diff --git a/src/gateway/interactive-readline.test.ts b/src/gateway/interactive-readline.test.ts
new file mode 100644
index 0000000..e904f4f
--- /dev/null
+++ b/src/gateway/interactive-readline.test.ts
@@ -0,0 +1,93 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import {
+  createInteractiveReadline,
+  disposeInteractiveReadline,
+  __resetInteractiveReadlineForTests,
+  __getInteractiveReadlineInvocationCountForTests,
+} from "./interactive-readline.js";
+
+describe("interactive-readline factory", () => {
+  beforeEach(() => {
+    __resetInteractiveReadlineForTests();
+  });
+
+  afterEach(() => {
+    __resetInteractiveReadlineForTests();
+    delete process.env.LOG_LEVEL;
+  });
+
+  it("returns a fresh, independent interface per call", () => {
+    const rl1 = createInteractiveReadline();
+    const rl2 = createInteractiveReadline();
+
+    expect(rl1).not.toBe(rl2);
+    expect(__getInteractiveReadlineInvocationCountForTests()).toBe(2);
+  });
+
+  it("uses terminal:false (cooked mode) to avoid Windows raw-mode issues", () => {
+    // With terminal:false, readline does NOT attach a keypress listener
+    // to stdin. We can't directly read the option from the public API,
+    // but we can assert the side effect: no keypress listener growth.
+    const before = process.stdin.listenerCount("keypress");
+
+    const rl = createInteractiveReadline();
+
+    expect(process.stdin.listenerCount("keypress")).toBe(before);
+
+    disposeInteractiveReadline(rl);
+  });
+
+  it("disposeInteractiveReadline brings keypress listener count back down", () => {
+    const before = process.stdin.listenerCount("keypress");
+
+    const rl = createInteractiveReadline();
+    disposeInteractiveReadline(rl);
+
+    expect(process.stdin.listenerCount("keypress")).toBeLessThanOrEqual(before);
+  });
+
+  it("does not remove keypress listeners that existed before the prompt", () => {
+    const existingListener = () => undefined;
+    const leakedPromptListener = () => undefined;
+    process.stdin.on("keypress", existingListener);
+
+    try {
+      const rl = createInteractiveReadline();
+      process.stdin.on("keypress", leakedPromptListener);
+      disposeInteractiveReadline(rl);
+
+      expect(process.stdin.listeners("keypress")).toContain(existingListener);
+      expect(process.stdin.listeners("keypress")).not.toContain(
+        leakedPromptListener,
+      );
+    } finally {
+      process.stdin.removeListener("keypress", existingListener);
+      process.stdin.removeListener("keypress", leakedPromptListener);
+    }
+  });
+
+  it("disposeInteractiveReadline is safe to call on an already-closed interface", () => {
+    const rl = createInteractiveReadline();
+    rl.close();
+    expect(() => disposeInteractiveReadline(rl)).not.toThrow();
+  });
+
+  it("does not accumulate keypress listeners across create/dispose cycles", () => {
+    const before = process.stdin.listenerCount("keypress");
+
+    for (let i = 0; i < 5; i += 1) {
+      const rl = createInteractiveReadline();
+      disposeInteractiveReadline(rl);
+    }
+
+    expect(process.stdin.listenerCount("keypress")).toBeLessThanOrEqual(before);
+  });
+
+  it("does not throw when debug logging is enabled", () => {
+    process.env.LOG_LEVEL = "debug";
+    expect(() => {
+      const rl = createInteractiveReadline();
+      disposeInteractiveReadline(rl);
+    }).not.toThrow();
+  });
+});
diff --git a/src/gateway/interactive-readline.ts b/src/gateway/interactive-readline.ts
new file mode 100644
index 0000000..4595814
--- /dev/null
+++ b/src/gateway/interactive-readline.ts
@@ -0,0 +1,104 @@
+import readline from "node:readline/promises";
+import { stdin as input, stdout as output } from "node:process";
+import { appendStderrDevLog } from "../runtime/stderr-dev-log.js";
+
+/**
+ * Create a readline interface for one-shot prompts (tool approval, user
+ * clarification). Use `disposeInteractiveReadline` in the prompt's
+ * `finally` block to tear it down.
+ *
+ * Uses `terminal: false` deliberately. The previous `terminal: true`
+ * configuration put stdin into raw mode and attached a `keypress` listener,
+ * both of which are unreliable on Windows (ConHost / Windows Terminal):
+ *
+ *   1. `rl.close()` does not reliably remove the keypress listener, causing
+ *      listener accumulation across prompts. At the Nth prompt, each leaked
+ *      listener echoed the same keystroke, so pressing `y` once rendered as
+ *      N `y` characters.
+ *   2. Windows console focus / IME / mode-switch events leak through raw
+ *      mode as spurious empty line events, so `rl.question()` resolved with
+ *      `""` on its own — the "auto-advance" symptom where each prompt
+ *      disappeared without user input.
+ *
+ * `terminal: false` keeps stdin in cooked mode: the OS handles line editing
+ * and delivers complete lines only when the user presses Enter. No raw
+ * mode, no keypress listener, no spurious events.
+ *
+ * Trade-off: no in-line editing (backspace, arrow keys, history). For y/n
+ * approval prompts that's acceptable; users type one char + Enter.
+ */
+let promptInvocationCount = 0;
+const keypressListenersByReadline = new WeakMap<
+  readline.Interface,
+  Function[]
+>();
+
+function isDebugLogEnabled(): boolean {
+  const level = process.env.LOG_LEVEL;
+  return level === "debug" || level === "trace";
+}
+
+function logApprovalReadlineDebug(message: string): void {
+  if (!isDebugLogEnabled()) return;
+  void appendStderrDevLog(`[debug] event=approval-readline ${message}\n`);
+}
+
+export function createInteractiveReadline(): readline.Interface {
+  promptInvocationCount += 1;
+  const keypressListenersBeforeCreate = input.listeners("keypress");
+  logApprovalReadlineDebug(
+    `create invocation=${promptInvocationCount} terminal=false`,
+  );
+  const rl = readline.createInterface({
+    input,
+    output,
+    terminal: false,
+  });
+  keypressListenersByReadline.set(rl, keypressListenersBeforeCreate);
+  return rl;
+}
+
+export function disposeInteractiveReadline(rl: readline.Interface): void {
+  const keypressListenersBeforeCreate =
+    keypressListenersByReadline.get(rl) ?? [];
+  logApprovalReadlineDebug(
+    `dispose invocation=${promptInvocationCount} keypressListeners=${input.listenerCount("keypress")}`,
+  );
+
+  try {
+    rl.close();
+  } catch {
+    // Ignore: may already be closed.
+  }
+
+  // A console host can still leave a keypress listener behind. Remove only
+  // listeners added after this interface was created, never ones owned by
+  // the long-lived REPL readline interface.
+  const retainedListenerCounts = new Map<Function, number>();
+  for (const listener of keypressListenersBeforeCreate) {
+    retainedListenerCounts.set(
+      listener,
+      (retainedListenerCounts.get(listener) ?? 0) + 1,
+    );
+  }
+  for (const listener of input.listeners("keypress")) {
+    const retainedCount = retainedListenerCounts.get(listener) ?? 0;
+    if (retainedCount > 0) {
+      retainedListenerCounts.set(listener, retainedCount - 1);
+      continue;
+    }
+    input.removeListener("keypress", listener);
+  }
+
+  keypressListenersByReadline.delete(rl);
+}
+
+/** Test-only: reset invocation counter between unit tests. */
+export function __resetInteractiveReadlineForTests(): void {
+  promptInvocationCount = 0;
+}
+
+/** Test-only: observe invocation count. */
+export function __getInteractiveReadlineInvocationCountForTests(): number {
+  return promptInvocationCount;
+}
diff --git a/src/gateway/runtime.ts b/src/gateway/runtime.ts
index 8dc4281..d1e7b01 100644
--- a/src/gateway/runtime.ts
+++ b/src/gateway/runtime.ts
@@ -115,6 +115,10 @@ import {
   type StepCliInteractiveUi,
   type StepCliInteractiveUiFactory,
 } from "./interactive-ui.js";
+import {
+  createInteractiveReadline,
+  disposeInteractiveReadline,
+} from "./interactive-readline.js";
 import { createFilesystemAgentRunArtifactStore } from "./artifacts/run-artifact-store.js";
 import { FilesystemConversationTranscriptStore } from "./memory/filesystem-conversation-transcript-store.js";
 import { FilesystemFreshAttemptProgressStore } from "./memory/filesystem-fresh-attempt-progress-store.js";
@@ -4606,11 +4610,10 @@ async function promptForToolApproval(
       : "deny";
   }
 
