Woodstock Docs
Proposals

Reading what you drop

A proposal for review — what Snoopy says back when you drop a file or a link, in every case it can hit.

Proposal — nothing here is built yet. This page is for review. Every reply below is draft copy for a behaviour we are about to build, not something you can try today. Comments on wording, tone, and when the agent should speak are exactly what we are looking for.

Today, dropping a file into a channel is a leap of faith. Something may happen to it. You will not be told what.

This proposal makes one promise: whatever you drop, you get told what happened to it, in the same thread, in plain language — and if something got in the way, you get one clear next step. Behind that, the file becomes searchable, page by page, so you can point at page 7 later and be right.

Below is every case we could find, with the reply we would give. Read it as a script.


The five outcomes

Every drop lands in exactly one of these. The words matter more than the labels — a person should never have to learn this vocabulary to understand the reply.

Read it allEverything is now searchable.
Read some of itNames exactly which part, and offers the rest.
Needs youSomething only you can fix — a password, a full link.
Can't read this yetHonest about the limit, and offers what it can do.
Something went wrongSays nothing was lost, and what to try.

1 · A PDF it can read

📄 Q3-expenses.pdf
Snoopy is reading 10 pages…
Snoopy
Read all 10 pages of Q3-expenses.pdf — a quarterly expense ledger, ten vendor sections, totals from $45.00 to $3,772.65.

You can ask me about any page now and I'll be able to point at it.
Why the page count is in the reply. It is the shortest possible proof that the whole thing was read, and it is the number a person will check.

2 · A PDF it can only partly read

📄 Board-pack.pdf
Snoopy
Read pages 1–30 of Board-pack.pdf. Pages 31–40 are scanned images with no text I can pull.

I can read those ten by eye if they matter — want me to?
It names the range, not "some pages". And it ends with an offer rather than an apology — the agent can read scanned pages, it just costs more, so it asks first.

3 · A scan — short enough to just read

📄 supplier-invoice.pdf
No text in it — reading 3 pages by eye…
Snoopy
Done — read all 3 pages. Invoice from Ferrous Supply Co, ฿77,400, due 30 Sep.

That's my reading of the scan rather than its own text, so I'll quote it as a description, not word-for-word.
No permission step, because there is nothing worth asking about. Three pages by eye costs about what the ordinary text read costs, so asking would be a chore dressed as a safeguard. The question is reserved for spend that deserves one — see case 9.

The most important sentence here is the last one. When the agent reads a picture rather than lifting real text, it says so — and it will never later quote that back as if it were the document's own words. Does that read as trustworthy, or as hedging? This is the wording we most want a second opinion on.

4 · A locked file

📄 payroll-aug.pdf
Snoopy
payroll-aug.pdf needs a password to open, so I couldn't get into it at all — not even to see how long it is.

Save it again without the password, or paste the part you need.
No offer here, deliberately — reading it by eye would not help either, and offering something that cannot work is worse than saying nothing.

5 · A damaged file

📄 contract-final.pdf
Snoopy
contract-final.pdf arrived damaged — the file is cut short, so there's nothing I can read in it.

Your upload is still here and nothing was thrown away. Sending it again usually fixes this.
"Nothing was thrown away" is load-bearing. The fear when a file fails is that it is gone. Say it before the person has to ask.

6 · A photo

🖼 IMG_4471.jpg
Snoopy
Looked at IMG_4471.jpg — a receipt from Sablefish Analytics, ฿3,772.65, dated 14 Aug. Written down so it turns up in search.

That's what I can see in the photo, not text I lifted off it.

7 · An ordinary message

let's move the standup to 9:30
— no reply, nothing happens —
Silence is the correct answer here, and it is a deliberate design decision rather than an oversight. The agent speaks when something was dropped, never on ordinary conversation.
Snoopy is reading the page…
Snoopy
Saved "The Cloudflare Blog" — I've kept a copy of the page as it reads today, so it'll still turn up in search even if the post changes later.
"As it reads today" is the honest bit. We keep a snapshot, not a live mirror. If the page changes next month, search still finds what you actually shared.

9 · Several files at once

📄 Q3-expenses.pdf📄 scan.pdf📄 payroll.pdf
Snoopy
Three files:

• Q3-expenses.pdf — read, all 10 pages
• scan.pdf — no text in it, so I read its 2 pages by eye
• payroll.pdf — needs a password

Can you re-save payroll unlocked?
One reply, one line per file, and only the thing a person actually has to act on is asked. The small scan was simply read — the only question left is the one nobody but the person can answer. Is this the right shape at five or ten files, or does it need to collapse?
Snoopy
That link forwards somewhere else rather than being the page itself, and I only open links that point straight at the real page — so I can't be sent somewhere I shouldn't go.

Open it once and paste the address it lands on, and I'll read that.
Rewritten twice, and the second time is the honest one. This case used to refuse the link and claim to name its destination — which prompted exactly the right question in review: if it knows where the link goes, why can't it just read it? It couldn't. It had never resolved the destination; the host it named was the shortener you pasted.

We briefly made it follow the link. A security pass found that following redirects hands an attacker the choice of which address gets safety-checked, and the check underneath is weaker than it looks — so following is deferred until that check is made binding. What stays is the part that was actually wrong: it no longer claims to know where the link goes. Is "paste the address it lands on" a reasonable thing to ask someone?

11 · Something far too big

📄 archive-2019.pdf
Snoopy
archive-2019.pdf is 180 scanned pages — too many for me to read by eye in one go.

Tell me which pages matter and I'll do those.
Reading 180 scanned pages by eye is slow and expensive, so there is a limit. The reply gives the real number and turns the limit into a question worth answering.

What we would like you to react to

  1. The description disclaimer (cases 3 and 6) — "that's my reading of the scan rather than its own text". It is there so the agent never passes off a guess as a quote. Does it build trust, or undercut the answer?
  2. Speaking on every drop (case 1). Silence would be quieter, but silence is indistinguishable from a file being lost. Is one line the right price?
  3. The offer pattern. Cases 2, 3 and 9 end with a question. Is asking the right default, or should the agent just do it when the document looks important?
  4. Case 9 at scale. Ten files in one drop — list, or summary?
  5. Tone. These replies are plain and slightly clipped. Right for a work channel used by Thai SME teams?

Not in this proposal: nothing changes visually anywhere else in the product — no new screen, no new button, no settings. The whole change is what the agent says in a thread, plus files becoming findable in search later. Reading a scan by eye and reading a link both happen only when the agent asks and you say yes.

On this page