diff --git a/changelog.d/fixes/13575-proxy-pool-chat-path-rotation.md b/changelog.d/fixes/13575-proxy-pool-chat-path-rotation.md
new file mode 100644
index 0000000000..32539342e2
--- /dev/null
+++ b/changelog.d/fixes/13575-proxy-pool-chat-path-rotation.md
@@ -0,0 +1 @@
+- fix(db): make the chat-path proxy resolver (`resolveProxyForConnection`) rotate a multi-member pool the same way the registry resolver already does — its per-connection cache was freezing on the first pool member forever instead of re-running the scope's round-robin/sticky/random strategy on each request, unless the connection needs a stable egress (opencode's egress-bucketed quota, grok-web's IP-pinned `cf_clearance`) (#13575)
diff --git a/src/lib/db/settings.ts b/src/lib/db/settings.ts
index cb4f410579..448c38e6d7 100644
--- a/src/lib/db/settings.ts
+++ b/src/lib/db/settings.ts
@@ -15,6 +15,7 @@ import { isProxySkipRecentlyFailedEnabled } from "@/shared/utils/featureFlags";
 import { invalidateDbCache } from "./readCache";
 import { encrypt, decrypt } from "./encryption";
 import { getProxyRegistryGeneration, resolveProxyForScopeFromRegistry } from "./proxies";
+import { isEgressBucketedLockScope } from "@omniroute/open-sse/config/providerErrorRules.ts";
 import { getComboModelProvider as getComboEntryProvider } from "@/lib/combos/steps";
 import { requestBodyLimitMbFromEnv } from "@/shared/constants/bodySize";
 import { DEFAULT_RESPONSES_PREVIOUS_RESPONSE_ID_MODE } from "@/shared/constants/responsesPreviousResponseId";
@@ -527,6 +528,41 @@ function isCachedPoolMemberSetAside(entry: ProxyResolutionCacheEntry): boolean {
   return isProxySkipRecentlyFailedEnabled();
 }
 
+// Providers that need a STABLE egress across requests, never rotated under them by this
+// cache-invalidation path (#13575): opencode's free-tier quota is bucketed by egress IP
+// (EGRESS_BUCKETED_LOCK_PROVIDERS — rotating would fragment one connection's quota across
+// several IPs), and grok-web's cf_clearance cookie is pinned to the IP/User-Agent/TLS
+// fingerprint that earned it (src/shared/providers/webSessionCredentials.ts "grok-web" —
+// rotating the egress would turn every subsequent request into a Cloudflare 403).
+function requiresStableEgress(provider: string | null): boolean {
+  if (!provider) return false;
+  return isEgressBucketedLockScope(provider) || provider.toLowerCase() === "grok-web";
+}
+
+// The chat-path cache (below) exists so a hot connection does not pay the full resolution
+// cascade on every request, but it must not FREEZE a rotating pool's choice: the registry
+// resolver (resolveProxyForScopeFromRegistry, called directly by every #6365 rotation test)
+// re-runs its strategy on every call and rotates correctly, while the cache here returned
+// the same first-resolved member forever (#13575). A cached member is stale whenever it came
+// from a live scope pool (source: "registry") and the connection is not in the two populations
+// above that need a pinned egress instead: the caller then falls through to the full cascade,
+// which re-invokes resolveProxyForScopeFromRegistry and applies the pool's own selection
+// strategy (round-robin advances, sticky holds until its window elapses, random reshuffles) —
+// no new strategy is introduced here.
+function isCachedPoolMemberDue(
+  entry: ProxyResolutionCacheEntry,
+  db: ReturnType<typeof getDbInstance>,
+  connectionId: string
+): boolean {
+  const { result } = entry;
+  if (result.source !== "registry" || result.proxy == null) return false;
+  const row = db
+    .prepare("SELECT provider FROM provider_connections WHERE id = ?")
+    .get(connectionId) as { provider?: string } | undefined;
+  const provider = typeof row?.provider === "string" ? row.provider : null;
+  return !requiresStableEgress(provider);
+}
+
 export async function resolveProxyForConnection(
   connectionId: string,
   apiKeyId?: string,
@@ -542,18 +578,18 @@ export async function resolveProxyForConnection(
     registryGeneration: getProxyRegistryGeneration(),
     refusalSeq: getProxyRefusalSeq(),
   };
+  const db = getDbInstance();
   const cached = proxyResolutionCache.get(cacheKey);
   if (
     cached &&
     cached.generation === stamp.generation &&
     cached.registryGeneration === stamp.registryGeneration &&
-    !isCachedPoolMemberSetAside(cached)
+    !isCachedPoolMemberSetAside(cached) &&
+    !isCachedPoolMemberDue(cached, db, connectionId)
   ) {
     return cached.result;
   }
 
