diff --git a/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequest.java b/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequest.java
index 49bf7cbae8a..6a0e52803da 100644
--- a/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequest.java
+++ b/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2022, 2023 Oracle and/or its affiliates.
+ * Copyright (c) 2022, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -388,6 +388,16 @@ default <T> ClientResponseTyped<T> outputStream(OutputStreamHandler outputStream
      */
     T readContinueTimeout(Duration readContinueTimeout);
 
+    /**
+     * Whether Expect 100-Continue header is sent to verify server availability before sending an entity.
+     * Can be used to override the setting inherited from {@link HttpClientConfig#sendExpectContinue()}
+     * on a per-request basis.
+     *
+     * @param sendExpectContinue value to override behavior for a single request
+     * @return whether Expect 100-Continue header should be sent on streamed transfers
+     */
+    T sendExpectContinue(boolean sendExpectContinue);
+
     /**
      * Handle output stream.
      */
diff --git a/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequestBase.java b/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequestBase.java
index d1cec37df6e..ee467cdd90a 100644
--- a/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequestBase.java
+++ b/webclient/api/src/main/java/io/helidon/webclient/api/ClientRequestBase.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2023, 2024 Oracle and/or its affiliates.
+ * Copyright (c) 2023, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -87,6 +87,7 @@ public abstract class ClientRequestBase<T extends ClientRequest<T>, R extends Ht
     private Proxy proxy;
     private boolean keepAlive;
     private ClientConnection connection;
+    private Boolean sendExpectContinue;
 
     protected ClientRequestBase(HttpClientConfig clientConfig,
                                 WebClientCookieManager cookieManager,
@@ -94,11 +95,22 @@ protected ClientRequestBase(HttpClientConfig clientConfig,
                                 Method method,
                                 ClientUri clientUri,
                                 Map<String, String> properties) {
+        this(clientConfig, cookieManager, protocolId, method, clientUri, null, properties);
+    }
+
+    protected ClientRequestBase(HttpClientConfig clientConfig,
+                                WebClientCookieManager cookieManager,
+                                String protocolId,
+                                Method method,
+                                ClientUri clientUri,
+                                Boolean sendExpectContinue,
+                                Map<String, String> properties) {
         this.clientConfig = clientConfig;
         this.cookieManager = cookieManager;
         this.protocolId = protocolId;
         this.method = method;
         this.clientUri = clientUri;
+        this.sendExpectContinue = sendExpectContinue;
         this.properties = new HashMap<>(properties);
 
         this.headers = clientConfig.defaultRequestHeaders();
@@ -277,6 +289,12 @@ public R outputStream(OutputStreamHandler outputStreamConsumer) {
         return doOutputStream(outputStreamConsumer);
     }
 
+    @Override
+    public T sendExpectContinue(boolean sendExpectContinue) {
+        this.sendExpectContinue = sendExpectContinue;
+        return identity();
+    }
+
     /**
      * Append additional headers before sending the request.
      */
@@ -364,6 +382,11 @@ public boolean skipUriEncoding() {
         return skipUriEncoding;
     }
 
+    @Override
+    public Optional<Boolean> sendExpectContinue() {
+        return Optional.ofNullable(sendExpectContinue);
+    }
+
     protected abstract R doSubmit(Object entity);
 
