diff --git a/.changeset/seven-colts-flash.md b/.changeset/seven-colts-flash.md
new file mode 100644
index 00000000..4c37bc2b
--- /dev/null
+++ b/.changeset/seven-colts-flash.md
@@ -0,0 +1,5 @@
+---
+"agent-base": patch
+---
+
+Synchronously update internal sockets length so `http.Agent` pooling is used
diff --git a/packages/agent-base/src/index.ts b/packages/agent-base/src/index.ts
index f3758fb9..fcf2b57c 100644
--- a/packages/agent-base/src/index.ts
+++ b/packages/agent-base/src/index.ts
@@ -1,6 +1,7 @@
 import * as net from 'net';
 import * as tls from 'tls';
 import * as http from 'http';
+import { Agent as HttpsAgent } from 'https';
 import type { Duplex } from 'stream';
 
 export * from './helpers';
@@ -77,6 +78,65 @@ export abstract class Agent extends http.Agent {
 			);
 	}
 
+	// In order to support async signatures in `connect()` and Node's native
+	// connection pooling in `http.Agent`, the array of sockets for each origin
+	// has to be updated synchronously. This is so the length of the array is
+	// accurate when `addRequest()` is next called. We achieve this by creating a
+	// fake socket and adding it to `sockets[origin]` and incrementing
+	// `totalSocketCount`.
+	private incrementSockets(name: string) {
+		// If `maxSockets` and `maxTotalSockets` are both Infinity then there is no
+		// need to create a fake socket because Node.js native connection pooling
+		// will never be invoked.
+		if (this.maxSockets === Infinity && this.maxTotalSockets === Infinity) {
+			return null;
+		}
+		// All instances of `sockets` are expected TypeScript errors. The
+		// alternative is to add it as a private property of this class but that
+		// will break TypeScript subclassing.
+		if (!this.sockets[name]) {
+			// @ts-expect-error `sockets` is readonly in `@types/node`
+			this.sockets[name] = [];
+		}
+		const fakeSocket = new net.Socket({ writable: false });
+		(this.sockets[name] as net.Socket[]).push(fakeSocket);
+		// @ts-expect-error `totalSocketCount` isn't defined in `@types/node`
+		this.totalSocketCount++;
+		return fakeSocket;
+	}
+
+	private decrementSockets(name: string, socket: null | net.Socket) {
+		if (!this.sockets[name] || socket === null) {
+			return;
+		}
+		const sockets = this.sockets[name] as net.Socket[];
+		const index = sockets.indexOf(socket);
+		if (index !== -1) {
+			sockets.splice(index, 1);
+			// @ts-expect-error  `totalSocketCount` isn't defined in `@types/node`
+			this.totalSocketCount--;
+			if (sockets.length === 0) {
+				// @ts-expect-error `sockets` is readonly in `@types/node`
+				delete this.sockets[name];
+			}
+		}
+	}
+
+	// In order to properly update the socket pool, we need to call `getName()` on
+	// the core `https.Agent` if it is a secureEndpoint.
+	getName(options: AgentConnectOpts): string {
+		const secureEndpoint =
+			typeof options.secureEndpoint === 'boolean'
+				? options.secureEndpoint
+				: this.isSecureEndpoint(options);
+		if (secureEndpoint) {
+			// @ts-expect-error `getName()` isn't defined in `@types/node`
+			return HttpsAgent.prototype.getName.call(this, options);
+		}
+		// @ts-expect-error `getName()` isn't defined in `@types/node`
+		return super.getName(options);
+	}
+
 	createSocket(
 		req: http.ClientRequest,
 		options: AgentConnectOpts,
@@ -86,17 +146,26 @@ export abstract class Agent extends http.Agent {
 			...options,
 			secureEndpoint: this.isSecureEndpoint(options),
 		};
+		const name = this.getName(connectOpts);
+		const fakeSocket = this.incrementSockets(name);
 		Promise.resolve()
 			.then(() => this.connect(req, connectOpts))
-			.then((socket) => {
-				if (socket instanceof http.Agent) {
-					// @ts-expect-error `addRequest()` isn't defined in `@types/node`
-					return socket.addRequest(req, connectOpts);
+			.then(
+				(socket) => {
+					this.decrementSockets(name, fakeSocket);
+					if (socket instanceof http.Agent) {
+						// @ts-expect-error `addRequest()` isn't defined in `@types/node`
+						return socket.addRequest(req, connectOpts);
+					}
+					this[INTERNAL].currentSocket = socket;
+					// @ts-expect-error `createSocket()` isn't defined in `@types/node`
+					super.createSocket(req, options, cb);
+				},
+				(err) => {
+					this.decrementSockets(name, fakeSocket);
+					cb(err);
 				}
-				this[INTERNAL].currentSocket = socket;
-				// @ts-expect-error `createSocket()` isn't defined in `@types/node`
-				super.createSocket(req, options, cb);
-			}, cb);
+			);
 	}
 
