How to attach files
- Click the paperclip in the message box, or
- drag files from your computer or Outlook onto the chat window. You'll see "Drop files to attach to message".
Limits
- Up to 20 files per message.
- A combined size limit per message. As a rough guide, about 20 MB of PDF/Word/Excel files together. Text-heavy files (.txt, .csv, .html) count much more heavily per MB.
- Long conversations also count towards the limit. If you get a "message is too large" error, start a New Chat.
Supported file types
| Type | Extensions |
|---|---|
| Documents | .pdf, .docx, .xlsx, .pptx, .rtf, .txt, .csv, .html |
| Emails | .msg (Outlook), .eml. Attachments inside the email are read too. |
| Images | .png, .jpg, .jpeg, .webp, .heic, .heif |
Not supported
| File | What to do |
|---|---|
| Old Office formats: .doc, .xls, .ppt | Open the file and use Save As → .docx / .xlsx / .pptx, or save as PDF. |
| Zip / archive files: .zip, .rar, .7z | Extract the files and attach them individually. |
Tips
- Say what each file is: "Attached: 1) current schedule, 2) Insurer B quote, 3) Insurer C quote."
- Photos of documents work, but a clear, straight, well-lit photo gives better results.
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