     protected abstract R doOutputStream(OutputStreamHandler outputStreamHandler);
diff --git a/webclient/api/src/main/java/io/helidon/webclient/api/FullClientRequest.java b/webclient/api/src/main/java/io/helidon/webclient/api/FullClientRequest.java
index 806ea34318f..d0170e1ca8e 100644
--- a/webclient/api/src/main/java/io/helidon/webclient/api/FullClientRequest.java
+++ b/webclient/api/src/main/java/io/helidon/webclient/api/FullClientRequest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2023 Oracle and/or its affiliates.
+ * Copyright (c) 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -112,4 +112,12 @@ public interface FullClientRequest<T extends ClientRequest<T>> extends ClientReq
      * @return whether to skip encoding
      */
     boolean skipUriEncoding();
+
+    /**
+     * Whether Expect 100-Continue header is sent to verify server availability before sending
+     * an entity. Overrides the setting from {@link HttpClientConfig#sendExpectContinue()}.
+     *
+     * @return Expect 100-Continue value if set
+     */
+    Optional<Boolean> sendExpectContinue();
 }
diff --git a/webclient/api/src/main/java/io/helidon/webclient/api/HttpClientRequest.java b/webclient/api/src/main/java/io/helidon/webclient/api/HttpClientRequest.java
index 20618f33c9d..92ad73d91f8 100644
--- a/webclient/api/src/main/java/io/helidon/webclient/api/HttpClientRequest.java
+++ b/webclient/api/src/main/java/io/helidon/webclient/api/HttpClientRequest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2023, 2024 Oracle and/or its affiliates.
+ * Copyright (c) 2023, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -51,7 +51,22 @@ public class HttpClientRequest extends ClientRequestBase<HttpClientRequest, Http
                       List<LoomClient.ProtocolSpi> tcpProtocols,
                       List<String> tcpProtocolIds,
                       LruCache<LoomClient.EndpointKey, HttpClientSpi> clientSpiCache) {
-        super(clientConfig, webClient.cookieManager(), "any", method, clientUri, clientConfig.properties());
+        this(webClient, clientConfig, method, clientUri, protocolsToClients, protocols, tcpProtocols,
+             tcpProtocolIds, null, clientSpiCache);
+    }
+
+    HttpClientRequest(WebClient webClient,
+                      WebClientConfig clientConfig,
+                      Method method,
+                      ClientUri clientUri,
+                      Map<String, LoomClient.ProtocolSpi> protocolsToClients,
+                      List<LoomClient.ProtocolSpi> protocols,
+                      List<LoomClient.ProtocolSpi> tcpProtocols,
+                      List<String> tcpProtocolIds,
+                      Boolean send100Continue,
+                      LruCache<LoomClient.EndpointKey, HttpClientSpi> clientSpiCache) {
+        super(clientConfig, webClient.cookieManager(), "any", method, clientUri,
+              send100Continue, clientConfig.properties());
         this.webClient = webClient;
         this.clients = protocolsToClients;
         this.protocols = protocols;
diff --git a/webclient/api/src/test/java/io/helidon/webclient/api/HttpClientTest.java b/webclient/api/src/test/java/io/helidon/webclient/api/HttpClientTest.java
index 0f0e20461f6..e3ea72af258 100644
--- a/webclient/api/src/test/java/io/helidon/webclient/api/HttpClientTest.java
+++ b/webclient/api/src/test/java/io/helidon/webclient/api/HttpClientTest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2023 Oracle and/or its affiliates.
+ * Copyright (c) 2023, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -114,6 +114,11 @@ public FakeHttpClientRequest readContinueTimeout(Duration readContinueTimeout) {
             return this;
         }
 
+        @Override
+        public FakeHttpClientRequest sendExpectContinue(boolean sendExpectContinue) {
+            return null;
+        }
+
         @Override
         public FakeHttpClientRequest tls(Tls tls) {
             return this;
diff --git a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1CallOutputStreamChain.java b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1CallOutputStreamChain.java
index 1532f9d4777..e410621bf65 100644
--- a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1CallOutputStreamChain.java
+++ b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1CallOutputStreamChain.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2023, 2024 Oracle and/or its affiliates.
+ * Copyright (c) 2023, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -354,7 +354,10 @@ private void writeContent(BufferData buffer) throws IOException {
         }
 
         private void sendPrologueAndHeader() {
-            boolean expects100Continue = clientConfig.sendExpectContinue() && !noData;
+            // setting for expect 100 header, can be overridden for each request
+            boolean expects100Continue = !noData;
+            Boolean override100Continue = originalRequest.sendExpectContinue().orElse(null);
+            expects100Continue &= (override100Continue != null) ? override100Continue : clientConfig.sendExpectContinue();
             if (expects100Continue) {
                 headers.add(HeaderValues.EXPECT_100);
             }
diff --git a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientImpl.java b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientImpl.java
index f06c4300837..548ee3f0334 100644
--- a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientImpl.java
+++ b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientImpl.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2022, 2023 Oracle and/or its affiliates.
+ * Copyright (c) 2022, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -74,6 +74,7 @@ public ClientRequest<?> clientRequest(FullClientRequest<?> clientRequest, Client
         Http1ClientRequest request = new Http1ClientRequestImpl(this,
                                                                 clientRequest.method(),
                                                                 clientUri,
+                                                                clientRequest.sendExpectContinue().orElse(null),
                                                                 clientRequest.properties());
 
