diff --git a/lib/Server.js b/lib/Server.js
index f351263f33..34320d23c2 100644
--- a/lib/Server.js
+++ b/lib/Server.js
@@ -492,8 +492,12 @@ class Server {
      * }
      */
     if (typeof options.proxy !== "undefined") {
+      // TODO remove in the next major release, only accept `Array`
       if (!Array.isArray(options.proxy)) {
-        if (Object.prototype.hasOwnProperty.call(options.proxy, "target")) {
+        if (
+          Object.prototype.hasOwnProperty.call(options.proxy, "target") ||
+          Object.prototype.hasOwnProperty.call(options.proxy, "router")
+        ) {
           options.proxy = [options.proxy];
         } else {
           options.proxy = Object.keys(options.proxy).map((context) => {
@@ -513,38 +517,42 @@ class Server {
               proxyOptions.context = correctedContext;
             }
 
-            const getLogLevelForProxy = (level) => {
-              if (level === "none") {
-                return "silent";
-              }
+            return proxyOptions;
+          });
+        }
+      }
 
-              if (level === "log") {
-                return "info";
-              }
+      options.proxy = options.proxy.map((item) => {
+        const getLogLevelForProxy = (level) => {
+          if (level === "none") {
+            return "silent";
+          }
 
-              if (level === "verbose") {
-                return "debug";
-              }
+          if (level === "log") {
+            return "info";
+          }
 
-              return level;
-            };
+          if (level === "verbose") {
+            return "debug";
+          }
 
-            if (typeof proxyOptions.logLevel === "undefined") {
-              proxyOptions.logLevel = getLogLevelForProxy(
-                compilerOptions.infrastructureLogging
-                  ? compilerOptions.infrastructureLogging.level
-                  : "info"
-              );
-            }
+          return level;
+        };
 
-            if (typeof proxyOptions.logProvider === "undefined") {
-              proxyOptions.logProvider = () => this.logger;
-            }
+        if (typeof item.logLevel === "undefined") {
+          item.logLevel = getLogLevelForProxy(
+            compilerOptions.infrastructureLogging
+              ? compilerOptions.infrastructureLogging.level
+              : "info"
+          );
+        }
 
-            return proxyOptions;
-          });
+        if (typeof item.logProvider === "undefined") {
+          item.logProvider = () => this.logger;
         }
-      }
+
+        return item;
+      });
     }
 
     if (typeof options.setupExitSignals === "undefined") {
@@ -875,22 +883,24 @@ class Server {
 
       // It is possible to use the `bypass` method without a `target`.
       // However, the proxy middleware has no use in this case, and will fail to instantiate.
-      if (proxyConfig.target) {
+      if (context) {
         return createProxyMiddleware(context, proxyConfig);
       }
+
+      return createProxyMiddleware(proxyConfig);
     };
     /**
      * Assume a proxy configuration specified as:
      * proxy: [
      *   {
-     *     context: ...,
-     *     ...options...
+     *     context: "value",
+     *     ...options,
      *   },
      *   // or:
      *   function() {
      *     return {
-     *       context: ...,
-     *       ...options...
+     *       context: "context",
+     *       ...options,
      *     };
      *   }
      * ]
@@ -903,7 +913,9 @@ class Server {
           ? proxyConfigOrCallback()
           : proxyConfigOrCallback;
 
-      proxyMiddleware = getProxyMiddleware(proxyConfig);
+      if (!proxyConfig.bypass) {
+        proxyMiddleware = getProxyMiddleware(proxyConfig);
+      }
 
       if (proxyConfig.ws) {
         this.webSocketProxies.push(proxyMiddleware);
@@ -922,6 +934,7 @@ class Server {
         // - Check if we have a bypass function defined
         // - In case the bypass function is defined we'll retrieve the
         // bypassUrl from it otherwise bypassUrl would be null
+        // TODO remove in the next major in favor `context` and `router` options
         const isByPassFuncDefined = typeof proxyConfig.bypass === "function";
         const bypassUrl = isByPassFuncDefined
           ? await proxyConfig.bypass(req, res, proxyConfig)
diff --git a/test/server/proxy-option.test.js b/test/server/proxy-option.test.js
index 8f23637bd4..cc7f2e872a 100644
--- a/test/server/proxy-option.test.js
+++ b/test/server/proxy-option.test.js
@@ -66,6 +66,7 @@ const proxyOptionOfArray = [
       bypass: () => {
         if (req && req.query.foo) {
           res.end(`foo+${next.name}+${typeof next}`);
+
           return false;
         }
       },
@@ -73,6 +74,27 @@ const proxyOptionOfArray = [
   },
 ];
 
