diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9358cfe79a3..f48245320ec 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,7 @@ Docs: https://docs.openclaw.ai
 - CLI/directory: report unsupported directory operations for installed channel plugins instead of prompting to reinstall the plugin when it lacks a directory adapter. Fixes #75770. Thanks @lawong888.
 - Web search: keep public provider requests on the strict SSRF guard and reserve private-network access for explicit self-hosted SearXNG/Firecrawl endpoints. Fixes #74357 and supersedes #74360. Thanks @fede-kamel.
 - Web search/Firecrawl: allow self-hosted private/internal Firecrawl `baseUrl` endpoints, including HTTP for private targets, while keeping hosted Firecrawl on the strict official endpoint. Fixes #63877 and supersedes #59666, #63941, and #74013. Thanks @jhthompson12, @jzakirov, @Mlightsnow, and @shad0wca7.
+- Providers/OpenRouter: strip trailing assistant prefill turns from verified OpenRouter Anthropic model requests when reasoning is enabled, so Claude 4.6 routes no longer fail with Anthropic's prefill rejection through the OpenAI-compatible adapter. Fixes #75395. Thanks @sbmilburn.
 - Feishu: preserve Feishu/Lark HTTP error bodies for message sends, media sends, and chat member lookups, so HTTP 400 failures include vendor code, message, log id, and troubleshooter details. Fixes #73860. Thanks @desksk.
 - Agents/transcripts: avoid reopening large Pi transcript files through the synchronous session manager for maintenance rewrites, persisted tool-result truncation, manual compaction boundary hardening, and queued compaction rotation. Thanks @mariozechner.
 - Web search/Exa: accept `plugins.entries.exa.config.webSearch.baseUrl`, normalize it to the Exa `/search` endpoint, and partition cached results by endpoint. Fixes #54928 and supersedes #54939. Thanks @mrpl327 and @lyfuci.
diff --git a/docs/providers/openrouter.md b/docs/providers/openrouter.md
index 9ef2957aad4..d8cc51bda28 100644
--- a/docs/providers/openrouter.md
+++ b/docs/providers/openrouter.md
@@ -159,6 +159,13 @@ does **not** inject those OpenRouter-specific headers or Anthropic cache markers
     better prompt-cache reuse on system/developer prompt blocks.
   </Accordion>
 
+  <Accordion title="Anthropic reasoning prefill">
+    On verified OpenRouter routes, Anthropic model refs with reasoning enabled
+    drop trailing assistant prefill turns before the request reaches OpenRouter,
+    matching Anthropic's requirement that reasoning conversations end with a user
+    turn.
+  </Accordion>
+
   <Accordion title="Thinking / reasoning injection">
     On supported non-`auto` routes, OpenClaw maps the selected thinking level to
     OpenRouter proxy reasoning payloads. Unsupported model hints and
diff --git a/docs/reference/transcript-hygiene.md b/docs/reference/transcript-hygiene.md
index c53ee188cdb..fa79ca86123 100644
--- a/docs/reference/transcript-hygiene.md
+++ b/docs/reference/transcript-hygiene.md
@@ -177,6 +177,12 @@ inter-session user turns that only have provenance metadata.
 
 - Thought signature cleanup: strip non-base64 `thought_signature` values (keep base64).
 
+**OpenRouter Anthropic**
+
+- Trailing assistant prefill turns are stripped from verified OpenRouter
+  OpenAI-compatible Anthropic model payloads when reasoning is enabled, matching
+  direct Anthropic and Cloudflare Anthropic replay behavior.
+
 **Everything else**
 
