From d58f7af082169ea4705012d49d2677b42cc2e30d Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 14:06:13 -0400
Subject: [PATCH 1/8] Add sent mail listing

---
 .surface                                 |   4 +
 docs/cli.md                              |   6 +-
 go.mod                                   |   2 +-
 go.sum                                   |   4 +-
 internal/cmd/help.go                     |   2 +-
 internal/cmd/help_test.go                |   1 +
 internal/cmd/root.go                     |   1 +
 internal/cmd/sent.go                     | 257 +++++++++++++++++++++++
 internal/cmd/sent_test.go                | 201 ++++++++++++++++++
 internal/mcpserver/model/PROVENANCE.json |   9 +-
 internal/mcpserver/model/openapi.json    |  15 +-
 tests/smoke/sent_test.go                 |  55 +++++
 12 files changed, 548 insertions(+), 9 deletions(-)
 create mode 100644 internal/cmd/sent.go
 create mode 100644 internal/cmd/sent_test.go
 create mode 100644 tests/smoke/sent_test.go

diff --git a/.surface b/.surface
index 9dee36fb..ec09927b 100644
--- a/.surface
+++ b/.surface
@@ -316,6 +316,10 @@ hey search --subject
 hey search --to
 hey search filters
 hey seen
+hey sent
+hey sent --all
+hey sent --limit
+hey sent --page
 hey set-aside
 hey set-aside group
 hey set-aside group add
diff --git a/docs/cli.md b/docs/cli.md
index 72cbb684..aca42303 100644
--- a/docs/cli.md
+++ b/docs/cli.md
@@ -112,7 +112,7 @@ Listing commands also answer `--markdown` for a table, `--styled` to force the h
 rendering when the output is piped, `--ids-only` for one ID per line, and `--count` for a
 bare number. `--ids-only` and `--count` need list data, so they work on `hey box list`,
 `hey box view`, `hey bundle view`, `hey label list`, `hey label view`, `hey collection list`, `hey collection view`,
-`hey workflow list`, `hey workflow view`, `hey clip list`, `hey snippet list`, `hey draft list`, `hey search`, `hey contact list`, `hey contact threads`, `hey screener list`, `hey screener history`, `hey calendar list`,
+`hey workflow list`, `hey workflow view`, `hey clip list`, `hey snippet list`, `hey draft list`, `hey sent`, `hey search`, `hey contact list`, `hey contact threads`, `hey screener list`, `hey screener history`, `hey calendar list`,
 `hey event list`, `hey event day`, `hey event week`, `hey todo list`, `hey habit list`,
 `hey timetrack list` and `hey journal list`.
 The
@@ -193,6 +193,8 @@ hey snippet list                                  # list reusable email snippets
 hey snippet create --name "Scheduling reply" --content "Tuesday works for me."
 hey snippet update 44 --content "Wednesday works for me."
 hey snippet delete 44
+hey sent                            # list the latest sent message in each thread
+hey sent --all --json               # exact To, CC, BCC, sent time, and app URL
 hey search "quarterly planning"    # search threads and matching messages
 hey search --from jane@example.com --date last_30_days  # refine a search
 hey search filters                 # list available refinement values
@@ -270,6 +272,8 @@ Drafts are the review-before-send lane: `hey compose --draft` (and `hey reply --
 
 `hey share <thread_id>` gets a sharing link for a thread. Anyone with the link can see the entire thread and future emails or replies sent to it. `hey unshare <thread_id>` turns off the sharing link.
 
