diff --git a/packages/playwright-core/src/server/fetch.ts b/packages/playwright-core/src/server/fetch.ts
index b154ce63079fb..4905f22f8369a 100644
--- a/packages/playwright-core/src/server/fetch.ts
+++ b/packages/playwright-core/src/server/fetch.ts
@@ -87,7 +87,7 @@ export type APIRequestFinishedEvent = {
   securityDetails?: har.SecurityDetails;
 };
 
-type SendRequestOptions = https.RequestOptions & {
+type SendRequestOptions = Omit<https.RequestOptions, 'agent'> & {
   maxRedirects: number,
   headers: HeadersObject,
   __testHookLookup?: (hostname: string) => LookupAddress[]
@@ -168,6 +168,13 @@ export abstract class APIRequestContext extends SdkObject {
     this.emit(APIRequestContext.Events.Dispose);
   }
 
+  private _proxyAgentForUrl(url: URL): http.Agent | undefined {
+    const proxy = this._defaultOptions().proxy;
+    // We skip 'per-context' in order to not break existing users. 'per-context' was previously used to
+    // workaround an upstream Chromium bug. Can be removed in the future.
+    return createProxyAgent(proxy?.server === 'per-context' ? undefined : proxy, url);
+  }
+
   private _ensureAgent(protocol: string): http.Agent {
     let agent = this._agentForProtocol.get(protocol);
     if (!agent) {
@@ -221,22 +228,13 @@ export abstract class APIRequestContext extends SdkObject {
       setBasicAuthorizationHeader(headers, credentials);
 
     const method = params.method?.toUpperCase() || 'GET';
-    const proxy = defaults.proxy;
-    let agent;
-    // We skip 'per-context' in order to not break existing users. 'per-context' was previously used to
-    // workaround an upstream Chromium bug. Can be removed in the future.
-    if (proxy?.server !== 'per-context')
-      agent = createProxyAgent(proxy, requestUrl);
-
     let maxRedirects = params.maxRedirects ?? (defaults.maxRedirects ?? 20);
     maxRedirects = maxRedirects === 0 ? -1 : maxRedirects;
 
     const options: SendRequestOptions = {
       method,
       headers,
-      agent,
       maxRedirects,
-      ...getMatchingTLSOptionsForOrigin(this._defaultOptions().clientCertificates, requestUrl.origin),
       __testHookLookup: (params as any).__testHookLookup,
     };
     // rejectUnauthorized = undefined is treated as true in Node.js 12.
@@ -362,11 +360,15 @@ export abstract class APIRequestContext extends SdkObject {
     const resultPromise = new Promise<SendRequestResult>((fulfill, reject) => {
       const requestConstructor: ((url: URL, options: http.RequestOptions, callback?: (res: http.IncomingMessage) => void) => http.ClientRequest)
         = (url.protocol === 'https:' ? https : http).request;
-      // Without an explicit proxy agent, use this context's own agent, which has
-      // keep-alive enabled and connects with Happy Eyeballs (autoSelectFamily).
-      // Resolved per request so that a cross-protocol redirect picks the right agent.
-      const requestOptions = { ...options, ...happyEyeballsOptions };
-      requestOptions.agent = options.agent ?? this._ensureAgent(url.protocol);
+      // Proxy bypass rules and client certificates are resolved per hop, so that
+      // a redirect target picks its own agent and TLS options. Without a proxy agent,
+      // use this context's own agent (keep-alive, Happy Eyeballs).
+      const requestOptions: https.RequestOptions = {
+        ...options,
+        ...happyEyeballsOptions,
+        ...getMatchingTLSOptionsForOrigin(this._defaultOptions().clientCertificates, url.origin),
+        agent: this._proxyAgentForUrl(url) ?? this._ensureAgent(url.protocol),
+      };
       if (options.__testHookLookup)
         requestOptions.lookup = lookupWithTestHook(options.__testHookLookup);
 
@@ -484,7 +486,6 @@ export abstract class APIRequestContext extends SdkObject {
           const redirectOptions: SendRequestOptions = {
             method,
             headers,
-            agent: options.agent,
             maxRedirects: options.maxRedirects - 1,
             __testHookLookup: options.__testHookLookup,
           };
@@ -512,11 +513,6 @@ export abstract class APIRequestContext extends SdkObject {
             if (locationURL.origin !== url.origin)
               removeHeader(headers, 'authorization');
 
-            // Client certificates are origin-scoped — pick them based on the redirect
-            // target, not the original URL.
-            Object.assign(redirectOptions,
-                getMatchingTLSOptionsForOrigin(this._defaultOptions().clientCertificates, locationURL.origin));
-
             notifyRequestFinished();
             fulfill(this._sendRequest(progress, log, locationURL, redirectOptions, postData));
             request.destroy();
diff --git a/tests/library/fetch-proxy.spec.ts b/tests/library/fetch-proxy.spec.ts
index 5d35bef85b063..a8ec03a7f6247 100644
--- a/tests/library/fetch-proxy.spec.ts
+++ b/tests/library/fetch-proxy.spec.ts
@@ -171,3 +171,32 @@ it('should send correct ALPN protocol to HTTPS proxy', { annotation: { type: 'is
   proxy.close();
   await request.dispose();
 });
+
+it('should apply proxy.bypass to redirect targets', { annotation: { type: 'issue', description: 'https://github.com/microsoft/playwright/issues/42815' } }, async ({ contextFactory, server, proxyServer }) => {
+  const crossProcessHost = new URL(server.CROSS_PROCESS_PREFIX).host;
+  it.skip(crossProcessHost === server.HOST, 'Needs two different host names for the same server');
+
+  proxyServer.forwardTo(server.PORT, { allowConnectRequests: true });
+  server.setRedirect('/redirect-to-cross-process', server.CROSS_PROCESS_PREFIX + '/simple.json');
+  server.setRedirect('/redirect-to-same-origin', server.PREFIX + '/simple.json');
+  const context = await contextFactory({
+    proxy: { server: `localhost:${proxyServer.PORT}`, bypass: server.HOSTNAME }
+  });
+
+  {
+    // Bypassed first hop redirects to a host that must go through the proxy.
+    const response = await context.request.get(server.PREFIX + '/redirect-to-cross-process');
+    expect(response.url()).toBe(server.CROSS_PROCESS_PREFIX + '/simple.json');
+    expect(await response.json()).toEqual({ foo: 'bar' });
+    expect(proxyServer.connectHosts).toEqual([crossProcessHost]);
+    proxyServer.connectHosts = [];
+  }
+
+  {
+    // Proxied first hop redirects to a bypassed host.
+    const response = await context.request.get(server.CROSS_PROCESS_PREFIX + '/redirect-to-same-origin');
+    expect(response.url()).toBe(server.PREFIX + '/simple.json');
+    expect(await response.json()).toEqual({ foo: 'bar' });
+    expect(proxyServer.connectHosts).toEqual([crossProcessHost]);
+  }
+});