diff --git a/src/client/http.ts b/src/client/http.ts
index c77ba79..d4edbc2 100644
--- a/src/client/http.ts
+++ b/src/client/http.ts
@@ -18,6 +18,50 @@ export interface RequestOpts {
   authStyle?: 'bearer' | 'x-api-key';
 }
 
+const MAX_ATTEMPTS = 3;
+const BASE_RETRY_DELAY_MS = 250;
+const MAX_RETRY_DELAY_MS = 30_000;
+const RETRYABLE_STATUSES = new Set([408, 429, 500, 502, 503, 504]);
+
+function parseRetryAfter(value: string | null, now: number): number | undefined {
+  if (value === null) return undefined;
+
+  const seconds = Number(value);
+  if (Number.isFinite(seconds) && seconds >= 0) {
+    return seconds * 1000;
+  }
+
+  const date = Date.parse(value);
+  if (Number.isNaN(date)) return undefined;
+  return Math.max(0, date - now);
+}
+
+export function retryDelayMs(
+  retryNumber: number,
+  retryAfter: string | null,
+  now = Date.now(),
+  random = Math.random(),
+): number {
+  const serverDelay = parseRetryAfter(retryAfter, now);
+  if (serverDelay !== undefined) {
+    return Math.min(serverDelay, MAX_RETRY_DELAY_MS);
+  }
+
+  const exponentialDelay = BASE_RETRY_DELAY_MS * 2 ** (retryNumber - 1);
+  return Math.min(exponentialDelay * Math.max(0, Math.min(random, 1)), MAX_RETRY_DELAY_MS);
+}
+
+function isRetryableNetworkError(error: unknown): boolean {
+  return error instanceof TypeError ||
+    (error instanceof DOMException && error.name === 'TimeoutError');
+}
+
+async function waitBeforeRetry(retryNumber: number, retryAfter: string | null): Promise<void> {
+  const delay = retryDelayMs(retryNumber, retryAfter);
+  if (delay <= 0) return;
+  await new Promise(resolve => setTimeout(resolve, delay));
+}
+
 export async function request(config: Config, opts: RequestOpts): Promise<Response> {
   const isFormData = typeof FormData !== 'undefined' && opts.body instanceof FormData;
 
@@ -53,17 +97,37 @@ export async function request(config: Config, opts: RequestOpts): Promise<Respon
   }
 
   const timeoutMs = (opts.timeout ?? config.timeout) * 1000;
+  const requestBody = opts.body
+    ? isFormData
+      ? (opts.body as FormData)
+      : JSON.stringify(opts.body)
+    : undefined;
+
+  let res: Response | undefined;
+  for (let attempt = 1; attempt <= MAX_ATTEMPTS; attempt++) {
+    try {
+      res = await fetch(opts.url, {
+        method: opts.method ?? 'GET',
+        headers,
+        body: requestBody,
+        signal: opts.stream ? undefined : AbortSignal.timeout(timeoutMs),
+      });
+    } catch (error) {
+      if (attempt === MAX_ATTEMPTS || !isRetryableNetworkError(error)) throw error;
+      await waitBeforeRetry(attempt, null);
+      continue;
+    }
 
-  const res = await fetch(opts.url, {
-    method: opts.method ?? 'GET',
-    headers,
-    body: opts.body
-      ? isFormData
-        ? (opts.body as FormData)
-        : JSON.stringify(opts.body)
-      : undefined,
-    signal: opts.stream ? undefined : AbortSignal.timeout(timeoutMs),
-  });
+    if (!RETRYABLE_STATUSES.has(res.status) || attempt === MAX_ATTEMPTS) break;
+
+    const retryAfter = res.headers.get('retry-after');
+    await res.body?.cancel();
+    await waitBeforeRetry(attempt, retryAfter);
+  }
+
+  if (!res) {
+    throw new Error('HTTP request completed without a response');
+  }
 
   if (config.verbose) {
     process.stderr.write(`< ${res.status} ${res.statusText}\n`);
diff --git a/test/client/http.test.ts b/test/client/http.test.ts
index 07c0aeb..60d8b74 100644
--- a/test/client/http.test.ts
+++ b/test/client/http.test.ts
@@ -1,5 +1,5 @@
 import { describe, it, expect, afterEach } from 'bun:test';
-import { requestJson } from '../../src/client/http';
+import { requestJson, retryDelayMs } from '../../src/client/http';
 import { CLI_VERSION } from '../../src/version';
 import { createMockServer, jsonResponse, type MockServer } from '../helpers/mock-server';
 import type { Config } from '../../src/config/schema';
@@ -23,9 +23,11 @@ function makeConfig(baseUrl: string): Config {
 
 describe('HTTP client', () => {
   let server: MockServer;
+  const originalFetch = globalThis.fetch;
 
   afterEach(() => {
     server?.close();
+    globalThis.fetch = originalFetch;
   });
 