-  const db = getDbInstance();
-
   // Step 1: Check global proxyEnabled setting
   // Read only the proxyEnabled key for performance instead of loading all settings.
   let globalProxyEnabled = true;
diff --git a/tests/unit/proxy-pool-chat-path-rotation-13575.test.ts b/tests/unit/proxy-pool-chat-path-rotation-13575.test.ts
new file mode 100644
index 0000000000..a11f79668c
--- /dev/null
+++ b/tests/unit/proxy-pool-chat-path-rotation-13575.test.ts
@@ -0,0 +1,120 @@
+/**
+ * Regression test for issue #13575.
+ *
+ * The chat path (`resolveProxyForConnection`) must rotate across a multi-member
+ * pool the same way the registry-level resolver does (`resolveProxyForScopeFromRegistry`),
+ * instead of freezing on the first pick for the life of the per-connection cache.
+ * Providers with a stable-egress requirement (egress-bucketed quota, IP-pinned web
+ * session credentials) must stay pinned to a single member.
+ */
+import test from "node:test";
+import assert from "node:assert/strict";
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+
+const TEST_DATA_DIR = fs.mkdtempSync(path.join(os.tmpdir(), "omniroute-proxy-13575-rotation-"));
+process.env.DATA_DIR = TEST_DATA_DIR;
+process.env.API_KEY_SECRET = "test-secret";
+
+const core = await import("../../src/lib/db/core.ts");
+const proxiesDb = await import("../../src/lib/db/proxies.ts");
+const providersDb = await import("../../src/lib/db/providers.ts");
+const settingsDb = await import("../../src/lib/db/settings.ts");
+
+let proxySeq = 0;
+async function makeProxy() {
+  proxySeq++;
+  const proxy = await proxiesDb.createProxy({
+    name: `Pool proxy ${proxySeq}`,
+    type: "http",
+    host: `10.9.1.${proxySeq}`,
+    port: 9100 + proxySeq,
+    status: "active",
+  });
+  return proxy!;
+}
+
+async function makeConnection(provider = "openai"): Promise<string> {
+  const conn = await providersDb.createProviderConnection({
+    provider,
+    authType: "apiKey",
+    name: `Conn ${Date.now()} ${Math.random()}`,
+    apiKey: "sk-test",
+  });
+  return (conn as { id: string }).id;
+}
+
+test.after(async () => {
+  core.resetDbInstance();
+  fs.rmSync(TEST_DATA_DIR, { recursive: true, force: true, maxRetries: 5, retryDelay: 100 });
+});
+
+test("#13575: resolveProxyForConnection rotates round-robin across a multi-member pool", async () => {
+  const a = await makeProxy();
+  const b = await makeProxy();
+  const c = await makeProxy();
+  const connId = await makeConnection("openai");
+  await proxiesDb.addProxyToScopePool("account", connId, a.id);
+  await proxiesDb.addProxyToScopePool("account", connId, b.id);
+  await proxiesDb.addProxyToScopePool("account", connId, c.id);
+
+  const chatPathHosts: string[] = [];
+  for (let i = 0; i < 6; i++) {
+    const r = (await settingsDb.resolveProxyForConnection(connId)) as {
+      proxy?: { host?: string } | null;
+    };
+    chatPathHosts.push(r.proxy?.host ?? "null");
+  }
+
+  const distinctChatHosts = new Set(chatPathHosts);
+  assert.ok(
+    distinctChatHosts.size > 1,
+    `expected resolveProxyForConnection to rotate across the pool, but got: ${JSON.stringify(chatPathHosts)}`
+  );
+  assert.deepEqual(distinctChatHosts, new Set([a.host, b.host, c.host]));
+});
+
+test("#13575: egress-bucketed-quota providers (opencode) stay pinned on the chat path", async () => {
+  const a = await makeProxy();
+  const b = await makeProxy();
+  const connId = await makeConnection("opencode");
+  await proxiesDb.addProxyToScopePool("account", connId, a.id);
+  await proxiesDb.addProxyToScopePool("account", connId, b.id);
+
+  const hosts: string[] = [];
+  for (let i = 0; i < 6; i++) {
+    const r = (await settingsDb.resolveProxyForConnection(connId)) as {
+      proxy?: { host?: string } | null;
+    };
+    hosts.push(r.proxy?.host ?? "null");
+  }
+
+  assert.deepEqual(
+    new Set(hosts),
+    new Set([hosts[0]]),
+    `expected an egress-bucketed-quota connection to stay pinned to one member, got: ${JSON.stringify(hosts)}`
+  );
+});
+
+test("#13575: IP-pinned web-session providers (grok-web) stay pinned on the chat path", async () => {
+  const a = await makeProxy();
+  const b = await makeProxy();
+  const connId = await makeConnection("grok-web");
+  await proxiesDb.addProxyToScopePool("account", connId, a.id);
+  await proxiesDb.addProxyToScopePool("account", connId, b.id);
+
+  const hosts: string[] = [];
+  for (let i = 0; i < 6; i++) {
+    const r = (await settingsDb.resolveProxyForConnection(connId)) as {
+      proxy?: { host?: string } | null;
+    };
+    hosts.push(r.proxy?.host ?? "null");
+  }
+
+  assert.deepEqual(
+    new Set(hosts),
+    new Set([hosts[0]]),
+    `expected an IP-pinned web-session connection to stay pinned to one member, got: ${JSON.stringify(hosts)}`
+  );
+});
diff --git a/tests/unit/proxy-pool-skips-refused-member.test.ts b/tests/unit/proxy-pool-skips-refused-member.test.ts
index c2dc6c293c..56e2b6ec4e 100644
--- a/tests/unit/proxy-pool-skips-refused-member.test.ts
+++ b/tests/unit/proxy-pool-skips-refused-member.test.ts
@@ -5,9 +5,10 @@ import os from "node:os";
 import path from "node:path";
 
