diff --git a/clis/chatwise/ask.js b/clis/chatwise/ask.js
index 7178697ef..71b2ecdab 100644
--- a/clis/chatwise/ask.js
+++ b/clis/chatwise/ask.js
@@ -1,5 +1,11 @@
 import { cli, Strategy } from '@jackwener/opencli/registry';
-import { selectorError } from '@jackwener/opencli/errors';
+import { selectorError, TimeoutError } from '@jackwener/opencli/errors';
+import {
+    buildChatwiseInjectTextJs,
+    buildChatwiseMessageCountJs,
+    buildChatwiseResponseAfterJs,
+    normalizeTimeout,
+} from './utils.js';
 export const askCommand = cli({
     site: 'chatwise',
     name: 'ask',
@@ -15,34 +21,11 @@ export const askCommand = cli({
     columns: ['Role', 'Text'],
     func: async (page, kwargs) => {
         const text = kwargs.text;
-        const timeout = parseInt(kwargs.timeout, 10) || 30;
+        const timeout = normalizeTimeout(kwargs.timeout);
         // Snapshot content length
-        const beforeLen = await page.evaluate(`
-      (function() {
-        const msgs = document.querySelectorAll('[data-message-id], [class*="message"], [class*="bubble"]');
-        return msgs.length;
-      })()
-    `);
+        const beforeLen = await page.evaluate(buildChatwiseMessageCountJs());
         // Send message
-        const injected = await page.evaluate(`
-      (function(text) {
-        let composer = document.querySelector('textarea');
-        if (!composer) {
-          const editables = Array.from(document.querySelectorAll('[contenteditable="true"]'));
-          composer = editables.length > 0 ? editables[editables.length - 1] : null;
-        }
-        if (!composer) return false;
-        composer.focus();
-        if (composer.tagName === 'TEXTAREA') {
-          const setter = Object.getOwnPropertyDescriptor(window.HTMLTextAreaElement.prototype, 'value').set;
-          setter.call(composer, text);
-          composer.dispatchEvent(new Event('input', { bubbles: true }));
-        } else {
-          document.execCommand('insertText', false, text);
-        }
-        return true;
-      })(${JSON.stringify(text)})
-    `);
+        const injected = await page.evaluate(buildChatwiseInjectTextJs(text));
         if (!injected)
             throw selectorError('ChatWise input element');
         await page.wait(0.5);
@@ -53,25 +36,15 @@ export const askCommand = cli({
         let response = '';
         for (let i = 0; i < maxPolls; i++) {
             await page.wait(pollInterval);
-            const result = await page.evaluate(`
-        (function(prevLen) {
-          const msgs = document.querySelectorAll('[data-message-id], [class*="message"], [class*="bubble"]');
-          if (msgs.length <= prevLen) return null;
-          const last = msgs[msgs.length - 1];
-          const text = last.innerText || last.textContent;
-          return text ? text.trim() : null;
-        })(${beforeLen})
-      `);
+            const result = await page.evaluate(buildChatwiseResponseAfterJs(beforeLen, text));
             if (result) {
-                response = result;
-                break;
+                const next = String(result).trim();
+                if (next === response) break;
+                response = next;
             }
         }
         if (!response) {
-            return [
-                { Role: 'User', Text: text },
-                { Role: 'System', Text: `No response within ${timeout}s.` },
-            ];
+            throw new TimeoutError('ChatWise response', timeout, 'Confirm ChatWise is done generating, then retry with a larger --timeout if needed.');
         }
         return [
             { Role: 'User', Text: text },
diff --git a/clis/chatwise/composer.test.js b/clis/chatwise/composer.test.js
new file mode 100644
index 000000000..f0a92270b
--- /dev/null
+++ b/clis/chatwise/composer.test.js
@@ -0,0 +1,186 @@
+import { JSDOM } from 'jsdom';
+import { describe, expect, it, vi } from 'vitest';
