diff --git a/packages/opencode/src/session/retry.ts b/packages/opencode/src/session/retry.ts
index 284c0f0ade41..612a7dff63e4 100644
--- a/packages/opencode/src/session/retry.ts
+++ b/packages/opencode/src/session/retry.ts
@@ -29,6 +29,7 @@ export const RETRY_JITTER_FACTOR = 0.25
 export const RETRY_MAX_DELAY_NO_HEADERS = 30_000 // 30 seconds
 export const RETRY_MAX_DELAY = 2_147_483_647 // max 32-bit signed integer for setTimeout
 export const RETRY_MAX_RETRIES = 5
+export const RETRY_MAX_WAIT = 300_000 // longest provider-requested wait worth sleeping through - waits above this stop the retry loop instead of sleeping, see policy(). Distinct from RETRY_MAX_DELAY (backoff cap).
 
 const RETRYABLE_MESSAGE_PATTERNS = [
   /429|500|502|503|504|524/i,
@@ -198,8 +199,12 @@ export function policy(opts: {
           attempt: meta.attempt,
           message: retry.message,
           action: retry.action,
-          next: now + wait,
+          next: wait > RETRY_MAX_WAIT ? now : now + wait,
         })
+        // Status is published first so the limit dialog still fires, then we stop: a wait
+        // this long is an exhausted quota window, and sleeping through it leaves the
+        // session pending for hours with no visible error.
+        if (wait > RETRY_MAX_WAIT) return yield* Cause.done(meta.attempt)
         return [meta.attempt, Duration.millis(wait)] as [number, Duration.Duration]
       })
     }),
diff --git a/packages/opencode/test/session/retry.test.ts b/packages/opencode/test/session/retry.test.ts
index 20c8678cf0a7..093ea93b69ca 100644
--- a/packages/opencode/test/session/retry.test.ts
+++ b/packages/opencode/test/session/retry.test.ts
@@ -4,7 +4,7 @@ import { SessionV1 } from "@opencode-ai/core/v1/session"
 import type { NamedError } from "@opencode-ai/core/util/error"
 import { APICallError } from "ai"
 import { setTimeout as sleep } from "node:timers/promises"
-import { Effect, Schedule, Schema } from "effect"
+import { Duration, Effect, Exit, Schedule, Schema } from "effect"
 import { CrossSpawnSpawner } from "@opencode-ai/core/cross-spawn-spawner"
 import { SessionRetry } from "../../src/session/retry"
 import { MessageV2 } from "../../src/session/message-v2"
@@ -146,6 +146,51 @@ describe("session.retry.delay", () => {
       expect(attempts).toStrictEqual([1, 2, 3, 4, 5])
     }),
   )
+
+  it.instance("policy stops when the provider asks for a wait past the ceiling", () =>
+    Effect.gen(function* () {
+      const seen: { message: string; reason?: string }[] = []
+      // opencode zen answers an exhausted free tier with 429 and a retry-after pointing
+      // at the next daily reset, so the wait can be most of a day
+      const error = Schema.decodeUnknownSync(SessionV1.APIError.Schema)(
+        new SessionV1.APIError({
+          message: "Rate limit exceeded. Please try again later.",
+          statusCode: 429,
+          isRetryable: true,
+          responseHeaders: { "retry-after": "43200" },
+          responseBody: JSON.stringify({ type: "error", error: { type: "FreeUsageLimitError" } }),
+        }).toObject(),
+      )
+      const step = yield* Schedule.toStep(
+        SessionRetry.policy({
+          provider: "opencode",
+          parse: Schema.decodeUnknownSync(SessionV1.APIError.Schema),
+          set: (info) =>
+            Effect.sync(() => {
+              seen.push({ message: info.message, reason: info.action?.reason })
+            }),
+        }),
+      )
+
+      expect(Exit.isFailure(yield* Effect.exit(step(Date.now(), error)))).toBe(true)
+      expect(seen).toStrictEqual([{ message: SessionRetry.GO_UPSELL_MESSAGE, reason: "free_tier_limit" }])
+    }),
+  )
+
+  it.instance("policy keeps retrying a wait within the ceiling", () =>
+    Effect.gen(function* () {
+      const error = apiError({ "retry-after-ms": String(SessionRetry.RETRY_MAX_WAIT) })
+      const step = yield* Schedule.toStep(
+        SessionRetry.policy({
+          provider: "test",
+          parse: Schema.decodeUnknownSync(SessionV1.APIError.Schema),
+          set: () => Effect.void,
+        }),
+      )
+
+      expect(Duration.toMillis((yield* step(Date.now(), error))[1])).toBe(SessionRetry.RETRY_MAX_WAIT)
+    }),
+  )
 })
 
 describe("session.retry.retryable", () => {