chore(release): default installer to v0.5.2

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

USER-MANUAL.md

@@ -33,8 +33,9 @@ This manual is for **using and administering** `emcli`. It assumes you have the
 ## 1. Key concepts
 
 **Two kinds of commands.**
-- **Admin commands** (`init`, `account`, `whitelist`, `config`, `audit`) require `EMCLI_ADMIN_KEY`
-  and are for *you*, the human. They print human-readable text or open an interactive form.
+- **Admin commands** (`init`, `account add/edit/remove`, `whitelist`, `config`, `audit`) require
+  `EMCLI_ADMIN_KEY` and are for *you*, the human. They print human-readable text or open an
+  interactive form. (`account list` is the one exception — it is also an agent command; see below.)
 - **Agent commands** (`list`, `get`, `search`, `ack`, `send`, `doctor`) require `EMCLI_KEY` (or
   `EMCLI_ADMIN_KEY` as a superset) and are for the *agent*. They print one line of JSON and
   nothing else, so a program can consume them reliably. (`doctor` prints human-readable text but
@@ -124,8 +125,12 @@ DEK for an admin command, even if it somehow knows the agent key.
 
 | Command | Role required |
 |---|---|
-| `list`, `get`, `search`, `ack`, `send`, `doctor` | Agent (`EMCLI_KEY` or `EMCLI_ADMIN_KEY`) |
-| `account`, `whitelist`, `config`, `audit` | Admin (`EMCLI_ADMIN_KEY` required) |
+| `list`, `get`, `search`, `ack`, `send`, `doctor`, `account list` | Agent (`EMCLI_KEY` or `EMCLI_ADMIN_KEY`) |
+| `account add/edit/remove`, `whitelist`, `config`, `audit` | Admin (`EMCLI_ADMIN_KEY` required) |
+
+`account list` is dual-role: with the admin key it prints the full `NAME MODE IMAP USER` table;
+with only `EMCLI_KEY` (an agent) it prints a JSON envelope exposing just `name`, `from`, and
+`can_send` — no host or login username.
 | `init` | Both keys required (writes both wrap slots) |
 
 ### Agent launcher guidance
@@ -191,6 +196,7 @@ emcli account add --name work --mode RW \
 | `--smtp-security` | `tls` | `tls` or `starttls` |
 | `--username` | — | Login username, usually your full email (required) |
 | `--password` | — | Login password or app password |
+| `--from` | — | Send-as address (blank = use username); bare or `"Display Name <addr>"` |
 | `--subject-regex` | — | Inbound subject filter (optional) |
 | `--whitelist-in` | off | Enable inbound whitelist |
 | `--whitelist-out` | off | Enable outbound whitelist |
@@ -260,9 +266,15 @@ emcli account edit --name work --mode RW --smtp-host smtp.example.com --smtp-por
 emcli account edit --name gmail --password 'new-app-password'   # rotate the app password
 ```
 
-> Note: the flag form of `account edit` covers connection/auth fields and `--subject-regex`. To
-> toggle whitelists or `process-backlog`, use the interactive form (`emcli account edit --name X`
-> with no other flags), or the `whitelist` commands in section 6.
+```bash
+emcli account edit --name work --from 'Work Team <you@yourdomain.com>'   # set the send-as address
+emcli account edit --name work --from ''                                 # clear it (revert to username)
+```
+
+> Note: the flag form of `account edit` covers connection/auth fields, `--from`, and
+> `--subject-regex`. Passing `--from ''` clears the send-as address so mail falls back to the login
+> username. To toggle whitelists or `process-backlog`, use the interactive form (`emcli account edit
+> --name X` with no other flags), or the `whitelist` commands in section 6.
 
 **Remove an account** (requires `--yes`):
 
@@ -420,6 +432,11 @@ emcli send --account gmail --to a@x.com --subject "Re: Hi" --body "thanks" \
 client. The source is subject to the inbound whitelist — you can't reply to mail you aren't allowed
 to see.
 
+The message's `From:` is the account's send-as address (`--from`, set on `account add`/`edit`); if
+none is configured it falls back to the login username. A display-name address like
+`Steve Cliff <me@example.com>` shows the name in the recipient's client while the bare address is
+used for the SMTP envelope.
+
 ---
 
 ## 8. The JSON envelope
@@ -540,8 +557,8 @@ base64-encoded 32-byte key (section 2). Agent commands (`list`, `get`, `search`,
 `doctor`) need this key.
 
 **"this command requires EMCLI_ADMIN_KEY (admin privilege)".** Set `EMCLI_ADMIN_KEY` (section 2).
-Admin commands (`account`, `whitelist`, `config`, `audit`, `init`) need this key; `EMCLI_KEY`
-alone is not enough for them.
+Admin commands (`account add/edit/remove`, `whitelist`, `config`, `audit`, `init`) need this key;
+`EMCLI_KEY` alone is not enough for them. (`account list` is the exception — an agent can run it.)
 
 **A command fails to decrypt / wrong key.** The key doesn't match the one used when the database
 was initialised. Restore the original key, or re-run `emcli init` (idempotent — it won't regenerate
@@ -582,7 +599,7 @@ emcli <command> --help # usage and flags for one command
 # Admin (requires EMCLI_ADMIN_KEY)
 emcli init                                            # create DB + add first account (form)
 emcli account add [flags | none for form]            # add an account
-emcli account list                                    # list accounts (no secrets)
+emcli account list                                    # full table (admin) / name+from+can_send JSON (agent)
 emcli account edit --name N [flags | none for form]  # change an account
 emcli account remove --name N --yes                   # delete an account
 emcli whitelist in|out add|remove|list --account N [--address A]

docs/superpowers/plans/2026-06-23-agent-account-list.md

@@ -0,0 +1,497 @@
+# Agent-readable `account list` Implementation Plan
+
+> **For agentic workers:** REQUIRED SUB-SKILL: Use superpowers:subagent-driven-development (recommended) or superpowers:executing-plans to implement this plan task-by-task. Steps use checkbox (`- [ ]`) syntax for tracking.
+
+**Goal:** Let an agent holding only `EMCLI_KEY` run `emcli account list` and get a reduced JSON view (name, from, can_send), while admin keeps the full text table and `account add/edit/remove` stay admin-only.
+
+**Architecture:** Make `commandRole` subcommand-aware so `account list` routes to the agent role; branch the `list` renderer on whether the admin key is present (admin → existing text table; agent → standard `Success` JSON envelope). No schema change; `ListAccounts` already avoids decrypting secrets.
+
+**Tech Stack:** Go, standard library (`flag`, `encoding/json`), existing `internal/cli` envelope helpers and `internal/crypto` key loaders.
+
+## Global Constraints
+
+- Agent output is the existing JSON envelope shape: `{"error":bool,"error_detail":{...},"data":{...}}` via `Success(...)` / `Failure(...)` in `internal/cli/envelope.go`.
+- Admin `account list` output stays byte-for-byte the current human-readable table (`NAME MODE IMAP USER`).
+- The agent (reduced) view exposes only `name`, `from`, `can_send` — never the IMAP host/port or login username.
+- `from = Account.SendFrom()` (explicit `FromAddress`, else `Username`). `can_send = (Mode == "RW")`.
+- `account add/edit/remove` remain admin-only (hard-require `EMCLI_ADMIN_KEY`, no fallback).
+- Privilege detection: a caller is "admin" iff `crypto.AdminKeyFromEnv()` returns no error.
+- Spec: `docs/superpowers/specs/2026-06-23-agent-account-list-design.md`.
+
+---
+
+### Task 1: Route `account list` to the agent role and render by privilege
+
+**Files:**
+- Modify: `internal/cli/run.go` (`commandRole`, its call site in `Run`)
+- Modify: `internal/cli/admin.go` (the `list` branch of `runAccount`; add `crypto` import)
+- Modify: `internal/cli/role_test.go` (`TestCommandRole`)
+- Modify: `internal/cli/security_invariant_test.go` (refused-commands set)
+- Create/Test: `internal/cli/account_list_test.go`
+
+**Interfaces:**
+- Consumes: `store.Account.SendFrom() string`, `store.Account.Mode string`, `store.Store.ListAccounts() ([]store.Account, error)`, `crypto.AdminKeyFromEnv() ([]byte, error)`, `Success(map[string]any) Envelope`, `Failure(code, msg string) Envelope`, `Envelope.Write(io.Writer) error`, test helpers `adminEnv(t)`, `run(t, args...)`.
+- Produces: `commandRole(args []string) store.Role` (signature changes from `commandRole(cmd string)`). Agent `account list` emits `{"data":{"accounts":[{"name":string,"from":string,"can_send":bool}]}}`.
+
+- [ ] **Step 1: Rewrite `TestCommandRole` for the new signature and subcommand routing**
+
+Replace the body of `TestCommandRole` in `internal/cli/role_test.go` with:
+
+```go
+func TestCommandRole(t *testing.T) {
+	adminCmds := [][]string{
+		{"whitelist"}, {"config"}, {"audit"},
+		{"account"}, {"account", "add"}, {"account", "edit"}, {"account", "remove"},
+	}
+	agentCmds := [][]string{
+		{"list"}, {"get"}, {"search"}, {"ack"}, {"send"}, {"doctor"},
+		{"account", "list"},
+	}
+	for _, c := range adminCmds {
+		if commandRole(c) != store.RoleAdmin {
+			t.Errorf("%v should be admin", c)
+		}
+	}
+	for _, c := range agentCmds {
+		if commandRole(c) != store.RoleAgent {
+			t.Errorf("%v should be agent", c)
+		}
+	}
+}
+```
+
+Note: `init` is intentionally absent from this table. `commandRole({"init"})` falls through to the agent arm, but `Run` dispatches `init` via its own bootstrap path (which requires both keys), so its `commandRole` result is never used — asserting a role for it here would be both wrong and meaningless.
+
+- [ ] **Step 2: Run the routing test to verify it fails to compile**
+
+Run: `go test ./internal/cli/ -run TestCommandRole`
+Expected: FAIL — compile error, `commandRole` takes `string`, called with `[]string`.
+
+- [ ] **Step 3: Make `commandRole` subcommand-aware, update its call site, and fix the security invariant**
+
+In `internal/cli/run.go`, replace:
+
+```go
+func commandRole(cmd string) store.Role {
+	switch cmd {
+	case "account", "whitelist", "config", "audit":
+		return store.RoleAdmin
+	default: // list, get, search, ack, send, doctor
+		return store.RoleAgent
+	}
+}
+```
+
+with:
+
+```go
+func commandRole(args []string) store.Role {
+	switch args[0] {
+	case "account":
+		// account list is a read-only discovery view available to agents;
+		// add/edit/remove mutate config and require admin.
+		if len(args) >= 2 && args[1] == "list" {
+			return store.RoleAgent
+		}
+		return store.RoleAdmin
+	case "whitelist", "config", "audit":
+		return store.RoleAdmin
+	default: // list, get, search, ack, send, doctor
+		return store.RoleAgent
+	}
+}
+```
+
+In `Run`, change the call site from `role := commandRole(cmd)` to `role := commandRole(args)`.
+
+In `internal/cli/security_invariant_test.go`, in `TestAgentKeyCannotRunAdminCommands`, replace the `adminAttempts` entry `{"account", "list"}` so the set covers a *mutating* account command instead (account list is now allowed for agents):
+
+```go
+	adminAttempts := [][]string{
+		{"account", "add", "--name", "x", "--imap-host", "h", "--username", "u@x.com"},
+		{"config", "set", "audit_retention_days", "30"},
+		{"audit"},
+	}
+```
+
+- [ ] **Step 4: Run the cli package tests to verify routing + invariant pass**
+
+Run: `go test ./internal/cli/ -run 'TestCommandRole|TestAgentKeyCannotRunAdminCommands'`
+Expected: PASS (both). The agent can no longer be proven to refuse `account list` — that is intended; the invariant now proves `account add` is refused and the DB is unchanged.
+
+- [ ] **Step 5: Add the rendering tests (agent JSON view + admin text view)**
+
+Create `internal/cli/account_list_test.go`:
+
+```go
+package cli
+
+import (
+	"encoding/json"
+	"strings"
+	"testing"
+)
+
+// With only EMCLI_KEY set, `account list` emits the reduced JSON envelope:
+// name/from/can_send, and never the IMAP host or login username.
+func TestAccountListAgentJSONView(t *testing.T) {
+	adminEnv(t) // both keys + initialized temp DB
+	run(t, "account", "add", "--name", "work", "--mode", "RW",
+		"--imap-host", "imap.example.com", "--smtp-host", "smtp.example.com",
+		"--username", "login@example.com", "--from", "me@example.com")
+	run(t, "account", "add", "--name", "alerts", "--mode", "RO",
+		"--imap-host", "imap.example.com", "--username", "alerts@example.com")
+
+	// Drop the admin key → caller is an agent.
+	t.Setenv("EMCLI_ADMIN_KEY", "")
+	code, out, errOut := run(t, "account", "list")
+	if code != 0 {
+		t.Fatalf("agent account list should succeed: code=%d err=%q", code, errOut)
+	}
+
+	var env struct {
+		Error bool `json:"error"`
+		Data  struct {
+			Accounts []struct {
+				Name    string `json:"name"`
+				From    string `json:"from"`
+				CanSend bool   `json:"can_send"`
+			} `json:"accounts"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal([]byte(out), &env); err != nil {
+		t.Fatalf("output is not the agent envelope: %v\n%s", err, out)
+	}
+	if env.Error || len(env.Data.Accounts) != 2 {
+		t.Fatalf("want 2 accounts and no error, got %+v", env)
+	}
+	// The reduced view must not leak the IMAP host or the login username.
+	if strings.Contains(out, "imap.example.com") || strings.Contains(out, "login@example.com") {
+		t.Fatalf("agent view leaked host/username:\n%s", out)
+	}
+
+	got := map[string]struct {
+		from    string
+		canSend bool
+	}{}
+	for _, a := range env.Data.Accounts {
+		got[a.Name] = struct {
+			from    string
+			canSend bool
+		}{a.From, a.CanSend}
+	}
+	if g := got["work"]; g.from != "me@example.com" || !g.canSend {
+		t.Errorf("work: want from=me@example.com can_send=true, got %+v", g)
+	}
+	// alerts has no --from → SendFrom() falls back to the username.
+	if g := got["alerts"]; g.from != "alerts@example.com" || g.canSend {
+		t.Errorf("alerts: want from=alerts@example.com can_send=false, got %+v", g)
+	}
+}
+
+// With the admin key present, `account list` stays the full human-readable table.