+import { ArgumentError, TimeoutError } from '@jackwener/opencli/errors';
+import {
+    buildChatwiseInjectTextJs,
+    buildChatwiseMessageCountJs,
+    buildChatwiseResponseAfterJs,
+    normalizeTimeout,
+    scoreChatwiseComposerCandidate,
+    selectBestChatwiseComposer,
+} from './utils.js';
+import { askCommand } from './ask.js';
+
+function candidate(overrides = {}) {
+    return {
+        index: 0,
+        hidden: false,
+        role: 'textbox',
+        classes: 'cm-content cm-lineWrapping',
+        editorClasses: 'cm-editor',
+        ariaLabel: '',
+        placeholder: '',
+        text: '',
+        rect: { y: 0, h: 30 },
+        ...overrides,
+    };
+}
+
+function runBrowserScript(html, script) {
+    const dom = new JSDOM(html, { url: 'app://chatwise.local/', runScripts: 'outside-only' });
+    Object.defineProperty(dom.window.HTMLElement.prototype, 'offsetWidth', { configurable: true, get: () => 400 });
+    Object.defineProperty(dom.window.HTMLElement.prototype, 'offsetHeight', { configurable: true, get: () => 32 });
+    dom.window.HTMLElement.prototype.getClientRects = () => [{ length: 1 }];
+    dom.window.document.execCommand = () => false;
+    return { dom, result: dom.window.eval(script) };
+}
+
+function makePage(evaluateResults = []) {
+    const evaluate = vi.fn();
+    for (const result of evaluateResults) evaluate.mockResolvedValueOnce(result);
+    evaluate.mockResolvedValue(null);
+    return {
+        evaluate,
+        wait: vi.fn().mockResolvedValue(undefined),
+        pressKey: vi.fn().mockResolvedValue(undefined),
+    };
+}
+
+describe('chatwise composer selection', () => {
+    it('prefers the main composer over auxiliary contenteditable editors', () => {
+        const mainComposer = candidate({
+            index: 0,
+            placeholder: 'placeholder Enter a message here, press ⏎ to send',
+            rect: { y: 860, h: 32 },
+        });
+        const optionalDescription = candidate({
+            index: 1,
+            placeholder: 'placeholder Optional description',
+            editorClasses: 'cm-editor simple-editor',
+            rect: { y: 400, h: 32 },
+        });
+        const userContext = candidate({
+            index: 2,
+            text: '# User Context Document',
+            editorClasses: 'cm-editor simple-editor',
+            rect: { y: 460, h: 1200 },
+        });
+
+        expect(scoreChatwiseComposerCandidate(mainComposer, 900)).toBeGreaterThan(
+            scoreChatwiseComposerCandidate(optionalDescription, 900),
+        );
+        expect(scoreChatwiseComposerCandidate(mainComposer, 900)).toBeGreaterThan(
+            scoreChatwiseComposerCandidate(userContext, 900),
+        );
+
+        expect(selectBestChatwiseComposer([
+            optionalDescription,
+            userContext,
+            mainComposer,
+        ], 900)?.index).toBe(0);
+    });
+
+    it('rejects hidden or low-confidence candidates instead of injecting into the wrong editor', () => {
+        expect(selectBestChatwiseComposer([
+            candidate({
+                index: 0,
+                hidden: true,
+                placeholder: 'Enter a message here, press ⏎ to send',
+                rect: { y: 860, h: 32 },
+            }),
+        ], 900)).toBeNull();
+
+        expect(selectBestChatwiseComposer([
+            candidate({
+                index: 1,
+                placeholder: 'Optional description',
+                editorClasses: 'cm-editor simple-editor',
+                rect: { y: 860, h: 32 },
+            }),
+            candidate({
+                index: 2,
+                text: '# User Context Document',
+                editorClasses: 'cm-editor simple-editor',
+                rect: { y: 870, h: 32 },
+            }),
+        ], 900)).toBeNull();
+    });
+
+    it('injects text into the scored main composer instead of the last contenteditable', () => {
+        const html = `
