diff --git a/common/testing/http-junit5/src/main/java/io/helidon/common/testing/http/junit5/SocketHttpClient.java b/common/testing/http-junit5/src/main/java/io/helidon/common/testing/http/junit5/SocketHttpClient.java
index 074bf961598..159d5c3341d 100644
--- a/common/testing/http-junit5/src/main/java/io/helidon/common/testing/http/junit5/SocketHttpClient.java
+++ b/common/testing/http-junit5/src/main/java/io/helidon/common/testing/http/junit5/SocketHttpClient.java
@@ -534,6 +534,7 @@ public SocketHttpClient manualRequest(String formatString, Object... args) throw
 
     /**
      * Continue sending more to text to socket.
+     *
      * @param payload text to be sent
      * @return this http client
      * @throws IOException
@@ -548,6 +549,18 @@ public SocketHttpClient continuePayload(String payload)
         return this;
     }
 
+    /**
+     * Send single chunk as defined by RFC 9112 §7.1.
+     *
+     * @param payload of the chunk
+     * @return this http client
+     * @throws IOException
+     */
+    public SocketHttpClient sendChunk(String payload) throws IOException {
+        continuePayload(Integer.toHexString(payload.length()) + EOL + payload + EOL);
+        return this;
+    }
+
     /**
      * Override this to send a specific payload.
      *
diff --git a/nima/tests/integration/webserver/webserver/src/test/java/io/helidon/nima/tests/integration/server/Continue100Test.java b/nima/tests/integration/webserver/webserver/src/test/java/io/helidon/nima/tests/integration/server/Continue100Test.java
index 136ace714d5..4ace9e21e44 100644
--- a/nima/tests/integration/webserver/webserver/src/test/java/io/helidon/nima/tests/integration/server/Continue100Test.java
+++ b/nima/tests/integration/webserver/webserver/src/test/java/io/helidon/nima/tests/integration/server/Continue100Test.java
@@ -24,7 +24,11 @@
 import io.helidon.nima.webserver.http.Handler;
 import io.helidon.nima.webserver.http.HttpRouting;
 import org.junit.jupiter.api.Test;
+
+import java.io.ByteArrayInputStream;
 import java.io.IOException;
+import java.io.InputStream;
+import java.io.OutputStream;
 import java.time.Duration;
 import java.util.Map;
 import java.util.Optional;
@@ -90,6 +94,13 @@ static void routing(HttpRouting.Builder router) {
                 )
                 .route(Http.Method.predicate(Http.Method.PUT, Http.Method.POST),
                         PathMatchers.exact("/"), anyHandler)
+                .route(Http.Method.predicate(Http.Method.PUT),
+                       PathMatchers.exact("/chunked"), (req, res) -> {
+                            try (InputStream is = req.content().inputStream();
+                                    OutputStream os = res.outputStream()) {
+                                new ByteArrayInputStream(is.readAllBytes()).transferTo(os);
+                            }
+                        })
                 .route(Http.Method.predicate(Http.Method.GET),
                         PathMatchers.exact("/"), (req, res) -> res.status(Http.Status.OK_200).send("GET TEST"));
     }
@@ -98,6 +109,32 @@ public Continue100Test(WebServer server) {
         defaultPort = server.port();
     }
 
+    @Test
+    void continue100ChunkedPut() throws Exception {
+        try (SocketHttpClient socketHttpClient = SocketHttpClient.create(defaultPort)) {
+            socketHttpClient
+                    .manualRequest("""                            
+                            PUT /chunked HTTP/1.1
+                            Host: localhost:%d
+                            Expect: 100-continue
+                            Accept: */*
+                            Transfer-Encoding: chunked
+                            Content-Type: text/plain
+                                                             
+                            """, defaultPort)
+                    .awaitResponse("HTTP/1.1 100 Continue", "\n\n")
+                    .sendChunk("This ")
+                    .sendChunk("is ")
+                    .sendChunk("chunked!")
+                    .sendChunk("");
+
+            String received = socketHttpClient.receive();
+            assertThat(received, startsWith("HTTP/1.1 200 OK"));
+            assertThat(received, endsWith("This is chunked!"));
+
+            checkKeepAlive(socketHttpClient);
+        }
+    }
     @Test
     void continue100Post() throws Exception {
         try (SocketHttpClient socketHttpClient = SocketHttpClient.create(defaultPort)) {
diff --git a/nima/webserver/webserver/src/main/java/io/helidon/nima/webserver/http1/Http1ServerResponse.java b/nima/webserver/webserver/src/main/java/io/helidon/nima/webserver/http1/Http1ServerResponse.java
index 72bfe1515b3..105cb7deb17 100644
--- a/nima/webserver/webserver/src/main/java/io/helidon/nima/webserver/http1/Http1ServerResponse.java
+++ b/nima/webserver/webserver/src/main/java/io/helidon/nima/webserver/http1/Http1ServerResponse.java
@@ -152,8 +152,6 @@ public OutputStream outputStream() {
         }
         streamingEntity = true;
 
-        request.reset();
-
         this.outputStream = new BlockingOutputStream(headers,
                                                      trailers,
                                                      this::status,
@@ -162,6 +160,7 @@ public OutputStream outputStream() {
                                                      () -> {
                                                          this.isSent = true;
                                                          afterSend();
+                                                         request.reset();
                                                      },
                                                      ctx,
                                                      sendListener,