diff --git a/README.md b/README.md
index a403ea19e..eb787f3fd 100644
--- a/README.md
+++ b/README.md
@@ -70,12 +70,34 @@ This property allows a user to pass the list of HTTP request methods accepted by
 
 ### headers
 
-Type: `Object`  
+Type: `Object|Function`
 Default: `undefined`
 
 This property allows a user to pass custom HTTP headers on each request.
 eg. `{ "X-Custom-Header": "yes" }`
 
+or
+
+```js
+webpackDevMiddleware(compiler, {
+  headers: () => {
+    return {
+      'Last-Modified': new Date(),
+    };
+  },
+});
+```
+
+or
+
+```js
+webpackDevMiddleware(compiler, {
+  headers: (req, res, context) => {
+    res.setHeader('Last-Modified', new Date());
+  },
+});
+```
+
 ### index
 
 Type: `Boolean|String`  
diff --git a/src/middleware.js b/src/middleware.js
index e22393db1..8f6aab6f1 100644
--- a/src/middleware.js
+++ b/src/middleware.js
@@ -42,7 +42,12 @@ export default function wrapper(context) {
 
     async function processRequest() {
       const filename = getFilenameFromUrl(context, req.url);
-      const { headers } = context.options;
+      let { headers } = context.options;
+
+      if (typeof headers === 'function') {
+        headers = headers(req, res, context);
+      }
+
       let content;
 
       if (!filename) {
diff --git a/src/options.json b/src/options.json
index 0969a0154..a6c605696 100644
--- a/src/options.json
+++ b/src/options.json
@@ -25,7 +25,14 @@
       }
     },
     "headers": {
-      "type": "object"
+      "anyOf": [
+        {
+          "type": "object"
+        },
+        {
+          "instanceof": "Function"
+        }
+      ]
     },
     "publicPath": {
       "description": "The `publicPath` specifies the public URL address of the output files when referenced in a browser.",
diff --git a/test/__snapshots__/validation-options.test.js.snap.webpack4 b/test/__snapshots__/validation-options.test.js.snap.webpack4
index 3b46c1351..4cb0a3ea8 100644
--- a/test/__snapshots__/validation-options.test.js.snap.webpack4
+++ b/test/__snapshots__/validation-options.test.js.snap.webpack4
@@ -1,9 +1,23 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
+exports[`validation should throw an error on the "headers" option with "1" value 1`] = `
+"Invalid options object. Dev Middleware has been initialized using an options object that does not match the API schema.
+ - options.headers should be one of these:
+   object { … } | function
+   Details:
+    * options.headers should be an object:
+      object { … }
+    * options.headers should be an instance of function."
+`;
+
 exports[`validation should throw an error on the "headers" option with "true" value 1`] = `
 "Invalid options object. Dev Middleware has been initialized using an options object that does not match the API schema.
- - options.headers should be an object:
-   object { … }"
+ - options.headers should be one of these:
+   object { … } | function
+   Details:
+    * options.headers should be an object:
+      object { … }
+    * options.headers should be an instance of function."
 `;
 
 exports[`validation should throw an error on the "index" option with "{}" value 1`] = `
diff --git a/test/__snapshots__/validation-options.test.js.snap.webpack5 b/test/__snapshots__/validation-options.test.js.snap.webpack5
index 3b46c1351..4cb0a3ea8 100644
--- a/test/__snapshots__/validation-options.test.js.snap.webpack5
+++ b/test/__snapshots__/validation-options.test.js.snap.webpack5
@@ -1,9 +1,23 @@
 // Jest Snapshot v1, https://goo.gl/fbAQLP
 
+exports[`validation should throw an error on the "headers" option with "1" value 1`] = `
+"Invalid options object. Dev Middleware has been initialized using an options object that does not match the API schema.
+ - options.headers should be one of these:
+   object { … } | function
+   Details:
+    * options.headers should be an object:
+      object { … }
+    * options.headers should be an instance of function."
+`;
+
 exports[`validation should throw an error on the "headers" option with "true" value 1`] = `
 "Invalid options object. Dev Middleware has been initialized using an options object that does not match the API schema.
- - options.headers should be an object:
-   object { … }"
+ - options.headers should be one of these:
+   object { … } | function
+   Details:
+    * options.headers should be an object:
+      object { … }
+    * options.headers should be an instance of function."
 `;
 
 exports[`validation should throw an error on the "index" option with "{}" value 1`] = `
diff --git a/test/middleware.test.js b/test/middleware.test.js
index 0f2657f55..99b000ad3 100644
--- a/test/middleware.test.js
+++ b/test/middleware.test.js
@@ -2392,45 +2392,137 @@ describe.each([
     });
 
     describe('headers option', () => {
-      beforeEach((done) => {
-        const compiler = getCompiler(webpackConfig);
+      describe('works with object', () => {
+        beforeEach((done) => {
+          const compiler = getCompiler(webpackConfig);
 
-        instance = middleware(compiler, {
-          headers: { 'X-nonsense-1': 'yes', 'X-nonsense-2': 'no' },
+          instance = middleware(compiler, {
+            headers: { 'X-nonsense-1': 'yes', 'X-nonsense-2': 'no' },
+          });
+
+          app = framework();
+          app.use(instance);
+
+          listen = listenShorthand(done);
         });
 