+          <div class="cm-editor simple-editor">
+            <div class="cm-placeholder">Optional description</div>
+            <div id="optional" contenteditable="true" role="textbox"></div>
+          </div>
+          <div class="cm-editor">
+            <div class="cm-placeholder">Enter a message here, press ⏎ to send</div>
+            <div id="main" class="cm-content" contenteditable="true" role="textbox"></div>
+          </div>
+          <div class="cm-editor simple-editor">
+            <div id="context" contenteditable="true" role="textbox"># User Context Document</div>
+          </div>
+        `;
+
+        const { dom, result } = runBrowserScript(html, buildChatwiseInjectTextJs('hello'));
+
+        expect(result).toBe(true);
+        expect(dom.window.document.querySelector('#main')?.textContent).toBe('hello');
+        expect(dom.window.document.querySelector('#optional')?.textContent).toBe('');
+        expect(dom.window.document.querySelector('#context')?.textContent).toBe('# User Context Document');
+    });
+
+    it('fails injection when only auxiliary editors are present', () => {
+        const html = `
+          <div class="cm-editor simple-editor">
+            <div class="cm-placeholder">Optional description</div>
+            <div id="optional" contenteditable="true" role="textbox"></div>
+          </div>
+          <div class="cm-editor simple-editor">
+            <div id="context" contenteditable="true" role="textbox"># User Context Document</div>
+          </div>
+        `;
+
+        const { dom, result } = runBrowserScript(html, buildChatwiseInjectTextJs('hello'));
+
+        expect(result).toBe(false);
+        expect(dom.window.document.querySelector('#optional')?.textContent).toBe('');
+        expect(dom.window.document.querySelector('#context')?.textContent).toBe('# User Context Document');
+    });
+
+    it('reads only real message wrapper content after the previous count', () => {
+        const html = `
+          <div class="group/message">old message</div>
+          <div class="timestamp">12:00</div>
+          <div class="group/message">new assistant answer</div>
+        `;
+
+        expect(runBrowserScript(html, buildChatwiseMessageCountJs()).result).toBe(2);
+        expect(runBrowserScript(html, buildChatwiseResponseAfterJs(1, 'user prompt')).result).toBe('new assistant answer');
+    });
+
+    it('does not treat the user prompt wrapper as an assistant response', () => {
+        const html = `
+          <div class="group/message">old message</div>
+          <div class="group/message">user prompt</div>
+        `;
+
+        expect(runBrowserScript(html, buildChatwiseResponseAfterJs(1, 'user prompt')).result).toBeNull();
+    });
+
+    it('validates timeout explicitly', () => {
+        expect(normalizeTimeout(undefined)).toBe(30);
+        expect(() => normalizeTimeout('0')).toThrow(ArgumentError);
+        expect(() => normalizeTimeout('301')).toThrow(ArgumentError);
+    });
+
+    it('fails fast when ask times out instead of returning a System success row', async () => {
+        const page = makePage([
+            1,
+            true,
+            null,
+        ]);
+
+        await expect(askCommand.func(page, { text: 'hello', timeout: 1 }))
+            .rejects.toBeInstanceOf(TimeoutError);
+    });
+});
diff --git a/clis/chatwise/send.js b/clis/chatwise/send.js
index 7f7ca9883..f18967b15 100644
--- a/clis/chatwise/send.js
+++ b/clis/chatwise/send.js
@@ -1,5 +1,6 @@
 import { cli, Strategy } from '@jackwener/opencli/registry';
 import { selectorError } from '@jackwener/opencli/errors';
+import { buildChatwiseInjectTextJs } from './utils.js';
 export const sendCommand = cli({
     site: 'chatwise',
     name: 'send',
@@ -12,30 +13,7 @@ export const sendCommand = cli({
     columns: ['Status', 'InjectedText'],
     func: async (page, kwargs) => {
         const text = kwargs.text;
