diff --git a/packages/core/src/cachekeep.ts b/packages/core/src/cachekeep.ts
index 3d9621ad..8a88a007 100644
--- a/packages/core/src/cachekeep.ts
+++ b/packages/core/src/cachekeep.ts
@@ -339,7 +339,7 @@ export type CacheKeepPrewarmResult =
         cache_read_input_tokens?: number
       }
     }
-  | { ok: false; reason: string; status?: number }
+  | { ok: false; reason: string; status?: number; transient?: true }
 
 export class CacheKeepManager {
   private readonly targets = new Map<string, CacheKeepTarget>()
@@ -576,7 +576,15 @@ export class CacheKeepManager {
     const dueAt = now + CACHE_KEEP_PREWARM_LEAD_MS
     for (const target of this.targets.values()) {
       if (target.cacheExpiresAt > dueAt) continue
-      await this.prewarm(target, now)
+      try {
+        await this.prewarm(target, now)
+      } catch (error) {
+        logger.warn('cachekeep', 'prewarm failed', {
+          session: target.id,
+          reason: error instanceof Error ? error.message : String(error),
+        })
+        target.cacheExpiresAt = now + CACHE_KEEP_PREWARM_LEAD_MS + 5 * 60_000
+      }
     }
     this.publishTrackedSessions()
   }
@@ -597,14 +605,23 @@ export class CacheKeepManager {
       : new Headers(target.headers)
     headers.delete('content-length')
     headers.delete('transfer-encoding')
-    const response = await fetchImpl(target.url, {
-      method: 'POST',
-      headers,
-      body: prewarm.bodyText,
-      signal: AbortSignal.timeout(
-        this.options.prewarmTimeoutMs ?? CACHE_KEEP_PREWARM_TIMEOUT_MS,
-      ),
-    })
+    let response: Response
+    try {
+      response = await fetchImpl(target.url, {
+        method: 'POST',
+        headers,
+        body: prewarm.bodyText,
+        signal: AbortSignal.timeout(
+          this.options.prewarmTimeoutMs ?? CACHE_KEEP_PREWARM_TIMEOUT_MS,
+        ),
+      })
+    } catch (error) {
+      return {
+        ok: false,
+        reason: error instanceof Error ? error.message : String(error),
+        transient: true,
+      }
+    }
     if (!response.ok) {
       return {
         ok: false,
@@ -632,7 +649,7 @@ export class CacheKeepManager {
   private async prewarm(target: CacheKeepTarget, now: number) {
     const result = await this.sendPrewarm(target)
     if (!result.ok) {
-      if (result.status == null) {
+      if (result.status == null && !result.transient) {
         logger.debug('cachekeep', 'prewarm skipped', {
           session: target.id,
           reason: result.reason,
diff --git a/packages/opencode/src/tests/cachekeep.test.ts b/packages/opencode/src/tests/cachekeep.test.ts
index a350dad8..3d0de358 100644
--- a/packages/opencode/src/tests/cachekeep.test.ts
+++ b/packages/opencode/src/tests/cachekeep.test.ts
@@ -314,7 +314,7 @@ describe('CacheKeepManager', () => {
       prewarmTimeoutMs: 5,
     })
 
-    const result = manager.prewarmNow({
+    const result = await manager.prewarmNow({
       sessionId: 'ses_timeout',
       url: 'https://api.anthropic.com/v1/messages?beta=true',
       headers: new Headers(),
@@ -330,7 +330,10 @@ describe('CacheKeepManager', () => {
       }),
     })
 
-    await expect(result).rejects.toMatchObject({ name: 'TimeoutError' })
+    expect(result.ok).toBe(false)
+    if (result.ok) throw new Error('expected prewarm to fail')
+    expect(result.transient).toBe(true)
+    expect(result.reason).toContain('timed out')
   })
 
   test('passes OAuth account identity to prewarm header refresh', async () => {
@@ -651,4 +654,98 @@ describe('CacheKeepManager', () => {
     expect(fetchImpl).toHaveBeenCalledTimes(1)
     manager.stop()
   })
+
+  test('contains thrown prewarm errors and continues with later targets', async () => {
+    let now = new Date('2026-05-18T10:00:00').getTime()
+    const attempts: string[] = []
+    let publishCount = 0
+    const timeout = new Error('The operation timed out.')
+    timeout.name = 'TimeoutError'
+    const fetchImpl = mock((input: string | URL | Request) => {
+      const url = String(input)
+      attempts.push(url)
+      if (url.endsWith('/A')) throw timeout
+      return Promise.resolve(new Response('{}', { status: 200 }))
+    }) as unknown as typeof fetch
+    const manager = new CacheKeepManager({
+      loadStorage: () => Promise.resolve(hybridStorage()),
+      fetchImpl,
+      now: () => now,
+      onTrackedSessionsChanged: () => {
+        publishCount++
+      },
+    })
+    const body = JSON.stringify({
+      system: [
+        { type: 'text', text: 'stable', cache_control: { type: 'ephemeral' } },
+      ],
+      messages: [{ role: 'user', content: 'hello' }],
+    })
+
+    for (const id of ['A', 'B', 'C']) {
+      await manager.track({
+        sessionId: `ses_${id}`,
+        url: `https://api.anthropic.com/v1/messages/${id}`,
+        headers: new Headers(),
+        bodyText: body,
+        storage: hybridStorage(),
+        cacheMode: 'hybrid',
+      })
+    }
+
+    const publishedBeforeTick = publishCount
+    now += 55 * 60_000
+    await manager.tick()
+
+    expect(attempts).toEqual([
+      'https://api.anthropic.com/v1/messages/A',
+      'https://api.anthropic.com/v1/messages/B',
+      'https://api.anthropic.com/v1/messages/C',
+    ])
+    expect(manager.trackedSessions().map((session) => session.id)).toEqual([
+      'ses_A',
+      'ses_B',
+      'ses_C',
+    ])
+    expect(
+      manager.trackedSessions().find((session) => session.id === 'ses_A')
+        ?.cacheExpiresAt,
+    ).toBe(now + 10 * 60_000)
+    expect(publishCount).toBeGreaterThan(publishedBeforeTick)
+
+    attempts.length = 0
+    now += 60_000
+    await manager.tick()
+    expect(attempts).toEqual([])
+    manager.stop()
+  })
+
+  test('deletes a tracked target when its prewarm body is unbuildable', async () => {
+    let now = new Date('2026-05-18T10:00:00').getTime()
+    const fetchImpl = mock(() =>
+      Promise.resolve(new Response('{}', { status: 200 })),
+    ) as unknown as typeof fetch
+    const manager = new CacheKeepManager({
+      loadStorage: () => Promise.resolve(hybridStorage()),
+      fetchImpl,
+      now: () => now,
+    })
+
+    await manager.track({
+      sessionId: 'ses_unbuildable',
+      url: 'https://api.anthropic.com/v1/messages/unbuildable',
+      headers: new Headers(),
+      bodyText: JSON.stringify({
+        messages: [{ role: 'user', content: 'hello' }],
+      }),
+      storage: hybridStorage(),
+      cacheMode: 'hybrid',
+    })
+
+    now += 55 * 60_000
+    await manager.tick()
+    expect(fetchImpl).not.toHaveBeenCalled()
+    expect(manager.trackedCount()).toBe(0)
+    manager.stop()
+  })
 })