diff --git a/src/index.test.ts b/src/index.test.ts
index 4922d07..bcf149b 100644
--- a/src/index.test.ts
+++ b/src/index.test.ts
@@ -29,6 +29,7 @@ import {
   shouldInjectClaudeTools,
   stripAssistantPrefillForClaude,
   stripSystemCacheControl,
+  stripMessageCacheControlPreservingTail,
 } from "./index.js";
 import { createSseProcessor, parseSseEvent, buildSseEvent } from "./stream.js";
 
@@ -171,12 +172,59 @@ describe("Claude assistant prefill stripping", () => {
     ]);
   });
 
-  it("keeps non-synthetic assistant messages intact", () => {
-    const input = [
+  it("appends a user turn after a real assistant tail so the request ends on a user message", () => {
+    const out = stripAssistantPrefillForClaude([
+      { role: "user", content: [{ type: "text", text: "hello" }] },
+      { role: "assistant", content: "Real assistant content" },
+    ]);
+    assert.deepEqual(out, [
+      { role: "user", content: [{ type: "text", text: "hello" }] },
+      { role: "assistant", content: "Real assistant content" },
+      { role: "user", content: "Continue." },
+    ]);
+  });
+
+  it("drops the nudge then appends a user turn when it trails a real assistant turn", () => {
+    const out = stripAssistantPrefillForClaude([
       { role: "user", content: [{ type: "text", text: "hello" }] },
       { role: "assistant", content: "Real assistant content" },
+      { role: "assistant", content: "Continue with your tasks." },
+    ]);
+    assert.deepEqual(out, [
+      { role: "user", content: [{ type: "text", text: "hello" }] },
+      { role: "assistant", content: "Real assistant content" },
+      { role: "user", content: "Continue." },
+    ]);
+  });
+
+  it("ends on a user turn after opencode's max-steps assistant prefill", () => {
+    const maxSteps = "CRITICAL - MAXIMUM STEPS REACHED\n\nTools are disabled until next user input. Respond with text only.";
+    for (const content of [maxSteps, [{ type: "text", text: maxSteps }]]) {
+      const out = stripAssistantPrefillForClaude([
+        { role: "user", content: [{ type: "text", text: "hello" }] },
+        { role: "assistant", content },
+      ]);
+      assert.deepEqual(out, [
+        { role: "user", content: [{ type: "text", text: "hello" }] },
+        { role: "assistant", content },
+        { role: "user", content: "Continue." },
+      ]);
+    }
+  });
+
+  it("leaves a user-tailed conversation unchanged", () => {
+    const input = [
+      { role: "assistant", content: "earlier answer" },
+      { role: "user", content: [{ type: "text", text: "hello" }] },
     ];
-    assert.deepEqual(stripAssistantPrefillForClaude(input), input);
+    const out = stripAssistantPrefillForClaude(input);
+    // Assert against a fresh literal (not the same reference) so the test would
+    // fail if the function mutated the input or appended a synthetic turn.
+    assert.deepEqual(out, [
+      { role: "assistant", content: "earlier answer" },
+      { role: "user", content: [{ type: "text", text: "hello" }] },
+    ]);
+    assert.equal(out.length, 2);
   });
 });
 
@@ -192,6 +240,59 @@ describe("system cache control", () => {
   });
 });
 
+describe("message cache control (tail breakpoint)", () => {
+  it("preserves the tail message's text cache_control but strips earlier ones", () => {
+    const messages = [
+      {
+        role: "user",
+        content: [{ type: "text", text: "old", cache_control: { type: "ephemeral" } }],
+      },
+      {
+        role: "assistant",
+        content: [{ type: "text", text: "mid", cache_control: { type: "ephemeral" } }],
+      },
+      {
+        role: "user",
+        content: [{ type: "text", text: "tail", cache_control: { type: "ephemeral" } }],
+      },
+    ];
+    stripMessageCacheControlPreservingTail(messages);
+    // Earlier messages: cache_control stripped.
+    assert.equal("cache_control" in messages[0].content[0], false);
+    assert.equal("cache_control" in messages[1].content[0], false);
+    // Tail message: cache_control preserved (the surviving breakpoint).
+    assert.deepEqual(messages[2].content[0].cache_control, { type: "ephemeral" });
+  });
+
+  it("preserves a tail breakpoint even when the tail block is text (text-tailed request)", () => {
+    const messages = [
+      { role: "user", content: [{ type: "text", text: "q", cache_control: { type: "ephemeral" } }] },
+    ];
+    stripMessageCacheControlPreservingTail(messages);
+    assert.deepEqual(messages[0].content[0].cache_control, { type: "ephemeral" });
+  });
+
+  it("leaves non-text blocks and messages without content untouched", () => {
+    const messages: Array<{ role: string; content?: unknown }> = [
+      {
+        role: "user",
+        content: [
+          { type: "tool_result", tool_use_id: "t1", content: "r", cache_control: { type: "ephemeral" } },
+          { type: "text", text: "x", cache_control: { type: "ephemeral" } },
+        ],
+      },
+      { role: "assistant", content: undefined },
+      { role: "user", content: [{ type: "text", text: "tail" }] },
+    ];
+    stripMessageCacheControlPreservingTail(messages);
+    const first = messages[0].content as Array<Record<string, unknown>>;
+    // Non-text block: never stripped.
+    assert.deepEqual(first[0].cache_control, { type: "ephemeral" });
+    // Earlier text block: stripped.
+    assert.equal("cache_control" in first[1], false);
+  });
+});
+
 describe("tool schema selection", () => {
   it("uses Claude schemas for native Anthropic requests", () => {
     assert.equal(shouldUseClaudeToolSchemas({
diff --git a/src/index.ts b/src/index.ts
index d9fcaac..1d4ad15 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -226,6 +226,37 @@ export function stripSystemCacheControl(
   });
 }
 
