diff --git a/fluxer_desktop/src/main/DesktopHappyEyeballs.test.mjs b/fluxer_desktop/src/main/DesktopHappyEyeballs.test.mjs
new file mode 100644
index 000000000..7ec4a16ec
--- /dev/null
+++ b/fluxer_desktop/src/main/DesktopHappyEyeballs.test.mjs
@@ -0,0 +1,55 @@
+// SPDX-License-Identifier: AGPL-3.0-or-later
+
+import assert from 'node:assert/strict';
+import net from 'node:net';
+import {describe, test} from 'node:test';
+
+const {connectToFirstAnsweringAddress} = await import('./DesktopHappyEyeballs.ts');
+
+function race(addresses, port, options) {
+	return new Promise((resolve) => {
+		connectToFirstAnsweringAddress(addresses, port, options, (error, socket) => resolve({error, socket}));
+	});
+}
+
+describe('DesktopHappyEyeballs', () => {
+	test('a slow first address keeps racing after the next one fails fast', async () => {
+		const server = net.createServer((socket) => socket.end());
+		await new Promise((resolve) => server.listen(0, '127.0.0.1', resolve));
+		const {port} = server.address();
+		const dial = (options) => {
+			if (options.host !== '127.0.0.1') {
+				return net.connect(options);
+			}
+			const socket = new net.Socket();
+			setTimeout(() => socket.connect(options), 150);
+			return socket;
+		};
+		try {
+			const {error, socket} = await race(
+				[
+					{address: '127.0.0.1', family: 4},
+					{address: '::1', family: 6},
+				],
+				port,
+				{attemptDelayMs: 20, dial},
+			);
+			assert.equal(error, null, 'a connect slower than the attempt delay must not be abandoned');
+			assert.equal(socket.remoteAddress, '127.0.0.1');
+			socket.destroy();
+		} finally {
+			server.close();
+		}
+	});
+
+	test('when every address fails the error names each attempt', async () => {
+		const server = net.createServer();
+		await new Promise((resolve) => server.listen(0, '127.0.0.1', resolve));
+		const {port} = server.address();
+		await new Promise((resolve) => server.close(resolve));
+		const {error, socket} = await race([{address: '127.0.0.1', family: 4}], port, {});
+		assert.equal(socket, null);
+		assert.equal(error.code, 'ECONNREFUSED');
+		assert.match(error.message, /ECONNREFUSED 127\.0\.0\.1/);
+	});
+});
diff --git a/fluxer_desktop/src/main/DesktopHappyEyeballs.ts b/fluxer_desktop/src/main/DesktopHappyEyeballs.ts
new file mode 100644
index 000000000..538cb896b
--- /dev/null
+++ b/fluxer_desktop/src/main/DesktopHappyEyeballs.ts
@@ -0,0 +1,214 @@
+// SPDX-License-Identifier: AGPL-3.0-or-later
+
+import http from 'node:http';
+import https from 'node:https';
+import net, {type LookupFunction} from 'node:net';
+import type {Duplex} from 'node:stream';
+
+const HAPPY_EYEBALLS_ATTEMPT_DELAY_MS = 250;
+const HAPPY_EYEBALLS_CONNECT_TIMEOUT_MS = 30_000;
+
+interface ConnectAddress {
+	readonly address: string;
+	readonly family: 4 | 6;
+}
+
+type ConnectCallback = (error: Error | null, socket: net.Socket | null) => void;
+type Dial = (options: net.TcpNetConnectOpts) => net.Socket;
+
+interface RaceOptions {
+	readonly attemptDelayMs?: number;
+	readonly dial?: Dial;
+	readonly keepAlive?: boolean;
+	readonly keepAliveInitialDelay?: number;
+	readonly noDelay?: boolean;
+}
+
+type CreatedConnectionCallback = (error: Error | null, stream: Duplex) => void;
+
+interface HappyEyeballsConnectOptions {
+	readonly host?: string | null;
+	readonly hostname?: string | null;
+	readonly keepAlive?: boolean;
