# 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 `). 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 " if got := a.SendFrom(); got != "Steve Cliff " { t.Fatalf("set from-address should win, got %q", got) } } func TestAddGetAccountRoundTripsFromAddress(t *testing.T) { s := openTemp(t) a := sampleAccount() a.FromAddress = "Steve Cliff " 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 " { 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) " ``` --- ### 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 `. - 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", "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 ", 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 ") 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) " ``` --- ### 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 " 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 " acc, _ := f.ToAccount() if acc.FromAddress != "Steve Cliff " { t.Fatalf("ToAccount lost FromAddress: %q", acc.FromAddress) } back := FieldsFromAccount(acc) if back.FromAddress != "Steve Cliff " { 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 "). 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 " 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 " { 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) " ``` --- ## 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.