-        const injected = await page.evaluate(`
-      (function(text) {
-        // ChatWise input can be textarea or contenteditable
-        let composer = document.querySelector('textarea');
-        if (!composer) {
-          const editables = Array.from(document.querySelectorAll('[contenteditable="true"]'));
-          composer = editables.length > 0 ? editables[editables.length - 1] : null;
-        }
-
-        if (!composer) return false;
-
-        composer.focus();
-        
-        if (composer.tagName === 'TEXTAREA') {
-          // For textarea, set value and dispatch input event
-          const nativeInputValueSetter = Object.getOwnPropertyDescriptor(window.HTMLTextAreaElement.prototype, 'value').set;
-          nativeInputValueSetter.call(composer, text);
-          composer.dispatchEvent(new Event('input', { bubbles: true }));
-        } else {
-          document.execCommand('insertText', false, text);
-        }
-        return true;
-      })(${JSON.stringify(text)})
-    `);
+        const injected = await page.evaluate(buildChatwiseInjectTextJs(text));
         if (!injected)
             throw selectorError('ChatWise input element');
         await page.wait(0.5);
diff --git a/clis/chatwise/utils.js b/clis/chatwise/utils.js
new file mode 100644
index 000000000..dfa8673d9
--- /dev/null
+++ b/clis/chatwise/utils.js
@@ -0,0 +1,147 @@
+import { ArgumentError } from '@jackwener/opencli/errors';
+
+export const MESSAGE_WRAPPER_SELECTOR = '[class*="group/message"]';
+export const MIN_COMPOSER_SCORE = 120;
+
+export function normalizeTimeout(value, defaultSeconds = 30, maxSeconds = 300) {
+    const raw = value ?? defaultSeconds;
+    const timeout = Number(raw);
+    if (!Number.isInteger(timeout) || timeout <= 0) {
+        throw new ArgumentError('timeout must be a positive integer', `Example: opencli chatwise ask "hello" --timeout ${defaultSeconds}`);
+    }
+    if (timeout > maxSeconds) {
+        throw new ArgumentError(`timeout must be <= ${maxSeconds}`, `Example: opencli chatwise ask "hello" --timeout ${maxSeconds}`);
+    }
+    return timeout;
+}
+
+export function scoreChatwiseComposerCandidate(candidate, viewportHeight = 0) {
+    if (candidate.hidden) return -1000;
+
+    let score = 0;
+    const normalizedRole = String(candidate.role || '').toLowerCase();
+    if (normalizedRole === 'textbox') score += 10;
+
+    const normalizedClasses = `${candidate.classes || ''} ${candidate.editorClasses || ''} ${candidate.ariaLabel || ''}`.toLowerCase();
+    if (normalizedClasses.includes('cm-content')) score += 20;
+    if (normalizedClasses.includes('cm-editor')) score += 30;
+    if (normalizedClasses.includes('simple-editor')) score -= 140;
+
+    const searchableText = `${candidate.placeholder || ''} ${candidate.ariaLabel || ''} ${candidate.text || ''}`.toLowerCase();
+    if (searchableText.includes('enter a message here')) score += 220;
+    if (searchableText.includes('press ⏎ to send')) score += 80;
+    if (searchableText.includes('press enter to send')) score += 80;
+    if (searchableText.includes('message')) score += 20;
+    if (searchableText.includes('optional description')) score -= 140;
+    if (searchableText.includes('user context document')) score -= 220;
+
+    if (viewportHeight > 0 && candidate.rect) {
+        const bottom = candidate.rect.y + candidate.rect.h;
+        const distanceFromBottom = Math.abs(viewportHeight - bottom);
+        score += Math.max(0, 80 - distanceFromBottom / 8);
+    }
+
+    return score;
+}
+
+export function selectBestChatwiseComposer(candidates, viewportHeight = 0, minScore = MIN_COMPOSER_SCORE) {
+    if (!Array.isArray(candidates) || candidates.length === 0) return null;
+    const best = [...candidates]
+        .sort((left, right) => {
+            const delta = scoreChatwiseComposerCandidate(right, viewportHeight)
