emcli/specifications/SPEC.md

# emcli — Specification

**Status:** Draft for implementation
**Source:** `specifications/PRD.md`
**Date:** 2026-06-21

## 1. Summary

`emcli` is a single cross-platform Go binary that mediates all email access for an AI
agent. The agent never holds email credentials and never connects to IMAP/SMTP directly —
every read and send passes through `emcli`, which enforces user-configured restrictions.
The goal is to contain the blast radius of agent hallucination when operating on live
email: even with faulty instructions, the agent cannot read mail it is not permitted to
see or send mail to recipients it is not permitted to contact.

## 2. Goals & non-goals

### Goals
- Single static binary, no runtime dependencies, cross-compiled per OS/arch.
- Email credentials and OAuth tokens are encrypted at rest and never exposed to the agent.
- Per-account enforcement of read-only/read-write mode, inbound/outbound whitelists, and
  subject filtering.
- Machine-readable JSON for agent commands; human-readable/interactive output for admin.
- Auditable history of agent actions with configurable retention.

### Non-goals
- Not a full email client (no threading UI, no flags/labels management beyond what is
  needed, no draft management).
- No graphical UI. TUI is used only for init and (re)configuration.
- No multi-user/server mode — `emcli` is a local utility invoked per-process.

## 3. Technology choices

| Concern | Choice |
| --- | --- |
| Language/runtime | Go (no CGO) |
| IMAP | `github.com/emersion/go-imap` |
| SMTP | `github.com/emersion/go-smtp` |
| MIME parsing/building | `github.com/emersion/go-message` |
| SASL / XOAUTH2 | `github.com/emersion/go-sasl` |
| SQLite | `modernc.org/sqlite` (pure Go) |
| TUI | `github.com/charmbracelet/bubbletea` (+ `lipgloss`) |
| Crypto | Go stdlib `crypto/aes` + `crypto/cipher` (AES-256-GCM) |

Rationale: the emersion email libraries are mature and designed to be used together,
including XOAUTH2 for Gmail. Pure-Go SQLite avoids CGO so the binary is genuinely static
and trivially cross-compiled.

## 4. Architecture

The binary is organized into independently testable packages:

- **`store`** — encrypted SQLite config and state. Owns the schema, migrations, and
  field-level encryption of secret columns.
- **`policy`** — pure enforcement functions: mode (RO/RW), whitelist-in, whitelist-out,
  subject regex, folder access. No I/O. The single gate every agent action passes through.
- **`mail`** — IMAP read and SMTP send, including SASL XOAUTH2 and password auth.
- **`oauth`** — loopback-redirect consent flow, refresh-token storage, automatic
  access-token refresh.
- **`audit`** — append-only action log with retention-based purge.
- **`cli`** — command dispatch and the two output surfaces (agent JSON, admin
  human-readable/TUI).

### Trust boundary

Two keys enforce a hard privilege split — this is not convention; it is structurally enforced by
the DEK-wrapping scheme:

- **`EMCLI_ADMIN_KEY`** — base64-encoded 32-byte key held by the human operator. Authorises ALL
  commands. Admin commands unwrap the DEK from the `dek_wrap_admin` slot only; there is no fallback
  to the agent slot. A process holding only `EMCLI_KEY` cannot run admin commands.
- **`EMCLI_KEY`** — base64-encoded 32-byte key supplied to the agent orchestrator. Authorises agent
  commands (`list`, `get`, `search`, `ack`, `send`, `doctor`) only. `EMCLI_ADMIN_KEY` is a superset:
  a process with only the admin key can also run agent commands.
- Agent commands use `EMCLI_KEY`; if only `EMCLI_ADMIN_KEY` is set, they fall back to it.
  If a process holding only `EMCLI_KEY` attempts an admin command, `emcli` exits with:
  `emcli: this command requires EMCLI_ADMIN_KEY (admin privilege)`.
  (An agent command with no key set at all yields a different `config` error: `EMCLI_KEY is not set`.)
- `EMCLI_KEY` is supplied by the orchestrator that launches `emcli`, never as an argument the agent
  constructs. The agent has no command that reveals secret values.
- All policy decisions happen inside `emcli`; the agent cannot bypass them because it has no other
  path to the mail servers.