-  const rl = readline.createInterface({
-    input,
-    output,
-    terminal: true,
-  });
+  // Per-call readline in cooked mode (terminal:false). See
+  // `interactive-readline.ts` for why `terminal:true` is unreliable on
+  // Windows (listener leak + spurious empty line events).
+  const rl = createInteractiveReadline();
 
   const preview =
     request.rawArgs.length > 240
@@ -4692,7 +4695,7 @@ async function promptForToolApproval(
       output.write(`Unrecognized decision: ${answer}. Type '?' for help.\n`);
     }
   } finally {
-    rl.close();
+    disposeInteractiveReadline(rl);
   }
 }
 
@@ -4708,11 +4711,8 @@ async function promptForUserClarification(
     };
   }
 
-  const rl = readline.createInterface({
-    input,
-    output,
-    terminal: true,
-  });
+  // Per-call readline in cooked mode. See `interactive-readline.ts`.
+  const rl = createInteractiveReadline();
 
   const options = Array.isArray(request.options) ? request.options : [];
   const helpLines = buildClarificationHelpLines(request);
@@ -4779,7 +4779,7 @@ async function promptForUserClarification(
       output.write(`${parsed.message}\n`);
     }
   } finally {
-    rl.close();
+    disposeInteractiveReadline(rl);
   }
 }
 
diff --git a/vitest.config.ts b/vitest.config.ts
index 2ea1608..8bf09f1 100644
--- a/vitest.config.ts
+++ b/vitest.config.ts
@@ -76,6 +76,7 @@ export default defineConfig({
         "src/bootstrap/config/defaults.ts",
         "src/commands/option-parsers.ts",
         "src/gateway/storage/layout.ts",
+        "src/gateway/interactive-readline.ts",
         "src/gateway/verifier.ts",
         "src/runtime/runtime-config.ts",
         "src/runtime/runtime-utils.ts",