diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
index 28e5ce19a2c..54ace6faf68 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpConnection.java
@@ -134,10 +134,14 @@ public abstract class HttpConnection implements Connection
         CookieStore cookieStore = getHttpClient().getCookieStore();
         if (cookieStore != null)
         {
-            StringBuilder cookies = convertCookies(cookieStore.get(request.getURI()), null);
-            cookies = convertCookies(request.getCookies(), cookies);
-            if (cookies != null)
-                request.header(HttpHeader.COOKIE.asString(), cookies.toString());
+            URI uri = request.getURI();
+            if (uri != null)
+            {
+                StringBuilder cookies = convertCookies(cookieStore.get(uri), null);
+                cookies = convertCookies(request.getCookies(), cookies);
+                if (cookies != null)
+                    request.header(HttpHeader.COOKIE.asString(), cookies.toString());
+            }
         }
 
         // Authorization
diff --git a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
index 57c79facc4e..2dd02292c5c 100644
--- a/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
+++ b/jetty-client/src/main/java/org/eclipse/jetty/client/HttpRequest.java
@@ -22,6 +22,7 @@ import java.io.IOException;
 import java.io.UnsupportedEncodingException;
 import java.net.HttpCookie;
 import java.net.URI;
+import java.net.URISyntaxException;
 import java.net.URLDecoder;
 import java.net.URLEncoder;
 import java.nio.ByteBuffer;
@@ -57,6 +58,8 @@ import org.eclipse.jetty.util.Fields;
 
 public class HttpRequest implements Request
 {
+    private static final URI NULL_URI = URI.create("null:0");
+
     private final HttpFields headers = new HttpFields();
     private final Fields params = new Fields(true);
     private final List<Response.ResponseListener> responseListeners = new ArrayList<>();
@@ -158,22 +161,30 @@ public class HttpRequest implements Request
     @Override
     public Request path(String path)
     {
-        URI uri = URI.create(path);
-        String rawPath = uri.getRawPath();
-        if (uri.isOpaque())
-            rawPath = path;
-        if (rawPath == null)
-            rawPath = "";
-        this.path = rawPath;
-        String query = uri.getRawQuery();
-        if (query != null)
+        URI uri = newURI(path);
+        if (uri == null)
         {
-            this.query = query;
-            params.clear();
-            extractParams(query);
+            this.path = path;
+            this.query = null;
+        }
+        else
+        {
+            String rawPath = uri.getRawPath();
+            if (uri.isOpaque())
+                rawPath = path;
+            if (rawPath == null)
+                rawPath = "";
+            this.path = rawPath;
+            String query = uri.getRawQuery();
+            if (query != null)
+            {
+                this.query = query;
+                params.clear();
+                extractParams(query);
+            }
+            if (uri.isAbsolute())
+                this.path = buildURI(false).toString();
         }
-        if (uri.isAbsolute())
-            this.path = buildURI(false).toString();
         this.uri = null;
         return this;
     }
@@ -187,9 +198,9 @@ public class HttpRequest implements Request
     @Override
     public URI getURI()
     {
-        if (uri != null)
-            return uri;
-        return uri = buildURI(true);
+        if (uri == null)
+            uri = buildURI(true);
+        return uri == NULL_URI ? null : uri;
     }
 
     @Override
@@ -762,12 +773,28 @@ public class HttpRequest implements Request
         String query = getQuery();
         if (query != null && withQuery)
             path += "?" + query;
-        URI result = URI.create(path);
+        URI result = newURI(path);
+        if (result == null)
+            return NULL_URI;
         if (!result.isAbsolute() && !result.isOpaque())
             result = URI.create(new Origin(getScheme(), getHost(), getPort()).asString() + path);
         return result;
     }
 
+    private URI newURI(String uri)
+    {
+        try
+        {
+            return new URI(uri);
+        }
+        catch (URISyntaxException x)
+        {
+            // The "path" of a HTTP request may not be a URI,
+            // for example for CONNECT 127.0.0.1:8080 or OPTIONS *.
+            return null;
+        }
+    }
+
     @Override
     public String toString()
     {
diff --git a/jetty-proxy/src/test/java/org/eclipse/jetty/proxy/ProxyTunnellingTest.java b/jetty-proxy/src/test/java/org/eclipse/jetty/proxy/ProxyTunnellingTest.java
index eab6ca76719..dd89a0715b1 100644
--- a/jetty-proxy/src/test/java/org/eclipse/jetty/proxy/ProxyTunnellingTest.java
+++ b/jetty-proxy/src/test/java/org/eclipse/jetty/proxy/ProxyTunnellingTest.java
@@ -18,8 +18,6 @@
 
 package org.eclipse.jetty.proxy;
 
-import static org.junit.Assert.assertEquals;
-
 import java.io.IOException;
 import java.net.ConnectException;
 import java.net.Socket;
@@ -28,7 +26,6 @@ import java.util.concurrent.CountDownLatch;
 import java.util.concurrent.ExecutionException;
 import java.util.concurrent.TimeUnit;
 import java.util.concurrent.atomic.AtomicReference;
-
 import javax.servlet.ServletException;
 import javax.servlet.ServletOutputStream;
 import javax.servlet.http.HttpServletRequest;
@@ -64,6 +61,8 @@ import org.junit.Ignore;
 import org.junit.Rule;
 import org.junit.Test;
 
+import static org.junit.Assert.assertEquals;
+
 public class ProxyTunnellingTest
 {
     @Rule
@@ -148,8 +147,10 @@ public class ProxyTunnellingTest
 
         try
         {
+            // Use a numeric host to test the URI of the CONNECT request.
+            String host = "127.0.0.1";
             String body = "BODY";
-            ContentResponse response = httpClient.newRequest("localhost", serverConnector.getLocalPort())
+            ContentResponse response = httpClient.newRequest(host, serverConnector.getLocalPort())
                     .scheme(HttpScheme.HTTPS.asString())
                     .method(HttpMethod.GET)
                     .path("/echo?body=" + URLEncoder.encode(body, "UTF-8"))