diff --git a/.changeset/flat-pumpkins-accept.md b/.changeset/flat-pumpkins-accept.md
new file mode 100644
index 0000000..efe8632
--- /dev/null
+++ b/.changeset/flat-pumpkins-accept.md
@@ -0,0 +1,5 @@
+---
+"@astrojs/cli-kit": patch
+---
+
+Allow Houston to line wrap
diff --git a/index.mjs b/index.mjs
new file mode 100644
index 0000000..826a992
--- /dev/null
+++ b/index.mjs
@@ -0,0 +1,5 @@
+import { say } from './dist/index.js'
+
+await say([
+    'Hello world lorem ipsum et dolor sic amor sucks to suck mother fucker'
+])
diff --git a/src/messages/index.ts b/src/messages/index.ts
index a9f89dc..ca82e38 100644
--- a/src/messages/index.ts
+++ b/src/messages/index.ts
@@ -3,7 +3,7 @@ import color from 'chalk';
 import { createLogUpdate } from 'log-update';
 import { random, randomBetween, sleep, useAscii } from '../utils/index.js'
 import { action } from '../prompt/util/action.js';
-import { strip } from '../prompt/util/clear.js';
+import { strip, wrap } from '../prompt/util/clear.js';
 
 type Message = string | Promise<string>;
 
@@ -49,10 +49,13 @@ export const say = async (msg: Message | Message[] = [], { clear = false, hat =
         const [h, v] = walls;
         const [tl, tr, bl, br] = corners;
         const head = h.repeat(3 - strip(hat).split('').length);
+        const prefix = ' '.repeat(9);
+        const [message, secondMessage = '', ...lines] = wrap(`${prefix}${msg}`, prefix).split('\n');
         return [
             `${tl}${h.repeat(2)}${hat}${head}${tr}  ${color.bold(color.cyan('Houston:'))}`,
-            `${v} ${eye} ${color.cyanBright(mouth)} ${eye}  ${msg}`,
-            `${bl}${h.repeat(5)}${br}`,
+            `${v} ${eye} ${color.cyanBright(mouth)} ${eye}  ${message.trimStart()}`,
+            `${bl}${h.repeat(5)}${br}  ${secondMessage.trimStart()}`,
+            ...lines
         ].join('\n')
     };
 
diff --git a/src/prompt/util/clear.ts b/src/prompt/util/clear.ts
index 4eabe28..7028148 100644
--- a/src/prompt/util/clear.ts
+++ b/src/prompt/util/clear.ts
@@ -30,7 +30,7 @@ export const wrap = (str: string, indent = '', max = process.stdout.columns) =>
   for (const raw of words) {
     const len = strip(raw).length;
     if (i + len > max) {
-      i = 0;
+      i = indent.length;
       lines.push('\n' + indent, raw);
     } else {
       lines.push(raw);