-        app = framework();
-        app.use(instance);
+        afterEach(close);
 
-        listen = listenShorthand(done);
+        it('should return the "200" code for the "GET" request to the bundle file and return headers', (done) => {
+          request(app)
+            .get('/bundle.js')
+            .expect('X-nonsense-1', 'yes')
+            .expect('X-nonsense-2', 'no')
+            .expect(200, done);
+        });
+
+        it('should return the "200" code for the "GET" request to path not in outputFileSystem but not return headers', async () => {
+          app.use('/file.jpg', (req, res) => {
+            // Express API
+            if (res.send) {
+              res.send('welcome');
+            }
+            // Connect API
+            else {
+              res.end('welcome');
+            }
+          });
+
+          const res = await request(app).get('/file.jpg');
+          expect(res.statusCode).toEqual(200);
+          expect(res.headers['X-nonsense-1']).toBeUndefined();
+          expect(res.headers['X-nonsense-2']).toBeUndefined();
+        });
       });
+      describe('works with function', () => {
+        beforeEach((done) => {
+          const compiler = getCompiler(webpackConfig);
 
-      afterEach(close);
+          instance = middleware(compiler, {
+            headers: () => {
+              return { 'X-nonsense-1': 'yes', 'X-nonsense-2': 'no' };
+            },
+          });
 
-      it('should return the "200" code for the "GET" request to the bundle file and return headers', (done) => {
-        request(app)
-          .get('/bundle.js')
-          .expect('X-nonsense-1', 'yes')
-          .expect('X-nonsense-2', 'no')
-          .expect(200, done);
+          app = framework();
+          app.use(instance);
+
+          listen = listenShorthand(done);
+        });
+
+        afterEach(close);
+
+        it('should return the "200" code for the "GET" request to the bundle file and return headers', (done) => {
+          request(app)
+            .get('/bundle.js')
+            .expect('X-nonsense-1', 'yes')
+            .expect('X-nonsense-2', 'no')
+            .expect(200, done);
+        });
+
+        it('should return the "200" code for the "GET" request to path not in outputFileSystem but not return headers', async () => {
+          app.use('/file.jpg', (req, res) => {
+            // Express API
+            if (res.send) {
+              res.send('welcome');
+            }
+            // Connect API
+            else {
+              res.end('welcome');
+            }
+          });
+
+          const res = await request(app).get('/file.jpg');
+          expect(res.statusCode).toEqual(200);
+          expect(res.headers['X-nonsense-1']).toBeUndefined();
+          expect(res.headers['X-nonsense-2']).toBeUndefined();
+        });
       });
+      describe('works with headers function with params', () => {
+        beforeEach((done) => {
+          const compiler = getCompiler(webpackConfig);
 
-      it('should return the "200" code for the "GET" request to path not in outputFileSystem but not return headers', async () => {
-        app.use('/file.jpg', (req, res) => {
-          // Express API
-          if (res.send) {
-            res.send('welcome');
-          }
-          // Connect API
-          else {
-            res.end('welcome');
-          }
+          instance = middleware(compiler, {
+            // eslint-disable-next-line no-unused-vars
+            headers: (req, res, context) => {
+              res.setHeader('X-nonsense-1', 'yes');
+              res.setHeader('X-nonsense-2', 'no');
+            },
+          });
+
+          app = framework();
+          app.use(instance);
+
+          listen = listenShorthand(done);
         });
 
-        const res = await request(app).get('/file.jpg');
-        expect(res.statusCode).toEqual(200);
-        expect(res.headers['X-nonsense-1']).toBeUndefined();
-        expect(res.headers['X-nonsense-2']).toBeUndefined();
+        afterEach(close);
+
+        it('should return the "200" code for the "GET" request to the bundle file and return headers', (done) => {
+          request(app)
+            .get('/bundle.js')
+            .expect('X-nonsense-1', 'yes')
+            .expect('X-nonsense-2', 'no')
+            .expect(200, done);
+        });
+
+        it('should return the "200" code for the "GET" request to path not in outputFileSystem but not return headers', async () => {
+          app.use('/file.jpg', (req, res) => {
+            // Express API
+            if (res.send) {
+              res.send('welcome');
+            }
+            // Connect API
+            else {
+              res.end('welcome');
+            }
+          });
+
+          const res = await request(app).get('/file.jpg');
+          expect(res.statusCode).toEqual(200);
+          expect(res.headers['X-nonsense-1']).toBeUndefined();
+          expect(res.headers['X-nonsense-2']).toBeUndefined();
+        });
       });
     });
 
diff --git a/test/validation-options.test.js b/test/validation-options.test.js
index 300d6ba80..9607aa557 100644
--- a/test/validation-options.test.js
+++ b/test/validation-options.test.js
@@ -28,8 +28,8 @@ describe('validation', () => {
       failure: [{}, true],
     },
     headers: {
-      success: [{ 'X-Custom-Header': 'yes' }],
-      failure: [true],
+      success: [{ 'X-Custom-Header': 'yes' }, () => {}],
+      failure: [true, 1],
     },
     publicPath: {
       success: ['/foo', '', 'auto', () => '/public/path'],