 - Image sanitization only.
diff --git a/extensions/openrouter/index.test.ts b/extensions/openrouter/index.test.ts
index 66d77857d1e..2bea1091f5f 100644
--- a/extensions/openrouter/index.test.ts
+++ b/extensions/openrouter/index.test.ts
@@ -218,4 +218,111 @@ describe("openrouter provider hooks", () => {
     expect(capturedPayload).toEqual({});
     expect(baseStreamFn).toHaveBeenCalledOnce();
   });
+
+  it("strips OpenRouter-routed Anthropic assistant prefill when reasoning is enabled", async () => {
+    const provider = await registerSingleProviderPlugin(openrouterPlugin);
+    let capturedPayload: Record<string, unknown> | undefined;
+    const baseStreamFn = vi.fn(
+      (
+        ...args: Parameters<import("@mariozechner/pi-agent-core").StreamFn>
+      ): ReturnType<import("@mariozechner/pi-agent-core").StreamFn> => {
+        const payload = {
+          messages: [
+            { role: "user", content: "Return JSON." },
+            { role: "assistant", content: "{" },
+          ],
+        };
+        void args[2]?.onPayload?.(payload, args[0]);
+        capturedPayload = payload;
+        return { async *[Symbol.asyncIterator]() {} } as never;
+      },
+    );
+
+    const wrapped = provider.wrapStreamFn?.({
+      provider: "openrouter",
+      modelId: "anthropic/claude-opus-4.6",
+      streamFn: baseStreamFn,
+      thinkingLevel: "high",
+    } as never);
+
+    void wrapped?.(
+      {
+        provider: "openrouter",
+        api: "openai-completions",
+        id: "anthropic/claude-opus-4.6",
+        baseUrl: "https://openrouter.ai/api/v1",
+        compat: {},
+      } as never,
+      { messages: [] } as never,
+      {},
+    );
+
+    expect(capturedPayload).toMatchObject({
+      messages: [{ role: "user", content: "Return JSON." }],
+      reasoning: { effort: "high" },
+    });
+    expect(baseStreamFn).toHaveBeenCalledOnce();
+  });
+
+  it("keeps OpenRouter Anthropic prefill when reasoning is disabled or the route is custom", async () => {
+    const provider = await registerSingleProviderPlugin(openrouterPlugin);
+    const payloads: Array<Record<string, unknown>> = [];
+    const baseStreamFn = vi.fn(
+      (
+        ...args: Parameters<import("@mariozechner/pi-agent-core").StreamFn>
+      ): ReturnType<import("@mariozechner/pi-agent-core").StreamFn> => {
+        const payload = {
+          messages: [
+            { role: "user", content: "Return JSON." },
+            { role: "assistant", content: "{" },
+          ],
+        };
+        void args[2]?.onPayload?.(payload, args[0]);
+        payloads.push(payload);
+        return { async *[Symbol.asyncIterator]() {} } as never;
+      },
+    );
+
+    const disabled = provider.wrapStreamFn?.({
+      provider: "openrouter",
+      modelId: "anthropic/claude-opus-4.6",
+      streamFn: baseStreamFn,
+      thinkingLevel: "off",
+    } as never);
+    void disabled?.(
+      {
+        provider: "openrouter",
+        api: "openai-completions",
+        id: "anthropic/claude-opus-4.6",
+        baseUrl: "https://openrouter.ai/api/v1",
+        compat: {},
+      } as never,
+      { messages: [] } as never,
+      {},
+    );
+
+    const customRoute = provider.wrapStreamFn?.({
+      provider: "openrouter",
