diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3c720dd3edb..56b19d84dc5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -45,6 +45,7 @@ Docs: https://docs.openclaw.ai
 - Plugins/uninstall: remove empty managed git install parent directories after deleting cloned plugin repos and cover npm/git uninstall residue in Docker plugin lifecycle tests. Thanks @vincentkoc.
 - Plugins/install: resolve bare official external plugin IDs such as `brave` through the official catalog when no bundled source is available, so packaged installs fetch the intended scoped npm package instead of an unrelated unscoped package. Fixes #76373. Thanks @bek91 and @vincentkoc.
 - Plugins/install: require OpenClaw-owned install provenance before granting official npm plugin scanner trust, so direct npm package names no longer bypass launch-code scanning while catalog, onboarding, and doctor installs stay trusted. Thanks @fede-kamel and @vincentkoc.
+- Network proxy: preserve target TLS hostname validation for Node HTTPS requests routed through the managed HTTP proxy, so Discord-style CONNECT traffic no longer validates certificates against the local proxy host. Fixes #74809. (#76442) Thanks @jesse-merhi and @abnershang.
 - Gateway/sessions: keep async `sessions.list` title and preview hydration bounded to transcript head/tail reads so Control UI polling cannot full-scan large session transcripts every refresh. Thanks @vincentkoc.
 - Gateway/sessions: keep agent runtime metadata on lightweight `sessions.list` rows so model-only session patches do not make Control UI lose runtime identity. Thanks @vincentkoc.
 - Gateway/sessions: keep bulk `sessions.list` rows lightweight by skipping per-row transcript usage fallback, display model inference, and plugin projection, avoiding event-loop stalls in large session stores. Thanks @Marvinthebored and @vincentkoc.
diff --git a/src/infra/net/proxy/external-proxy.e2e.test.ts b/src/infra/net/proxy/external-proxy.e2e.test.ts
index cbd0d4977c7..2b5daaa3e67 100644
--- a/src/infra/net/proxy/external-proxy.e2e.test.ts
+++ b/src/infra/net/proxy/external-proxy.e2e.test.ts
@@ -1,11 +1,106 @@
-import { spawn } from "node:child_process";
+import { execFileSync, spawn } from "node:child_process";
+import { mkdtempSync, readFileSync, rmSync, writeFileSync } from "node:fs";
 import { createServer, request as httpRequest, type Server } from "node:http";
+import { createServer as createHttpsServer } from "node:https";
 import * as net from "node:net";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import type { Duplex } from "node:stream";
 import { afterEach, describe, expect, it } from "vitest";
 import { WebSocketServer } from "ws";
 
 const CHILD_PROCESS_TIMEOUT_MS = process.env.CI ? 45_000 : 15_000;
 const PROBE_TIMEOUT_MS = process.env.CI ? 15_000 : 5_000;
+const PROXY_TUNNEL_SOCKETS = new WeakMap<Server, Set<Duplex>>();
+type DiscordTlsFixture = {
+  caPath: string;
+  cert: string;
+  cleanup: () => void;
+  key: string;
+};
+
+function createDiscordTlsFixture(): DiscordTlsFixture {
+  const dir = mkdtempSync(join(tmpdir(), "openclaw-discord-tls-"));
+  try {
+    const caKeyPath = join(dir, "ca-key.pem");
+    const caCertPath = join(dir, "ca-cert.pem");
+    const serverKeyPath = join(dir, "server-key.pem");
+    const serverCsrPath = join(dir, "server.csr");
+    const serverCertPath = join(dir, "server-cert.pem");
+    const extPath = join(dir, "server-ext.cnf");
+
+    execFileSync(
+      "openssl",
+      [
+        "req",
+        "-x509",
+        "-newkey",
+        "rsa:2048",
+        "-nodes",
+        "-keyout",
+        caKeyPath,
+        "-out",
+        caCertPath,
+        "-days",
+        "1",
+        "-subj",
+        "/CN=OpenClaw Proxy Test CA",
+      ],
+      { stdio: "ignore" },
+    );
+    execFileSync(
+      "openssl",
+      [
+        "req",
+        "-newkey",
+        "rsa:2048",
+        "-nodes",
+        "-keyout",
+        serverKeyPath,
+        "-out",
+        serverCsrPath,
+        "-subj",
+        "/CN=discord.com",
+      ],
+      { stdio: "ignore" },
+    );
+    writeFileSync(extPath, "subjectAltName=DNS:discord.com\n");
+    execFileSync(
+      "openssl",
+      [
+        "x509",
+        "-req",
+        "-in",
+        serverCsrPath,
+        "-CA",
+        caCertPath,
+        "-CAkey",
+        caKeyPath,
+        "-CAcreateserial",
+        "-out",
+        serverCertPath,
+        "-days",
+        "1",
+        "-sha256",
+        "-extfile",
+        extPath,
+      ],
+      { stdio: "ignore" },
+    );
+
+    return {
+      caPath: caCertPath,
+      cert: readFileSync(serverCertPath, "utf8"),
+      cleanup: () => {
+        rmSync(dir, { force: true, recursive: true });
+      },
+      key: readFileSync(serverKeyPath, "utf8"),
+    };
+  } catch (err) {
+    rmSync(dir, { force: true, recursive: true });
+    throw err;
+  }
+}
 
