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Documents and spreadsheets

Kind	Formats
Documents	PDF, DOC, DOCX, TXT
Spreadsheets	CSV, XLS, XLSX
Slides	PPT, PPTX

Pages, Numbers and Keynote files are not on the list. Export to PDF, Word or Excel first.

Images

JPEG, PNG, WebP and GIF. HEIC — what an iPhone takes by default — is not accepted. Sharing a photo through Photos usually converts it to JPEG for you; if you are moving files off the phone yourself, convert or export as JPEG first.

Photographs of documents work: a picture of a receipt or a printed page can be read like any other image.

Your profile picture is separate and has a smaller limit — 5 MB — because it is not a conversation attachment.

Audio and video

Kind	Formats
Audio	MP3, M4A, OGG, WAV, WebM
Video	MP4, WebM, OGG, MOV

The 20 MB limit bites soonest here — a few minutes of video is often already over it. For a meeting you want captured, record it with the Meeting helper rather than uploading a file: it is built for long audio and gives you a transcript and a summary.

How many at once, and how large

Limit	Value
Size of one file	20 MB
Files in one message	5
Files in one conversation	No limit — five per message, as many messages as you like
Profile picture	5 MB

Why a supported file might still not work

It is a scan, not a document. A PDF from a scanner or a photocopier holds a picture of each page rather than text. Orsola indexes documents by their text, so there is nothing to find in one of these and it will tell you it cannot see the content. A photo of the same page, sent as an image, is often read better.
It is password-protected. Nothing can open it. Save an unlocked copy and send that.
It is over 20 MB. The commonest cause by far, and usually images inside a document rather than the text.
The Files dialog is hiding it. The picker filters to documents, images, audio and video, so spreadsheets and slide decks can look unsupported. Switch it to All files — they upload fine.
You attached it in a different conversation. Files belong to the conversation they were sent in. Orsola will not see one from somewhere else.

Where to go next

Add a document, photo, or spreadsheet walks through attaching one, and file will not upload, or Orsola ignored it? covers the failures that are not about format.

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