+func TestAccountListAdminTextView(t *testing.T) {
+	adminEnv(t)
+	run(t, "account", "add", "--name", "work", "--mode", "RW",
+		"--imap-host", "imap.example.com", "--smtp-host", "smtp.example.com",
+		"--username", "login@example.com", "--from", "me@example.com")
+
+	code, out, _ := run(t, "account", "list")
+	if code != 0 {
+		t.Fatalf("admin account list failed: code=%d", code)
+	}
+	for _, want := range []string{"NAME", "MODE", "IMAP", "USER", "imap.example.com:993", "login@example.com"} {
+		if !strings.Contains(out, want) {
+			t.Fatalf("admin view missing %q:\n%s", want, out)
+		}
+	}
+	if strings.Contains(out, `"accounts"`) {
+		t.Fatalf("admin view should be text, not JSON:\n%s", out)
+	}
+}
+```
+
+- [ ] **Step 6: Run the rendering tests to verify the agent view fails**
+
+Run: `go test ./internal/cli/ -run 'TestAccountListAgentJSONView|TestAccountListAdminTextView'`
+Expected: `TestAccountListAdminTextView` PASS (already text); `TestAccountListAgentJSONView` FAIL — output is still the text table, so `json.Unmarshal` errors.
+
+- [ ] **Step 7: Split the `list` branch by privilege in `runAccount`**
+
+In `internal/cli/admin.go`, add the crypto import. Change the import block:
+
+```go
+import (
+	"flag"
+	"fmt"
+	"io"
+	"strconv"
+
+	"git.dcglab.co.uk/steve/emcli/internal/crypto"
+	"git.dcglab.co.uk/steve/emcli/internal/store"
+	"git.dcglab.co.uk/steve/emcli/internal/tui"
+)
+```
+
+Replace the `case "list":` block (currently):
+
+```go
+	case "list":
+		accs, err := st.ListAccounts()
+		if err != nil {
+			fmt.Fprintf(errOut, "list: %v\n", err)
+			return 1
+		}
+		fmt.Fprintf(out, "%-16s %-4s %-28s %s\n", "NAME", "MODE", "IMAP", "USER")
+		for _, a := range accs {
+			fmt.Fprintf(out, "%-16s %-4s %-28s %s\n",
+				a.Name, a.Mode, fmt.Sprintf("%s:%d", a.IMAPHost, a.IMAPPort), a.Username)
+		}
+		return 0
+```
+
+with:
+
+```go
+	case "list":
+		// Holding the admin key means the caller is the human admin (full
+		// detail). An agent holds only EMCLI_KEY and gets a reduced JSON view.
+		_, adminErr := crypto.AdminKeyFromEnv()
+		isAdmin := adminErr == nil
+		accs, err := st.ListAccounts()
+		if err != nil {
+			if isAdmin {
+				fmt.Fprintf(errOut, "list: %v\n", err)
+			} else {
+				_ = Failure(CodeDB, err.Error()).Write(out)
+			}
+			return 1
+		}
+		if !isAdmin {
+			items := make([]map[string]any, 0, len(accs))
+			for _, a := range accs {
+				items = append(items, map[string]any{
+					"name":     a.Name,
+					"from":     a.SendFrom(),
+					"can_send": a.Mode == "RW",
+				})
+			}
+			_ = Success(map[string]any{"accounts": items}).Write(out)
+			return 0
+		}
+		fmt.Fprintf(out, "%-16s %-4s %-28s %s\n", "NAME", "MODE", "IMAP", "USER")
+		for _, a := range accs {
+			fmt.Fprintf(out, "%-16s %-4s %-28s %s\n",
+				a.Name, a.Mode, fmt.Sprintf("%s:%d", a.IMAPHost, a.IMAPPort), a.Username)
+		}
+		return 0
+```
+
+- [ ] **Step 8: Run the full cli package test suite**
+
+Run: `go test ./internal/cli/`
+Expected: PASS (all tests, including the two new rendering tests, the routing test, and the security invariant).
+
+- [ ] **Step 9: Run the whole module to confirm nothing else regressed**
+
+Run: `go build ./... && go test ./...`
+Expected: build clean; all packages PASS.
+
+- [ ] **Step 10: Commit**
+
+```bash
+git add internal/cli/run.go internal/cli/admin.go internal/cli/role_test.go \
+        internal/cli/security_invariant_test.go internal/cli/account_list_test.go
+git commit -m "feat(cli): agent-readable account list (reduced JSON view)
+
+account list now routes to the agent role; an agent (EMCLI_KEY only) gets a
+JSON envelope of name/from/can_send, while the admin keeps the full text
+table. account add/edit/remove stay admin-only.
+
+Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>"
+```
+
+---
+
+### Task 2: Update user and agent documentation
+
+**Files:**
+- Modify: `USER-MANUAL.md` (command-kinds note, role table, cheatsheet)
+- Modify: `skills/emcli/SKILL.md` (allowed-commands note, command table, do/don't)
+- Modify: `skills/emcli/AGENTIC-MANUAL.md` (§4 account discovery)
+
+**Interfaces:**
+- Consumes: behavior shipped in Task 1 (agent `account list` → `{"data":{"accounts":[{name,from,can_send}]}}`).
+- Produces: docs only; no code interface.
+
+- [ ] **Step 1: USER-MANUAL — note that `account list` is the one agent-readable admin view**
+
+In `USER-MANUAL.md`, in the "Two kinds of commands" block, change the Admin bullet (line ~36) from:
+
+```
+- **Admin commands** (`init`, `account`, `whitelist`, `config`, `audit`) require `EMCLI_ADMIN_KEY`
+  and are for *you*, the human. They print human-readable text or open an interactive form.
+```
+
+to:
+
+```
+- **Admin commands** (`init`, `account add/edit/remove`, `whitelist`, `config`, `audit`) require
+  `EMCLI_ADMIN_KEY` and are for *you*, the human. They print human-readable text or open an
+  interactive form. (`account list` is the one exception — it is also an agent command; see below.)
+```
+
+- [ ] **Step 2: USER-MANUAL — update the role table**
+
+Replace the role table rows (lines ~127-128):
+
+```
+| `list`, `get`, `search`, `ack`, `send`, `doctor` | Agent (`EMCLI_KEY` or `EMCLI_ADMIN_KEY`) |
+| `account`, `whitelist`, `config`, `audit` | Admin (`EMCLI_ADMIN_KEY` required) |
+```
+
+with:
+
+```
+| `list`, `get`, `search`, `ack`, `send`, `doctor`, `account list` | Agent (`EMCLI_KEY` or `EMCLI_ADMIN_KEY`) |
+| `account add/edit/remove`, `whitelist`, `config`, `audit` | Admin (`EMCLI_ADMIN_KEY` required) |
+
+`account list` is dual-role: with the admin key it prints the full `NAME MODE IMAP USER` table;
+with only `EMCLI_KEY` (an agent) it prints a JSON envelope exposing just `name`, `from`, and
+`can_send` — no host or login username.
+```
+
+- [ ] **Step 3: USER-MANUAL — annotate the cheatsheet**
+
+In the cheatsheet (line ~597), change:
+
+```
+emcli account list                                    # list accounts (no secrets)
+```
+
+to:
+
+```
+emcli account list                                    # full table (admin) / name+from+can_send JSON (agent)
+```
+
+- [ ] **Step 4: SKILL.md — carve `account list` out of the forbidden-commands rule**
+
+In `skills/emcli/SKILL.md`, change the first bullet (lines ~20-24):
+
+```
+- **You only run agent commands:** `list`, `get`, `search`, `ack`, `send`, `doctor`. You are
+  provided only `EMCLI_KEY` (the agent key), which authorises these commands and nothing else.
+  Account setup, passwords, whitelists, and config are the **user's** job (admin commands that
+  require `EMCLI_ADMIN_KEY`) — do not run or suggest running `account`, `whitelist`, `config`,
+  `audit`, or `init`. You have only `EMCLI_KEY` (agent key); `emcli` will refuse admin commands
+  with a privilege error.
+```
+
+to:
+
+```
+- **You only run agent commands:** `list`, `get`, `search`, `ack`, `send`, `doctor`, and
+  `account list` (to discover accounts). You are provided only `EMCLI_KEY` (the agent key), which
+  authorises these and nothing else. Account *setup* (`account add/edit/remove`), passwords,
+  whitelists, and config are the **user's** job (admin commands that require `EMCLI_ADMIN_KEY`) —
+  do not run or suggest running `account add/edit/remove`, `whitelist`, `config`, `audit`, or
+  `init`. `emcli` will refuse those with a privilege error.
+```
+
+- [ ] **Step 5: SKILL.md — add `account list` to the command table**
+
+In the command table (after the `send` row, line ~122), add:
+
+```
+| `emcli account list` | Discover accounts: JSON `name` / `from` / `can_send` per account |
+```
+
+- [ ] **Step 6: SKILL.md — fix the "don't" bullet**
+
+Change (lines ~147-148):
+
+```
+- ❌ Don't run admin commands (`account`/`whitelist`/`config`/`audit`/`init`) — you have only
+  `EMCLI_KEY` (agent key); `emcli` will refuse admin commands with a privilege error.
+```
+
+to:
+
+```
+- ❌ Don't run admin commands (`account add/edit/remove`, `whitelist`, `config`, `audit`, `init`) —
+  you have only `EMCLI_KEY` (agent key); `emcli` will refuse them with a privilege error.
+  (`account list` is allowed — use it to discover accounts.)
+```
+
+Also change the ✅ bullet (line ~145) from `Ask the user for the account name; keep bodies plain text.` to:
+
+```
+- ✅ Discover accounts with `emcli account list`, or ask the user; keep bodies plain text.
+```
+
+- [ ] **Step 7: AGENTIC-MANUAL — document discovery via `account list`**
+
+In `skills/emcli/AGENTIC-MANUAL.md`, replace the body of `## 4. Find the account(s)` (lines ~88-97):
+
+```
+You refer to an account by name (e.g. `gmail`, `work`). Ask the user which account to use.
+`emcli doctor` is an agent command (authorised by `EMCLI_KEY`), so you can run it to check that
+configured accounts connect and authenticate:
+
+```bash
+emcli doctor              # all accounts
+emcli doctor --account gmail
+```
+
+Just take the account name from the user and start with the workflow in `SKILL.md`.
+```
+
+with:
+
+```
+You refer to an account by name (e.g. `gmail`, `work`). Discover the configured accounts yourself
+with `emcli account list` (an agent command authorised by `EMCLI_KEY`); it prints a JSON envelope
+with one entry per account:
+
+```bash
+emcli account list
+# {"error":false,"error_detail":{},"data":{"accounts":[
+#   {"name":"gmail","from":"me@gmail.com","can_send":true},
+#   {"name":"alerts","from":"alerts@x.com","can_send":false}]}}
+```
+
+`name` is what you pass to `--account`; `from` is the send-as identity; `can_send` is false for
+read-only accounts (they reject `send`). If unsure which to use, ask the user. `emcli doctor`
+(also an agent command) checks that accounts connect and authenticate:
+
+```bash
+emcli doctor              # all accounts
+emcli doctor --account gmail
+```
+
+Then start with the workflow in `SKILL.md`.
+```
+
+- [ ] **Step 8: Sanity-check the docs render and reference reality**
+
+Run: `grep -n "account list" USER-MANUAL.md skills/emcli/SKILL.md skills/emcli/AGENTIC-MANUAL.md`
+Expected: each file shows the updated `account list` references; no remaining text claims the agent cannot run `account list`.
+
+- [ ] **Step 9: Commit**
+
+```bash
+git add USER-MANUAL.md skills/emcli/SKILL.md skills/emcli/AGENTIC-MANUAL.md
+git commit -m "docs: agent can discover accounts via account list
+
+Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>"
+```
+
+---
+
+## Notes for the implementer
+
+- Run all Go commands from the repo root (`/home/steve/src/emcli`).
+- The two intentional red states are Step 2 (compile error) and Step 6 (agent JSON test) in Task 1. Every other test run must be green.
+- Do not change the admin text table or add columns to it — admin output must stay identical.
+- `adminEnv(t)` and `run(t, ...)` live in `internal/cli/admin_test.go`; `b64Key`/`b64AgentKey` in `internal/cli/run_test.go`. No new helpers are needed.

docs/superpowers/plans/2026-06-23-send-from-address.md

@@ -0,0 +1,688 @@
+# Send-as "From" Address Implementation Plan
+
+> **For agentic workers:** REQUIRED SUB-SKILL: Use superpowers:subagent-driven-development (recommended) or superpowers:executing-plans to implement this plan task-by-task. Steps use checkbox (`- [ ]`) syntax for tracking.
+
+**Goal:** Let each account configure the email address used as the `From:` when sending, instead of always reusing the login username.
+
+**Architecture:** Add a single freeform RFC 5322 `from_address` field to the account (bare address or `Display Name <addr>`). When blank, sending falls back to the login username — no migration of existing data. The header `From:` carries the full identity; the SMTP envelope sender is derived as the bare address. A version-gated `ALTER TABLE` migration adds the column to existing databases.
+
+**Tech Stack:** Go, SQLite (`modernc.org/sqlite`), `github.com/emersion/go-message/mail` for MIME, `net/mail` (stdlib) for address validation, bubbletea TUI.
+
+## Global Constraints
+
+- Module path: `git.dcglab.co.uk/steve/emcli`.
+- The `from_address` field is **not** a secret — store as plaintext (like `username`), never encrypted.
+- A blank from-address is always valid and means "fall back to `Account.Username`".
+- Follow existing patterns: `nullStr` for nullable text columns, `sql.NullString` in `scanAccount`, `fs.Visit` overlay for `account edit` flags.
+- Tests are Go table/unit tests in the same package; reuse the existing `openTemp(t)` helper where keys are needed.
+
+---
+
+### Task 1: Store — field, migration, persistence
+
+**Files:**
+- Modify: `internal/store/account.go` (Account struct, AddAccount, GetAccount, ListAccounts, UpdateAccount, scanAccount)
+- Modify: `internal/store/schema.go` (add column, bump schemaVersion)
+- Modify: `internal/store/store.go` (run migration in Open)
+- Modify: `internal/store/store_test.go` (update schema_version expectations to "2")
+- Test: `internal/store/account_test.go` (SendFrom + round-trip), `internal/store/store_test.go` (migration)
+
+**Interfaces:**
+- Produces: `store.Account.FromAddress string` field; method `func (a Account) SendFrom() string`; schema at version 2 with `accounts.from_address TEXT` column.
