diff --git a/lib/sender.js b/lib/sender.js
index 060e55392..500bd98cd 100644
--- a/lib/sender.js
+++ b/lib/sender.js
@@ -27,6 +27,20 @@ class Sender {
     this._bufferedBytes = 0;
     this._deflating = false;
     this._queue = [];
+
+    if (this._extensions[PerMessageDeflate.extensionName]) {
+      this._socket.once('close', () => {
+        const err = new Error('WebSocket is not open: readyState 2 (CLOSING)');
+
+        while (this._queue.length) {
+          const params = this._queue.shift();
+          const cb = params[params.length - 1];
+
+          this._bufferedBytes -= params[1].length;
+          if (typeof cb === 'function') cb(err);
+        }
+      });
+    }
   }
 
   /**
diff --git a/lib/websocket.js b/lib/websocket.js
index 92cb0f891..845bd2dba 100644
--- a/lib/websocket.js
+++ b/lib/websocket.js
@@ -123,6 +123,11 @@ class WebSocket extends EventEmitter {
       maxPayload
     );
 
+    //
+    // `Sender` must be instantiated before adding the `socketOnClose` listener.
+    // This allows the sender queue, when used, to be emptied before
+    // `socketOnClose` is called.
+    //
     this._sender = new Sender(socket, this._extensions);
     this._receiver = receiver;
     this._socket = socket;
diff --git a/test/sender.test.js b/test/sender.test.js
index 623ce5954..e7c7dd104 100644
--- a/test/sender.test.js
+++ b/test/sender.test.js
@@ -5,6 +5,16 @@ const assert = require('assert');
 const PerMessageDeflate = require('../lib/permessage-deflate');
 const Sender = require('../lib/sender');
 
+class MockSocket {
+  constructor ({ write, once } = {}) {
+    if (write) this.write = write;
+    if (once) this.once = once;
+  }
+
+  write () {}
+  once () {}
+}
+
 describe('Sender', function () {
   describe('.frame', function () {
     it('does not mutate the input buffer if data is `readOnly`', function () {
@@ -38,12 +48,13 @@ describe('Sender', function () {
     it('compresses data if compress option is enabled', function (done) {
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
       let count = 0;
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           assert.strictEqual(data[0] & 0x40, 0x40);
           if (++count === 3) done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -57,14 +68,53 @@ describe('Sender', function () {
       sender.send('hi', options);
     });
 
+    it('does not compress enqueued messages after socket closes', function (done) {
+      const numMessages = 100;
+      let numErrors = 0;
+
+      const mockSocket = new MockSocket({
+        write: (data) => {
+          // Test that `PerMessageDeflate#compress()` and `Socket#write()` is
+          // called only once (for the first message that is not queued).
+          assert.strictEqual(numErrors, numMessages);
+          done();
+        },
+        once: (ev, cb) => {
+          if (ev === 'close') process.nextTick(cb);
+        }
+      });
+
+      const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
+      perMessageDeflate.accept([{}]);
+
+      const sender = new Sender(mockSocket, {
+        'permessage-deflate': perMessageDeflate
+      });
+
+      const options = { compress: true, fin: true };
+      sender.send('hi', options);
+
+      for (let i = 0; i < numMessages; i++) {
+        sender.send('hi', options, (err) => {
+          assert.ok(err instanceof Error);
+          assert.strictEqual(
+            err.message,
+            'WebSocket is not open: readyState 2 (CLOSING)'
+          );
+          numErrors++;
+        });
+      }
+    });
+
     it('does not compress data for small payloads', function (done) {
       const perMessageDeflate = new PerMessageDeflate();
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           assert.notStrictEqual(data[0] & 0x40, 0x40);
           done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -76,7 +126,7 @@ describe('Sender', function () {
     it('compresses all frames in a fragmented message', function (done) {
       const fragments = [];
       const perMessageDeflate = new PerMessageDeflate({ threshold: 3 });
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           fragments.push(data);
           if (fragments.length !== 2) return;
@@ -87,7 +137,8 @@ describe('Sender', function () {
           assert.strictEqual(fragments[1].length, 6);
           done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -100,7 +151,7 @@ describe('Sender', function () {
     it('compresses no frames in a fragmented message', function (done) {
       const fragments = [];
       const perMessageDeflate = new PerMessageDeflate({ threshold: 3 });
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           fragments.push(data);
           if (fragments.length !== 2) return;
@@ -111,7 +162,8 @@ describe('Sender', function () {
           assert.strictEqual(fragments[1].length, 5);
           done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -124,7 +176,7 @@ describe('Sender', function () {
     it('compresses empty buffer as first fragment', function (done) {
       const fragments = [];
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           fragments.push(data);
           if (fragments.length !== 2) return;
@@ -135,7 +187,8 @@ describe('Sender', function () {
           assert.strictEqual(fragments[1].length, 8);
           done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -148,7 +201,7 @@ describe('Sender', function () {
     it('compresses empty buffer as last fragment', function (done) {
       const fragments = [];
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           fragments.push(data);
           if (fragments.length !== 2) return;
@@ -159,7 +212,8 @@ describe('Sender', function () {
           assert.strictEqual(fragments[1].length, 3);
           done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -172,11 +226,12 @@ describe('Sender', function () {
     it('handles many send calls while processing without crashing on flush', function (done) {
       let count = 0;
       const perMessageDeflate = new PerMessageDeflate();
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: () => {
           if (++count > 1e4) done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -196,14 +251,15 @@ describe('Sender', function () {
     it('works with multiple types of data', function (done) {
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
       let count = 0;
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           if (++count === 1) return;
 