## 5. Configuration & secrets

- **Admin key:** `EMCLI_ADMIN_KEY` env var, a base64-encoded 32-byte key (AES-256). Required for
  admin commands and for `init`. If absent or malformed when an admin command is attempted, the
  command fails with `emcli: this command requires EMCLI_ADMIN_KEY (admin privilege)`.
- **Agent key:** `EMCLI_KEY` env var, a base64-encoded 32-byte key (AES-256). Required for agent
  commands. If absent or malformed, every agent command fails closed with a `config` error envelope;
  no plaintext fallback. `EMCLI_ADMIN_KEY` is accepted as a fallback for agent commands when
  `EMCLI_KEY` is not set.
- **Database path:** `EMCLI_DB` env var; default `~/.config/emcli/emcli.db`
  (`%AppData%\emcli\emcli.db` on Windows).
- **Envelope encryption (DEK):** `emcli init` generates a random data-encryption key (DEK) that
  protects all account secrets. The DEK is stored in the `settings` table sealed under both keys:
  - `dek_wrap_admin` — the DEK encrypted under `EMCLI_ADMIN_KEY` (AES-256-GCM).
  - `dek_wrap_agent` — the DEK encrypted under `EMCLI_KEY` (AES-256-GCM).
  The DEK is never written in cleartext. Admin commands unwrap from `dek_wrap_admin` only; agent
  commands unwrap from `dek_wrap_agent` (or `dek_wrap_admin` if only the admin key is present).
  There is no cross-slot fallback for admin commands — a holder of only `EMCLI_KEY` cannot unwrap
  the admin DEK slot.
- **`init` idempotency:** re-running `emcli init` does not regenerate the DEK; the existing wrapped
  DEK rows are preserved.
- **Field-level encryption:** secret columns are encrypted with the DEK using AES-256-GCM with a
  random 96-bit nonce per value, prefixed to the ciphertext. Non-secret config remains plaintext for
  debuggability. Decryption with the wrong key fails (GCM auth tag) and is surfaced as an error,
  never silently ignored.

Secret columns: account password, OAuth client secret, OAuth refresh token.

## 6. Data model (SQLite)

```
accounts
  id                   INTEGER PK
  name                 TEXT UNIQUE          -- agent-facing identifier
  mode                 TEXT                 -- 'RO' | 'RW'
  imap_host            TEXT
  imap_port            INTEGER
  imap_security        TEXT                 -- 'tls' | 'starttls'
  smtp_host            TEXT                 -- nullable for RO accounts
  smtp_port            INTEGER
  smtp_security        TEXT                 -- 'tls' | 'starttls'
  auth_type            TEXT                 -- 'password' | 'oauth2'
  username             TEXT
  enc_password         BLOB                 -- encrypted (password auth)
  enc_oauth_client_id  BLOB                 -- encrypted (oauth2)
  enc_oauth_client_secret BLOB              -- encrypted (oauth2)
  enc_oauth_refresh_token BLOB              -- encrypted (oauth2)
  whitelist_in_enabled  INTEGER             -- 0 | 1
  whitelist_out_enabled INTEGER             -- 0 | 1
  subject_regex        TEXT                 -- nullable; blank/null = no subject filter
  process_backlog      INTEGER              -- 0 | 1; baseline policy for newly-seen folders
                                            --   0 (default) = floor at current max UID
                                            --   1           = floor at 0 (process existing mail)

whitelist_in
  account_id           INTEGER FK
  address              TEXT                 -- exact addr or '@domain.com'

whitelist_out
  account_id           INTEGER FK
  address              TEXT

folder_state                              -- one row per folder ever seen
  account_id           INTEGER FK
  folder               TEXT
  uidvalidity          INTEGER
  floor_uid            INTEGER              -- nothing at or below this is ever "new"
  PRIMARY KEY (account_id, folder)

acked                                     -- individual processed UIDs above the floor
  account_id           INTEGER FK
  folder               TEXT
  uidvalidity          INTEGER
  uid                  INTEGER
  PRIMARY KEY (account_id, folder, uid)

audit_log
  id                   INTEGER PK
  ts                   TEXT                 -- RFC3339 UTC
  account              TEXT
  action               TEXT                 -- 'list' | 'get' | 'send' | 'ack' | 'search'
  target               TEXT                 -- folder, UID(s), or recipient set
  result               TEXT                 -- 'allowed' | 'blocked'
  reason               TEXT                 -- nullable; populated on block

settings
  key                  TEXT PK
  value                TEXT
  -- includes: audit_retention_days, schema_version,
  --           dek_wrap_admin (DEK sealed under EMCLI_ADMIN_KEY),
  --           dek_wrap_agent (DEK sealed under EMCLI_KEY)
```

