diff --git a/cloudinary-http5/src/main/java/com/cloudinary/http5/UploaderStrategy.java b/cloudinary-http5/src/main/java/com/cloudinary/http5/UploaderStrategy.java
index 5f87cbd8..589dff5b 100644
--- a/cloudinary-http5/src/main/java/com/cloudinary/http5/UploaderStrategy.java
+++ b/cloudinary-http5/src/main/java/com/cloudinary/http5/UploaderStrategy.java
@@ -8,16 +8,21 @@
 import com.cloudinary.utils.StringUtils;
 import org.apache.hc.client5.http.classic.methods.HttpPost;
 import org.apache.hc.client5.http.classic.methods.HttpUriRequestBase;
+import org.apache.hc.client5.http.config.RequestConfig;
 import org.apache.hc.client5.http.entity.mime.ByteArrayBody;
 import org.apache.hc.client5.http.entity.mime.FileBody;
 import org.apache.hc.client5.http.entity.mime.HttpMultipartMode;
 import org.apache.hc.client5.http.entity.mime.MultipartEntityBuilder;
 import org.apache.hc.client5.http.impl.classic.CloseableHttpClient;
 import org.apache.hc.client5.http.impl.classic.CloseableHttpResponse;
+import org.apache.hc.client5.http.impl.classic.HttpClientBuilder;
 import org.apache.hc.client5.http.impl.classic.HttpClients;
+import org.apache.hc.client5.http.io.HttpClientConnectionManager;
 import org.apache.hc.core5.http.ContentType;
+import org.apache.hc.core5.http.HttpHost;
 import org.apache.hc.core5.http.ParseException;
 import org.apache.hc.core5.http.io.entity.EntityUtils;
+import org.apache.hc.core5.util.Timeout;
 
 import java.io.File;
 import java.io.IOException;
@@ -35,11 +40,39 @@ public class UploaderStrategy extends AbstractUploaderStrategy {
     public void init(Uploader uploader) {
         super.init(uploader);
 
-        this.client = HttpClients.custom()
-                .setUserAgent(cloudinary().getUserAgent() + " ApacheHttpClient/" + APACHE_HTTP_CLIENT_VERSION)
+        HttpClientBuilder clientBuilder = HttpClients.custom();
+        clientBuilder.useSystemProperties().setUserAgent(cloudinary().getUserAgent() + " ApacheHttpClient/" + APACHE_HTTP_CLIENT_VERSION);
+
+        HttpClientConnectionManager connectionManager = (HttpClientConnectionManager) cloudinary().config.properties.get("connectionManager");
+        if (connectionManager != null) {
+            clientBuilder.setConnectionManager(connectionManager);
+        }
+
+        RequestConfig requestConfig = buildRequestConfig();
+
+        client = clientBuilder
+                .setDefaultRequestConfig(requestConfig)
                 .build();
     }
 
+    public RequestConfig buildRequestConfig() {
+        RequestConfig.Builder requestConfigBuilder = RequestConfig.custom();
+
+        if (cloudinary().config.proxyHost != null && cloudinary().config.proxyPort != 0) {
+            HttpHost proxy = new HttpHost(cloudinary().config.proxyHost, cloudinary().config.proxyPort);
+            requestConfigBuilder.setProxy(proxy);
+        }
+
+        int timeout = cloudinary().config.timeout;
+        if (timeout > 0) {
+            requestConfigBuilder.setResponseTimeout(Timeout.ofSeconds(timeout))
+                    .setConnectionRequestTimeout(Timeout.ofSeconds(timeout))
+                    .setConnectTimeout(Timeout.ofSeconds(timeout));
+        }
+
+        return requestConfigBuilder.build();
+    }
+
     @SuppressWarnings({"rawtypes", "unchecked"})
     @Override
     public Map callApi(String action, Map<String, Object> params, Map options, Object file, ProgressCallback progressCallback) throws IOException {
diff --git a/cloudinary-http5/src/test/java/com/cloudinary/test/ApiTest.java b/cloudinary-http5/src/test/java/com/cloudinary/test/ApiTest.java
index 4735d89f..53da8866 100644
--- a/cloudinary-http5/src/test/java/com/cloudinary/test/ApiTest.java
+++ b/cloudinary-http5/src/test/java/com/cloudinary/test/ApiTest.java
@@ -11,6 +11,9 @@
 import org.junit.experimental.categories.Category;
 
 import java.util.Map;
+import java.util.UUID;
+
+import static com.cloudinary.utils.ObjectUtils.asMap;
 
 
 public class ApiTest extends AbstractApiTest {
@@ -48,7 +51,7 @@ public void testBuildRequestConfig_withoutProxy() {
     @Category(TimeoutTest.class)
     @Test(expected = Exception.class)
     public void testConnectTimeoutParameter() throws Exception {
-        Map<String, Object> options = ObjectUtils.asMap(
+        Map<String, Object> options = asMap(
                 "max_results", 500,
                 "connect_timeout", 0.2);
 
@@ -65,7 +68,7 @@ public void testConnectTimeoutParameter() throws Exception {
     @Test(expected = Exception.class)
     public void testTimeoutParameter() throws Exception {
         // Set a very short request timeout to trigger a timeout exception
-        Map<String, Object> options = ObjectUtils.asMap(
+        Map<String, Object> options = asMap(
                 "max_results", 500,
                 "timeout", Timeout.ofMilliseconds(1000)); // Set the timeout to 1 second
 
@@ -76,4 +79,24 @@ public void testTimeoutParameter() throws Exception {
             throw new Exception("Socket timeout");
         }
     }
+
+    @Category(TimeoutTest.class)
+    @Test(expected = Exception.class)
+    public void testUploaderTimeoutParameter() throws Exception {
+        Cloudinary cloudinary = new Cloudinary("cloudinary://test:test@test.com");
+        cloudinary.config.uploadPrefix = "https://10.255.255.1";
+        String publicId = UUID.randomUUID().toString();
+        // Set a very short request timeout to trigger a timeout exception
+        Map<String, Object> options = asMap(
+                "max_results", 500,
+                "timeout", Timeout.ofMilliseconds(10)); // Set the timeout to 1 second
+
+        try {
+           Map result = cloudinary.uploader().addContext(asMap("caption", "new caption"), new String[]{publicId, "no-such-id"}, options);
+        } catch (Exception e) {
+            // Convert IOException to SocketTimeoutException if appropriate
+            throw new Exception("Socket timeout");
+        }
+    }
+
 }
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