+const proxyOptionOfArrayWithoutTarget = [
+  {
+    router: () => `http://localhost:${port1}`,
+  },
+];
+
+const proxyWithPath = {
+  "/proxy1": {
+    path: `http://localhost:${port1}`,
+    target: `http://localhost:${port1}`,
+  },
+};
+
+const proxyWithString = {
+  "/proxy1": `http://localhost:${port1}`,
+};
+
+const proxyWithRouterAsObject = {
+  router: () => `http://localhost:${port1}`,
+};
+
 describe("proxy option", () => {
   let proxyServer1;
   let proxyServer2;
@@ -204,7 +226,7 @@ describe("proxy option", () => {
     });
   });
 
-  describe("as an option is an object", () => {
+  describe("as an option is an object with the `context` option", () => {
     let server;
     let req;
 
@@ -243,6 +265,123 @@ describe("proxy option", () => {
     });
   });
 
+  describe("as an option is an object with `context` and `target` as string", () => {
+    let server;
+    let req;
+
+    beforeAll(async () => {
+      const compiler = webpack(config);
+
+      server = new Server(
+        {
+          static: {
+            directory: staticDirectory,
+            watch: false,
+          },
+          proxy: proxyWithString,
+          port: port3,
+        },
+        compiler
+      );
+
+      await server.start();
+
+      await listenProxyServers();
+
+      req = request(server.app);
+    });
+
+    afterAll(async () => {
+      await server.stop();
+      await closeProxyServers();
+    });
+
+    it("respects a proxy option", async () => {
+      const response = await req.get("/proxy1");
+
+      expect(response.status).toEqual(200);
+      expect(response.text).toContain("from proxy1");
+    });
+  });
+
+  describe("as an option is an object with the `path` option (`context` alias)", () => {
+    let server;
+    let req;
+
+    beforeAll(async () => {
+      const compiler = webpack(config);
+
+      server = new Server(
+        {
+          static: {
+            directory: staticDirectory,
+            watch: false,
+          },
+          proxy: proxyWithPath,
+          port: port3,
+        },
+        compiler
+      );
+
+      await server.start();
+
+      await listenProxyServers();
+
+      req = request(server.app);
+    });
+
+    afterAll(async () => {
+      await server.stop();
+      await closeProxyServers();
+    });
+
+    it("respects a proxy option", async () => {
+      const response = await req.get("/proxy1");
+
+      expect(response.status).toEqual(200);
+      expect(response.text).toContain("from proxy1");
+    });
+  });
+
+  describe("as an option is an object with the `router` option", () => {
+    let server;
+    let req;
+
+    beforeAll(async () => {
+      const compiler = webpack(config);
+
+      server = new Server(
+        {
+          static: {
+            directory: staticDirectory,
+            watch: false,
+          },
+          proxy: proxyWithRouterAsObject,
+          port: port3,
+        },
+        compiler
+      );
+
+      await server.start();
+
+      await listenProxyServers();
+
+      req = request(server.app);
+    });
+
+    afterAll(async () => {
+      await server.stop();
+      await closeProxyServers();
+    });
+
+    it("respects a proxy option", async () => {
+      const response = await req.get("/proxy1");
+
+      expect(response.status).toEqual(200);
+      expect(response.text).toContain("from proxy1");
+    });
+  });
+
   describe("as an array", () => {
     let server;
     let req;
@@ -296,6 +435,45 @@ describe("proxy option", () => {
     });
   });
 
+  describe("as an array without the `route` option", () => {
+    let server;
+    let req;
+
+    beforeAll(async () => {
+      const compiler = webpack(config);
+
+      server = new Server(
+        {
+          static: {
+            directory: staticDirectory,
+            watch: false,
+          },
+          proxy: proxyOptionOfArrayWithoutTarget,
+          port: port3,
+        },
+        compiler
+      );
+
+      await server.start();
+
+      await listenProxyServers();
+
+      req = request(server.app);
+    });
+
+    afterAll(async () => {
+      await server.stop();
+      await closeProxyServers();
+    });
+
+    it("respects a proxy option", async () => {
+      const response = await req.get("/proxy1");
+
+      expect(response.status).toEqual(200);
+      expect(response.text).toContain("from proxy1");
+    });
+  });
+
   describe("should sharing a proxy option", () => {
     let server;
     let req;