+	readonly keepAliveInitialDelay?: number;
+	readonly lookup?: LookupFunction;
+	readonly noDelay?: boolean;
+	readonly port?: number | string | null;
+}
+
+class HappyEyeballsConnectError extends AggregateError {
+	public readonly code: string | undefined;
+	public readonly syscall = 'connect';
+
+	public constructor(errors: ReadonlyArray<Error>) {
+		super(errors, `Could not connect to any resolved address (${errors.map((error) => error.message).join('; ')})`);
+		this.name = 'HappyEyeballsConnectError';
+		this.code = (errors[0] as NodeJS.ErrnoException | undefined)?.code;
+	}
+}
+
+function connectFailure(errors: ReadonlyArray<Error>): Error {
+	return errors.length === 1 ? errors[0] : new HappyEyeballsConnectError(errors);
+}
+
+function connectTimeoutError(): NodeJS.ErrnoException {
+	const error: NodeJS.ErrnoException = new Error('Connecting to the resolved addresses timed out');
+	error.code = 'ETIMEDOUT';
+	return error;
+}
+
+function interleaveFamilies(addresses: ReadonlyArray<ConnectAddress>): ReadonlyArray<ConnectAddress> {
+	const first = addresses[0]?.family;
+	const preferred = addresses.filter((address) => address.family === first);
+	const other = addresses.filter((address) => address.family !== first);
+	const ordered: Array<ConnectAddress> = [];
+	for (let index = 0; index < Math.max(preferred.length, other.length); index += 1) {
+		if (index < preferred.length) {
+			ordered.push(preferred[index]);
+		}
+		if (index < other.length) {
+			ordered.push(other[index]);
+		}
+	}
+	return ordered;
+}
+
+export function connectToFirstAnsweringAddress(
+	addresses: ReadonlyArray<ConnectAddress>,
+	port: number,
+	options: RaceOptions,
+	callback: ConnectCallback,
+): void {
+	const attemptDelayMs = options.attemptDelayMs ?? HAPPY_EYEBALLS_ATTEMPT_DELAY_MS;
+	const dial = options.dial ?? net.connect;
+	const ordered = interleaveFamilies(addresses);
+	const pending = new Set<net.Socket>();
+	const errors: Array<Error> = [];
+	let next = 0;
+	let settled = false;
+	let attemptTimer: NodeJS.Timeout | undefined;
+	const finish = (error: Error | null, winner: net.Socket | null): void => {
+		if (settled) {
+			return;
+		}
+		settled = true;
+		clearTimeout(attemptTimer);
+		clearTimeout(deadline);
+		for (const socket of pending) {
+			if (socket !== winner) {
+				socket.destroy();
+			}
+		}
+		pending.clear();
+		callback(error, winner);
+	};
+	const startNext = (): void => {
+		clearTimeout(attemptTimer);
+		if (settled || next >= ordered.length) {
+			return;
+		}
+		const {address, family} = ordered[next];
+		next += 1;
+		const socket = dial({
+			family,
+			host: address,
+			keepAlive: options.keepAlive,
+			keepAliveInitialDelay: options.keepAliveInitialDelay,
+			noDelay: options.noDelay,
+			port,
+		});
+		pending.add(socket);
+		const onError = (error: Error): void => {
+			pending.delete(socket);
+			errors.push(error);
+			if (settled) {
+				return;
+			}
+			if (next < ordered.length) {
+				startNext();
+			} else if (pending.size === 0) {
+				finish(connectFailure(errors), null);
+			}
+		};
+		socket.once('error', onError);
+		socket.once('connect', () => {
+			socket.removeListener('error', onError);
+			finish(null, socket);
+		});
+		if (next < ordered.length) {
+			attemptTimer = setTimeout(startNext, attemptDelayMs);
+		}
+	};
+	const deadline = setTimeout(() => {