+                - scoreChatwiseComposerCandidate(left, viewportHeight);
+            return delta !== 0 ? delta : left.index - right.index;
+        })[0] ?? null;
+    if (!best || scoreChatwiseComposerCandidate(best, viewportHeight) < minScore) return null;
+    return best;
+}
+
+export function buildChatwiseInjectTextJs(text) {
+    const scoreFn = scoreChatwiseComposerCandidate.toString();
+    const selectFn = selectBestChatwiseComposer.toString();
+    const textJs = JSON.stringify(String(text ?? ''));
+
+    return `
+      (function(text) {
+        const scoreChatwiseComposerCandidate = ${scoreFn};
+        const selectBestChatwiseComposer = ${selectFn};
+        const MIN_COMPOSER_SCORE = ${MIN_COMPOSER_SCORE};
+
+        const composers = Array.from(document.querySelectorAll([
+          'textarea[aria-label*="message" i]',
+          'textarea[placeholder*="message" i]',
+          '[contenteditable="true"][role="textbox"]',
+          '[contenteditable="true"]'
+        ].join(',')));
+        const candidates = composers.map((el, index) => {
+          const rect = el.getBoundingClientRect();
+          const editor = el.closest('.cm-editor');
+          const placeholderEl = editor?.querySelector('.cm-placeholder');
+          return {
+            index,
+            hidden: !(el.offsetWidth || el.offsetHeight || el.getClientRects().length),
+            role: el.getAttribute('role'),
+            classes: el.className || '',
+            editorClasses: editor?.className || '',
+            ariaLabel: el.getAttribute('aria-label') || '',
+            placeholder: placeholderEl?.getAttribute('aria-label') || placeholderEl?.textContent || el.getAttribute('placeholder') || '',
+            text: (el.textContent || '').trim(),
+            rect: { y: rect.y, h: rect.height },
+          };
+        });
+
+        const best = selectBestChatwiseComposer(candidates, window.innerHeight, MIN_COMPOSER_SCORE);
+        if (!best) return false;
+
+        const composer = composers[best.index];
+        composer.focus();
+
+        if (composer.tagName === 'TEXTAREA') {
+          const setter = Object.getOwnPropertyDescriptor(window.HTMLTextAreaElement.prototype, 'value')?.set;
+          if (setter) setter.call(composer, text);
+          else composer.value = text;
+          composer.dispatchEvent(new Event('input', { bubbles: true }));
+          return true;
+        }
+
+        const selection = window.getSelection();
+        const range = document.createRange();
+        range.selectNodeContents(composer);
+        selection?.removeAllRanges();
+        selection?.addRange(range);
+
+        const inserted = document.execCommand?.('insertText', false, text);
+        if (!inserted) {
+          composer.textContent = text;
+        }
+        composer.dispatchEvent(new Event('input', { bubbles: true }));
+        return true;
+      })(${textJs})
+    `;
+}
+
+export function buildChatwiseMessageCountJs() {
+    return `
+      (function() {
+        return Array.from(document.querySelectorAll(${JSON.stringify(MESSAGE_WRAPPER_SELECTOR)}))
+          .map(node => (node.innerText || node.textContent || '').trim())
+          .filter(Boolean)
+          .length;
+      })()
+    `;
+}
+
+export function buildChatwiseResponseAfterJs(previousCount, userText) {
+    return `
+      (function(previousCount, userText) {
+        const messages = Array.from(document.querySelectorAll(${JSON.stringify(MESSAGE_WRAPPER_SELECTOR)}))
+          .map(node => (node.innerText || node.textContent || '').trim())
+          .filter(Boolean);
+        if (messages.length <= previousCount) return null;
+        const fresh = messages.slice(previousCount)
+          .filter(text => text && text !== userText);
+        if (fresh.length === 0) return null;
+        return fresh[fresh.length - 1];
+      })(${Number(previousCount) || 0}, ${JSON.stringify(String(userText ?? ''))})
+    `;
+}