 // With PROXY_SKIP_RECENTLY_FAILED on, pool selection skips members that just failed, for
-// every rotation strategy, and the per-connection resolution cache stops re-serving such a
-// member (once per set-aside event, never a DB cascade per request). With every member set
-// aside, or the flag off (the default), selection is exactly what it was.
+// every rotation strategy. The per-connection resolution used by the chat path
+// (resolveProxyForConnection) re-runs the registry cascade on every call for a multi-member
+// pool (#13575) and skips a set-aside member on top of that. With every member set aside, or
+// the flag off (the default), set-aside skipping does not apply but rotation continues.
 
 const TEST_DATA_DIR = fs.mkdtempSync(path.join(os.tmpdir(), "omniroute-pool-skip-refused-"));
 process.env.DATA_DIR = TEST_DATA_DIR;
@@ -167,34 +168,39 @@ test("a DB override turning the flag off wins over the environment", async () =>
   assert.deepEqual(await picks(2), [members[0].host, members[2].host]);
 });
 
-test("a connection's cached pool member is not re-served once set aside", async () => {
+// #13575: the chat-path resolveProxyForConnection() no longer freezes a multi-member
+// pool's choice for the connection's lifetime — it re-runs the registry cascade on every
+// call (like every other pool consumer) so round-robin/sticky/random keep working exactly
+// as resolveProxyForScopeFromRegistry() already does when called directly. A member set
+// aside is still skipped on top of that rotation, same as before.
+test("a connection's chat-path resolution skips a member set aside", async () => {
   const [a, b, c] = await pool(3, "account", "conn-pool");
   const first = await settingsDb.resolveProxyForConnection("conn-pool");
   assert.equal((first as { proxy: { host: string } }).proxy.host, a.host);
-  assert.strictEqual(await settingsDb.resolveProxyForConnection("conn-pool"), first);
 
-  setAside(a);
+  setAside(b);
   const next = await settingsDb.resolveProxyForConnection("conn-pool");
-  assert.equal((next as { proxy: { host: string } }).proxy.host, b.host);
+  assert.equal((next as { proxy: { host: string } }).proxy.host, c.host);
 
-  memory.noteProxyRecovered(keyOf(a), "proxy_unreachable");
-  assert.equal(memory.isProxyAvoided(keyOf(a)), false);
+  memory.noteProxyRecovered(keyOf(b), "proxy_unreachable");
+  assert.equal(memory.isProxyAvoided(keyOf(b)), false);
   assert.deepEqual(
     [await pick("account", "conn-pool"), await pick("account", "conn-pool")],
-    [c.host, a.host]
+    [a.host, b.host]
   );
 });
 
-test("with the flag off a connection keeps its cached pool member even once set aside", async () => {
-  const [a] = await pool(3, "account", "conn-off");
+test("with the flag off a connection's chat-path resolution still rotates normally", async () => {
+  const [a, b] = await pool(3, "account", "conn-off");
   delete process.env.PROXY_SKIP_RECENTLY_FAILED;
   const first = await settingsDb.resolveProxyForConnection("conn-off");
   assert.equal((first as { proxy: { host: string } }).proxy.host, a.host);
   setAside(a);
-  assert.strictEqual(await settingsDb.resolveProxyForConnection("conn-off"), first);
+  const next = await settingsDb.resolveProxyForConnection("conn-off");
+  assert.equal((next as { proxy: { host: string } }).proxy.host, b.host);
 });
 
-test("with every member set aside the cascade re-runs once, not on every request", async () => {
+test("with every member set aside, chat-path resolution keeps rotating like the registry", async () => {
   // Round-robin advances its persisted cursor on each cascade run, so the cursor counts
   // how many times the registry pool was actually queried for this connection.
   const [a, b] = await pool(2, "account", "conn-all");
@@ -218,10 +224,9 @@ test("with every member set aside the cascade re-runs once, not on every request
   assert.equal((second as { proxy: { host: string } }).proxy.host, b.host);
   assert.equal(cursor(), 2);
 
-  for (let i = 0; i < 5; i++) {
-    assert.strictEqual(await settingsDb.resolveProxyForConnection("conn-all"), second);
-  }
-  assert.equal(cursor(), 2, "a member set aside before the entry was cached must not bypass it");
+  const third = await settingsDb.resolveProxyForConnection("conn-all");
+  assert.equal((third as { proxy: { host: string } }).proxy.host, a.host);
+  assert.equal(cursor(), 3);
 });
 
 test("a legacy single-proxy level stays cached even when its proxy is set aside", async () => {