+      modelId: "anthropic/claude-opus-4.6",
+      streamFn: baseStreamFn,
+      thinkingLevel: "high",
+    } as never);
+    void customRoute?.(
+      {
+        provider: "openrouter",
+        api: "openai-completions",
+        id: "anthropic/claude-opus-4.6",
+        baseUrl: "https://proxy.example.com/v1",
+        compat: {},
+      } as never,
+      { messages: [] } as never,
+      {},
+    );
+
+    expect(payloads).toHaveLength(2);
+    expect(payloads[0]?.messages).toHaveLength(2);
+    expect(payloads[0]).not.toHaveProperty("reasoning");
+    expect(payloads[1]?.messages).toHaveLength(2);
+    expect(payloads[1]).toMatchObject({ reasoning: { effort: "high" } });
+  });
 });
diff --git a/extensions/openrouter/stream.ts b/extensions/openrouter/stream.ts
index 37573c455cb..48fa6d3c379 100644
--- a/extensions/openrouter/stream.ts
+++ b/extensions/openrouter/stream.ts
@@ -1,7 +1,65 @@
 import type { StreamFn } from "@mariozechner/pi-agent-core";
 import type { ProviderWrapStreamFnContext } from "openclaw/plugin-sdk/plugin-entry";
 import { OPENROUTER_THINKING_STREAM_HOOKS } from "openclaw/plugin-sdk/provider-stream-family";
-import { isOpenRouterProxyReasoningUnsupportedModel } from "./provider-catalog.js";
+import {
+  createPayloadPatchStreamWrapper,
+  stripTrailingAssistantPrefillMessages,
+} from "openclaw/plugin-sdk/provider-stream-shared";
+import { createSubsystemLogger } from "openclaw/plugin-sdk/runtime-env";
+import {
+  isOpenRouterProxyReasoningUnsupportedModel,
+  normalizeOpenRouterBaseUrl,
+  OPENROUTER_BASE_URL,
+} from "./provider-catalog.js";
+
+const log = createSubsystemLogger("openrouter-stream");
+
+function readString(value: unknown): string | undefined {
+  return typeof value === "string" ? value.trim() : undefined;
+}
+
+function isOpenRouterAnthropicModelId(modelId: unknown): boolean {
+  const normalized = readString(modelId)?.toLowerCase();
+  return (
+    normalized?.startsWith("anthropic/") === true ||
+    normalized?.startsWith("openrouter/anthropic/") === true
+  );
+}
+
+function isVerifiedOpenRouterRoute(model: Parameters<StreamFn>[0]): boolean {
+  const provider = readString(model.provider)?.toLowerCase();
+  const baseUrl = readString(model.baseUrl);
+  if (baseUrl) {
+    return normalizeOpenRouterBaseUrl(baseUrl) === OPENROUTER_BASE_URL;
+  }
+  return provider === "openrouter";
+}
+
+function shouldPatchAnthropicOpenRouterPayload(model: Parameters<StreamFn>[0]): boolean {
+  const api = readString(model.api);
+  return (
+    (api === undefined || api === "openai-completions") &&
+    isOpenRouterAnthropicModelId(model.id) &&
+    isVerifiedOpenRouterRoute(model)
+  );
+}
+
+function isEnabledReasoningValue(value: unknown): boolean {
+  if (value === undefined || value === null || value === false) {
+    return false;
+  }
+  if (typeof value === "string") {
+    const normalized = value.trim().toLowerCase();
+    return normalized !== "" && normalized !== "off" && normalized !== "none";
+  }
+  return true;
+}
+
+function isOpenRouterReasoningPayloadEnabled(payload: Record<string, unknown>): boolean {
+  return (
+    isEnabledReasoningValue(payload.reasoning) || isEnabledReasoningValue(payload.reasoning_effort)
+  );
+}
 
