## Thinking Path
> - Paperclip is the open source app people use to manage AI agents for
work
> - With Cases enabled, a person can ask chat to open a case from a
brief and hand it to an agent
> - The case scenario expects the brief and a workflow document on the
primary task before work starts
> - In one run the CEO copied the brief's facts into case fields but
saved only the workflow document
> - The Cases chat guidance says nothing about where the person's brief
belongs
> - This pull request adds one guidance sentence: save the brief with
`initialDocuments` in the same case-handoff request
> - The benefit is that the assignee always has the person's source,
saved before its run begins
## Linked Issues or Issue Description
**What happened**
In the chat eval `cases.create-case` (run 43107042937), the person
attached a customer bug brief and asked the CEO to open a case and have
Morgan investigate. The CEO created the case, its fields, the workflow
document and the kickoff. It did not save the brief on the primary task.
In an earlier run (43101125481) the CEO did save it, so the behavior
depends on the model's choice.
**Expected behavior**
The new primary task has the person's brief as a document, saved in the
request that creates it, before the assignee starts.
**Steps to reproduce**
1. Enable Cases. Attach a brief in chat with the CEO.
2. Ask: "Open a case for this customer bug, record the facts from my
brief, and have Morgan investigate first."
3. Read the primary task's documents: in some runs only `workflow`
exists.
## What Changed
- `CASES_CHAT_DIRECTIVE` (rendered only while Cases is enabled): one
sentence. When the person opens a case from a brief, save the brief as a
document on the primary task with `initialDocuments` on `POST
/api/companies/{companyId}/case-handoffs`. Case fields do not replace
the brief.
- `case-history-api-discovery.test.ts`: a regression test for the new
guidance.
## Verification
- Red: the new test failed before the change. Green: `npx vitest run
src/__tests__/case-history-api-discovery.test.ts
src/__tests__/agent-conversations.test.ts` (67 passed).
- The route already accepts `initialDocuments` for a newly created
primary task (`packages/shared/src/case-handoffs.ts`).
- End-to-end: chat eval run linked in a comment below.
## Risks
- Low risk. The sentence renders only when Cases is enabled. No API or
permission changes.
## Model Used
- Anthropic Claude Opus 5.5 (`claude-opus-5-5`), tool use and code
execution in Claude Code.
## Checklist
- [x] I have included a thinking path that traces from project context
to this change
- [x] I have specified the model used (with version and capability
details)
- [x] I have checked ROADMAP.md and confirmed this PR does not duplicate
planned core work
- [x] I have searched GitHub for duplicate or related PRs and linked
them above
- [x] I have either (a) linked existing issues with `Fixes: #` / `Closes
#` / `Refs #` OR (b) described the issue in-PR following the relevant
issue template
- [x] I have not referenced internal/instance-local Paperclip issues or
links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip`
URLs)
- [x] My branch name describes the change (e.g. `docs/...`, `fix/...`)
and contains no internal Paperclip ticket id or instance-derived details
- [x] I have run tests locally and they pass
- [x] I have added or updated tests where applicable
- [x] I have updated relevant documentation to reflect my changes
- [x] I have considered and documented any risks above
- [ ] All Paperclip CI gates are green
- [ ] Greptile is 5/5 with no open P2s, recommendations, or follow-ups
- [x] I will address all Greptile and reviewer comments before
requesting merge
🤖 Generated with [Claude Code](https://claude.com/claude-code)
---------
Co-authored-by: Claude Opus 5.5 <noreply@anthropic.com>