Notes:
- Folders are agent-specified; there is no folder whitelist. Read state is tracked per
  `(account, folder)`.
- **"New" is a seen-set, not a watermark.** A message is "new" when it exists in the
  folder, its `uid > floor_uid`, and its `uid` is not in `acked`. This makes
  acknowledgement per-message and order-independent — essential when the agent fans
  processing out to concurrent subagents that finish out of order.
- **Floor baseline.** On first contact with a folder, `floor_uid` is set from the
  account's `process_backlog` policy: the current highest UID (default — existing mail is
  treated as already handled) or `0` (process the existing backlog).
- **Compaction (internal, invisible to the agent).** When `acked` holds a contiguous run
  of UIDs immediately above `floor_uid`, that run is collapsed: `floor_uid` advances past
  it and the rows are deleted. This bounds storage without changing what counts as new. A
  folder processed strictly in order degenerates to a single floor value with an empty
  `acked` set (i.e. the watermark case); out-of-order processing leaves short-lived holes
  above the floor until they fill in.
- **UIDVALIDITY change.** If the server reports a different `UIDVALIDITY` for a folder than
  the stored value, UIDs are no longer comparable: `folder_state` and `acked` for that
  folder are reset and the floor re-baselined per `process_backlog`.

## 7. Command surface

### 7.1 Agent commands (JSON output only)

All agent commands emit a single JSON object (Section 8) and nothing else on stdout.

All read commands are **stateless** — they never mutate floor or ack state. The only
command that advances read state is `ack`.

**`emcli list --account <name> --folder <folder> [--new] [--before <uid>] [--since <uid>] [--limit N]`**
- Returns message headers only: `uid`, `from`, `to`, `subject`, `date`, `message_id`,
  `has_attachments`. Newest-first.
- `--new` filters to messages that are new per the seen-set rule (`uid > floor_uid` and
  not in `acked`). It does **not** advance any state.
- `--before <uid>` / `--since <uid>` page through history by UID cursor (e.g. page older by
  passing the lowest UID from the previous page as `--before`).
- `--limit` caps results (default applied if omitted; see 7.3).
- Whitelist-in and subject-regex filtering are applied before results are returned
  (Section 9); filtered messages are invisible in every mode.

**`emcli get --account <name> --folder <folder> --uid <uid>`**
- Returns full message: headers, decoded plain-text body, and attachments as
  `{name, size, mime, content_b64}`.
- Does **not** ack the message — fetching to inspect is distinct from consuming.
- If the message is filtered by whitelist-in or subject-regex, returns an error envelope
  (not-found) — the agent cannot retrieve filtered mail.

**`emcli search --account <name> --folder <folder> [--from <addr>] [--subject-contains <s>] [--text <s>] [--since <date>] [--before <date>] [--limit N]`**
- Server-side IMAP SEARCH across the whole folder, regardless of floor/ack state. Returns
  the same headers-only shape as `list`. Useful for finding specific historical mail.
- Subject to the same inbound filtering as `list`/`get`: filtered messages never appear.
- Stateless.

**`emcli ack --account <name> --folder <folder> --uid <uid>…`**
- Marks one or more UIDs as processed (adds them to the `acked` set; triggers compaction).
- Idempotent, batchable, and order-independent — safe to call from concurrent subagents.
- After ack, those UIDs no longer appear under `list --new`.
- A filtered/invisible UID cannot be acked (returns not-found), preventing the agent from
  manipulating state for mail it isn't allowed to see.

**`emcli send --account <name> --to <addr>… [--cc <addr>…] [--bcc <addr>…] --subject <s> --body <text> [--attach <path>]… [--reply-to <uid>]`**
- Sends a plain-text message via the account's SMTP endpoint.
- `--reply-to <uid>` fetches the source message's `Message-ID` and `References` and sets
  `In-Reply-To`/`References` headers so the reply threads correctly. The referenced UID is
  read from the same account (subject to inbound filtering — a filtered source UID cannot
  be replied to).
- Enforcement: RO accounts are rejected; whitelist-out (if enabled) must pass for every
  recipient across to/cc/bcc or the entire send is blocked (Section 9).

### 7.2 Admin commands (human-readable / TUI)

Require `EMCLI_ADMIN_KEY`.

- **`emcli init`** — TUI flow: creates the DB (generating schema + DEK), adds the first account,
  and runs OAuth consent if the account is OAuth2. Requires both `EMCLI_ADMIN_KEY` and `EMCLI_KEY`
  (writes both DEK wrap slots). Idempotent — re-running does not regenerate the DEK.
- **`emcli account add | edit | remove | list`** — interactive add/edit; `list` prints a
  table (never secrets). `account add` accepts `--process-backlog` (default off) which sets
  the account's baseline policy: off ⇒ newly-seen folders floor at their current max UID
  (existing mail treated as handled); on ⇒ floor at 0 (existing mail is processed).
- **`emcli whitelist in|out add|remove|list --account <name>`** — manage whitelist entries.
- **`emcli config set|get`** — global settings (e.g. `audit_retention_days`).
- **`emcli audit list [--account <name>] [--limit N]`** — view recent audit entries.