           assert.ok(data.equals(Buffer.from([0x89, 0x02, 0x68, 0x69])));
           if (count === 4) done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -222,14 +278,15 @@ describe('Sender', function () {
     it('works with multiple types of data', function (done) {
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
       let count = 0;
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data) => {
           if (++count === 1) return;
 
           assert.ok(data.equals(Buffer.from([0x8a, 0x02, 0x68, 0x69])));
           if (count === 4) done();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
@@ -249,12 +306,13 @@ describe('Sender', function () {
       const perMessageDeflate = new PerMessageDeflate({ threshold: 0 });
 
       let count = 0;
-      const sender = new Sender({
+      const mockSocket = new MockSocket({
         write: (data, cb) => {
           count++;
           if (cb) cb();
         }
-      }, {
+      });
+      const sender = new Sender(mockSocket, {
         'permessage-deflate': perMessageDeflate
       });
 
diff --git a/test/websocket.test.js b/test/websocket.test.js
index 25bdc8f8e..b78429e1c 100644
--- a/test/websocket.test.js
+++ b/test/websocket.test.js
@@ -2040,6 +2040,40 @@ describe('WebSocket', function () {
       });
     });
 
+    it('reports the state as `CLOSING` in callbacks of discarded queued messages', function (done) {
+      const wss = new WebSocket.Server({
+        perMessageDeflate: { threshold: 0 },
+        port: 0
+      }, () => {
+        const ws = new WebSocket(`ws://localhost:${wss.address().port}`);
+      });
+
+      wss.on('connection', (ws) => {
+        const map = () => crypto.randomBytes(16);
+        let count = 100;
+
+        Array.from({ length: count }).map(map).forEach((data, i) => {
+          ws.send(data, (err) => {
+            assert.ok(err instanceof Error);
+
+            if (i > 0) {
+              // The first message is not queued and compression completes after
+              // the `'close'` event is emitted on the `net.Socket`.
+              assert.strictEqual(ws.readyState, WebSocket.CLOSING);
+              assert.strictEqual(
+                err.message,
+                'WebSocket is not open: readyState 2 (CLOSING)'
+              );
+            }
+
+            if (--count === 0) done();
+          });
+        });
+
+        wss.close();
+      });
+    });
+
     describe('#send', function () {
       it('ignores the `compress` option if the extension is disabled', function (done) {
         const wss = new WebSocket.Server({ port: 0 }, () => {