style: fix test name typo, table-test reporting, validator wording

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

USER-MANUAL.md

@@ -191,6 +191,7 @@ 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 |

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-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/admin.go

@@ -45,6 +45,7 @@ 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 +57,14 @@ 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 +91,7 @@ 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 +103,10 @@ 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 +133,8 @@ 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
 			}

internal/cli/admin_test.go

@@ -132,3 +132,17 @@ 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/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

@@ -42,15 +42,39 @@ 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() }
 
 // DefaultDBPath resolves EMCLI_DB or the per-OS default location.

internal/store/store_test.go

@@ -1,6 +1,7 @@
 package store
 
 import (
+	"database/sql"
 	"path/filepath"
 	"testing"
 )
@@ -28,7 +29,7 @@ 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 +40,7 @@ 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 +105,66 @@ 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)
+	}
+}