 async function listenOnLoopback(server: Server): Promise<number> {
   return new Promise((resolve, reject) => {
@@ -26,6 +121,10 @@ async function closeServer(server: Server | null): Promise<void> {
   if (server === null || !server.listening) {
     return;
   }
+  for (const socket of PROXY_TUNNEL_SOCKETS.get(server) ?? []) {
+    socket.destroy();
+  }
+  server.closeAllConnections?.();
   await new Promise<void>((resolve, reject) => {
     server.close((err) => {
       if (err) {
@@ -37,7 +136,16 @@ async function closeServer(server: Server | null): Promise<void> {
   });
 }
 
-function createTunnelProxy(seenConnectTargets: string[]): Server {
+type ConnectTargetOverride = {
+  hostname: string;
+  port: number;
+};
+
+function createTunnelProxy(
+  seenConnectTargets: string[],
+  connectTargetOverrides: Record<string, ConnectTargetOverride> = {},
+): Server {
+  const tunnelSockets = new Set<Duplex>();
   const proxy = createServer((req, res) => {
     const target = req.url ?? "";
     seenConnectTargets.push(target);
@@ -71,6 +179,7 @@ function createTunnelProxy(seenConnectTargets: string[]): Server {
     });
     req.pipe(upstream);
   });
+  PROXY_TUNNEL_SOCKETS.set(proxy, tunnelSockets);
 
   proxy.on("connect", (req, clientSocket, head) => {
     const target = req.url ?? "";
@@ -84,13 +193,26 @@ function createTunnelProxy(seenConnectTargets: string[]): Server {
       return;
     }
 
-    const upstream = net.connect(Number(targetUrl.port), targetUrl.hostname, () => {
-      clientSocket.write("HTTP/1.1 200 Connection Established\r\n\r\n");
-      if (head.length > 0) {
-        upstream.write(head);
-      }
-      upstream.pipe(clientSocket);
-      clientSocket.pipe(upstream);
+    const override = connectTargetOverrides[target];
+    tunnelSockets.add(clientSocket);
+    clientSocket.once("close", () => {
+      tunnelSockets.delete(clientSocket);
+    });
+    const upstream = net.connect(
+      override?.port ?? Number(targetUrl.port),
+      override?.hostname ?? targetUrl.hostname,
+      () => {
+        clientSocket.write("HTTP/1.1 200 Connection Established\r\n\r\n");
+        if (head.length > 0) {
+          upstream.write(head);
+        }
+        upstream.pipe(clientSocket);
+        clientSocket.pipe(upstream);
+      },
+    );
+    tunnelSockets.add(upstream);
+    upstream.once("close", () => {
+      tunnelSockets.delete(upstream);
     });
 
     upstream.on("error", () => {
@@ -155,6 +277,7 @@ async function runNodeModule(
 describe("SSRF external proxy routing", () => {
   let target: Server | null = null;
   let httpsLikeTarget: Server | null = null;
+  let tlsTarget: Server | null = null;
   let proxy: Server | null = null;
   let wss: WebSocketServer | null = null;
 