 	createConnection(): Duplex {
diff --git a/packages/agent-base/test/test.ts b/packages/agent-base/test/test.ts
index 6f49a84d..deeed875 100644
--- a/packages/agent-base/test/test.ts
+++ b/packages/agent-base/test/test.ts
@@ -79,6 +79,7 @@ describe('Agent (TypeScript)', () => {
 				) {
 					gotCallback = true;
 					assert(opts.secureEndpoint === false);
+					assert.equal(this.getName(opts), `127.0.0.1:${port}:`);
 					return net.connect(opts);
 				}
 			}
@@ -308,6 +309,60 @@ describe('Agent (TypeScript)', () => {
 				server2.close();
 			}
 		});
+
+		it('should support `keepAlive: true` with `maxSockets`', async () => {
+			let reqCount = 0;
+			let connectCount = 0;
+
+			class MyAgent extends Agent {
+				async connect(
+					_req: http.ClientRequest,
+					opts: AgentConnectOpts
+				) {
+					connectCount++;
+					assert(opts.secureEndpoint === false);
+					await sleep(10);
+					return net.connect(opts);
+				}
+			}
+			const agent = new MyAgent({ keepAlive: true, maxSockets: 1 });
+
+			const server = http.createServer(async (req, res) => {
+				expect(req.headers.connection).toEqual('keep-alive');
+				reqCount++;
+				await sleep(10);
+				res.end();
+			});
+			const addr = await listen(server);
+
+			try {
+				const resPromise = req(new URL('/foo', addr), { agent });
+				const res2Promise = req(new URL('/another', addr), {
+					agent,
+				});
+
+				const res = await resPromise;
+				expect(reqCount).toEqual(1);
+				expect(connectCount).toEqual(1);
+				expect(res.headers.connection).toEqual('keep-alive');
+
+				res.resume();
+				const s1 = res.socket;
+				await once(s1, 'free');
+
+				const res2 = await res2Promise;
+				expect(reqCount).toEqual(2);
+				expect(connectCount).toEqual(1);
+				expect(res2.headers.connection).toEqual('keep-alive');
+				assert(res2.socket === s1);
+
+				res2.resume();
+				await once(res2.socket, 'free');
+			} finally {
+				agent.destroy();
+				server.close();
+			}
+		});
 	});
 
 	describe('"https" module', () => {
@@ -322,6 +377,10 @@ describe('Agent (TypeScript)', () => {
 				): net.Socket {
 					gotCallback = true;
 					assert(opts.secureEndpoint === true);
+					assert.equal(
+						this.getName(opts),
+						`127.0.0.1:${port}::::::::false:::::::::::::`
+					);
 					return tls.connect(opts);
 				}
 			}
@@ -509,5 +568,63 @@ describe('Agent (TypeScript)', () => {
 				server.close();
 			}
 		});
+
+		it('should support `keepAlive: true` with `maxSockets`', async () => {
+			let reqCount = 0;
+			let connectCount = 0;
+
+			class MyAgent extends Agent {
+				async connect(
+					_req: http.ClientRequest,
+					opts: AgentConnectOpts
+				) {
+					connectCount++;
+					assert(opts.secureEndpoint === true);
+					await sleep(10);
+					return tls.connect(opts);
+				}
+			}
+			const agent = new MyAgent({ keepAlive: true, maxSockets: 1 });
+
+			const server = https.createServer(sslOptions, async (req, res) => {
+				expect(req.headers.connection).toEqual('keep-alive');
+				reqCount++;
+				await sleep(10);
+				res.end();
+			});
+			const addr = await listen(server);
+
+			try {
+				const resPromise = req(new URL('/foo', addr), {
+					agent,
+					rejectUnauthorized: false,
+				});
+				const res2Promise = req(new URL('/another', addr), {
+					agent,
+					rejectUnauthorized: false,
+				});
+
+				const res = await resPromise;
+				expect(reqCount).toEqual(1);
+				expect(connectCount).toEqual(1);
+				expect(res.headers.connection).toEqual('keep-alive');
+
+				res.resume();
+				const s1 = res.socket;
+				await once(s1, 'free');
+
+				const res2 = await res2Promise;
+				expect(reqCount).toEqual(2);
+				expect(connectCount).toEqual(1);
+				expect(res2.headers.connection).toEqual('keep-alive');
+				assert(res2.socket === s1);
+
+				res2.resume();
+				await once(res2.socket, 'free');
+			} finally {
+				agent.destroy();
+				server.close();
+			}
+		});
 	});
 });