+/**
+ * Strip OpenCode's cache_control from message TEXT blocks, but PRESERVE the
+ * breakpoint on the tail (last) message.
+ *
+ * OpenCode's automatic cache policy marks the tail message's final content part
+ * with cache_control (the prompt-prefix cache breakpoint). We must strip the
+ * client-set cache_control on the Claude Code subscription endpoint — EXCEPT the
+ * single tail breakpoint. Without it, a text-tailed request (e.g. a plain user
+ * turn, or a compaction/summary request whose last message is text) has no
+ * surviving breakpoint and Anthropic never reads the warm prefix (cache_read 0);
+ * only tool-block-tailed requests cached, because non-text blocks are never
+ * stripped here. Keeping the one tail breakpoint restores caching for every
+ * request shape without ADDING breakpoints (stays within Anthropic's 4-breakpoint
+ * cap — OpenCode already placed and capped it). Mutates in place.
+ */
+export function stripMessageCacheControlPreservingTail(
+  messages: Array<{ content?: unknown }>,
+): void {
+  const tailIndex = messages.length - 1;
+  for (let index = 0; index < messages.length; index++) {
+    if (index === tailIndex) continue; // preserve the tail message's breakpoint
+    const content = messages[index]?.content;
+    if (!Array.isArray(content)) continue;
+    for (const block of content) {
+      if (block && block.type === "text" && "cache_control" in block) {
+        delete block.cache_control;
+      }
+    }
+  }
+}
+
 export function shouldInjectClaudeTools(input: {
   model?: string;
   requestUrl?: string;
@@ -487,15 +518,44 @@ function maybeUnquoteText(text: string): string {
   return text;
 }
 
+/** opencode's synthetic continuation nudge — a content-free assistant turn, safe to drop. */
+const OPENCODE_CONTINUATION_NUDGE = "Continue with your tasks.";
+/**
+ * Appended after any remaining assistant tail so the request ends on a user turn.
+ * The Claude subscription endpoint rejects assistant-message prefill
+ * ("does not support assistant message prefill. The conversation must end with a user message").
+ */
+const ASSISTANT_TAIL_USER_CONTINUATION = "Continue.";
+
+// The Claude subscription endpoint (unlike the raw Anthropic API) does NOT support
+// assistant-message prefill: the messages array must end with a user turn. Drop
+// opencode's content-free continuation nudge, then guarantee a user tail for ANY
+// other assistant-tailed request (e.g. a resumed session whose last saved turn was
+// the assistant's) by appending a minimal user turn — preserving the assistant
+// content instead of discarding it. Previously only the exact nudge string was
+// handled, so every other assistant tail hit a 400.
 export function stripAssistantPrefillForClaude(
   messages: Array<{ role?: string; content?: unknown }>,
 ): Array<{ role?: string; content?: unknown }> {
   if (messages.length === 0) return messages;
-  const last = messages[messages.length - 1];
-  if (last?.role !== "assistant") return messages;
-  if (typeof last.content !== "string") return messages;
-  if (last.content.trim() !== "Continue with your tasks.") return messages;
-  return messages.slice(0, -1);
+  let result = messages;
+  const last = result[result.length - 1];
+  if (
+    last?.role === "assistant" &&
+    typeof last.content === "string" &&
+    last.content.trim() === OPENCODE_CONTINUATION_NUDGE
+  ) {
+    result = result.slice(0, -1);
+  }
+  const tail = result[result.length - 1];
+  if (tail?.role === "assistant") {
+    // Assumes the assistant tail is a final/text turn. A dangling tool_use tail
+    // (a turn interrupted between the tool call and its result) would make this
+    // appended user turn violate Anthropic's tool_use/tool_result pairing — but
+    // that corrupted-resume shape already fails the endpoint's prefill rule too.
+    result = [...result, { role: "user", content: ASSISTANT_TAIL_USER_CONTINUATION }];
+  }
+  return result;
 }
 
 function normalizeSystemBlocks(
@@ -849,12 +909,15 @@ const OpenCodeClaudeBridge = async ({ client }: { client: PluginClient }) => {
                 // - Translate tool_use input arguments (camelCase → snake_case)
                 // - Clean up text blocks
                 if (parsed.messages && Array.isArray(parsed.messages)) {
+                  // Preserve the tail cache_control breakpoint so text-tailed
+                  // requests still cache on the subscription route (earlier text
+                  // blocks are still stripped). See the helper for the rationale.
+                  stripMessageCacheControlPreservingTail(parsed.messages);
                   for (const msg of parsed.messages) {
                     if (!Array.isArray(msg.content)) continue;
                     for (const block of msg.content) {
                       if (block.type === "text" && typeof block.text === "string") {
                         block.text = maybeUnquoteText(block.text);
-                        delete block.cache_control;
                       }
                       if (block.type === "tool_use" && block.name) {
                         block.name = mapOutboundToolName(block.name);