@@ -167,10 +290,12 @@ describe("SSRF external proxy routing", () => {
       wss.close(() => resolve());
     });
     await closeServer(proxy);
+    await closeServer(tlsTarget);
     await closeServer(httpsLikeTarget);
     await closeServer(target);
     wss = null;
     proxy = null;
+    tlsTarget = null;
     httpsLikeTarget = null;
     target = null;
   });
@@ -328,4 +453,75 @@ describe("SSRF external proxy routing", () => {
     expect(seenConnectTargets).toContain(`http://127.0.0.1:${targetPort}/websocket-proxied`);
     expect(seenConnectTargets).not.toContain(`http://127.0.0.1:${targetPort}/gateway-bypass`);
   });
+
+  it("preserves the target TLS hostname for Node HTTPS requests through the managed proxy", async () => {
+    const tlsFixture = createDiscordTlsFixture();
+    try {
+      tlsTarget = createHttpsServer({ key: tlsFixture.key, cert: tlsFixture.cert }, (_req, res) => {
+        res.writeHead(209, { "content-type": "text/plain" });
+        res.end("discord target tls ok");
+      });
+      const tlsTargetPort = await listenOnLoopback(tlsTarget);
+
+      const seenConnectTargets: string[] = [];
+      proxy = createTunnelProxy(seenConnectTargets, {
+        [`discord.com:${tlsTargetPort}`]: { hostname: "127.0.0.1", port: tlsTargetPort },
+      });
+      const proxyPort = await listenOnLoopback(proxy);
+
+      const child = await runNodeModule(
+        `
+        import https from "node:https";
+        import { startProxy, stopProxy } from "./src/infra/net/proxy/proxy-lifecycle.ts";
+
+        async function nodeHttpsGet(url) {
+          return new Promise((resolve, reject) => {
+            const req = https.get(url, (response) => {
+              let body = "";
+              response.setEncoding("utf8");
+              response.on("data", (chunk) => {
+                body += chunk;
+              });
+              response.on("end", () => {
+                resolve({ status: response.statusCode, body });
+              });
+            });
+            req.setTimeout(${PROBE_TIMEOUT_MS}, () => {
+              req.destroy(new Error("node:https request timed out"));
+            });
+            req.on("error", reject);
+          });
+        }
+
+        const handle = await startProxy({ enabled: true });
+        if (handle === null) {
+          throw new Error("expected external proxy routing to start");
+        }
+        try {
+          const response = await nodeHttpsGet(process.env.OPENCLAW_TEST_DISCORD_TLS_URL);
+          console.log(JSON.stringify(response));
+        } finally {
+          await stopProxy(handle);
+        }
+      `,
+        {
+          ...process.env,
+          NODE_EXTRA_CA_CERTS: tlsFixture.caPath,
+          OPENCLAW_PROXY_URL: `http://127.0.0.1:${proxyPort}`,
+          OPENCLAW_TEST_DISCORD_TLS_URL: `https://discord.com:${tlsTargetPort}/tls-proxy-proof`,
+          NO_PROXY: "127.0.0.1,localhost",
+          no_proxy: "localhost",
+          GLOBAL_AGENT_NO_PROXY: "localhost",
+        },
+      );
+
+      expect(child.stderr).toBe("");
+      expect(child.code).toBe(0);
+      expect(child.stdout).toContain('"status":209');
+      expect(child.stdout).toContain('"body":"discord target tls ok"');
+      expect(seenConnectTargets).toContain(`discord.com:${tlsTargetPort}`);
+    } finally {
+      tlsFixture.cleanup();
+    }
+  });
 });
diff --git a/src/infra/net/proxy/proxy-lifecycle.ts b/src/infra/net/proxy/proxy-lifecycle.ts
index 91aca8f3bd9..605ee62e79b 100644
--- a/src/infra/net/proxy/proxy-lifecycle.ts
+++ b/src/infra/net/proxy/proxy-lifecycle.ts
@@ -9,6 +9,7 @@
 