+`hey sent` lists the latest message you sent in each thread, newest first. Its `id` is the thread ID accepted by `hey thread read`; `sent_at` is when HEY delivered that message, not when an earlier draft was created. JSON separates exact recipients into `to`, `cc`, and `bcc` arrays and includes the subject, summary, and `app_url`. Styled and Markdown output use HEY's compact `Me → first recipient + N` summary. One page arrives by default; `--limit` reads enough pages for the requested count, `--all` follows HEY's next-page links for up to 100 pages, and `--page` continues from a reported page.
+
 Search accepts free text plus `--required`, `--any`, `--none`, `--exact`, `--from`, `--to`, `--subject`, `--date`, `--in`, `--label`, and `--attachment`. `--in`, `--date`, `--label` and `--attachment` take one of the values `hey search filters` lists — the attachment kinds are `any`, `images`, `pdfs`, `calendar_invites`, `documents`, `spreadsheets`, `presentations`, `media` and `zip_files`, so it is `--attachment pdfs` rather than `pdf`, and an unrecognized `--in`, `--date` or `--attachment` is refused with the values it accepts before anything is sent. Use `--page` for one page or `--all` to fetch up to 100 pages; capped searches report the next page for continuation. Search results include `topic_id` for reading the thread and the matching message summaries. Results with an active box item also include `id` for organization actions.
 