+
+- [ ] **Step 1: Write the failing test for SendFrom + round-trip**
+
+Add to `internal/store/account_test.go`:
+
+```go
+func TestSendFromFallsBackToUsername(t *testing.T) {
+	a := Account{Username: "login@example.com"}
+	if got := a.SendFrom(); got != "login@example.com" {
+		t.Fatalf("blank from-address should fall back to username, got %q", got)
+	}
+	a.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if got := a.SendFrom(); got != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("set from-address should win, got %q", got)
+	}
+}
+
+func TestAddGetAccountRoundTripsFromAddress(t *testing.T) {
+	s := openTemp(t)
+	a := sampleAccount()
+	a.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if _, err := s.AddAccount(a); err != nil {
+		t.Fatalf("AddAccount: %v", err)
+	}
+	got, err := s.GetAccount("work")
+	if err != nil {
+		t.Fatalf("GetAccount: %v", err)
+	}
+	if got.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("FromAddress not round-tripped: %q", got.FromAddress)
+	}
+}
+```
+
+- [ ] **Step 2: Run tests to verify they fail**
+
+Run: `go test ./internal/store/ -run 'TestSendFrom|TestAddGetAccountRoundTripsFromAddress' -v`
+Expected: FAIL — `a.SendFrom undefined` and `a.FromAddress undefined`.
+
+- [ ] **Step 3: Add the field and SendFrom method**
+
+In `internal/store/account.go`, add `FromAddress` to the struct (right after `Username`) and the method. The struct becomes:
+
+```go
+type Account struct {
+	ID                  int64
+	Name                string
+	Mode                string // RO | RW
+	IMAPHost            string
+	IMAPPort            int
+	IMAPSecurity        string // tls | starttls
+	SMTPHost            string // nullable for RO accounts
+	SMTPPort            int
+	SMTPSecurity        string // tls | starttls
+	AuthType            string // password | oauth2
+	Username            string
+	FromAddress         string // send-as identity; blank ⇒ fall back to Username
+	Password            string // decrypted; empty in ListAccounts
+	WhitelistInEnabled  bool
+	WhitelistOutEnabled bool
+	SubjectRegex        string
+	ProcessBacklog      bool
+}
+
+// SendFrom returns the From identity for outgoing mail, falling back to the
+// login username when no explicit from-address is configured.
+func (a Account) SendFrom() string {
+	if a.FromAddress != "" {
+		return a.FromAddress
+	}
+	return a.Username
+}
+```
+
+- [ ] **Step 4: Thread from_address through persistence**
+
+In `internal/store/account.go`:
+
+AddAccount — add `from_address` to the column list and a value placeholder. The INSERT becomes:
+
+```go
+	res, err := s.db.Exec(`
+		INSERT INTO accounts
+		  (name,mode,imap_host,imap_port,imap_security,smtp_host,smtp_port,smtp_security,
+		   auth_type,username,from_address,
+		   enc_password,whitelist_in_enabled,whitelist_out_enabled,subject_regex,process_backlog)
+		VALUES (?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?)`,
+		a.Name, a.Mode, a.IMAPHost, a.IMAPPort, a.IMAPSecurity,
+		nullStr(a.SMTPHost), nullInt(a.SMTPPort), nullStr(a.SMTPSecurity),
+		a.AuthType, a.Username, nullStr(a.FromAddress),
+		encPw, b2i(a.WhitelistInEnabled), b2i(a.WhitelistOutEnabled),
+		nullStr(a.SubjectRegex), b2i(a.ProcessBacklog))
+```
+
+GetAccount and ListAccounts — add `from_address` to both SELECT column lists, right after `username`:
+
+```go
+		SELECT id,name,mode,imap_host,imap_port,imap_security,smtp_host,smtp_port,smtp_security,
+		       auth_type,username,from_address,
+		       enc_password,whitelist_in_enabled,whitelist_out_enabled,subject_regex,process_backlog
+```
+
+UpdateAccount — add `from_address=?` to the SET clause and its arg (after `username=?` / `a.Username`):
+
+```go
+	set := `mode=?, imap_host=?, imap_port=?, imap_security=?,
+	        smtp_host=?, smtp_port=?, smtp_security=?,
+	        auth_type=?, username=?, from_address=?,
+	        whitelist_in_enabled=?, whitelist_out_enabled=?, subject_regex=?, process_backlog=?`
+	args := []any{
+		a.Mode, a.IMAPHost, a.IMAPPort, a.IMAPSecurity,
+		nullStr(a.SMTPHost), nullInt(a.SMTPPort), nullStr(a.SMTPSecurity),
+		a.AuthType, a.Username, nullStr(a.FromAddress),
+		b2i(a.WhitelistInEnabled), b2i(a.WhitelistOutEnabled),
+		nullStr(a.SubjectRegex), b2i(a.ProcessBacklog),
+	}
+```
+
+scanAccount — add a `fromAddr sql.NullString` local, scan it after `&a.Username`, and assign. The var block gains `fromAddr sql.NullString`; the Scan call becomes:
+
+```go
+	err := sc.Scan(&a.ID, &a.Name, &a.Mode, &a.IMAPHost, &a.IMAPPort, &a.IMAPSecurity,
+		&smtpHost, &smtpPort, &smtpSec,
+		&a.AuthType, &a.Username, &fromAddr, &encPw, &wlIn, &wlOut, &subj, &backlog)
+```
+
+and after the existing assignments add:
+
+```go
+	a.FromAddress = fromAddr.String
+```
+
+- [ ] **Step 5: Add the column to the schema and bump the version**
+
+In `internal/store/schema.go`, change `const schemaVersion = 1` to `const schemaVersion = 2`, and add the column to the `accounts` CREATE TABLE, right after the `username` line:
+
+```sql
+  username                TEXT NOT NULL,
+  from_address            TEXT,
+  enc_password            BLOB,
+```
+
+- [ ] **Step 6: Run the round-trip + SendFrom tests to verify they pass**
+
+Run: `go test ./internal/store/ -run 'TestSendFrom|TestAddGetAccountRoundTripsFromAddress' -v`
+Expected: PASS.
+
+- [ ] **Step 7: Write the failing migration test**
+
+The existing `TestOpenCreatesSchemaAndIsIdempotent` will now fail because it expects `schema_version == "1"`. Update both assertions in `internal/store/store_test.go` from `"1"` to `"2"`. Then add a new migration test in `internal/store/store_test.go`:
+
+```go
+func TestOpenMigratesV1AddsFromAddress(t *testing.T) {
+	p := filepath.Join(t.TempDir(), "emcli.db")
+
+	// Hand-build a v1 database: accounts table WITHOUT from_address, a settings
+	// table pinned at schema_version=1, and one pre-existing account row.
+	raw, err := sql.Open("sqlite", p)
+	if err != nil {
+		t.Fatalf("sql.Open: %v", err)
+	}
+	const v1Schema = `
+CREATE TABLE settings (key TEXT PRIMARY KEY, value TEXT NOT NULL);
+CREATE TABLE accounts (
+  id            INTEGER PRIMARY KEY AUTOINCREMENT,
+  name          TEXT UNIQUE NOT NULL,
+  mode          TEXT NOT NULL,
+  imap_host     TEXT NOT NULL,
+  imap_port     INTEGER NOT NULL,
+  imap_security TEXT NOT NULL,
+  smtp_host     TEXT, smtp_port INTEGER, smtp_security TEXT,
+  auth_type     TEXT NOT NULL,
+  username      TEXT NOT NULL,
+  enc_password  BLOB,
+  enc_oauth_client_id BLOB, enc_oauth_client_secret BLOB, enc_oauth_refresh_token BLOB,
+  whitelist_in_enabled INTEGER NOT NULL DEFAULT 0,
+  whitelist_out_enabled INTEGER NOT NULL DEFAULT 0,
+  subject_regex TEXT,
+  process_backlog INTEGER NOT NULL DEFAULT 0
+);
+INSERT INTO settings(key,value) VALUES ('schema_version','1');
+INSERT INTO accounts(name,mode,imap_host,imap_port,imap_security,auth_type,username)
+  VALUES ('legacy','RO','imap.example.com',993,'tls','password','login@example.com');
+`
+	if _, err := raw.Exec(v1Schema); err != nil {
+		t.Fatalf("seed v1 schema: %v", err)
+	}
+	raw.Close()
+
+	// Open via the store: the migration must add from_address and bump to v2.
+	s, err := Open(p)
+	if err != nil {
+		t.Fatalf("Open (migrate): %v", err)
+	}
+	defer s.Close()
+
+	if v, _ := s.GetSetting("schema_version"); v != "2" {
+		t.Fatalf("schema_version after migrate: %q, want 2", v)
+	}
+	// ListAccounts SELECTs from_address; it would error if the column were missing.
+	accs, err := s.ListAccounts()
+	if err != nil {
+		t.Fatalf("ListAccounts after migrate: %v", err)
+	}
+	if len(accs) != 1 || accs[0].FromAddress != "" {
+		t.Fatalf("legacy account wrong after migrate: %+v", accs)
+	}
+	if got := accs[0].SendFrom(); got != "login@example.com" {
+		t.Fatalf("legacy account should send from username, got %q", got)
+	}
+}
+```
+
+Ensure `internal/store/store_test.go` imports `"database/sql"` (add it to the import block).
+
+- [ ] **Step 8: Run the migration test to verify it fails**
+
+Run: `go test ./internal/store/ -run 'TestOpenMigratesV1AddsFromAddress|TestOpenCreatesSchemaAndIsIdempotent' -v`
+Expected: migration test FAILS with a "no such column: from_address" error from `ListAccounts` (the column is in the schema for new DBs but not added to the seeded v1 DB).
+
+- [ ] **Step 9: Add the migration runner to Open**
+
+In `internal/store/store.go`, replace the post-schema version block with a call to a new `migrate` method. Change the tail of `Open` from:
+
+```go
+	s := &Store{db: db}
+	if _, err := s.GetSetting("schema_version"); err != nil {
+		if err := s.SetSetting("schema_version", strconv.Itoa(schemaVersion)); err != nil {
+			db.Close()
+			return nil, err
+		}
+	}
+	return s, nil
+```
+
+to:
+
+```go
+	s := &Store{db: db}
+	if err := s.migrate(); err != nil {
+		db.Close()
+		return nil, err
+	}
+	return s, nil
+```
+
+and add the method:
+
+```go
+// migrate brings an existing database up to the current schemaVersion. A brand-
+// new database (no schema_version yet) already has every column from schemaSQL,
+// so it is simply stamped at the current version. Each older version runs its
+// forward step. The version gate makes every step idempotent across reopens.
+func (s *Store) migrate() error {
+	v, err := s.GetSetting("schema_version")
+	if err != nil {
+		// Fresh database: schemaSQL created all columns already.
+		return s.SetSetting("schema_version", strconv.Itoa(schemaVersion))
+	}
+	ver, _ := strconv.Atoi(v)
+	if ver < 2 {
+		if _, err := s.db.Exec(`ALTER TABLE accounts ADD COLUMN from_address TEXT`); err != nil {
+			return fmt.Errorf("migrate to v2: %w", err)
+		}
+		if err := s.SetSetting("schema_version", "2"); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+```
+
+Confirm `internal/store/store.go` already imports `fmt` and `strconv` (it does); no import changes needed.
+
+- [ ] **Step 10: Run the full store test suite to verify it passes**
+
+Run: `go test ./internal/store/ -v`
+Expected: PASS (migration, idempotency, round-trip, and existing tests all green).
+
+- [ ] **Step 11: Commit**
+
+```bash
+git add internal/store/account.go internal/store/schema.go internal/store/store.go internal/store/account_test.go internal/store/store_test.go
+git commit -m "feat(store): add account from_address field + v2 migration
+
+Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>"
+```
+
+---
+
+### Task 2: Mail — envelope sender vs header From
+
+**Files:**
+- Modify: `internal/mail/send.go` (add `envelopeFrom` helper, use it in `SendSMTP`)
+- Test: `internal/mail/send_test.go` (envelopeFrom table test + BuildMIME display-name assertion)
+
+**Interfaces:**
+- Consumes: `OutgoingMessage.From` may now hold `Display Name <addr>`.
+- Produces: `func envelopeFrom(from string) string` (package-private) — bare address for the SMTP envelope.
+
+- [ ] **Step 1: Write the failing test for envelopeFrom and the display-name header**
+
+Add to `internal/mail/send_test.go`:
+
+```go
+func TestEnvelopeFromStripsDisplayName(t *testing.T) {
+	cases := map[string]string{
+		"Steve Cliff <me@stevecliff.com>": "me@stevecliff.com",
+		"me@stevecliff.com":               "me@stevecliff.com",
+		"<me@stevecliff.com>":             "me@stevecliff.com",
+		"not a valid address":             "not a valid address", // unparseable ⇒ passthrough
+	}
+	for in, want := range cases {
+		if got := envelopeFrom(in); got != want {
+			t.Fatalf("envelopeFrom(%q) = %q, want %q", in, got, want)
+		}
+	}
+}
+
+func TestBuildMIMEKeepsDisplayNameInHeader(t *testing.T) {
+	raw, err := BuildMIME(OutgoingMessage{
+		From:     "Steve Cliff <me@stevecliff.com>",
+		To:       []string{"you@example.com"},
+		Subject:  "hi",
+		BodyText: "body",
+		Date:     time.Date(2026, 6, 23, 12, 0, 0, 0, time.UTC),
+	})
+	if err != nil {
+		t.Fatalf("BuildMIME: %v", err)
+	}
+	if !strings.Contains(string(raw), "Steve Cliff") {
+		t.Fatalf("From header lost display name:\n%s", raw)
+	}
+}
+```
+
+- [ ] **Step 2: Run the tests to verify they fail**
+
+Run: `go test ./internal/mail/ -run 'TestEnvelopeFromStripsDisplayName|TestBuildMIMEKeepsDisplayNameInHeader' -v`
+Expected: FAIL — `envelopeFrom` undefined. (The BuildMIME test may already pass, since `SetAddressList` renders display names; the envelopeFrom test is the gating failure.)
+
+- [ ] **Step 3: Add the envelopeFrom helper and use it in SendSMTP**
+
+In `internal/mail/send.go`, add the helper (near `addrList`):
+
+```go
+// envelopeFrom returns the bare address for the SMTP envelope sender, stripping
+// any display name. A display-name From (e.g. "Name <addr>") is a valid header
+// but an invalid envelope sender, so it must be reduced to the bare address.
+// Unparseable input is passed through unchanged (preserves prior behaviour for
+// plain addresses).