 function injectOpenRouterRouting(
   baseStreamFn: StreamFn | undefined,
@@ -28,6 +86,26 @@ function injectOpenRouterRouting(
     );
 }
 
+function createOpenRouterAnthropicPrefillWrapper(baseStreamFn: StreamFn | undefined): StreamFn {
+  return createPayloadPatchStreamWrapper(
+    baseStreamFn,
+    ({ payload }) => {
+      if (!isOpenRouterReasoningPayloadEnabled(payload)) {
+        return;
+      }
+      const stripped = stripTrailingAssistantPrefillMessages(payload);
+      if (stripped > 0) {
+        log.warn(
+          `removed ${stripped} trailing assistant prefill message${stripped === 1 ? "" : "s"} because OpenRouter-routed Anthropic reasoning requires conversations to end with a user turn`,
+        );
+      }
+    },
+    {
+      shouldPatch: ({ model }) => shouldPatchAnthropicOpenRouterPayload(model),
+    },
+  );
+}
+
 export function wrapOpenRouterProviderStream(
   ctx: ProviderWrapStreamFnContext,
 ): StreamFn | null | undefined {
@@ -40,15 +118,22 @@ export function wrapOpenRouterProviderStream(
     : ctx.streamFn;
   const wrapStreamFn = OPENROUTER_THINKING_STREAM_HOOKS.wrapStreamFn ?? undefined;
   if (!wrapStreamFn) {
-    return routedStreamFn;
+    return createOpenRouterAnthropicPrefillWrapper(routedStreamFn);
   }
-  return (
+  const wrappedStreamFn =
     wrapStreamFn({
       ...ctx,
       streamFn: routedStreamFn,
       thinkingLevel: isOpenRouterProxyReasoningUnsupportedModel(ctx.modelId)
         ? undefined
         : ctx.thinkingLevel,
-    }) ?? undefined
-  );
+    }) ?? undefined;
+  return createOpenRouterAnthropicPrefillWrapper(wrappedStreamFn);
 }
+
+export const __testing = {
+  isOpenRouterAnthropicModelId,
+  isOpenRouterReasoningPayloadEnabled,
+  isVerifiedOpenRouterRoute,
+  shouldPatchAnthropicOpenRouterPayload,
+};
diff --git a/src/plugin-sdk/provider-stream-shared.test.ts b/src/plugin-sdk/provider-stream-shared.test.ts
index 97f035e82c8..9a68ce9d6e3 100644
--- a/src/plugin-sdk/provider-stream-shared.test.ts
+++ b/src/plugin-sdk/provider-stream-shared.test.ts
@@ -10,6 +10,7 @@ import {
   decodeHtmlEntitiesInObject,
   hasCopilotVisionInput,
   isOpenAICompatibleThinkingEnabled,
+  stripTrailingAssistantPrefillMessages,
   stripTrailingAnthropicAssistantPrefillWhenThinking,
 } from "./provider-stream-shared.js";
 
@@ -301,6 +302,18 @@ describe("createPayloadPatchStreamWrapper", () => {
 });
 
 describe("stripTrailingAnthropicAssistantPrefillWhenThinking", () => {
+  it("exposes unconditional assistant prefill stripping for proxy reasoning wrappers", () => {
+    const payload = {
+      messages: [
+        { role: "user", content: "Return JSON." },
+        { role: "assistant", content: "{" },
+      ],
+    };
+
+    expect(stripTrailingAssistantPrefillMessages(payload)).toBe(1);
+    expect(payload.messages).toEqual([{ role: "user", content: "Return JSON." }]);
+  });
+
   it("removes trailing assistant text turns when Anthropic thinking is enabled", () => {
     const payload = {
       thinking: { type: "enabled", budget_tokens: 1024 },
diff --git a/src/plugin-sdk/provider-stream-shared.ts b/src/plugin-sdk/provider-stream-shared.ts
index 5250c7cc747..a1ee1428bb7 100644
--- a/src/plugin-sdk/provider-stream-shared.ts
+++ b/src/plugin-sdk/provider-stream-shared.ts
@@ -179,10 +179,8 @@ function assistantMessageHasAnthropicToolUse(message: Record<string, unknown>):
   );
 }
 
-export function stripTrailingAnthropicAssistantPrefillWhenThinking(
-  payload: Record<string, unknown>,
-): number {
-  if (!isAnthropicThinkingEnabled(payload) || !Array.isArray(payload.messages)) {
+export function stripTrailingAssistantPrefillMessages(payload: Record<string, unknown>): number {
+  if (!Array.isArray(payload.messages)) {
     return 0;
   }
 
@@ -204,6 +202,15 @@ export function stripTrailingAnthropicAssistantPrefillWhenThinking(
   return stripped;
 }
 
+export function stripTrailingAnthropicAssistantPrefillWhenThinking(
+  payload: Record<string, unknown>,
+): number {
+  if (!isAnthropicThinkingEnabled(payload)) {
+    return 0;
+  }
+  return stripTrailingAssistantPrefillMessages(payload);
+}
+
 export function createAnthropicThinkingPrefillPayloadWrapper(
   baseStreamFn: StreamFn | undefined,
   onStripped?: (stripped: number) => void,