diff --git a/library/ssl_tls.c b/library/ssl_tls.c
index e06c06d34b..f4bca87d21 100644
--- a/library/ssl_tls.c
+++ b/library/ssl_tls.c
@@ -11950,6 +11950,10 @@ static int ssl_context_load( mbedtls_ssl_context *ssl,
     ssl->major_ver = MBEDTLS_SSL_MAJOR_VERSION_3;
     ssl->minor_ver = MBEDTLS_SSL_MINOR_VERSION_3;
 
+    /* Adjust pointers for header fields of outgoing records to
+     * the given transform, accounting for explicit IV and CID. */
+    ssl_update_out_pointers( ssl, ssl->transform );
+
 #if defined(MBEDTLS_SSL_PROTO_DTLS)
     ssl->in_epoch = 1;
 #endif
diff --git a/tests/ssl-opt.sh b/tests/ssl-opt.sh
index 67d3b9f85a..55a4fe1efe 100755
--- a/tests/ssl-opt.sh
+++ b/tests/ssl-opt.sh
@@ -1283,49 +1283,199 @@ run_test    "Truncated HMAC, DTLS: client enabled, server enabled" \
 # Tests for Context serialization
 
 requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, client serializes" \
+run_test    "Context serialization, client serializes, CCM" \
             "$P_SRV dtls=1 serialize=0 exchanges=2" \
-            "$P_CLI dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
             0 \
             -c "Deserializing connection..." \
             -S "Deserializing connection..."
 
 requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, server serializes" \
-            "$P_SRV dtls=1 serialize=1 exchanges=2" \
-            "$P_CLI dtls=1 serialize=0 exchanges=2" \
-            0 \
-            -C "Deserializing connection..." \
-            -s "Deserializing connection..."
-
-requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, both serialize" \
-            "$P_SRV dtls=1 serialize=1 exchanges=2" \
-            "$P_CLI dtls=1 serialize=1 exchanges=2" \
-            0 \
-            -c "Deserializing connection..." \
-            -s "Deserializing connection..."
-
-requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, re-init, client serializes" \
+run_test    "Context serialization, client serializes, ChaChaPoly" \
             "$P_SRV dtls=1 serialize=0 exchanges=2" \
-            "$P_CLI dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
             0 \
             -c "Deserializing connection..." \
             -S "Deserializing connection..."
 
 requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, re-init, server serializes" \
-            "$P_SRV dtls=1 serialize=2 exchanges=2" \
-            "$P_CLI dtls=1 serialize=0 exchanges=2" \
+run_test    "Context serialization, client serializes, GCM" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-GCM-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, client serializes, with CID" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 cid=1 cid_val=beef" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, server serializes, CCM" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
             0 \
             -C "Deserializing connection..." \
             -s "Deserializing connection..."
 
 requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
-run_test    "Context serialization, re-init, both serialize" \
+run_test    "Context serialization, server serializes, ChaChaPoly" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, server serializes, GCM" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-GCM-SHA256" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, server serializes, with CID" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 cid=1 cid_val=beef" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, both serialize, CCM" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, both serialize, ChaChaPoly" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, both serialize, GCM" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-GCM-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, both serialize, with CID" \
+            "$P_SRV dtls=1 serialize=1 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=1 exchanges=2 cid=1 cid_val=beef" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, client serializes, CCM" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, client serializes, ChaChaPoly" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, client serializes, GCM" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-GCM-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, re-init, client serializes, with CID" \
+            "$P_SRV dtls=1 serialize=0 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 cid=1 cid_val=beef" \
+            0 \
+            -c "Deserializing connection..." \
+            -S "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, server serializes, CCM" \
             "$P_SRV dtls=1 serialize=2 exchanges=2" \
-            "$P_CLI dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, server serializes, ChaChaPoly" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, server serializes, GCM" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, re-init, server serializes, with CID" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=0 exchanges=2 cid=1 cid_val=beef" \
+            0 \
+            -C "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, both serialize, CCM" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-AES-128-CCM-8" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, both serialize, ChaChaPoly" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+run_test    "Context serialization, re-init, both serialize, GCM" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 force_ciphersuite=TLS-ECDHE-ECDSA-WITH-CHACHA20-POLY1305-SHA256" \
+            0 \
+            -c "Deserializing connection..." \
+            -s "Deserializing connection..."
+
+requires_config_enabled MBEDTLS_SSL_CONTEXT_SERIALIZATION
+requires_config_enabled MBEDTLS_SSL_DTLS_CONNECTION_ID
+run_test    "Context serialization, re-init, both serialize, with CID" \
+            "$P_SRV dtls=1 serialize=2 exchanges=2 cid=1 cid_val=dead" \
+            "$P_CLI dtls=1 serialize=2 exchanges=2 cid=1 cid_val=beef" \
             0 \
             -c "Deserializing connection..." \
             -s "Deserializing connection..."