diff --git a/src/aws_encryption_sdk/internal/formatting/encryption_context.py b/src/aws_encryption_sdk/internal/formatting/encryption_context.py
index 949ebe6f2..febf1f5fb 100644
--- a/src/aws_encryption_sdk/internal/formatting/encryption_context.py
+++ b/src/aws_encryption_sdk/internal/formatting/encryption_context.py
@@ -16,6 +16,14 @@
 _LOGGER = logging.getLogger(__name__)
 
 
+def _validate_encryption_context_entry(key, value):
+    max_entry_length = aws_encryption_sdk.internal.defaults.MAX_BYTE_ARRAY_SIZE
+    if len(key) > max_entry_length:
+        raise SerializationError("The encryption context contains a key that is too large.")
+    if len(value) > max_entry_length:
+        raise SerializationError("The encryption context contains a value that is too large.")
+
+
 def assemble_content_aad(message_id, aad_content_string, seq_num, length):
     """Assembles the Body AAD string for a message body structure.
 
@@ -72,6 +80,7 @@ def serialize_encryption_context(encryption_context):
             )
 
     for key, value in sorted(encryption_context_list, key=lambda x: x[0]):
+        _validate_encryption_context_entry(key, value)
         serialized_context.extend(
             struct.pack(
                 ">H{key_size}sH{value_size}s".format(key_size=len(key), value_size=len(value)),
diff --git a/test/unit/test_encryption_context.py b/test/unit/test_encryption_context.py
index bd717fbd8..6871f0d71 100644
--- a/test/unit/test_encryption_context.py
+++ b/test/unit/test_encryption_context.py
@@ -64,6 +64,22 @@ def test_serialize_encryption_context_too_large(self):
             )
         excinfo.match("The serialized context is too large")
 
+    def test_serialize_encryption_context_key_too_large(self):
+        oversized_key = "a" * (aws_encryption_sdk.internal.defaults.MAX_BYTE_ARRAY_SIZE + 1)
+        with pytest.raises(SerializationError) as excinfo:
+            aws_encryption_sdk.internal.formatting.encryption_context.serialize_encryption_context(
+                {oversized_key: "value"}
+            )
+        excinfo.match("The encryption context contains a key that is too large.")
+
+    def test_serialize_encryption_context_value_too_large(self):
+        oversized_value = "a" * (aws_encryption_sdk.internal.defaults.MAX_BYTE_ARRAY_SIZE + 1)
+        with pytest.raises(SerializationError) as excinfo:
+            aws_encryption_sdk.internal.formatting.encryption_context.serialize_encryption_context(
+                {"key": oversized_value}
+            )
+        excinfo.match("The encryption context contains a value that is too large.")
+
     def test_serialize_encryption_context_unencodable(self):
         """Validate that the serialize_encryption_context
         function behaves as expected when presented