+func envelopeFrom(from string) string {
+	if a, err := gomail.ParseAddress(from); err == nil {
+		return a.Address
+	}
+	return from
+}
+```
+
+In `SendSMTP`, change the send line from:
+
+```go
+	if err := c.SendMail(m.From, m.Recipients(), bytes.NewReader(raw)); err != nil {
+```
+
+to:
+
+```go
+	if err := c.SendMail(envelopeFrom(m.From), m.Recipients(), bytes.NewReader(raw)); err != nil {
+```
+
+- [ ] **Step 4: Run the tests to verify they pass**
+
+Run: `go test ./internal/mail/ -run 'TestEnvelopeFromStripsDisplayName|TestBuildMIMEKeepsDisplayNameInHeader' -v`
+Expected: PASS.
+
+- [ ] **Step 5: Run the full mail suite**
+
+Run: `go test ./internal/mail/`
+Expected: PASS (`imap_integration_test` may skip without a live server — that is fine).
+
+- [ ] **Step 6: Commit**
+
+```bash
+git add internal/mail/send.go internal/mail/send_test.go
+git commit -m "feat(mail): derive bare envelope sender from display-name From
+
+Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>"
+```
+
+---
+
+### Task 3: CLI + TUI — inputs, validation, and send wiring
+
+**Files:**
+- Modify: `internal/cli/send.go:26` (use `acc.SendFrom()`)
+- Modify: `internal/cli/admin.go` (`--from` flag on `account add` and `account edit`)
+- Modify: `internal/tui/account.go` (Fields field, fieldDef, ToAccount, FieldsFromAccount, fieldValue, collect, validation helper, Validate)
+- Test: `internal/tui/account_test.go` (validation + round-trip), `internal/cli/send_test.go` (send uses configured from)
+
+**Interfaces:**
+- Consumes: `store.Account.FromAddress`, `store.Account.SendFrom()` (Task 1).
+- Produces: `func ValidFromAddress(s string) error` exported from `tui` package, used by both `Fields.Validate` and `internal/cli/admin.go`.
+
+- [ ] **Step 1: Write the failing TUI validation + round-trip tests**
+
+Add to `internal/tui/account_test.go`:
+
+```go
+func TestValidateRejectsBadFromAddress(t *testing.T) {
+	f := validFields()
+	f.FromAddress = "not an address"
+	if err := f.Validate(); err == nil {
+		t.Fatal("malformed from-address should fail validation")
+	}
+	f.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if err := f.Validate(); err != nil {
+		t.Fatalf("display-name from-address should validate: %v", err)
+	}
+	f.FromAddress = "me@stevecliff.com"
+	if err := f.Validate(); err != nil {
+		t.Fatalf("bare from-address should validate: %v", err)
+	}
+	f.FromAddress = "" // blank ⇒ fall back, always valid
+	if err := f.Validate(); err != nil {
+		t.Fatalf("blank from-address should validate: %v", err)
+	}
+}
+
+func TestFieldsFromToAccountCarriesFromAddress(t *testing.T) {
+	f := validFields()
+	f.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	acc, _ := f.ToAccount()
+	if acc.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("ToAccount lost FromAddress: %q", acc.FromAddress)
+	}
+	back := FieldsFromAccount(acc)
+	if back.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("FieldsFromAccount lost FromAddress: %q", back.FromAddress)
+	}
+}
+```
+
+- [ ] **Step 2: Run the tests to verify they fail**
+
+Run: `go test ./internal/tui/ -run 'TestValidateRejectsBadFromAddress|TestFieldsFromToAccountCarriesFromAddress' -v`
+Expected: FAIL — `f.FromAddress` undefined.
+
+- [ ] **Step 3: Add the field, validation helper, and wiring in tui/account.go**
+
+In `internal/tui/account.go`:
+
+Add `"net/mail"` to the import block.
+
+Add `FromAddress` to `Fields` (after the `Username, Password` line):
+
+```go
+type Fields struct {
+	Name, Mode                                string
+	IMAPHost, IMAPPort, IMAPSecurity          string
+	SMTPHost, SMTPPort, SMTPSecurity          string
+	Username, Password                        string
+	FromAddress                               string
+	WhitelistIn, WhitelistOut, ProcessBacklog bool
+	SubjectRegex                              string
+}
+```
+
+Add the exported validator:
+
+```go
+// ValidFromAddress returns an error if s is set but is not a valid RFC 5322
+// address (bare or "Display Name <addr>"). A blank value is valid: sending
+// falls back to the login username.
+func ValidFromAddress(s string) error {
+	if strings.TrimSpace(s) == "" {
+		return nil
+	}
+	if _, err := mail.ParseAddress(s); err != nil {
+		return errors.New("from address must be a valid email address")
+	}
+	return nil
+}
+```
+
+In `Fields.Validate`, add before the final `return nil`:
+
+```go
+	if err := ValidFromAddress(f.FromAddress); err != nil {
+		return err
+	}
+```
+
+In `ToAccount`, set the field on the assembled account (add to the struct literal, after `Username/Password`):
+
+```go
+		AuthType: "password", Username: f.Username, Password: f.Password,
+		FromAddress: f.FromAddress,
+```
+
+In `FieldsFromAccount`, prefill it (after `Username: a.Username,`):
+
+```go
+		Username:    a.Username,
+		FromAddress: a.FromAddress,
+```
+
+Add a `fieldDef` to `fieldDefs`, immediately after the `username` entry (so it appears next to it in the form):
+
+```go
+	{key: "username", label: "Username"},
+	{key: "from_address", label: "From address (optional)"},
+	{key: "password", label: "Password", password: true},
+```
+
+- [ ] **Step 4: Wire from_address through fieldValue and collect**
+
+In `internal/tui/account.go`, find `fieldValue` (≈ line 147) and add a `case "from_address": return f.FromAddress` alongside the other string cases. Find `collect` (≈ line 228) and add the inverse mapping so the typed value is written back to `f.FromAddress` (mirror exactly how `username` is handled in that function's switch).
+
+- [ ] **Step 5: Run the tui tests to verify they pass**
+
+Run: `go test ./internal/tui/ -v`
+Expected: PASS (new validation/round-trip tests plus existing form tests).
+
+- [ ] **Step 6: Write the failing CLI send test**
+
+The harness in `internal/cli/send_test.go` records every sent message into `*sent`, so assert directly on `m.From`. Add:
+
+```go
+func TestSendUsesConfiguredFromAddress(t *testing.T) {
+	acc := rwAccount()
+	acc.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	d, sent, _ := sendDeps(t, acc, nil)
+	if err := SendCmd(d, "send", []string{"me@stevecliff.com"}, nil, nil, "hi", "body", nil, 0, "INBOX"); err != nil {
+		t.Fatalf("SendCmd: %v", err)
+	}
+	if len(*sent) != 1 {
+		t.Fatalf("want 1 send, got %d", len(*sent))
+	}
+	if got := (*sent)[0].From; got != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("From = %q, want configured from-address", got)
+	}
+}
+
+func TestSendFallsBackToUsernameAsFrom(t *testing.T) {
+	// rwAccount has no FromAddress, so From must be the login username.
+	d, sent, _ := sendDeps(t, rwAccount(), nil)
+	if err := SendCmd(d, "send", []string{"me@stevecliff.com"}, nil, nil, "hi", "body", nil, 0, "INBOX"); err != nil {
+		t.Fatalf("SendCmd: %v", err)
+	}
+	if got := (*sent)[0].From; got != "emcli@stevecliff.com" {
+		t.Fatalf("From = %q, want username fallback", got)
+	}
+}
+```
+
+- [ ] **Step 7: Run the CLI send test to verify it fails**
+
+Run: `go test ./internal/cli/ -run 'TestSendUsesConfiguredFromAddress' -v`
+Expected: FAIL — `send.go` still sets `From: acc.Username`.
+
+- [ ] **Step 8: Wire send.go and add the --from flags**
+
+In `internal/cli/send.go`, change:
+
+```go
+	msg := mail.OutgoingMessage{
+		From: acc.Username, To: to, Cc: cc, Bcc: bcc,
+		Subject: subject, BodyText: body,
+	}
+```
+
+to:
+
+```go
+	msg := mail.OutgoingMessage{
+		From: acc.SendFrom(), To: to, Cc: cc, Bcc: bcc,
+		Subject: subject, BodyText: body,
+	}
+```
+
+In `internal/cli/admin.go`, `account add`: register the flag and validate it.
+
+Add alongside the other `add` flags:
+
+```go
+		from := fs.String("from", "", "send-as address (blank = use username)")
+```
+
+After the required-fields check, before building `acc`:
+
+```go
+		if err := tui.ValidFromAddress(*from); err != nil {
+			fmt.Fprintln(errOut, err)
+			return 2
+		}
+```
+
+Add `FromAddress: *from,` to the `store.Account{...}` literal.
+
+In `account edit`: register the flag:
+
+```go
+		from := fs.String("from", "", "send-as address (blank keeps existing)")
+```
+
+Add a case to the `fs.Visit` switch:
+
+```go
+			case "from":
+				if err := tui.ValidFromAddress(*from); err != nil {
+					fmt.Fprintln(errOut, err)
+					return // see note below
+				}
+				acc.FromAddress = *from
+```
+
+Because `fs.Visit`'s callback cannot return an exit code, instead validate `--from` before the `fs.Visit` block (the flag value is available regardless of Visit) and set the field inside Visit:
+
+```go
+		if err := tui.ValidFromAddress(*from); err != nil {
+			fmt.Fprintln(errOut, err)
+			return 2
+		}
+		// ... existing GetAccount + fs.Visit ...
+			case "from":
+				acc.FromAddress = *from
+```
+
+Use this pre-Visit validation form (not the in-callback `return`).
+
+- [ ] **Step 9: Run the CLI suite to verify it passes**
+
+Run: `go test ./internal/cli/ -v`
+Expected: PASS.
+
+- [ ] **Step 10: Build and vet the whole module**
+
+Run: `go build ./... && go vet ./... && go test ./...`
+Expected: clean build, no vet complaints, all tests PASS.
+
+- [ ] **Step 11: Commit**
+
+```bash
+git add internal/cli/send.go internal/cli/admin.go internal/cli/send_test.go internal/tui/account.go internal/tui/account_test.go
+git commit -m "feat(cli): configurable send-as From address (flags, TUI, validation)
+
+Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>"
+```
+
+---
+
+## Notes for the implementer
+
+- The `account list` output (`admin.go`, `case "list"`) shows NAME/MODE/IMAP/USER. Adding a FROM column is optional polish, not required — leave it unless asked.
+- `USER-MANUAL.md` / `README.md` mention `account add` flags; if they enumerate flags explicitly, add `--from` there in the relevant commit. Grep first: `grep -rn 'account add\|--username' README.md USER-MANUAL.md docs/`.
+- Existing send tests in `internal/cli/send_test.go` define the harness shape — read them before writing Task 3 Step 6 rather than inventing a new fake.

docs/superpowers/specs/2026-06-23-agent-account-list-design.md

@@ -0,0 +1,141 @@
+# Agent-readable `account list` — design
+
+**Date:** 2026-06-23
+**Status:** Approved (brainstorm), ready for implementation plan
+**Author:** Steve + Claude
+
+## Problem
+
+An agent process is launched with only `EMCLI_KEY` (the two-key model — see
+`2026-06-22-two-key-privilege-design.md`). Every agent command takes
+`--account NAME`, but the agent has no way to *discover* which accounts exist:
+`account list` is classified admin-only and is refused under the agent key. So
+account names must be supplied to the agent out of band, which is brittle and
+defeats the point of a self-directed agent.
+
+The two-key spec deliberately gated the whole `account` command to admin because
+`account add/edit/remove` mutate configuration. But `account list` is read-only
+and exposes no secrets — `store.ListAccounts` never decrypts the password
+(`enc_password` is scanned and discarded). Gating *discovery* behind admin is
+stricter than the threat model requires.
+
+## Goal
+
+Let an agent holding only `EMCLI_KEY` run `account list` to discover the
+accounts it may operate on, while:
+
+- keeping `account add/edit/remove` admin-only (mutation stays gated);
+- exposing to the agent only what it needs — **account name, the send-as From
+  address, and whether the account can send** — and *not* the IMAP host/port or
+  login username;
+- preserving the admin's existing full-detail view unchanged.
+
+## Constraints / decisions
+
+Settled during brainstorming:
+
+1. **Scope is exactly `account list`.** `whitelist list`, `config get`, and
+   `audit list` stay admin-only. `audit` in particular is oversight data and
+   must remain invisible to the agent.
+2. **Privilege-dependent rendering.** The admin keeps the current full table
+   (`NAME  MODE  IMAP  USER`, human-readable). The agent gets a *reduced* view
+   containing only name, From, and send-capability.
+3. **Agent output is JSON.** The agent is a machine consumer, so its
+   `account list` emits the standard agent envelope (like `list`/`get`/`search`),
+   not a text table. The admin path stays human-readable text.
+4. **No secret exposure, no schema change.** `ListAccounts` already avoids
+   decrypting passwords; nothing about the data model changes.
+
+## Approach
+
+Reclassify `account list` to the agent role, and branch rendering on the
+caller's actual privilege (presence of the admin key).
+
+### Routing (`internal/cli/run.go`)
+
+`commandRole` becomes subcommand-aware for `account`:
+
+- `account list` → `RoleAgent`
+- `account add | edit | remove` (and bare `account`) → `RoleAdmin`
+- all other commands unchanged.
+
+`commandRole` currently takes `cmd string`; it changes to take the full
+`args []string` so it can peek at the `account` subcommand. `Run` passes
+`args` through. This keeps `commandRole` the single source of truth for the
+classification table.
+
+Authorization mechanics are unchanged: `openStore(RoleAgent)` requires
+`EMCLI_KEY` (falling back to the admin key for a human who holds only that and
+runs `account list`). `account add/edit/remove` still hard-require
+`EMCLI_ADMIN_KEY` with no fallback.
+
+### Rendering (`internal/cli/admin.go`, the `list` branch)
+
+Determine privilege from the environment: `_, err := crypto.AdminKeyFromEnv()`;
+`isAdmin := err == nil`. (Holding the admin key *is* being the admin in this
+trust model. A human with only the admin key still gets the admin view; an agent
+with only `EMCLI_KEY` gets the reduced view.)
