERT_REQUIRED requires server_hostname"));
     }
 
+    #ifdef MBEDTLS_SSL_PROTO_DTLS
+    mbedtls_ssl_set_timer_cb(&o->ssl, o,
+        _mbedtls_timing_set_delay,
+        _mbedtls_timing_get_delay);
+    #endif
+
     mbedtls_ssl_set_bio(&o->ssl, &o->sock, _mbedtls_ssl_send, _mbedtls_ssl_recv, NULL);
 
     if (do_handshake_on_connect) {
@@ -760,6 +823,12 @@ STATIC const mp_rom_map_elem_t ssl_socket_locals_dict_table[] = {
     { MP_ROM_QSTR(MP_QSTR_readinto), MP_ROM_PTR(&mp_stream_readinto_obj) },
     { MP_ROM_QSTR(MP_QSTR_readline), MP_ROM_PTR(&mp_stream_unbuffered_readline_obj) },
     { MP_ROM_QSTR(MP_QSTR_write), MP_ROM_PTR(&mp_stream_write_obj) },
+    #ifdef MBEDTLS_SSL_PROTO_DTLS
+    { MP_ROM_QSTR(MP_QSTR_recv), MP_ROM_PTR(&mp_stream_read1_obj) },
+    { MP_ROM_QSTR(MP_QSTR_recv_into), MP_ROM_PTR(&mp_stream_readinto_obj) },
+    { MP_ROM_QSTR(MP_QSTR_send), MP_ROM_PTR(&mp_stream_write1_obj) },
+    { MP_ROM_QSTR(MP_QSTR_sendall), MP_ROM_PTR(&mp_stream_write_obj) },
+    #endif
     { MP_ROM_QSTR(MP_QSTR_setblocking), MP_ROM_PTR(&socket_setblocking_obj) },
     { MP_ROM_QSTR(MP_QSTR_close), MP_ROM_PTR(&mp_stream_close_obj) },
     #if MICROPY_PY_SSL_FINALISER
@@ -853,8 +922,12 @@ STATIC const mp_rom_map_elem_t mp_module_ssl_globals_table[] = {
 
     // Constants.
     { MP_ROM_QSTR(MP_QSTR_MBEDTLS_VERSION), MP_ROM_PTR(&mbedtls_version_obj)},
-    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_TLS_CLIENT), MP_ROM_INT(MBEDTLS_SSL_IS_CLIENT) },
-    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_TLS_SERVER), MP_ROM_INT(MBEDTLS_SSL_IS_SERVER) },
+    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_TLS_CLIENT), MP_ROM_INT(MP_PROTOCOL_TLS_CLIENT) },
+    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_TLS_SERVER), MP_ROM_INT(MP_PROTOCOL_TLS_SERVER) },
+    #ifdef MBEDTLS_SSL_PROTO_DTLS
+    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_DTLS_CLIENT), MP_ROM_INT(MP_PROTOCOL_DTLS_CLIENT) },
+    { MP_ROM_QSTR(MP_QSTR_PROTOCOL_DTLS_SERVER), MP_ROM_INT(MP_PROTOCOL_DTLS_SERVER) },
+    #endif
     { MP_ROM_QSTR(MP_QSTR_CERT_NONE), MP_ROM_INT(MBEDTLS_SSL_VERIFY_NONE) },
     { MP_ROM_QSTR(MP_QSTR_CERT_OPTIONAL), MP_ROM_INT(MBEDTLS_SSL_VERIFY_OPTIONAL) },
     { MP_ROM_QSTR(MP_QSTR_CERT_REQUIRED), MP_ROM_INT(MBEDTLS_SSL_VERIFY_REQUIRED) },
diff --git a/ports/esp32/boards/sdkconfig.base b/ports/esp32/boards/sdkconfig.base
index 05624f0d7409..4eb7e165fc33 100644
--- a/ports/esp32/boards/sdkconfig.base
+++ b/ports/esp32/boards/sdkconfig.base
@@ -62,6 +62,8 @@ CONFIG_MBEDTLS_ASYMMETRIC_CONTENT_LEN=y
 CONFIG_MBEDTLS_HAVE_TIME_DATE=y
 CONFIG_MBEDTLS_PLATFORM_TIME_ALT=y
 CONFIG_MBEDTLS_HAVE_TIME=y
+# Enable DTLS
+CONFIG_MBEDTLS_SSL_PROTO_DTLS=y
 
 # Disable ALPN support as it's not implemented in MicroPython
 CONFIG_MBEDTLS_SSL_ALPN=n
diff --git a/ports/unix/mbedtls/mbedtls_config.h b/ports/unix/mbedtls/mbedtls_config.h
index 629064abcf29..88f31469c121 100644
--- a/ports/unix/mbedtls/mbedtls_config.h
+++ b/ports/unix/mbedtls/mbedtls_config.h
@@ -29,6 +29,9 @@
 // Set mbedtls configuration
 #define MBEDTLS_CIPHER_MODE_CTR // needed for MICROPY_PY_CRYPTOLIB_CTR
 
+// Enable DTLS
+#define MBEDTLS_SSL_PROTO_DTLS
+
 // Enable mbedtls modules
 #define MBEDTLS_HAVEGE_C
 #define MBEDTLS_TIMING_C