29:I[816506,["/_next/static/chunks/36uob8i9riz8e.js","/_next/static/chunks/2j1lo1fp07j9f.js","/_next/static/chunks/33-6ln_ih2mwl.js","/_next/static/chunks/3wynbyhe9d79p.js","/_next/static/chunks/1cufwwl27tnp0.js","/_next/static/chunks/3-hoj0i8bw9f-.js","/_next/static/chunks/0dhqcsged49j8.js","/_next/static/chunks/1w8tw3u-839kd.js","/_next/static/chunks/298z1bczrkys1.js","/_next/static/chunks/2jv2uwhvyk171.js","/_next/static/chunks/3dwu-tydqwcsg.js","/_next/static/chunks/0686dxrv110za.js","/_next/static/chunks/3enadu5lhaloa.js","/_next/static/chunks/1u2ly6m0msti0.js","/_next/static/chunks/1i-rgcouojpqg.js","/_next/static/chunks/3sw5u78bcew8u.js","/_next/static/chunks/2upqokmvbvcc-.js","/_next/static/chunks/2iodr7v0j7s_a.js","/_next/static/chunks/1-8mo38-h124u.js","/_next/static/chunks/0ic8rmdz-hyww.js","/_next/static/chunks/0bxnssgp1vx3w.js","/_next/static/chunks/0k9flt0fwbu2-.js","/_next/static/chunks/2nm7r1rohp8s6.js","/_next/static/chunks/1hiusxxv1h9t6.js","/_next/static/chunks/3z47ruhe3--mc.js","/_next/static/chunks/1jp-7_do785j2.js","/_next/static/chunks/3e_lh4xcmyx9q.js","/_next/static/chunks/20hmc0ojgel--.js"],""] 2a:I[35455,["/_next/static/chunks/36uob8i9riz8e.js","/_next/static/chunks/2j1lo1fp07j9f.js","/_next/static/chunks/33-6ln_ih2mwl.js","/_next/static/chunks/3wynbyhe9d79p.js","/_next/static/chunks/1cufwwl27tnp0.js","/_next/static/chunks/3-hoj0i8bw9f-.js","/_next/static/chunks/0dhqcsged49j8.js","/_next/static/chunks/1w8tw3u-839kd.js","/_next/static/chunks/298z1bczrkys1.js","/_next/static/chunks/2jv2uwhvyk171.js","/_next/static/chunks/3dwu-tydqwcsg.js","/_next/static/chunks/0686dxrv110za.js","/_next/static/chunks/3enadu5lhaloa.js","/_next/static/chunks/1u2ly6m0msti0.js","/_next/static/chunks/1i-rgcouojpqg.js","/_next/static/chunks/3sw5u78bcew8u.js","/_next/static/chunks/2upqokmvbvcc-.js","/_next/static/chunks/2iodr7v0j7s_a.js","/_next/static/chunks/1-8mo38-h124u.js","/_next/static/chunks/0ic8rmdz-hyww.js","/_next/static/chunks/0bxnssgp1vx3w.js","/_next/static/chunks/0k9flt0fwbu2-.js","/_next/static/chunks/2nm7r1rohp8s6.js","/_next/static/chunks/1hiusxxv1h9t6.js","/_next/static/chunks/3z47ruhe3--mc.js","/_next/static/chunks/1jp-7_do785j2.js","/_next/static/chunks/3e_lh4xcmyx9q.js","/_next/static/chunks/20hmc0ojgel--.js"],"SupportArticleContent"] 2c:I[312843,["/_next/static/chunks/36uob8i9riz8e.js","/_next/static/chunks/2j1lo1fp07j9f.js","/_next/static/chunks/33-6ln_ih2mwl.js","/_next/static/chunks/3wynbyhe9d79p.js","/_next/static/chunks/1cufwwl27tnp0.js","/_next/static/chunks/3-hoj0i8bw9f-.js","/_next/static/chunks/0dhqcsged49j8.js","/_next/static/chunks/1w8tw3u-839kd.js","/_next/static/chunks/298z1bczrkys1.js","/_next/static/chunks/2jv2uwhvyk171.js","/_next/static/chunks/3dwu-tydqwcsg.js"],"IconMark"] 2b:Teb3,

What you are seeing

One of two different problems, and they have different answers:

The file never went through — it was rejected, or the upload failed.
The file went through but Orsola did not use it — it is sitting in the conversation and the answer ignores it.

If you got a message, it names the cause exactly. The three below cover nearly everything.

Check the type and the size

"File … exceeds 20MB limit" — every attachment is capped at 20 MB. Usually it is images inside a document rather than the text. Export a smaller version, compress it, or split it.

"File … type is not allowed" — the format is not one Orsola reads. Documents, spreadsheets and slides, images, audio and video are all accepted; the exact list is in what Orsola can read, and the limits. Exporting to PDF works for almost anything that is not on it.

Two formats catch people out. HEIC — what an iPhone takes by default — is not accepted, so use Photos rather than moving the file yourself, or export as JPEG. And Pages, Numbers and Keynote files need exporting to PDF, Word or Excel first.

If a spreadsheet or slide deck looks unavailable in the file picker, that is the dialog filtering, not a rejection. Switch it to All files and it will upload.

Check how many you attached at once

"Maximum 5 files allowed" — five per message is the limit. Send the rest in a second message; the first batch stays available in the conversation, so Orsola can still work across all of them.

Scanned or image-only documents

This is the commonest cause of a file that uploads perfectly and is then apparently ignored.

A PDF from a scanner or photocopier contains a picture of each page rather than text. Orsola indexes documents by their text, so there is nothing in one of these for it to find, and it will tell you it cannot see the content.

Two ways round it:

Send the page as an image instead — a photo or a screenshot of the same page is often read well, because images are looked at rather than searched.
Find the original. The document as it was written, rather than as it was scanned, works normally.

Files from a connected account

If you asked Orsola to use a file in Google Drive and it says it cannot find it, that is expected rather than broken. Orsola is given access to individual Drive items rather than to your whole Drive, so anything it did not create and you have not specifically opened with it is invisible to it — what connecting an account lets Orsola do explains the boundary.

Download the file and attach it from the message box; that always works. OneDrive is not limited this way and can be searched.

Also worth checking: files belong to the conversation they were sent in. Orsola will not see a file you attached in a different conversation.

Still stuck

If the file is a supported type, under 20 MB, on its own, and still will not go through, try once in a different browser to rule out an extension blocking the upload.

Then get in touch with the file's type and rough size, the exact message you saw, and what you were asking Orsola to do with it.

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