### 7.2a `doctor` — agent-role diagnostics

`doctor` is authorised by `EMCLI_KEY` (or `EMCLI_ADMIN_KEY`). It verifies the key is present and
valid, the DB opens, and each account's IMAP/SMTP connectivity and auth succeed. Prints
human-readable diagnostics. Can be run by the agent or by a human; does not require admin privilege.

### 7.3 Defaults & limits
- `list --limit` default: 50; maximum: 500.
- Attachment handling in `get`: full base64 contents are returned. (No size cap in v1; the
  caller is responsible for limits. Revisit if payloads prove unwieldy.)

## 8. JSON output envelope

Every agent command prints exactly one object:

```json
{
  "error": false,
  "error_detail": {},
  "data": {}
}
```

- `error` — boolean.
- `error_detail` — object; empty `{}` on success, otherwise `{ "code": "...", "message": "..." }`.
  Never contains secret values.
- `data` — command-specific payload; `{}` or `[]` when not applicable.
- Process exit code mirrors `error` (0 on success, non-zero on error) for scripting, but
  the JSON is authoritative.

## 9. Enforcement semantics

Enforcement lives entirely in the `policy` package and is exercised on every agent action.

### Inbound (read: `list`, `get`, `search`, `ack`)
- If `whitelist_in_enabled`, the message sender must match a `whitelist_in` entry.
- If `subject_regex` is set (non-empty), the subject must match the regex.
- A message that fails either check is **invisible**: excluded from `list` and `search`
  results, not retrievable via `get`, and not ackable via `ack` (all return not-found). The
  agent has no way to learn that the message exists or to alter read state for it.

### Outbound (send)
- If account `mode` is `RO`, `send` is rejected.
- If `whitelist_out_enabled`, every recipient (to + cc + bcc) must match a `whitelist_out`
  entry. If any recipient fails, the **entire** send is blocked — no partial send.

### Address matching (both directions)
- Case-insensitive.
- An entry of the form `@domain.com` matches any address at that domain.
- Any other entry matches a full address exactly.

### Audit
- Every action (`list`, `get`, `search`, `ack`, `send`), allowed or blocked, writes one
  `audit_log` row.
- Blocked actions record a `reason` (e.g. `ro_mode`, `whitelist_out`, `filtered`).
- On each run that opens the DB, audit rows older than `audit_retention_days` are purged.

## 10. OAuth2 (Gmail and compatible)

- The user supplies their own OAuth client ID/secret (registered in their Google Cloud
  project) during account configuration.
- Consent uses the **loopback redirect** flow: `emcli` starts a temporary listener on
  `127.0.0.1:<ephemeral-port>`, opens the consent URL, captures the authorization code on
  redirect, exchanges it for tokens, and stores the **refresh token** (encrypted).
- Access tokens are obtained/refreshed automatically before IMAP/SMTP use and held only in
  memory.
- IMAP and SMTP authenticate via SASL XOAUTH2 using the current access token.

## 11. Error handling

- All agent-command failures return the JSON error envelope; they never crash with an
  uncaught panic or emit partial non-JSON output on stdout.
- Categories: configuration/key errors, DB errors, network/connection errors, auth
  errors, policy blocks, and not-found. Each maps to a stable `error_detail.code`.
- Secrets never appear in output, error details, or the audit log.

## 12. Testing

- **`policy`** — table-driven unit tests covering the matrix of mode × whitelist-in ×
  whitelist-out × subject-regex, including domain-match and case-insensitivity, and the
  "any recipient fails ⇒ whole send blocked" rule.
- **`store`** — encryption round-trip; decryption with the wrong key fails closed; schema
  migration; floor baseline per `process_backlog`; seen-set membership (`uid > floor` and
  not acked); out-of-order ack correctness; compaction collapses contiguous runs into the
  floor; `folder_state`/`acked` reset on `UIDVALIDITY` change.
- **`mail`** — integration tests against a containerized IMAP/SMTP server (e.g. GreenMail
  or Dovecot) for list/get/send and threading headers.
- **`oauth`** — token exchange/refresh against a mocked authorization server; loopback
  capture logic unit-tested.
- **CLI** — golden-file tests of the JSON envelope for representative success and error
  cases; assert no secret ever appears in output.

## 13. Open items / future work

- Optional attachment size cap on `get` if payloads prove unwieldy.
- Additional auth mechanisms (e.g. OAuth for non-Google providers) follow the same model.
- Whitelist semantics are currently per-account only; global defaults with overrides are
  explicitly out of scope for v1.
- No `unack` / re-process command in v1; the agent acks deliberately and acks are final
  (short of an admin reset). Add if a re-processing workflow proves necessary.