+
+- **Admin** → existing full table, unchanged:
+  ```
+  NAME             MODE IMAP                         USER
+  work             RW   imap.example.com:993         me@example.com
+  ```
+- **Agent** → JSON envelope to stdout:
+  ```json
+  {"error":false,"error_detail":{},"data":{"accounts":[
+    {"name":"work","from":"me@example.com","can_send":true},
+    {"name":"alerts","from":"alerts@example.com","can_send":false}
+  ]}}
+  ```
+  where `from = Account.SendFrom()` (the configured From address, falling back
+  to the username) and `can_send = (Mode == "RW")` (RW accounts have SMTP
+  configured; RO cannot send). The IMAP host/port and the raw login username are
+  **not** emitted (when From falls back to the username it may coincide with it,
+  which is acceptable — the user asked for From specifically).
+
+The reduced view reuses the existing `Success(...)` envelope and `Envelope.Write`
+helper; no new output machinery.
+
+## Error handling
+
+- Agent key on `account add/edit/remove` → unchanged:
+  `emcli: this command requires EMCLI_ADMIN_KEY (admin privilege)`, non-zero.
+- Agent `account list` with neither key set → the agent-command config error
+  (`EMCLI_KEY is not set`), surfaced the same way other agent commands surface a
+  missing key. Because the agent path now emits JSON, a missing-key failure on
+  `account list` is a JSON `Failure(CodeConfig, …)` envelope, consistent with the
+  other agent commands.
+- DB/list errors on the agent path → `Failure(CodeDB, …)` envelope; on the admin
+  path → existing `list: <err>` text to stderr.
+
+## Testing
+
+- **Routing:** extend the `commandRole` table test — `account list` → agent;
+  `account add` / `account edit` / `account remove` → admin.
+- **Agent view:** with only `EMCLI_KEY`, `account list` exits 0, emits a valid
+  envelope, and the `data.accounts` entries carry `name`/`from`/`can_send` — and
+  the output does **not** contain the IMAP host or the login username.
+- **Admin view:** with `EMCLI_ADMIN_KEY`, `account list` still prints the full
+  `NAME MODE IMAP USER` table (regression guard).
+- **`can_send`:** an RW account yields `can_send:true`, an RO account
+  `can_send:false`; `from` reflects `SendFrom()` (explicit From, else username).
+- **Security invariant (`security_invariant_test.go`):** remove
+  `{"account","list"}` from the refused-commands set (it is now allowed) and
+  replace it with a *mutating* `account add …` attempt, so the "forced agent
+  cannot run admin commands and the DB is byte-for-byte unchanged" invariant
+  still covers the `account` family.
+
+## Documentation updates
+
+- **USER-MANUAL:** role/command table — `account list` is agent-readable
+  (reduced JSON view); `account add/edit/remove` remain admin.
+- **`skills/emcli` (SKILL.md / AGENTIC-MANUAL.md):** document that the agent
+  discovers accounts via `account list`, including the JSON shape
+  (`name`, `from`, `can_send`).
+
+## Out of scope
+
+- Agent access to `whitelist list`, `config get`, or `audit list`.
+- Any change to the admin `account list` columns or to the data model.
+- JSON output for the admin `account list` path (stays human-readable text).

docs/superpowers/specs/2026-06-23-send-from-address-design.md

@@ -0,0 +1,118 @@
+# Send-as "From" address — design
+
+**Date:** 2026-06-23
+**Status:** Approved (pending spec review)
+
+## Problem
+
+An account's configuration has no field for the email address used as the
+`From:` when sending mail. Today the From is silently aliased to the login
+username (`internal/cli/send.go:26`, `From: acc.Username`), and neither
+`store.Account` nor the `accounts` table has any `from`/`address`/`email`
+column.
+
+This works only when the login username is exactly the desired send-as
+address. It breaks for:
+
+- providers where the login is an account ID rather than an email,
+- sending from an **alias** of the mailbox,
+- wanting a **display name** (`Steve Cliff <me@…>`) rather than a bare address,
+- Gmail App Passwords where envelope-from and header-from may differ.
+
+## Decisions
+
+- **Field shape:** a single freeform RFC 5322 From identity — bare
+  (`me@stevecliff.com`) or with a display name
+  (`Steve Cliff <me@stevecliff.com>`). One field, not a split
+  address/display-name pair.
+- **Fallback:** when the from-address is blank, fall back to
+  `Account.Username` (current behaviour). No migration/backfill of existing
+  accounts required; they keep working unchanged.
+
+## Design
+
+### 1. Data model
+
+Add `FromAddress string` to `store.Account` and a `from_address TEXT` column to
+the `accounts` table. **Not encrypted** — it is not a secret (it appears in
+every outgoing header), so it is stored as plaintext like `username`.
+
+### 2. Fallback in one place
+
+Add a method so the fallback rule lives in exactly one spot:
+
+```go
+// SendFrom returns the From identity for outgoing mail, falling back to the
+// login username when no explicit from-address is configured.
+func (a Account) SendFrom() string {
+	if a.FromAddress != "" {
+		return a.FromAddress
+	}
+	return a.Username
+}
+```
+
+`internal/cli/send.go` changes `From: acc.Username` → `From: acc.SendFrom()`.
+
+### 3. Envelope sender vs header From
+
+A display-name From breaks the SMTP envelope: `c.SendMail("Steve <me@…>", …)`
+is invalid — the envelope sender must be the **bare** address.
+
+- `mail.BuildMIME` keeps using the full `m.From` for the `From:` header
+  (go-message renders `Name <addr>` correctly via `SetAddressList`).
+- `mail.SendSMTP` derives the envelope sender as the bare address:
+  `gomail.ParseAddress(m.From).Address`. If parsing fails, fall back to the raw
+  `m.From` (preserves today's behaviour for plain addresses).
+
+Header carries the display name; envelope carries the bare address.
+
+### 4. Migration
+
+The schema is v1, applied via `CREATE TABLE … IF NOT EXISTS`, which will not add
+a column to an existing DB, and there is no migration runner yet.
+
+- Add the `from_address` column to the `CREATE TABLE accounts` statement (new
+  DBs get it directly).
+- In `store.Open`, after applying the schema, run a version-gated migration: if
+  the stored `schema_version` is `< 2`, execute
+  `ALTER TABLE accounts ADD COLUMN from_address TEXT` and set `schema_version`
+  to `2`.
+- Bump the `schemaVersion` constant to `2`.
+
+SQLite `ALTER TABLE … ADD COLUMN` is cheap and safe. The migration is
+idempotent under the version gate.
+
+### 5. Inputs & validation
+
+- **CLI:** add a `--from` flag to `account add` and `account edit`. On `edit`,
+  follow the existing `fs.Visit` overlay pattern (only set when the flag was
+  passed).
+- **TUI:** add a `FromAddress` field to `tui.Fields`, a `fieldDef`
+  (`{key: "from_address", label: "From address (optional)"}`), and wire it
+  through `ToAccount`, `FieldsFromAccount`, `fieldValue`, and `collect`.
+- **Validation:** when the from-address is non-empty, reject it unless
+  `gomail.ParseAddress` accepts it (covers bare and display-name forms). A
+  blank from-address is always valid (→ fallback). Applied in
+  `Fields.Validate` and on the `account add`/`edit` flag path.
+- **Persistence:** thread `from_address` through `AddAccount`, `UpdateAccount`,
+  `scanAccount`, and the three `SELECT` column lists in
+  `internal/store/account.go`. Stored via `nullStr` (blank → NULL).
+
+### 6. Tests
+
+- `SendFrom()`: returns the from-address when set; returns username when blank.
+- `SendSMTP` envelope: when From is `Name <addr>`, the envelope sender passed to
+  the server is the bare `addr` (table test on the extraction helper).
+- Migration: open a v1 DB with no `from_address` column → column is added,
+  `schema_version` becomes 2, and an existing account still sends from its
+  username.
+- `Fields.Validate`: rejects a malformed from-address; accepts bare and
+  display-name forms; accepts blank.
+- Round-trip: `FieldsFromAccount` then `ToAccount` preserves `FromAddress`.
+
+## Out of scope (YAGNI)
+
+- Separate envelope-from override field (derive it from From instead).
+- Per-message From override at send time.
+- Multiple aliases per account.

internal/cli/account_list_test.go

@@ -0,0 +1,85 @@
+package cli
+
+import (
+	"encoding/json"
+	"strings"
+	"testing"
+)
+
+// With only EMCLI_KEY set, `account list` emits the reduced JSON envelope:
+// name/from/can_send, and never the IMAP host or login username.
+func TestAccountListAgentJSONView(t *testing.T) {
+	adminEnv(t) // both keys + initialized temp DB
+	run(t, "account", "add", "--name", "work", "--mode", "RW",
+		"--imap-host", "imap.example.com", "--smtp-host", "smtp.example.com",
+		"--username", "login@example.com", "--from", "me@example.com")
+	run(t, "account", "add", "--name", "alerts", "--mode", "RO",
+		"--imap-host", "imap.example.com", "--username", "alerts@example.com")
+
+	// Drop the admin key → caller is an agent.
+	t.Setenv("EMCLI_ADMIN_KEY", "")
+	code, out, errOut := run(t, "account", "list")
+	if code != 0 {
+		t.Fatalf("agent account list should succeed: code=%d err=%q", code, errOut)
+	}
+
+	var env struct {
+		Error bool `json:"error"`
+		Data  struct {
+			Accounts []struct {
+				Name    string `json:"name"`
+				From    string `json:"from"`
+				CanSend bool   `json:"can_send"`
+			} `json:"accounts"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal([]byte(out), &env); err != nil {
+		t.Fatalf("output is not the agent envelope: %v\n%s", err, out)
+	}
+	if env.Error || len(env.Data.Accounts) != 2 {
+		t.Fatalf("want 2 accounts and no error, got %+v", env)
+	}
+	// The reduced view must not leak the IMAP host or the login username.
+	if strings.Contains(out, "imap.example.com") || strings.Contains(out, "login@example.com") {
+		t.Fatalf("agent view leaked host/username:\n%s", out)
+	}
+
+	got := map[string]struct {
+		from    string
+		canSend bool
+	}{}
+	for _, a := range env.Data.Accounts {
+		got[a.Name] = struct {
+			from    string
+			canSend bool
+		}{a.From, a.CanSend}
+	}
+	if g := got["work"]; g.from != "me@example.com" || !g.canSend {
+		t.Errorf("work: want from=me@example.com can_send=true, got %+v", g)
+	}
+	// alerts has no --from → SendFrom() falls back to the username.
+	if g := got["alerts"]; g.from != "alerts@example.com" || g.canSend {
+		t.Errorf("alerts: want from=alerts@example.com can_send=false, got %+v", g)
+	}
+}
+
+// With the admin key present, `account list` stays the full human-readable table.
+func TestAccountListAdminTextView(t *testing.T) {
+	adminEnv(t)
+	run(t, "account", "add", "--name", "work", "--mode", "RW",
+		"--imap-host", "imap.example.com", "--smtp-host", "smtp.example.com",
+		"--username", "login@example.com", "--from", "me@example.com")
+
+	code, out, _ := run(t, "account", "list")
+	if code != 0 {
+		t.Fatalf("admin account list failed: code=%d", code)
+	}
+	for _, want := range []string{"NAME", "MODE", "IMAP", "USER", "imap.example.com:993", "login@example.com"} {
+		if !strings.Contains(out, want) {
+			t.Fatalf("admin view missing %q:\n%s", want, out)
+		}
+	}
+	if strings.Contains(out, `"accounts"`) {
+		t.Fatalf("admin view should be text, not JSON:\n%s", out)
+	}
+}

internal/cli/admin.go

@@ -6,6 +6,7 @@ import (
 	"io"
 	"strconv"
 
+	"git.dcglab.co.uk/steve/emcli/internal/crypto"
 	"git.dcglab.co.uk/steve/emcli/internal/store"
 	"git.dcglab.co.uk/steve/emcli/internal/tui"
 )
@@ -23,7 +24,14 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 	sub, rest := args[0], args[1:]
 	st, err := openStore(role)
 	if err != nil {
-		fmt.Fprintf(errOut, "emcli: %v\n", err)
+		// account list is an agent command (a JSON consumer), so its
+		// open/key failures are emitted as an envelope, like the other agent
+		// commands; the admin subcommands stay human-readable.
+		if sub == "list" {
+			_ = Failure(CodeConfig, err.Error()).Write(out)
+		} else {
+			fmt.Fprintf(errOut, "emcli: %v\n", err)
+		}
 		return 1
 	}
 	defer st.Close()
@@ -45,6 +53,7 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 		smtpSec := fs.String("smtp-security", "tls", "tls|starttls")
 		user := fs.String("username", "", "login username")
 		pass := fs.String("password", "", "login password")
+		from := fs.String("from", "", "send-as address (blank = use username)")
 		subj := fs.String("subject-regex", "", "inbound subject filter")
 		wlIn := fs.Bool("whitelist-in", false, "enable inbound whitelist")
 		wlOut := fs.Bool("whitelist-out", false, "enable outbound whitelist")
@@ -56,9 +65,14 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 			fmt.Fprintln(errOut, "name, imap-host, and username are required")
 			return 2
 		}
+		if err := tui.ValidFromAddress(*from); err != nil {
+			fmt.Fprintln(errOut, err)
+			return 2
+		}
 		acc := store.Account{
 			Name: *name, Mode: *mode, IMAPHost: *host, IMAPPort: *port, IMAPSecurity: *sec,
 			AuthType: "password", Username: *user, Password: *pass,
+			FromAddress: *from,
 			SubjectRegex: *subj, WhitelistInEnabled: *wlIn, WhitelistOutEnabled: *wlOut,
 			ProcessBacklog: *backlog,
 		}
@@ -85,6 +99,7 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 		smtpSec := fs.String("smtp-security", "", "tls|starttls")
 		user := fs.String("username", "", "login username")
 		pass := fs.String("password", "", "login password (blank keeps existing)")
+		from := fs.String("from", "", "send-as address (empty reverts to username)")
 		subj := fs.String("subject-regex", "", "inbound subject filter")
 		if err := fs.Parse(rest); err != nil {
 			return 2
@@ -96,6 +111,10 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 		if fs.NFlag() == 1 { // only --name → interactive TUI form, prefilled
 			return editInteractive(st, *name, out, errOut)
 		}
+		if err := tui.ValidFromAddress(*from); err != nil {
+			fmt.Fprintln(errOut, err)
+			return 2
+		}
 		acc, err := st.GetAccount(*name)
 		if err != nil {
 			fmt.Fprintf(errOut, "edit: %v\n", err)
@@ -122,6 +141,8 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 				acc.Username = *user
 			case "password":
 				acc.Password = *pass
+			case "from":
+				acc.FromAddress = *from
 			case "subject-regex":
 				acc.SubjectRegex = *subj
 			}
@@ -158,11 +179,31 @@ func runAccount(args []string, role store.Role, out, errOut io.Writer) int {
 		fmt.Fprintf(out, "account %q removed\n", *name)
 		return 0
 	case "list":
+		// Holding the admin key means the caller is the human admin (full
+		// detail). An agent holds only EMCLI_KEY and gets a reduced JSON view.