 import http from "node:http";
 import https from "node:https";
+import { isIP } from "node:net";
 import { bootstrap as bootstrapGlobalAgent } from "global-agent";
 import type { ProxyConfig } from "../../../config/zod-schema.proxy.js";
 import { logInfo, logWarn } from "../../../logger.js";
@@ -67,17 +68,23 @@ type ActiveProxyRegistration = {
   proxyUrl: string;
   stopped: boolean;
 };
+type GlobalAgentConnectConfiguration = Record<string, unknown> & {
+  host: string;
+  tls: Record<string, unknown>;
+};
 
 let globalAgentBootstrapped = false;
 let nodeHttpStackSnapshot: NodeHttpStackSnapshot | null = null;
 let activeProxyRegistrations: ActiveProxyRegistration[] = [];
 let baseProxyEnvSnapshot: ProxyEnvSnapshot | null = null;
+let patchedGlobalAgentHttpsAgents = new WeakSet<object>();
 
 export function _resetGlobalAgentBootstrapForTests(): void {
   globalAgentBootstrapped = false;
   nodeHttpStackSnapshot = null;
   activeProxyRegistrations = [];
   baseProxyEnvSnapshot = null;
+  patchedGlobalAgentHttpsAgents = new WeakSet<object>();
 }
 
 function captureProxyEnv(): ProxyEnvSnapshot {
@@ -212,6 +219,7 @@ function bootstrapNodeHttpStack(proxyUrl: string): void {
   if (!globalAgentBootstrapped) {
     nodeHttpStackSnapshot = captureNodeHttpStack();
     bootstrapGlobalAgent();
+    patchGlobalAgentHttpsConnectTlsTargetHost();
     globalAgentBootstrapped = true;
   }
 
@@ -226,6 +234,59 @@ function bootstrapNodeHttpStack(proxyUrl: string): void {
   }
 }
 
+function isRecord(value: unknown): value is Record<string, unknown> {
+  return typeof value === "object" && value !== null;
+}
+
+function isGlobalAgentConnectConfiguration(
+  value: unknown,
+): value is GlobalAgentConnectConfiguration {
+  if (!isRecord(value)) {
+    return false;
+  }
+  return typeof value["host"] === "string" && isRecord(value["tls"]);
+}
+
+function withTlsTargetHost(configuration: unknown): unknown {
+  if (!isGlobalAgentConnectConfiguration(configuration)) {
+    return configuration;
+  }
+
+  const tlsOptions: Record<string, unknown> = {
+    ...configuration.tls,
+    host: configuration.host,
+  };
+  if (tlsOptions["servername"] === undefined && isIP(configuration.host) === 0) {
+    tlsOptions["servername"] = configuration.host;
+  }
+  return {
+    ...configuration,
+    tls: tlsOptions,
+  };
+}
+
+function patchGlobalAgentHttpsConnectTlsTargetHost(): void {
+  const agent = https.globalAgent;
+  if (typeof agent !== "object" || agent === null || patchedGlobalAgentHttpsAgents.has(agent)) {
+    return;
+  }
+
+  const agentRecord = agent as unknown as Record<string, unknown>;
+  const createConnection = agentRecord["createConnection"];
+  if (typeof createConnection !== "function") {
+    return;
+  }
+
+  agentRecord["createConnection"] = function createConnectionWithTlsTargetHost(
+    this: unknown,
+    configuration: unknown,
+    callback: unknown,
+  ): unknown {
+    return createConnection.call(this, withTlsTargetHost(configuration), callback);
+  };
+  patchedGlobalAgentHttpsAgents.add(agent);
+}
+
 function findTopActiveProxyRegistration(): ActiveProxyRegistration | null {
   for (let index = activeProxyRegistrations.length - 1; index >= 0; index -= 1) {
     const registration = activeProxyRegistrations[index];