+		errors.push(connectTimeoutError());
+		finish(connectFailure(errors), null);
+	}, HAPPY_EYEBALLS_CONNECT_TIMEOUT_MS);
+	deadline.unref();
+	if (ordered.length === 0) {
+		finish(connectTimeoutError(), null);
+		return;
+	}
+	startNext();
+}
+
+function connectThroughLookup(options: HappyEyeballsConnectOptions, callback: ConnectCallback): void {
+	const lookup = options.lookup as LookupFunction;
+	const hostname = options.host ?? options.hostname ?? '';
+	lookup(hostname, {all: true}, (error, resolved) => {
+		if (error != null) {
+			callback(error, null);
+			return;
+		}
+		const addresses = (resolved as unknown as ReadonlyArray<{address: string; family: number}>).map(
+			(entry): ConnectAddress => ({address: entry.address, family: entry.family === 6 ? 6 : 4}),
+		);
+		connectToFirstAnsweringAddress(
+			addresses,
+			Number(options.port),
+			{
+				keepAlive: options.keepAlive,
+				keepAliveInitialDelay: options.keepAliveInitialDelay,
+				noDelay: options.noDelay,
+			},
+			callback,
+		);
+	});
+}
+
+export class HappyEyeballsHttpAgent extends http.Agent {
+	public override createConnection(
+		options: HappyEyeballsConnectOptions,
+		callback?: CreatedConnectionCallback,
+	): Duplex | null | undefined {
+		if (options.lookup == null || callback == null) {
+			return super.createConnection(options as http.ClientRequestArgs, callback);
+		}
+		connectThroughLookup(options, (error, socket) => {
+			if (error != null || socket == null) {
+				callback(error ?? connectTimeoutError(), undefined as unknown as Duplex);
+				return;
+			}
+			callback(null, socket);
+		});
+		return undefined;
+	}
+}
+
+export class HappyEyeballsHttpsAgent extends https.Agent {
+	public override createConnection(
+		options: HappyEyeballsConnectOptions,
+		callback?: CreatedConnectionCallback,
+	): Duplex | null | undefined {
+		if (options.lookup == null || callback == null) {
+			return super.createConnection(options as http.ClientRequestArgs, callback);
+		}
+		connectThroughLookup(options, (error, socket) => {
+			if (error != null || socket == null) {
+				callback(error ?? connectTimeoutError(), undefined as unknown as Duplex);
+				return;
+			}
+			callback(null, super.createConnection({...options, socket} as http.ClientRequestArgs) as Duplex);
+		});
+		return undefined;
+	}
+}
diff --git a/fluxer_desktop/src/main/DesktopOutboundHTTP.ts b/fluxer_desktop/src/main/DesktopOutboundHTTP.ts
index 4df23f28e..85d5e8c62 100644
--- a/fluxer_desktop/src/main/DesktopOutboundHTTP.ts
+++ b/fluxer_desktop/src/main/DesktopOutboundHTTP.ts
@@ -8,6 +8,7 @@ import {isIPv4, isIPv6, type LookupFunction} from 'node:net';
 import {Readable, Transform} from 'node:stream';
 import type {ReadableStream as NodeReadableStream} from 'node:stream/web';
 import {createChildLogger} from '@electron/common/Logger';
+import {HappyEyeballsHttpAgent, HappyEyeballsHttpsAgent} from '@electron/main/DesktopHappyEyeballs';
 import {
 	type DesktopProxyResolver,
 	type DesktopSessionHTTPSender,
@@ -88,11 +89,6 @@ export const DesktopOriginTrust = Object.freeze({
 
 export type DesktopOriginTrust = (typeof DesktopOriginTrust)[keyof typeof DesktopOriginTrust];
 
-const HAPPY_EYEBALLS_CONNECT_OPTIONS = Object.freeze({
-	autoSelectFamily: true,
-	autoSelectFamilyAttemptTimeout: 250,
-});
-
 interface PinnedAddress {
 	readonly address: string;