+		_, adminErr := crypto.AdminKeyFromEnv()
+		isAdmin := adminErr == nil
 		accs, err := st.ListAccounts()
 		if err != nil {
-			fmt.Fprintf(errOut, "list: %v\n", err)
+			if isAdmin {
+				fmt.Fprintf(errOut, "list: %v\n", err)
+			} else {
+				_ = Failure(CodeDB, err.Error()).Write(out)
+			}
 			return 1
 		}
+		if !isAdmin {
+			items := make([]map[string]any, 0, len(accs))
+			for _, a := range accs {
+				items = append(items, map[string]any{
+					"name":     a.Name,
+					"from":     a.SendFrom(),
+					"can_send": a.Mode == "RW",
+				})
+			}
+			_ = Success(map[string]any{"accounts": items}).Write(out)
+			return 0
+		}
 		fmt.Fprintf(out, "%-16s %-4s %-28s %s\n", "NAME", "MODE", "IMAP", "USER")
 		for _, a := range accs {
 			fmt.Fprintf(out, "%-16s %-4s %-28s %s\n",
@@ -289,7 +330,19 @@ func runWhitelist(args []string, role store.Role, out, errOut io.Writer) int {
 		return 2
 	}
 	dir := store.Direction(args[0])
+	if dir != store.DirIn && dir != store.DirOut {
+		fmt.Fprintf(errOut, "whitelist direction must be \"in\" or \"out\", got %q\n", args[0])
+		fmt.Fprintln(errOut, "usage: emcli whitelist <in|out> <add|remove|list> [flags]")
+		return 2
+	}
 	sub, rest := args[1], args[2:]
+	switch sub {
+	case "add", "remove", "list": // valid
+	default:
+		fmt.Fprintf(errOut, "unknown whitelist subcommand %q (want add|remove|list)\n", sub)
+		fmt.Fprintln(errOut, "usage: emcli whitelist <in|out> <add|remove|list> [flags]")
+		return 2
+	}
 	fs := flag.NewFlagSet("whitelist", flag.ContinueOnError)
 	fs.SetOutput(errOut)
 	account := fs.String("account", "", "account name")
@@ -330,9 +383,6 @@ func runWhitelist(args []string, role store.Role, out, errOut io.Writer) int {
 		for _, a := range addrs {
 			fmt.Fprintln(out, a)
 		}
-	default:
-		fmt.Fprintf(errOut, "unknown whitelist subcommand %q\n", sub)
-		return 2
 	}
 	return 0
 }

internal/cli/admin_test.go

@@ -110,6 +110,51 @@ func TestAccountEditPartialPreservesOtherFields(t *testing.T) {
 	}
 }
 
+// A missing direction (e.g. `whitelist list`) must report the real problem —
+// the in|out direction — not the misleading "--account is required".
+func TestWhitelistMissingDirectionReported(t *testing.T) {
+	adminEnv(t)
+	code, _, errOut := run(t, "whitelist", "list", "--account", "bobby")
+	if code == 0 {
+		t.Fatal("missing direction must be a usage error")
+	}
+	if strings.Contains(errOut, "--account is required") {
+		t.Fatalf("misleading error; want a direction complaint, got: %q", errOut)
+	}
+	if !strings.Contains(errOut, "in") || !strings.Contains(errOut, "out") {
+		t.Fatalf("error should name the in|out direction, got: %q", errOut)
+	}
+}
+
+// A missing subcommand (e.g. `whitelist out --account x`) must report the real
+// problem — the add|remove|list subcommand — not "--account is required".
+func TestWhitelistMissingSubcommandReported(t *testing.T) {
+	adminEnv(t)
+	code, _, errOut := run(t, "whitelist", "out", "--account", "bobby")
+	if code == 0 {
+		t.Fatal("missing subcommand must be a usage error")
+	}
+	if strings.Contains(errOut, "--account is required") {
+		t.Fatalf("misleading error; want a subcommand complaint, got: %q", errOut)
+	}
+	if !strings.Contains(errOut, "add") || !strings.Contains(errOut, "list") {
+		t.Fatalf("error should name the add|remove|list subcommand, got: %q", errOut)
+	}
+}
+
+// The happy path still works after the direction/subcommand validation.
+func TestWhitelistListWorks(t *testing.T) {
+	adminEnv(t)
+	run(t, "account", "add", "--name", "bobby", "--imap-host", "h", "--username", "u@x.com")
+	if code, _, e := run(t, "whitelist", "out", "add", "--account", "bobby", "--address", "@x.com"); code != 0 {
+		t.Fatalf("add failed: %s", e)
+	}
+	code, out, _ := run(t, "whitelist", "out", "list", "--account", "bobby")
+	if code != 0 || !strings.Contains(out, "@x.com") {
+		t.Fatalf("list: code=%d out=%q", code, out)
+	}
+}
+
 func TestAuditListCoreRenders(t *testing.T) {
 	st, err := store.Open(filepath.Join(t.TempDir(), "e.db"))
 	if err != nil {
@@ -132,3 +177,17 @@ func TestAuditListCoreRenders(t *testing.T) {
 	}
 }
 
+func TestAccountEditFromValidationRejectsMalformed(t *testing.T) {
+	adminEnv(t)
+	// Seed an account so the failure is from --from validation, not a missing account.
+	run(t, "account", "add", "--name", "valacc", "--imap-host", "imap.x.com", "--username", "u@x.com")
+	// A malformed --from value must be rejected with exit code 2 before touching the account.
+	code, _, errStr := run(t, "account", "edit", "--name", "valacc", "--from", "not an address")
+	if code != 2 {
+		t.Fatalf("expected exit code 2 for malformed --from, got %d (stderr: %q)", code, errStr)
+	}
+	if errStr == "" {
+		t.Fatal("expected an error message on stderr for malformed --from, got none")
+	}
+}
+

internal/cli/role_test.go

@@ -9,16 +9,22 @@ import (
 )
 
 func TestCommandRole(t *testing.T) {
-	admin := []string{"account", "whitelist", "config", "audit"}
-	agent := []string{"list", "get", "search", "ack", "send", "doctor"}
-	for _, c := range admin {
+	adminCmds := [][]string{
+		{"whitelist"}, {"config"}, {"audit"},
+		{"account"}, {"account", "add"}, {"account", "edit"}, {"account", "remove"},
+	}
+	agentCmds := [][]string{
+		{"list"}, {"get"}, {"search"}, {"ack"}, {"send"}, {"doctor"},
+		{"account", "list"},
+	}
+	for _, c := range adminCmds {
 		if commandRole(c) != store.RoleAdmin {
-			t.Errorf("%s should be admin", c)
+			t.Errorf("%v should be admin", c)
 		}
 	}
-	for _, c := range agent {
+	for _, c := range agentCmds {
 		if commandRole(c) != store.RoleAgent {
-			t.Errorf("%s should be agent", c)
+			t.Errorf("%v should be agent", c)
 		}
 	}
 }

internal/cli/run.go

@@ -27,9 +27,16 @@ func realMailer(acc store.Account) (Mailer, error) {
 
 // commandRole maps a command to the privilege it requires. Admin commands
 // mutate configuration or expose oversight data; everything else is agent.
-func commandRole(cmd string) store.Role {
-	switch cmd {
-	case "account", "whitelist", "config", "audit":
+func commandRole(args []string) store.Role {
+	switch args[0] {
+	case "account":
+		// account list is a read-only discovery view available to agents;
+		// add/edit/remove mutate config and require admin.
+		if len(args) >= 2 && args[1] == "list" {
+			return store.RoleAgent
+		}
+		return store.RoleAdmin
+	case "whitelist", "config", "audit":
 		return store.RoleAdmin
 	default: // list, get, search, ack, send, doctor
 		return store.RoleAgent
@@ -135,7 +142,7 @@ func Run(args []string, out, errOut io.Writer) int {
 		return 0
 	}
 	cmd, rest := args[0], args[1:]
-	role := commandRole(cmd)
+	role := commandRole(args)
 	switch cmd {
 	case "list", "get", "search", "ack":
 		return runAgent(cmd, rest, role, out, errOut)

internal/cli/run_test.go

@@ -18,9 +18,9 @@ func TestRunUnknownCommand(t *testing.T) {
 	}
 }
 
-func TestRunVersionIsJSONForAgentButTextHere(t *testing.T) {
-	// `account list` with no DB key should fail closed with a usage/config error,
-	// proving the key check happens before any DB work.
+func TestAccountListMissingKeyFailsClosedAsJSON(t *testing.T) {
+	// `account list` is an agent command: with no DB key it fails closed before
+	// any DB work, emitting a JSON config-error envelope that names EMCLI_KEY.
 	var out, errOut bytes.Buffer
 	t.Setenv("EMCLI_KEY", "")
 	t.Setenv("EMCLI_ADMIN_KEY", "")
@@ -28,8 +28,15 @@ func TestRunVersionIsJSONForAgentButTextHere(t *testing.T) {
 	if code == 0 {
 		t.Fatal("missing EMCLI_KEY must fail")
 	}
-	if !strings.Contains(out.String()+errOut.String(), "EMCLI_ADMIN_KEY") {
-		t.Fatalf("should mention EMCLI_ADMIN_KEY, got out=%q err=%q", out.String(), errOut.String())
+	var env map[string]any
+	if err := json.Unmarshal(out.Bytes(), &env); err != nil {
+		t.Fatalf("agent account list error must be JSON, got out=%q err=%q", out.String(), errOut.String())
+	}
+	if env["error"] != true {
+		t.Fatalf("want error envelope: %v", env)
+	}
+	if !strings.Contains(out.String(), "EMCLI_KEY") {
+		t.Fatalf("should name the missing EMCLI_KEY, got %q", out.String())
 	}
 }
 

internal/cli/security_invariant_test.go

@@ -49,7 +49,7 @@ func TestAgentKeyCannotRunAdminCommands(t *testing.T) {
 
 	before := dbBytes(t, db)
 	adminAttempts := [][]string{
-		{"account", "list"},
+		{"account", "add", "--name", "x", "--imap-host", "h", "--username", "u@x.com"},
 		{"config", "set", "audit_retention_days", "30"},
 		{"audit"},
 	}

internal/cli/send.go

@@ -23,7 +23,7 @@ func SendCmd(d Deps, account string, to, cc, bcc []string, subject, body string,
 	}
 
 	msg := mail.OutgoingMessage{
-		From: acc.Username, To: to, Cc: cc, Bcc: bcc,
+		From: acc.SendFrom(), To: to, Cc: cc, Bcc: bcc,
 		Subject: subject, BodyText: body,
 	}
 	recipients := msg.Recipients()

internal/cli/send_test.go

@@ -139,6 +139,32 @@ func TestSendReplyToThreadsHeaders(t *testing.T) {
 	}
 }
 
+func TestSendUsesConfiguredFromAddress(t *testing.T) {
+	acc := rwAccount()
+	acc.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	d, sent, _ := sendDeps(t, acc, nil)
+	if err := SendCmd(d, "send", []string{"me@stevecliff.com"}, nil, nil, "hi", "body", nil, 0, "INBOX"); err != nil {
+		t.Fatalf("SendCmd: %v", err)
+	}
+	if len(*sent) != 1 {
+		t.Fatalf("want 1 send, got %d", len(*sent))
+	}
+	if got := (*sent)[0].From; got != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("From = %q, want configured from-address", got)
+	}
+}
+
+func TestSendFallsBackToUsernameAsFrom(t *testing.T) {
+	// rwAccount has no FromAddress, so From must be the login username.
+	d, sent, _ := sendDeps(t, rwAccount(), nil)
+	if err := SendCmd(d, "send", []string{"me@stevecliff.com"}, nil, nil, "hi", "body", nil, 0, "INBOX"); err != nil {
+		t.Fatalf("SendCmd: %v", err)
+	}
+	if got := (*sent)[0].From; got != "emcli@stevecliff.com" {
+		t.Fatalf("From = %q, want username fallback", got)
+	}
+}
+
 func TestSendReplyToFilteredSourceNotFound(t *testing.T) {
 	acc := rwAccount()
 	acc.WhitelistInEnabled = true // inbound filter active

internal/mail/send.go

@@ -46,6 +46,18 @@ func (m OutgoingMessage) Recipients() []string {
 	return out
 }
 
+// envelopeFrom returns the bare address for the SMTP envelope sender, stripping
+// any display name. A display-name From (e.g. "Name <addr>") is a valid header
+// but an invalid envelope sender, so it must be reduced to the bare address.
+// Unparseable input is passed through unchanged (preserves prior behaviour for
+// plain addresses).
+func envelopeFrom(from string) string {
+	if a, err := gomail.ParseAddress(from); err == nil {
+		return a.Address
+	}
+	return from
+}
+
 func addrList(addrs []string) []*gomail.Address {
 	out := make([]*gomail.Address, 0, len(addrs))
 	for _, a := range addrs {
@@ -163,7 +175,7 @@ func SendSMTP(cfg SMTPConfig, m OutgoingMessage) error {
 	if err := c.Auth(auth); err != nil {
 		return fmt.Errorf("smtp auth: %w", err)
 	}
-	if err := c.SendMail(m.From, m.Recipients(), bytes.NewReader(raw)); err != nil {
+	if err := c.SendMail(envelopeFrom(m.From), m.Recipients(), bytes.NewReader(raw)); err != nil {
 		return fmt.Errorf("smtp send: %w", err)
 	}
 	return c.Quit()

internal/mail/send_test.go

@@ -100,6 +100,36 @@ func TestRecipientsCombinesAllFields(t *testing.T) {
 	}
 }
 
+func TestEnvelopeFromStripsDisplayName(t *testing.T) {
+	cases := map[string]string{
+		"Steve Cliff <me@stevecliff.com>": "me@stevecliff.com",
+		"me@stevecliff.com":               "me@stevecliff.com",
+		"<me@stevecliff.com>":             "me@stevecliff.com",
+		"not a valid address":             "not a valid address", // unparseable ⇒ passthrough
+	}
+	for in, want := range cases {
+		if got := envelopeFrom(in); got != want {
+			t.Errorf("envelopeFrom(%q) = %q, want %q", in, got, want)
+		}
+	}
+}
+
+func TestBuildMIMEKeepsDisplayNameInHeader(t *testing.T) {
+	raw, err := BuildMIME(OutgoingMessage{
+		From:     "Steve Cliff <me@stevecliff.com>",
+		To:       []string{"you@example.com"},
+		Subject:  "hi",
+		BodyText: "body",
+		Date:     time.Date(2026, 6, 23, 12, 0, 0, 0, time.UTC),
+	})
+	if err != nil {
+		t.Fatalf("BuildMIME: %v", err)
+	}
+	if !strings.Contains(string(raw), "Steve Cliff") {
+		t.Fatalf("From header lost display name:\n%s", raw)
+	}
+}
+
 func TestReadHeaderParsesReferences(t *testing.T) {
 	raw := "From: a@x.com\r\n" +
 		"To: b@x.com\r\n" +

internal/store/account.go

@@ -23,6 +23,7 @@ type Account struct {
 	SMTPSecurity        string // tls | starttls
 	AuthType            string // password | oauth2
 	Username            string
+	FromAddress         string // send-as identity; blank ⇒ fall back to Username
 	Password            string // decrypted; empty in ListAccounts
 	WhitelistInEnabled  bool
 	WhitelistOutEnabled bool
@@ -30,6 +31,15 @@ type Account struct {
 	ProcessBacklog      bool
 }
 
+// SendFrom returns the From identity for outgoing mail, falling back to the
+// login username when no explicit from-address is configured.
