Attach your files to Rolly

Add photos, PDFs and spreadsheets to your message so Rolly can read them, such as a photo to caption or a brief to turn into posts.

4 min readUpdated Nov 2, 2026Pro and Max only

Before you start

Steps

  1. Click Rolly at the top of any page.

  2. Click the paperclip in the bottom corner of the box.

  3. Pick up to 5 files from your computer. Each file shows above the box while it uploads, and a photo shows a small preview.

  4. Type what you want Rolly to do with your files, such as "Write alt text for this photo" or "Turn this brief into five LinkedIn posts."

  5. Press Enter or click the send arrow once your files finish uploading. Your files show above your message in the chat, and Rolly answers using what's in them.

Files Rolly can read

Rolly reads JPEG, PNG, GIF and WebP photos, PDFs, CSV files and plain text files. Each file can be up to 10MB, and you can add up to 5 files to one message. Rolly can't read videos, or HEIC photos from an iPhone, so save an iPhone photo as JPEG before you attach it.

How long Rolly keeps your files

Your files stay in the chat for 90 days, so you can open the chat again and still see them. After that, the chat shows only the file's name.

If you want ideas for what to ask

Go to Prompts under Rolly in the sidebar and click From your files. You'll see prompts made for files, such as Read an export and Turn a document into a plan. Caption what I attached is under Write and rewrite.

If you can't attach your file, it's likely one of these reasons

"is a HEIC image, which Rolly can't read. Save it as JPEG, PNG, GIF or WebP and attach it again." Your photo came from an iPhone in its own format. Save it as JPEG and attach it again.

"is a file Rolly can't read. It reads images (JPEG, PNG, GIF, WebP), PDFs, CSV and text." Your file is a type Rolly doesn't read, such as a video or a Word file. Save a Word file as PDF and attach it again.

"That file is too large. Attachments are limited to 10MB." Make your file smaller, or split a long PDF into parts.

Your file has a red border. It didn't upload, and your message would send without it. Click the retry button on the file, or remove it and attach it again.

The send arrow stays grey. A file is still uploading. Wait for it to finish, then send.

You can't add a sixth file. One message takes up to 5 files. Send them, then attach the rest in your next message.

"That message is too large. Try fewer or smaller attachments." Send fewer files at once, or make them smaller.

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