diff --git a/packages/core/src/session/model-request.ts b/packages/core/src/session/model-request.ts
index f744983afec8..359ff4624593 100644
--- a/packages/core/src/session/model-request.ts
+++ b/packages/core/src/session/model-request.ts
@@ -197,7 +197,9 @@ export const layer = Layer.effect(
         .filter((part) => part.length > 0)
         .map(SystemPart.make)
       const history = toLLMMessages(input.context.messages, resolved.ref, providerMetadataKey)
-      const messages = stepLimitReached ? [...history, Message.assistant(MAX_STEPS_PROMPT)] : history
+      // Anthropic rejects synthetic assistant prefills, so append the final-step
+      // guardrail as a synthetic user message.
+      const messages = stepLimitReached ? [...history, Message.user(MAX_STEPS_PROMPT)] : history
       const registry = new Map(tools.definitions.map((tool) => [tool.name, tool]))
       // The definition objects we hand to hooks, mapped back to their tools. Hooks rename a
       // tool by moving its definition to a new key; recognizing the object recovers the tool.
diff --git a/packages/core/test/session-runner.test.ts b/packages/core/test/session-runner.test.ts
index e55f1d8e2788..9ac1f7d1517a 100644
--- a/packages/core/test/session-runner.test.ts
+++ b/packages/core/test/session-runner.test.ts
@@ -43,6 +43,7 @@ import { SessionExecution } from "@opencode-ai/core/session/execution"
 import { SessionRunCoordinator } from "@opencode-ai/core/session/run-coordinator"
 import { SessionRunner } from "@opencode-ai/core/session/runner/index"
 import * as SessionRunnerLLM from "@opencode-ai/core/session/runner/llm"
+import { MAX_STEPS_PROMPT } from "@opencode-ai/core/session/runner/max-steps"
 import { SessionRunnerModel } from "@opencode-ai/core/session/runner/model"
 import { PromptCacheDiagnostics } from "@opencode-ai/core/session/prompt-cache-diagnostics"
 import { SessionUsage } from "@opencode-ai/core/session/usage"
@@ -4031,8 +4032,8 @@ describe("SessionRunnerLLM", () => {
       // Protocols with native "none" keep these definitions for prompt caching.
       expect(requests[1]?.tools.map((tool) => tool.name)).toContain("echo")
       expect(requests[1]?.messages.at(-1)).toMatchObject({
-        role: "assistant",
-        content: [{ type: "text", text: expect.stringContaining("MAXIMUM STEPS REACHED") }],
+        role: "user",
+        content: [{ type: "text", text: MAX_STEPS_PROMPT }],
       })
       expect(executions).toEqual(["done"])
       expect(yield* session.context(sessionID)).toMatchObject([
@@ -4583,16 +4584,13 @@ describe("SessionRunnerLLM", () => {
       expect(requests[0]?.tools.map((tool) => tool.name)).toContain("echo")
       expect(requests[1]?.toolChoice).toBeUndefined()
       expect(requests[1]?.tools.map((tool) => tool.name)).toContain("echo")
-      expect(requests[1]?.messages.at(-1)).not.toMatchObject({
-        role: "assistant",
-        content: [{ type: "text", text: expect.stringContaining("MAXIMUM STEPS REACHED") }],
-      })
+      expect(JSON.stringify(requests[1]?.messages)).not.toContain("MAXIMUM STEPS REACHED")
       expect(requests[2]?.toolChoice).toMatchObject({ type: "none" })
       // The final step keeps tool definitions to preserve provider prompt caching.
       expect(requests[2]?.tools.map((tool) => tool.name)).toContain("echo")
       expect(requests[2]?.messages.at(-1)).toMatchObject({
-        role: "assistant",
-        content: [{ type: "text", text: expect.stringContaining("MAXIMUM STEPS REACHED") }],
+        role: "user",
+        content: [{ type: "text", text: MAX_STEPS_PROMPT }],
       })
       expect(executions).toEqual(["recovered"])
       const eventTypes = yield* recordedEventTypes(sessionID)
@@ -4946,6 +4944,10 @@ describe("SessionRunnerLLM", () => {
       expect(requests).toHaveLength(2)
       expect(requests[0]?.toolChoice).toBeUndefined()
       expect(requests[1]?.toolChoice).toMatchObject({ type: "none" })
+      expect(requests[1]?.messages.at(-1)).toMatchObject({
+        role: "user",
+        content: [{ type: "text", text: MAX_STEPS_PROMPT }],
+      })
       expect((yield* recordedEventTypes(sessionID)).filter((type) => type === "session.tool.failed.2")).toHaveLength(2)
     }),
   )
diff --git a/packages/web/src/content/docs/agents.mdx b/packages/web/src/content/docs/agents.mdx
index 0c0a5e228465..62c8f166412f 100644
--- a/packages/web/src/content/docs/agents.mdx
+++ b/packages/web/src/content/docs/agents.mdx
@@ -306,7 +306,7 @@ If this is not set, the agent will continue to iterate until the model chooses t
 }
 ```
 
-When the limit is reached, the agent receives a special system prompt instructing it to respond with a summarization of its work and recommended remaining tasks.
+When the limit is reached, the agent receives a special user message instructing it to respond with a summarization of its work and recommended remaining tasks.
 
 :::caution
 The legacy `maxSteps` field is deprecated. Use `steps` instead.