+func (a Account) SendFrom() string {
+	if a.FromAddress != "" {
+		return a.FromAddress
+	}
+	return a.Username
+}
+
 func (s *Store) AddAccount(a Account) (int64, error) {
 	var encPw []byte
 	if a.Password != "" {
@@ -42,12 +52,12 @@ func (s *Store) AddAccount(a Account) (int64, error) {
 	res, err := s.db.Exec(`
 		INSERT INTO accounts
 		  (name,mode,imap_host,imap_port,imap_security,smtp_host,smtp_port,smtp_security,
-		   auth_type,username,
+		   auth_type,username,from_address,
 		   enc_password,whitelist_in_enabled,whitelist_out_enabled,subject_regex,process_backlog)
-		VALUES (?,?,?,?,?,?,?,?,?,?,?,?,?,?,?)`,
+		VALUES (?,?,?,?,?,?,?,?,?,?,?,?,?,?,?,?)`,
 		a.Name, a.Mode, a.IMAPHost, a.IMAPPort, a.IMAPSecurity,
 		nullStr(a.SMTPHost), nullInt(a.SMTPPort), nullStr(a.SMTPSecurity),
-		a.AuthType, a.Username,
+		a.AuthType, a.Username, nullStr(a.FromAddress),
 		encPw, b2i(a.WhitelistInEnabled), b2i(a.WhitelistOutEnabled),
 		nullStr(a.SubjectRegex), b2i(a.ProcessBacklog))
 	if err != nil {
@@ -59,7 +69,7 @@ func (s *Store) AddAccount(a Account) (int64, error) {
 func (s *Store) GetAccount(name string) (Account, error) {
 	row := s.db.QueryRow(`
 		SELECT id,name,mode,imap_host,imap_port,imap_security,smtp_host,smtp_port,smtp_security,
-		       auth_type,username,
+		       auth_type,username,from_address,
 		       enc_password,whitelist_in_enabled,whitelist_out_enabled,subject_regex,process_backlog
 		FROM accounts WHERE name = ?`, name)
 	a, encPw, err := scanAccount(row)
@@ -82,7 +92,7 @@ func (s *Store) GetAccount(name string) (Account, error) {
 func (s *Store) ListAccounts() ([]Account, error) {
 	rows, err := s.db.Query(`
 		SELECT id,name,mode,imap_host,imap_port,imap_security,smtp_host,smtp_port,smtp_security,
-		       auth_type,username,
+		       auth_type,username,from_address,
 		       enc_password,whitelist_in_enabled,whitelist_out_enabled,subject_regex,process_backlog
 		FROM accounts ORDER BY name`)
 	if err != nil {
@@ -108,12 +118,12 @@ func (s *Store) UpdateAccount(a Account) error {
 	// Build the SET clause, conditionally including secret columns.
 	set := `mode=?, imap_host=?, imap_port=?, imap_security=?,
 	        smtp_host=?, smtp_port=?, smtp_security=?,
-	        auth_type=?, username=?,
+	        auth_type=?, username=?, from_address=?,
 	        whitelist_in_enabled=?, whitelist_out_enabled=?, subject_regex=?, process_backlog=?`
 	args := []any{
 		a.Mode, a.IMAPHost, a.IMAPPort, a.IMAPSecurity,
 		nullStr(a.SMTPHost), nullInt(a.SMTPPort), nullStr(a.SMTPSecurity),
-		a.AuthType, a.Username,
+		a.AuthType, a.Username, nullStr(a.FromAddress),
 		b2i(a.WhitelistInEnabled), b2i(a.WhitelistOutEnabled),
 		nullStr(a.SubjectRegex), b2i(a.ProcessBacklog),
 	}
@@ -152,16 +162,16 @@ type scanner interface{ Scan(dest ...any) error }
 
 func scanAccount(sc scanner) (Account, []byte, error) {
 	var (
-		a                       Account
-		encPw                   []byte
-		subj, smtpHost, smtpSec sql.NullString
-		smtpPort                sql.NullInt64
-		wlIn, wlOut             int
-		backlog                 int
+		a                                Account
+		encPw                            []byte
+		subj, smtpHost, smtpSec, fromAddr sql.NullString
+		smtpPort                         sql.NullInt64
+		wlIn, wlOut                      int
+		backlog                          int
 	)
 	err := sc.Scan(&a.ID, &a.Name, &a.Mode, &a.IMAPHost, &a.IMAPPort, &a.IMAPSecurity,
 		&smtpHost, &smtpPort, &smtpSec,
-		&a.AuthType, &a.Username, &encPw, &wlIn, &wlOut, &subj, &backlog)
+		&a.AuthType, &a.Username, &fromAddr, &encPw, &wlIn, &wlOut, &subj, &backlog)
 	if err != nil {
 		return Account{}, nil, err
 	}
@@ -172,6 +182,7 @@ func scanAccount(sc scanner) (Account, []byte, error) {
 	a.WhitelistOutEnabled = wlOut != 0
 	a.ProcessBacklog = backlog != 0
 	a.SubjectRegex = subj.String
+	a.FromAddress = fromAddr.String
 	return a, encPw, nil
 }
 

internal/store/account_test.go

@@ -84,3 +84,30 @@ func TestListAccountsOmitsSecrets(t *testing.T) {
 		t.Fatal("ListAccounts must not return secrets")
 	}
 }
+
+func TestSendFromFallsBackToUsername(t *testing.T) {
+	a := Account{Username: "login@example.com"}
+	if got := a.SendFrom(); got != "login@example.com" {
+		t.Fatalf("blank from-address should fall back to username, got %q", got)
+	}
+	a.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if got := a.SendFrom(); got != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("set from-address should win, got %q", got)
+	}
+}
+
+func TestAddGetAccountRoundTripsFromAddress(t *testing.T) {
+	s := openTemp(t)
+	a := sampleAccount()
+	a.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if _, err := s.AddAccount(a); err != nil {
+		t.Fatalf("AddAccount: %v", err)
+	}
+	got, err := s.GetAccount("work")
+	if err != nil {
+		t.Fatalf("GetAccount: %v", err)
+	}
+	if got.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("FromAddress not round-tripped: %q", got.FromAddress)
+	}
+}

internal/store/schema.go

@@ -1,8 +1,8 @@
 package store
 
-const schemaVersion = 1
+const schemaVersion = 2
 
-// schemaSQL is the full v1 schema. All statements are idempotent via IF NOT EXISTS.
+// schemaSQL is the full current schema. All statements are idempotent via IF NOT EXISTS.
 const schemaSQL = `
 CREATE TABLE IF NOT EXISTS settings (
   key   TEXT PRIMARY KEY,
@@ -21,6 +21,7 @@ CREATE TABLE IF NOT EXISTS accounts (
   smtp_security           TEXT,
   auth_type               TEXT NOT NULL CHECK (auth_type IN ('password','oauth2')),
   username                TEXT NOT NULL,
+  from_address            TEXT,
   enc_password            BLOB,
   enc_oauth_client_id     BLOB,
   enc_oauth_client_secret BLOB,

internal/store/store.go

@@ -8,6 +8,7 @@ import (
 	"path/filepath"
 	"runtime"
 	"strconv"
+	"strings"
 
 	_ "modernc.org/sqlite"
 )
@@ -42,21 +43,59 @@ func Open(path string) (*Store, error) {
 		return nil, fmt.Errorf("apply schema: %w", err)
 	}
 	s := &Store{db: db}
-	if _, err := s.GetSetting("schema_version"); err != nil {
-		if err := s.SetSetting("schema_version", strconv.Itoa(schemaVersion)); err != nil {
-			db.Close()
-			return nil, err
-		}
+	if err := s.migrate(); err != nil {
+		db.Close()
+		return nil, err
 	}
 	return s, nil
 }
 
+// migrate brings an existing database up to the current schemaVersion. A brand-
+// new database (no schema_version yet) already has every column from schemaSQL,
+// so it is simply stamped at the current version. Each older version runs its
+// forward step. The version gate makes every step idempotent across reopens.
+func (s *Store) migrate() error {
+	v, err := s.GetSetting("schema_version")
+	if err != nil {
+		// Fresh database: schemaSQL created all columns already.
+		return s.SetSetting("schema_version", strconv.Itoa(schemaVersion))
+	}
+	var ver int
+	ver, err = strconv.Atoi(v)
+	if err != nil {
+		return fmt.Errorf("invalid schema_version %q: %w", v, err)
+	}
+	if ver < 2 {
+		if _, err := s.db.Exec(`ALTER TABLE accounts ADD COLUMN from_address TEXT`); err != nil {
+			return fmt.Errorf("migrate to v2: %w", err)
+		}
+		if err := s.SetSetting("schema_version", "2"); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
 func (s *Store) Close() error { return s.db.Close() }
 
+// expandUserHome replaces a leading "~" or "~/" in p with the user's home
+// directory. Only a leading tilde is expanded (the usual shell convention) —
+// "~user" and a tilde elsewhere in the path are left untouched. This guards
+// against an EMCLI_DB set to a literal "~/..." (no shell to expand it), which
+// would otherwise be opened relative to the cwd and create a stray "~" dir.
+func expandUserHome(p string) string {
+	if p == "~" || strings.HasPrefix(p, "~/") {
+		if home, err := os.UserHomeDir(); err == nil {
+			return filepath.Join(home, strings.TrimPrefix(p[1:], "/"))
+		}
+	}
+	return p
+}
+
 // DefaultDBPath resolves EMCLI_DB or the per-OS default location.
 func DefaultDBPath() (string, error) {
 	if p := os.Getenv("EMCLI_DB"); p != "" {
-		return p, nil
+		return expandUserHome(p), nil
 	}
 	if runtime.GOOS == "windows" {
 		if dir := os.Getenv("AppData"); dir != "" {

internal/store/store_test.go

@@ -1,10 +1,54 @@
 package store
 
 import (
+	"database/sql"
+	"os"
 	"path/filepath"
+	"strings"
 	"testing"
 )
 
+// A leading "~" in EMCLI_DB must be expanded to the home dir, so a literal
+// tilde (no shell to expand it) can't be opened relative to the cwd and
+// silently create a stray "~" directory.
+func TestDefaultDBPathExpandsLeadingTilde(t *testing.T) {
+	home, err := os.UserHomeDir()
+	if err != nil {
+		t.Skipf("no home dir: %v", err)
+	}
+	cases := map[string]string{
+		"~/.config/emcli/emcli.db": filepath.Join(home, ".config", "emcli", "emcli.db"),
+		"~":                        home,
+	}
+	for in, want := range cases {
+		t.Setenv("EMCLI_DB", in)
+		got, err := DefaultDBPath()
+		if err != nil {
+			t.Fatalf("DefaultDBPath(%q): %v", in, err)
+		}
+		if got != want {
+			t.Fatalf("EMCLI_DB=%q -> %q, want %q", in, got, want)
+		}
+		if strings.Contains(got, "~") {
+			t.Fatalf("EMCLI_DB=%q left a literal tilde: %q", in, got)
+		}
+	}
+}
+
+// A non-leading tilde or "~user" is NOT a path we should rewrite — leave it be.
+func TestDefaultDBPathLeavesOtherPathsUntouched(t *testing.T) {
+	for _, p := range []string{"/var/lib/emcli.db", "./rel/emcli.db", "~user/db"} {
+		t.Setenv("EMCLI_DB", p)
+		got, err := DefaultDBPath()
+		if err != nil {
+			t.Fatalf("DefaultDBPath(%q): %v", p, err)
+		}
+		if got != p {
+			t.Fatalf("EMCLI_DB=%q was rewritten to %q", p, got)
+		}
+	}
+}
+
 // openTemp opens a fresh store in a temp dir and initialises keys so that
 // account tests (which do crypto) work without needing their own setup.
 func openTemp(t *testing.T) *Store {
@@ -28,7 +72,7 @@ func TestOpenCreatesSchemaAndIsIdempotent(t *testing.T) {
 		t.Fatalf("first Open: %v", err)
 	}
 	v, err := s.GetSetting("schema_version")
-	if err != nil || v != "1" {
+	if err != nil || v != "2" {
 		t.Fatalf("schema_version: %q err=%v", v, err)
 	}
 	s.Close()
@@ -39,7 +83,7 @@ func TestOpenCreatesSchemaAndIsIdempotent(t *testing.T) {
 		t.Fatalf("second Open: %v", err)
 	}
 	defer s2.Close()
-	if v, _ := s2.GetSetting("schema_version"); v != "1" {
+	if v, _ := s2.GetSetting("schema_version"); v != "2" {
 		t.Fatalf("schema_version after reopen: %q", v)
 	}
 }
@@ -104,3 +148,66 @@ func TestForeignKeyCascade(t *testing.T) {
 		t.Fatalf("whitelist_in row not cascade-deleted: count=%d err=%v", count, err)
 	}
 }
+
+func TestOpenMigratesV1AddsFromAddress(t *testing.T) {
+	p := filepath.Join(t.TempDir(), "emcli.db")
+
+	// Hand-build a v1 database: accounts table WITHOUT from_address, a settings
+	// table pinned at schema_version=1, and one pre-existing account row.
