diff --git a/lib/agent.js b/lib/agent.js
index 8bd354e..7438d30 100644
--- a/lib/agent.js
+++ b/lib/agent.js
@@ -90,7 +90,13 @@ class Agent extends OriginalAgent {
     this.timeoutSocketCount = 0;
     this.timeoutSocketCountLastCheck = 0;
 
-    this.on('free', socket => {
+    this.on('free', (socket, options) => {
+      // Node's listener may assign the socket to a queued request before this
+      // listener runs. Only apply the free socket timeout if it was pooled.
+      const name = this.getName(options);
+      if (!this.freeSockets[name] || this.freeSockets[name].indexOf(socket) === -1) {
+        return;
+      }
       // https://github.com/nodejs/node/pull/32000
       // Node.js native agent will check socket timeout eqs agent.options.timeout.
       // Use the ttl or freeSocketTimeout to overwrite.
diff --git a/test/http_agent.test.js b/test/http_agent.test.js
index 4e1228b..b224e89 100644
--- a/test/http_agent.test.js
+++ b/test/http_agent.test.js
@@ -762,6 +762,42 @@ describe('test/agent.test.js', () => {
     assert(agent.requests[name].length === 1);
   });
 
+  it('should use active timeout when socket is assigned to a queued request', done => {
+    const name = 'localhost:' + port + ':';
+    const agent = new HttpAgent({
+      maxSockets: 1,
+      freeSocketTimeout: 50,
+      timeout: 1000,
+    });
+    let finished = false;
+    const finish = err => {
+      if (finished) return;
+      finished = true;
+      agent.destroy();
+      done(err);
+    };
+
+    http.get({
+      agent,
+      port,
+      path: '/?timeout=10',
+    }, res => {
+      res.resume();
+    }).on('error', finish);
+
+    http.get({
+      agent,
+      port,
+      path: '/?timeout=200',
+    }, res => {
+      assert(res.statusCode === 200);
+      res.resume();
+      res.on('end', finish);
+    }).on('error', finish);
+
+    assert(agent.requests[name].length === 1);
+  });
+
   it('should keep 1 free socket', done => {
     const name = 'localhost:' + port + ':';
     const agent = new HttpAgent({