         clientRequest.connection().ifPresent(request::connection);
diff --git a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientRequestImpl.java b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientRequestImpl.java
index 22260adcaed..50103c3bb12 100644
--- a/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientRequestImpl.java
+++ b/webclient/http1/src/main/java/io/helidon/webclient/http1/Http1ClientRequestImpl.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2022, 2024 Oracle and/or its affiliates.
+ * Copyright (c) 2022, 2025 Oracle and/or its affiliates.
  *
  * Licensed under the Apache License, Version 2.0 (the "License");
  * you may not use this file except in compliance with the License.
@@ -43,10 +43,20 @@ class Http1ClientRequestImpl extends ClientRequestBase<Http1ClientRequest, Http1
                            Method method,
                            ClientUri clientUri,
                            Map<String, String> properties) {
+        this(http1Client, method, clientUri, null, properties);
+    }
+
+    Http1ClientRequestImpl(Http1ClientImpl http1Client,
+                               Method method,
+                               ClientUri clientUri,
+                               Boolean sendExpectContinue,
+                               Map<String, String> properties) {
         super(http1Client.clientConfig(),
                 http1Client.webClient().cookieManager(),
                 Http1Client.PROTOCOL_ID,
-                method, clientUri,
+                method,
+                clientUri,
+                sendExpectContinue,
                 properties);
         this.http1Client = http1Client;
     }
@@ -59,6 +69,7 @@ class Http1ClientRequestImpl extends ClientRequestBase<Http1ClientRequest, Http1
         this(request.http1Client,
                 method,
                 clientUri,
+                null,
                 properties);
 
         followRedirects(request.followRedirects());
diff --git a/webclient/tests/http1/src/test/java/io/helidon/webclient/tests/Send100ContinueTest.java b/webclient/tests/http1/src/test/java/io/helidon/webclient/tests/Send100ContinueTest.java
new file mode 100644
index 00000000000..10af75a86cd
--- /dev/null
+++ b/webclient/tests/http1/src/test/java/io/helidon/webclient/tests/Send100ContinueTest.java
@@ -0,0 +1,90 @@
+/*
+ * Copyright (c) 2025 Oracle and/or its affiliates.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package io.helidon.webclient.tests;
+
+import io.helidon.http.HeaderValues;
+import io.helidon.http.Status;
+import io.helidon.webclient.api.HttpClientResponse;
+import io.helidon.webclient.api.WebClient;
+import io.helidon.webclient.http1.Http1Client;
+import io.helidon.webserver.http.HttpRouting;
+import io.helidon.webserver.testing.junit5.ServerTest;
+import io.helidon.webserver.testing.junit5.SetUpRoute;
+
+import org.junit.jupiter.api.Test;
+
+import static org.hamcrest.CoreMatchers.is;
+import static org.hamcrest.MatcherAssert.assertThat;
+
+@ServerTest
+class Send100ContinueTest {
+    private static final byte[] DATA = new byte[] { 1, 2, 3 };
+
+    private final WebClient webClient;
+    private final Http1Client http1Client;
+
+    Send100ContinueTest(WebClient webClient, Http1Client http1Client) {
+        this.webClient = webClient;
+        this.http1Client = http1Client;
+    }
+
+    @SetUpRoute
+    static void routing(HttpRouting.Builder router) {
+        router.post("/100Continue", (req, res) -> {
+                    res.status(req.headers().contains(HeaderValues.EXPECT_100) ?
+                                       Status.OK_200 : Status.BAD_REQUEST_400).send();
+                })
+                .post("/no100Continue", (req, res) -> {
+                    res.status(req.headers().contains(HeaderValues.EXPECT_100) ?
+                                       Status.BAD_REQUEST_400 : Status.OK_200).send();
+                });
+    }
+
+    @Test
+    public void test100ContinueDefaultWeb() {
+        try (HttpClientResponse response = webClient.post("/100Continue")
+                .outputStream(os -> { os.write(DATA); os.close(); })) {
+            assertThat(response.status(), is(Status.OK_200));
+        }
+    }
+
+    @Test
+    public void no100ContinueWeb() {
+        try (HttpClientResponse response = webClient.post("/no100Continue")
+                .sendExpectContinue(false)      // turns off 100 continue
+                .outputStream(os -> { os.write(DATA); os.close(); })) {
+            assertThat(response.status(), is(Status.OK_200));
+        }
+    }
+
+    @Test
+    public void test100ContinueDefaultHttp1() {
+        try (HttpClientResponse response = http1Client.post("/100Continue")
+                .outputStream(os -> { os.write(DATA); os.close(); })) {
+            assertThat(response.status(), is(Status.OK_200));
+        }
+    }
+
+    @Test
+    public void no100ContinueHttp1() {
+        try (HttpClientResponse response = http1Client.post("/no100Continue")
+                .sendExpectContinue(false)      // turns off 100 continue
+                .outputStream(os -> { os.write(DATA); os.close(); })) {
+            assertThat(response.status(), is(Status.OK_200));
+        }
+    }
+}