+	raw, err := sql.Open("sqlite", p)
+	if err != nil {
+		t.Fatalf("sql.Open: %v", err)
+	}
+	const v1Schema = `
+CREATE TABLE settings (key TEXT PRIMARY KEY, value TEXT NOT NULL);
+CREATE TABLE accounts (
+  id            INTEGER PRIMARY KEY AUTOINCREMENT,
+  name          TEXT UNIQUE NOT NULL,
+  mode          TEXT NOT NULL,
+  imap_host     TEXT NOT NULL,
+  imap_port     INTEGER NOT NULL,
+  imap_security TEXT NOT NULL,
+  smtp_host     TEXT, smtp_port INTEGER, smtp_security TEXT,
+  auth_type     TEXT NOT NULL,
+  username      TEXT NOT NULL,
+  enc_password  BLOB,
+  enc_oauth_client_id BLOB, enc_oauth_client_secret BLOB, enc_oauth_refresh_token BLOB,
+  whitelist_in_enabled INTEGER NOT NULL DEFAULT 0,
+  whitelist_out_enabled INTEGER NOT NULL DEFAULT 0,
+  subject_regex TEXT,
+  process_backlog INTEGER NOT NULL DEFAULT 0
+);
+INSERT INTO settings(key,value) VALUES ('schema_version','1');
+INSERT INTO accounts(name,mode,imap_host,imap_port,imap_security,auth_type,username)
+  VALUES ('legacy','RO','imap.example.com',993,'tls','password','login@example.com');
+`
+	if _, err := raw.Exec(v1Schema); err != nil {
+		t.Fatalf("seed v1 schema: %v", err)
+	}
+	raw.Close()
+
+	// Open via the store: the migration must add from_address and bump to v2.
+	s, err := Open(p)
+	if err != nil {
+		t.Fatalf("Open (migrate): %v", err)
+	}
+	defer s.Close()
+
+	if v, _ := s.GetSetting("schema_version"); v != "2" {
+		t.Fatalf("schema_version after migrate: %q, want 2", v)
+	}
+	// ListAccounts SELECTs from_address; it would error if the column were missing.
+	accs, err := s.ListAccounts()
+	if err != nil {
+		t.Fatalf("ListAccounts after migrate: %v", err)
+	}
+	if len(accs) != 1 {
+		t.Fatalf("want 1 account after migrate, got %d", len(accs))
+	}
+	if accs[0].FromAddress != "" {
+		t.Fatalf("legacy account FromAddress should be empty, got %q", accs[0].FromAddress)
+	}
+	if got := accs[0].SendFrom(); got != "login@example.com" {
+		t.Fatalf("legacy account should send from username, got %q", got)
+	}
+}

internal/tui/account.go

@@ -6,6 +6,7 @@ package tui
 import (
 	"errors"
 	"fmt"
+	"net/mail"
 	"strconv"
 	"strings"
 
@@ -22,10 +23,24 @@ type Fields struct {
 	IMAPHost, IMAPPort, IMAPSecurity          string
 	SMTPHost, SMTPPort, SMTPSecurity          string
 	Username, Password                        string
+	FromAddress                               string
 	WhitelistIn, WhitelistOut, ProcessBacklog bool
 	SubjectRegex                              string
 }
 
+// ValidFromAddress returns an error if s is set but is not a valid RFC 5322
+// address (bare or "Display Name <addr>"). A blank value is valid: sending
+// falls back to the login username.
+func ValidFromAddress(s string) error {
+	if strings.TrimSpace(s) == "" {
+		return nil
+	}
+	if _, err := mail.ParseAddress(s); err != nil {
+		return errors.New("from address must be a valid email address or \"Name <email>\"")
+	}
+	return nil
+}
+
 func validSecurity(s string) bool { return s == "tls" || s == "starttls" }
 
 // Validate checks required fields, enum fields, and numeric ports. RW accounts
@@ -60,6 +75,9 @@ func (f Fields) Validate() error {
 			return errors.New("smtp port must be a number")
 		}
 	}
+	if err := ValidFromAddress(f.FromAddress); err != nil {
+		return err
+	}
 	return nil
 }
 
@@ -71,6 +89,7 @@ func (f Fields) ToAccount() (store.Account, bool) {
 		Name: strings.TrimSpace(f.Name), Mode: f.Mode,
 		IMAPHost: f.IMAPHost, IMAPPort: ip, IMAPSecurity: f.IMAPSecurity,
 		AuthType: "password", Username: f.Username, Password: f.Password,
+		FromAddress: f.FromAddress,
 		WhitelistInEnabled: f.WhitelistIn, WhitelistOutEnabled: f.WhitelistOut,
 		SubjectRegex: f.SubjectRegex, ProcessBacklog: f.ProcessBacklog,
 	}
@@ -95,7 +114,8 @@ func FieldsFromAccount(a store.Account) Fields {
 		Name: a.Name, Mode: a.Mode,
 		IMAPHost: a.IMAPHost, IMAPPort: itoaPort(a.IMAPPort), IMAPSecurity: a.IMAPSecurity,
 		SMTPHost: a.SMTPHost, SMTPPort: itoaPort(a.SMTPPort), SMTPSecurity: a.SMTPSecurity,
-		Username:       a.Username,
+		Username:    a.Username,
+		FromAddress: a.FromAddress,
 		WhitelistIn:    a.WhitelistInEnabled,
 		WhitelistOut:   a.WhitelistOutEnabled,
 		ProcessBacklog: a.ProcessBacklog,
@@ -122,6 +142,7 @@ var fieldDefs = []fieldDef{
 	{key: "smtp_port", label: "SMTP port (RW)"},
 	{key: "smtp_security", label: "SMTP security (tls/starttls)"},
 	{key: "username", label: "Username"},
+	{key: "from_address", label: "From address (optional)"},
 	{key: "password", label: "Password", password: true},
 	{key: "whitelist_in", label: "Whitelist inbound (y/n)", isBool: true},
 	{key: "whitelist_out", label: "Whitelist outbound (y/n)", isBool: true},
@@ -164,6 +185,8 @@ func fieldValue(f Fields, key string) string {
 		return f.SMTPSecurity
 	case "username":
 		return f.Username
+	case "from_address":
+		return f.FromAddress
 	case "password":
 		return f.Password
 	case "whitelist_in":
@@ -249,6 +272,8 @@ func (m AccountForm) collect() Fields {
 			f.SMTPSecurity = strings.ToLower(v)
 		case "username":
 			f.Username = v
+		case "from_address":
+			f.FromAddress = v
 		case "password":
 			f.Password = m.inputs[i].Value() // do not trim a password
 		case "whitelist_in":

internal/tui/account_test.go

@@ -157,3 +157,36 @@ func TestAccountFormCancel(t *testing.T) {
 		t.Fatal("esc should cancel the form")
 	}
 }
+
+func TestValidateRejectsBadFromAddress(t *testing.T) {
+	f := validFields()
+	f.FromAddress = "not an address"
+	if err := f.Validate(); err == nil {
+		t.Fatal("malformed from-address should fail validation")
+	}
+	f.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	if err := f.Validate(); err != nil {
+		t.Fatalf("display-name from-address should validate: %v", err)
+	}
+	f.FromAddress = "me@stevecliff.com"
+	if err := f.Validate(); err != nil {
+		t.Fatalf("bare from-address should validate: %v", err)
+	}
+	f.FromAddress = "" // blank ⇒ fall back, always valid
+	if err := f.Validate(); err != nil {
+		t.Fatalf("blank from-address should validate: %v", err)
+	}
+}
+
+func TestFieldsFromToAccountCarriesFromAddress(t *testing.T) {
+	f := validFields()
+	f.FromAddress = "Steve Cliff <me@stevecliff.com>"
+	acc, _ := f.ToAccount()
+	if acc.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("ToAccount lost FromAddress: %q", acc.FromAddress)
+	}
+	back := FieldsFromAccount(acc)
+	if back.FromAddress != "Steve Cliff <me@stevecliff.com>" {
+		t.Fatalf("FieldsFromAccount lost FromAddress: %q", back.FromAddress)
+	}
+}

skills/emcli/AGENTIC-MANUAL.md

@@ -54,7 +54,7 @@ checksum, makes it executable in `~/.local/bin` (ensure that's on your PATH), an
 
 | Variable | Default | Purpose |
 |---|---|---|
-| `EMCLI_VERSION` | `v0.4.1` | Release tag to fetch |
+| `EMCLI_VERSION` | `v0.5.2` | Release tag to fetch |
 | `EMCLI_BASE_URL` | `https://gitea.dcglab.co.uk/steve/emcli` | Repo base URL |
 | `EMCLI_INSTALL_DIR` | `$HOME/.local/bin` | Install location |
 
@@ -85,16 +85,27 @@ with both keys exported. Account creation and other admin is the human's job —
 
 ## 4. Find the account(s)
 
-You refer to an account by name (e.g. `gmail`, `work`). Ask the user which account to use.
-`emcli doctor` is an agent command (authorised by `EMCLI_KEY`), so you can run it to check that
-configured accounts connect and authenticate:
+You refer to an account by name (e.g. `gmail`, `work`). Discover the configured accounts yourself
+with `emcli account list` (an agent command authorised by `EMCLI_KEY`); it prints a JSON envelope
+with one entry per account:
+
+```bash
+emcli account list
+# {"error":false,"error_detail":{},"data":{"accounts":[
+#   {"name":"gmail","from":"me@gmail.com","can_send":true},
+#   {"name":"alerts","from":"alerts@x.com","can_send":false}]}}
+```
+
+`name` is what you pass to `--account`; `from` is the send-as identity; `can_send` is false for
+read-only accounts (they reject `send`). If unsure which to use, ask the user. `emcli doctor`
+(also an agent command) checks that accounts connect and authenticate:
 
 ```bash
 emcli doctor              # all accounts
 emcli doctor --account gmail
 ```
 
-Just take the account name from the user and start with the workflow in `SKILL.md`.
+Then start with the workflow in `SKILL.md`.
 
 ## You're set up
 

skills/emcli/SKILL.md

@@ -17,12 +17,12 @@ sets its exit code to match.
 
 ## Security model — read this first
 
-- **You only run agent commands:** `list`, `get`, `search`, `ack`, `send`, `doctor`. You are
-  provided only `EMCLI_KEY` (the agent key), which authorises these commands and nothing else.
-  Account setup, passwords, whitelists, and config are the **user's** job (admin commands that
-  require `EMCLI_ADMIN_KEY`) — do not run or suggest running `account`, `whitelist`, `config`,
-  `audit`, or `init`. You have only `EMCLI_KEY` (agent key); `emcli` will refuse admin commands
-  with a privilege error.
+- **You only run agent commands:** `list`, `get`, `search`, `ack`, `send`, `doctor`, and
+  `account list` (to discover accounts). You are provided only `EMCLI_KEY` (the agent key), which
+  authorises these and nothing else. Account *setup* (`account add/edit/remove`), passwords,
+  whitelists, and config are the **user's** job (admin commands that require `EMCLI_ADMIN_KEY`) —
+  do not run or suggest running `account add/edit/remove`, `whitelist`, `config`, `audit`, or
+  `init`. `emcli` will refuse those with a privilege error.
 - **Never touch the secret key.** `EMCLI_KEY` is supplied in the environment by whoever launched
   you. Do not read it, print it, log it, pass it as an argument, or try to generate one. If it is
   missing, stop and tell the user (see "Files & first run").
@@ -120,6 +120,7 @@ read-only — tell the user; do not attempt another account without their say-so
 | `emcli search --account A [--folder F] [--from X] [--subject-contains X] [--text X] [--since-date D] [--before-date D]` | Server-side search |
 | `emcli ack --account A [--folder F] --uid-list U1,U2` | Mark message(s) processed |
 | `emcli send --account A --to X [--cc X] [--bcc X] --subject S --body B [--attach P]… [--reply-to U]` | Send / reply |
+| `emcli account list` | Discover accounts: JSON `name` / `from` / `can_send` per account |
 
 Defaults: `--folder INBOX`, `--limit 50` (max 500). Dates are RFC 3339 (e.g.
 `2026-06-01T00:00:00Z`). UIDs come from `list`/`search` output.
@@ -142,8 +143,9 @@ The user configures these; you cannot change them and shouldn't try.
 
 - ✅ Check `error` on every call; report `policy`/`not_found`/`auth` outcomes plainly to the user.
 - ✅ `get` to read, then `ack` only after you've truly processed a message.
-- ✅ Ask the user for the account name; keep bodies plain text.
+- ✅ Discover accounts with `emcli account list`, or ask the user; keep bodies plain text.
 - ❌ Don't read, print, or invent `EMCLI_KEY` or any password.
-- ❌ Don't run admin commands (`account`/`whitelist`/`config`/`audit`/`init`) — you have only
-  `EMCLI_KEY` (agent key); `emcli` will refuse admin commands with a privilege error.
+- ❌ Don't run admin commands (`account add/edit/remove`, `whitelist`, `config`, `audit`, `init`) —
+  you have only `EMCLI_KEY` (agent key); `emcli` will refuse them with a privilege error.
+  (`account list` is allowed — use it to discover accounts.)
 - ❌ Don't treat a blocked send or filtered message as a bug to route around — it's the user's policy.

skills/emcli/scripts/install.sh

@@ -7,17 +7,17 @@
 #   bash install.sh
 #
 # Environment overrides:
-#   EMCLI_VERSION      release tag to fetch          (default: v0.4.1)
+#   EMCLI_VERSION      release tag to fetch          (default: v0.5.2)
 #   EMCLI_BASE_URL     repo base URL                 (default: https://gitea.dcglab.co.uk/steve/emcli)
 #   EMCLI_INSTALL_DIR  where to put the binary        (default: $HOME/.local/bin)
 #
 # Release assets follow this naming scheme:
-#   emcli_<version>_<os>_<arch>[.exe]   e.g. emcli_0.4.1_linux_amd64
+#   emcli_<version>_<os>_<arch>[.exe]   e.g. emcli_0.5.2_linux_amd64
 #   checksums.txt                       (sha256, one "<sum>  <asset>" line per asset)
 
 set -euo pipefail
 
-VERSION="${EMCLI_VERSION:-v0.4.1}"
+VERSION="${EMCLI_VERSION:-v0.5.2}"
 BASE_URL="${EMCLI_BASE_URL:-https://gitea.dcglab.co.uk/steve/emcli}"
 INSTALL_DIR="${EMCLI_INSTALL_DIR:-$HOME/.local/bin}"