 	readonly family: 4 | 6;
@@ -710,9 +706,12 @@ interface DesktopProxiedSend {
 }
 
 export class DesktopOutboundHTTP {
-	private readonly httpAgent = new http.Agent({keepAlive: true, maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_SOCKETS});
+	private readonly httpAgent = new HappyEyeballsHttpAgent({
+		keepAlive: true,
+		maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_SOCKETS,
+	});
 	private readonly httpsAgent: https.Agent;
-	private readonly originRequestHttpAgent = new http.Agent({
+	private readonly originRequestHttpAgent = new HappyEyeballsHttpAgent({
 		keepAlive: true,
 		maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_IN_FLIGHT_PER_SERVICE,
 	});
@@ -735,8 +734,12 @@ export class DesktopOutboundHTTP {
 		this.sendThroughSession = options.sendThroughSession ?? sendThroughDesktopSession;
 		const certificates = options.trustedCertificates ?? resolveDesktopTrustedCertificates();
 		const trust = certificates.length > 0 ? {ca: [...certificates]} : {};
-		this.httpsAgent = new https.Agent({keepAlive: true, maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_SOCKETS, ...trust});
-		this.originRequestHttpsAgent = new https.Agent({
+		this.httpsAgent = new HappyEyeballsHttpsAgent({
+			keepAlive: true,
+			maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_SOCKETS,
+			...trust,
+		});
+		this.originRequestHttpsAgent = new HappyEyeballsHttpsAgent({
 			keepAlive: true,
 			maxSockets: DESKTOP_OUTBOUND_HTTP_MAX_IN_FLIGHT_PER_SERVICE,
 			...trust,
@@ -1074,7 +1077,6 @@ export class DesktopOutboundHTTP {
 			const clientRequest = transport.request(request.url, {
 				agent: secure ? this.httpsAgent : this.httpAgent,
 				lookup: createPinnedHostLookup(request.url.hostname, pinned),
-				...HAPPY_EYEBALLS_CONNECT_OPTIONS,
 				method: 'GET',
 			});
 			const deadline = setTimeout(() => {
@@ -1291,7 +1293,6 @@ export class DesktopOutboundHTTP {
 					agent: target.protocol === 'https:' ? this.originRequestHttpsAgent : this.originRequestHttpAgent,
 					headers: requestHeaders(request.headers),
 					lookup: createPinnedHostLookup(target.hostname, binding.addresses),
-					...HAPPY_EYEBALLS_CONNECT_OPTIONS,
 					method: request.method,
 				});
 				active = clientRequest;
diff --git a/fluxer_desktop/src/main/FileDownloads.test.mjs b/fluxer_desktop/src/main/FileDownloads.test.mjs
index d6a26d1dc..1b6c5f5ca 100644
--- a/fluxer_desktop/src/main/FileDownloads.test.mjs
+++ b/fluxer_desktop/src/main/FileDownloads.test.mjs
@@ -29,6 +29,7 @@ function transform(name) {
 	};
 }
 
+const happyEyeballsSource = transform('DesktopHappyEyeballs.ts');
 const outboundSource = transform('DesktopOutboundHTTP.ts');
 const fileDownloadsSource = transform('FileDownloads.ts');
 
@@ -102,6 +103,15 @@ async function loadFileDownloads({registerOrigin = true} = {}) {
 	};
 	const context = vm.createContext(sandbox);
 
+	const happyEyeballsModule = {exports: {}};
+	const happyEyeballsContext = vm.createContext({
+		...sandbox,
+		exports: happyEyeballsModule.exports,
+		module: happyEyeballsModule,
+	});
+	vm.runInContext(happyEyeballsSource.code, happyEyeballsContext, {filename: happyEyeballsSource.path});
+	stubs['@electron/main/DesktopHappyEyeballs'] = happyEyeballsModule.exports;
+
 	const outboundModule = {exports: {}};
 	sandbox.module = outboundModule;
 	sandbox.exports = outboundModule.exports;