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What you are seeing

Either a technically-correct answer that tells you nothing you did not know, or an answer that reads as though your attachment was never there.

Different causes, and both are usually fixed in one follow-up message rather than by starting again.

Say what you want back, more precisely

A generic answer is nearly always a generic question. Naming a topic gets a summary of the topic; naming an outcome gets the thing you needed.

Three additions do most of the work — the result you want, the form it should take, and what to leave out:

Instead of "what do you think of this proposal?" — "I have to approve or reject this by Friday. List the three things most likely to cost us money, with the section each is in. Skip the summary."

You do not have to start over. "Too general — give me the three specific risks with clause numbers" in the same conversation gets a better answer than a fresh attempt, because everything from before is still there.

Give it the background it was missing

Orsola knows the conversation and whatever it can reach through connected accounts. It does not know what is in your head — who the reader is, what has already been decided, what you cannot change.

An answer that feels wrong rather than vague is usually this: it made a reasonable assumption that happened to be untrue. Tell it plainly — "this is going to a client, not internally" — and ask again.

Check the file actually attached

Before assuming Orsola ignored it:

Look for the attachment on your message. If it is not shown there, it did not go with the message.
Check the conversation. Files belong to the conversation they were sent in — Orsola cannot see one you attached somewhere else.
Check it is not a scan. A PDF from a scanner is a picture of text with nothing to index, and Orsola will say it cannot see the content rather than reading it.
Ask directly. "What is the title and date on the document I attached?" settles it in one turn.

File will not upload, or Orsola ignored it? goes further on this.

Ask it to point at the source

When an answer matters, ask where it came from: "Which section says that?", "Quote the sentence you based that on."

Two benefits. You can check it, and a request to cite tends to produce a more careful answer in the first place. Numbers, dates, names and quotations are the things most worth verifying before you act on them.

Use a helper built for the job instead

Some requests go better in a purpose-built screen — scheduling in Task, a recording in Meeting, receipts in Expense. Choose the right helper for the job covers which is which.

Still stuck

If a rephrased, well-specified question with the right context still gives you something unusable, that is worth telling us — include what you asked and what came back. Report something that looks wrong or unsafe is the route for an answer that was not just unhelpful but wrong.

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