diff --git a/components/oblivious_http/oblivious_http_chunk_processor.cc b/components/oblivious_http/oblivious_http_chunk_processor.cc
index f9007230c0c..8bd81b17939 100644
--- a/components/oblivious_http/oblivious_http_chunk_processor.cc
+++ b/components/oblivious_http/oblivious_http_chunk_processor.cc
@@ -11,6 +11,10 @@
 
 namespace oblivious_http {
 
+namespace {
+constexpr size_t kMaxEncryptChunkSize = 16384;
+}  // namespace
+
 ObliviousHttpChunkProcessor::ObliviousHttpChunkProcessor(
     mojo::PendingRemote<network::mojom::ObliviousHttpChunkClient>
         chunk_client_remote,
@@ -55,12 +59,19 @@ ObliviousHttpChunkProcessor::Create(
 std::optional<std::string> ObliviousHttpChunkProcessor::EncryptRequest(
     std::string_view plaintext) {
   CHECK(ohttp_client_);
-  auto result =
-      ohttp_client_->EncryptRequestChunk(plaintext, /*is_final_chunk=*/true);
-  if (!result.ok()) {
-    return std::nullopt;
+
+  std::string result;
+  for (size_t offset = 0; offset < plaintext.size();
+       offset += kMaxEncryptChunkSize) {
+    const bool is_final = offset + kMaxEncryptChunkSize >= plaintext.size();
+    const auto chunk = plaintext.substr(offset, kMaxEncryptChunkSize);
+    auto encrypted = ohttp_client_->EncryptRequestChunk(chunk, is_final);
+    if (!encrypted.ok()) {
+      return std::nullopt;
+    }
+    result += std::move(*encrypted);
   }
-  return std::move(*result);
+  return result;
 }
 
 void ObliviousHttpChunkProcessor::OnDataReceived(std::string_view data,
diff --git a/components/oblivious_http/oblivious_http_chunk_processor_unittest.cc b/components/oblivious_http/oblivious_http_chunk_processor_unittest.cc
index 396700ec065..cf97f8f2e92 100644
--- a/components/oblivious_http/oblivious_http_chunk_processor_unittest.cc
+++ b/components/oblivious_http/oblivious_http_chunk_processor_unittest.cc
@@ -161,12 +161,13 @@ class ObliviousHttpChunkProcessorTest
     return result;
   }
 
-  void EncryptRequestAndGatewayDecrypt() {
-    auto encrypted_request = processor_->EncryptRequest(kTestRequestBody);
+  void EncryptRequestAndGatewayDecrypt(
+      std::string_view request_body = kTestRequestBody) {
+    auto encrypted_request = processor_->EncryptRequest(request_body);
     ASSERT_TRUE(encrypted_request.has_value());
     ASSERT_TRUE(
         gateway_->DecryptRequest(*encrypted_request, /*end_stream=*/true).ok());
-    EXPECT_EQ(kTestRequestBody, received_client_request_body_);
+    EXPECT_EQ(request_body, received_client_request_body_);
   }
 
   // Drives a full round-trip: encrypts kTestRequestBody, feeds the simulated
@@ -233,6 +234,18 @@ TEST_F(ObliviousHttpChunkProcessorTest,
   EncryptRequestAndGatewayDecrypt();
 }
 
+TEST_F(ObliviousHttpChunkProcessorTest,
+       EncryptRequest_LargeRequest_GatewayDecryptsCorrectly) {
+  constexpr std::string_view kAlphabet = "abcdefghijklmnopqrstuvwxyz";
+  constexpr size_t kLargeRequestSize = 50000;
+  std::string large_request;
+  large_request.reserve(kLargeRequestSize);
+  while (large_request.size() < kLargeRequestSize) {
+    large_request += kAlphabet;
+  }
+  EncryptRequestAndGatewayDecrypt(large_request);
+}
+
 TEST_F(ObliviousHttpChunkProcessorTest,
        RoundTrip_BodyChunksDeliveredToChunkClient) {
   auto future = RunRoundTrip("hello chunked", net::HTTP_OK,