   it('makes authenticated GET request', async () => {
@@ -93,4 +95,183 @@ describe('HTTP client', () => {
       requestJson(config, { url: `${server.url}/v1/test` }),
     ).rejects.toThrow('Rate limit');
   });
+
+  it.each([408, 429, 500, 502, 503, 504])('retries HTTP %d and then succeeds', async (status) => {
+    let attempts = 0;
+    server = createMockServer({
+      routes: {
+        '/v1/test': () => {
+          attempts++;
+          if (attempts < 3) {
+            return new Response('transient', {
+              status,
+              headers: { 'Retry-After': '0' },
+            });
+          }
+          return jsonResponse({ result: 'ok' });
+        },
+      },
+    });
+
+    const result = await requestJson<{ result: string }>(makeConfig(server.url), {
+      url: `${server.url}/v1/test`,
+    });
+
+    expect(result.result).toBe('ok');
+    expect(attempts).toBe(3);
+  });
+
+  it('stops after the bounded number of attempts', async () => {
+    let attempts = 0;
+    server = createMockServer({
+      routes: {
+        '/v1/test': () => {
+          attempts++;
+          return new Response('unavailable', {
+            status: 503,
+            headers: { 'Retry-After': '0' },
+          });
+        },
+      },
+    });
+
+    await expect(
+      requestJson(makeConfig(server.url), { url: `${server.url}/v1/test` }),
+    ).rejects.toThrow('HTTP 503');
+    expect(attempts).toBe(3);
+  });
+
+  it.each([400, 401, 403, 404, 409, 422])('does not retry permanent HTTP %d errors', async (status) => {
+    let attempts = 0;
+    server = createMockServer({
+      routes: {
+        '/v1/test': () => {
+          attempts++;
+          return jsonResponse({ error: { message: 'permanent' } }, status);
+        },
+      },
+    });
+
+    await expect(
+      requestJson(makeConfig(server.url), { url: `${server.url}/v1/test` }),
+    ).rejects.toBeInstanceOf(Error);
+    expect(attempts).toBe(1);
+  });
+
+  it('retries transient network failures', async () => {
+    let attempts = 0;
+    globalThis.fetch = Object.assign(
+      async (...args: Parameters<typeof fetch>) => {
+        attempts++;
+        if (attempts === 1) throw new TypeError('connection reset');
+        return originalFetch(...args);
+      },
+      { preconnect: originalFetch.preconnect },
+    );
+    server = createMockServer({
+      routes: { '/v1/test': () => jsonResponse({ result: 'ok' }) },
+    });
+
+    const result = await requestJson<{ result: string }>(makeConfig(server.url), {
+      url: `${server.url}/v1/test`,
+    });
+
+    expect(result.result).toBe('ok');
+    expect(attempts).toBe(2);
+  });
+
+  it('retries per-attempt timeout failures', async () => {
+    let attempts = 0;
+    globalThis.fetch = Object.assign(
+      async (...args: Parameters<typeof fetch>) => {
+        attempts++;
+        if (attempts === 1) throw new DOMException('timed out', 'TimeoutError');
+        return originalFetch(...args);
+      },
+      { preconnect: originalFetch.preconnect },
+    );
+    server = createMockServer({
+      routes: { '/v1/test': () => jsonResponse({ result: 'ok' }) },
+    });
+
+    const result = await requestJson<{ result: string }>(makeConfig(server.url), {
+      url: `${server.url}/v1/test`,
+    });
+
+    expect(result.result).toBe('ok');
+    expect(attempts).toBe(2);
+  });
+
+  it('replays JSON request bodies on retry', async () => {
+    const bodies: unknown[] = [];
+    server = createMockServer({
+      routes: {
+        '/v1/test': async (req) => {
+          bodies.push(await req.json());
+          if (bodies.length === 1) {
+            return new Response('unavailable', {
+              status: 503,
+              headers: { 'Retry-After': '0' },
+            });
+          }
+          return jsonResponse({ result: 'ok' });
+        },
+      },
+    });
+
+    await requestJson(makeConfig(server.url), {
+      url: `${server.url}/v1/test`,
+      method: 'POST',
+      body: { hello: 'world' },
+    });
+
+    expect(bodies).toEqual([{ hello: 'world' }, { hello: 'world' }]);
+  });
+
+  it('replays FormData request bodies on retry', async () => {
+    const values: string[] = [];
+    server = createMockServer({
+      routes: {
+        '/v1/test': async (req) => {
+          const form = await req.formData();
+          values.push(String(form.get('purpose')));
+          if (values.length === 1) {
+            return new Response('unavailable', {
+              status: 503,
+              headers: { 'Retry-After': '0' },
+            });
+          }
+          return jsonResponse({ result: 'ok' });
+        },
+      },
+    });
+    const body = new FormData();
+    body.append('purpose', 'retrieval');
+
+    await requestJson(makeConfig(server.url), {
+      url: `${server.url}/v1/test`,
+      method: 'POST',
+      body,
+    });
+
+    expect(values).toEqual(['retrieval', 'retrieval']);
+  });
+});
+
+describe('retryDelayMs', () => {
+  it('uses deterministic exponential backoff with injected jitter', () => {
+    expect(retryDelayMs(1, null, 0, 1)).toBe(250);
+    expect(retryDelayMs(2, null, 0, 0.5)).toBe(250);
+  });
+
+  it('supports Retry-After seconds and HTTP dates', () => {
+    const now = Date.parse('2026-08-05T00:00:00Z');
+    expect(retryDelayMs(1, '2', now, 0)).toBe(2_000);
+    expect(retryDelayMs(1, 'Wed, 05 Aug 2026 00:00:03 GMT', now, 0)).toBe(3_000);
+  });
+
+  it('caps Retry-After and falls back for invalid values', () => {
+    expect(retryDelayMs(1, '120', 0, 0)).toBe(30_000);
+    expect(retryDelayMs(1, 'invalid', 0, 1)).toBe(250);
+  });
 });