 Contact updates preserve omitted name, email, and alias fields. Supplying `--alias` replaces the complete alias list; `--alias=` clears it. Contact notes accept positional content, `--note`, stdin, or `$EDITOR`. HEY hides contacts rather than permanently deleting them; hidden contacts leave lists, autocomplete, and search, and can be shown again by ID. Bundling groups a contact's mail into one row without merging or deleting the underlying threads; unbundling lists those threads separately again. HEY applies bundling when the contact's current delivery setting supports bundles.
diff --git a/go.mod b/go.mod
index f1cadb43..a4782198 100644
--- a/go.mod
+++ b/go.mod
@@ -8,7 +8,7 @@ require (
 	charm.land/glamour/v2 v2.0.1
 	charm.land/lipgloss/v2 v2.0.6
 	github.com/basecamp/actioncable-go v1.1.0
-	github.com/basecamp/hey-sdk/go v0.31.1
+	github.com/basecamp/hey-sdk/go v0.31.2-0.20260920180340-2d40721c770f
 	github.com/basecamp/mcp v0.0.0-20260828100356-2d6f44b51e9d
 	github.com/charmbracelet/x/ansi v0.11.8
 	github.com/fsnotify/fsnotify v1.10.1
diff --git a/go.sum b/go.sum
index 656af9d5..79a05b6c 100644
--- a/go.sum
+++ b/go.sum
@@ -89,8 +89,8 @@ github.com/aymerick/douceur v0.2.0 h1:Mv+mAeH1Q+n9Fr+oyamOlAkUNPWPlA8PPGR0QAaYuP
 github.com/aymerick/douceur v0.2.0/go.mod h1:wlT5vV2O3h55X9m7iVYN0TBM0NH/MmbLnd30/FjWUq4=
 github.com/basecamp/actioncable-go v1.1.0 h1:AizmCxoKvmUMdqwMQCCLQrFaVbjp8RhkneWidxygc7E=
 github.com/basecamp/actioncable-go v1.1.0/go.mod h1:ezaV5z1GXQAsqyejqTs6wCFl2D8Wj+COLQkHc/kwoRs=
-github.com/basecamp/hey-sdk/go v0.31.1 h1:dFlCe4LMmLAHgRB05QRHaE26XPPkZVIMp0qCGEanVQU=
-github.com/basecamp/hey-sdk/go v0.31.1/go.mod h1:eCJOhTLOpi2FCQUXireHZQ7DzRs2TUqvYhRDTfVLoDY=
+github.com/basecamp/hey-sdk/go v0.31.2-0.20260920180340-2d40721c770f h1:pmgQYWhGNX7W6CAxrfKNTN+BEvfganLC2mgR87Uv5hs=
+github.com/basecamp/hey-sdk/go v0.31.2-0.20260920180340-2d40721c770f/go.mod h1:eCJOhTLOpi2FCQUXireHZQ7DzRs2TUqvYhRDTfVLoDY=
 github.com/basecamp/mcp v0.0.0-20260828100356-2d6f44b51e9d h1:zEQVGq1x1nhKMZ2TudFAcSJ32CHT8richI1vQakIKz4=
 github.com/basecamp/mcp v0.0.0-20260828100356-2d6f44b51e9d/go.mod h1:Ee2c/q1/pg+5T5741PIuA3s6VJMQC7I0XBNXIHIujzA=
 github.com/blang/semver v3.5.1+incompatible h1:cQNTCjp13qL8KC3Nbxr/y2Bqb63oX6wdnnjpJbkM4JQ=
diff --git a/internal/cmd/help.go b/internal/cmd/help.go
index 8c044833..63ffac5a 100644
--- a/internal/cmd/help.go
+++ b/internal/cmd/help.go
@@ -17,7 +17,7 @@ var curatedCategories = []struct {
 }{
 	{
 		heading: "CORE COMMANDS",
-		names:   []string{"tui", "box", "thread", "reply", "compose", "search", "contact", "calendar", "journal"},
+		names:   []string{"tui", "box", "thread", "reply", "compose", "sent", "search", "contact", "calendar", "journal"},
 	},
 	{
 		heading: "MAIL",
diff --git a/internal/cmd/help_test.go b/internal/cmd/help_test.go
index a09d6a83..be316459 100644
--- a/internal/cmd/help_test.go
+++ b/internal/cmd/help_test.go
@@ -110,6 +110,7 @@ CORE COMMANDS
   thread    Read email threads
   reply     Reply to a thread
   compose   Write and send a new email
+  sent      List sent email
   search    Search email threads and messages
   contact   Manage contacts
   calendar  Browse your calendars
diff --git a/internal/cmd/root.go b/internal/cmd/root.go
index eba54d9c..bee6c012 100644
--- a/internal/cmd/root.go
+++ b/internal/cmd/root.go
@@ -206,6 +206,7 @@ func newRootCmd() *cobra.Command {
 	root.AddCommand(newClipCommand().cmd)
 	root.AddCommand(newSnippetCommand().cmd)
 	root.AddCommand(newSearchCommand().cmd)
+	root.AddCommand(newSentCommand().cmd)
 	root.AddCommand(newContactsCommand().cmd)
 	root.AddCommand(newScreenerCommand().cmd)
 	root.AddCommand(newThreadCommand())
diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
new file mode 100644
index 00000000..9dde3fba
--- /dev/null
+++ b/internal/cmd/sent.go
@@ -0,0 +1,257 @@
+package cmd
+
+import (
+	"context"
+	"fmt"
+	"strconv"
+	"strings"
+	"time"
+
+	"github.com/spf13/cobra"
+
+	"github.com/basecamp/hey-sdk/go/pkg/generated"
+
+	"github.com/basecamp/hey-cli/internal/apierr"
+	"github.com/basecamp/hey-cli/internal/output"
+)
+
+// maxSentPages bounds one invocation even if the server returns a bad pagination loop.
+const maxSentPages = 100
+
+type sentCommand struct {
+	cmd   *cobra.Command
+	limit int
+	all   bool
+	page  int
+}
+
+type sentRecipient struct {
+	Name         string `json:"name,omitempty"`
+	EmailAddress string `json:"email_address"`
+}
+
+type sentMessage struct {
+	ID      int64           `json:"id"`
+	Subject string          `json:"subject"`
+	To      []sentRecipient `json:"to"`
+	CC      []sentRecipient `json:"cc"`
+	BCC     []sentRecipient `json:"bcc"`
+	Summary string          `json:"summary,omitempty"`
+	SentAt  time.Time       `json:"sent_at"`
+	AppURL  string          `json:"app_url"`
+}
+
+type sentTableRow struct {
+	ID         int64  `json:"id"`
+	Subject    string `json:"subject"`
+	Recipients string `json:"recipients"`
+	Summary    string `json:"summary,omitempty"`
+	Sent       string `json:"sent"`
+	AppURL     string `json:"app_url"`
+}
+
+func newSentCommand() *sentCommand {
+	sentCommand := &sentCommand{}
+	sentCommand.cmd = &cobra.Command{
+		Use:   "sent",
+		Short: "List sent email",
+		Long: `List the latest message you sent in each thread, newest first.
+
+One page arrives by default. --limit reads pages until it has enough messages, and
+--all reads up to 100 pages. Recipient lists in JSON preserve To, CC, and BCC separately.`,
+		Annotations: map[string]string{
+			"agent_notes": "Returns outbound mail with thread IDs, exact To/CC/BCC recipients, sent times, and HEY app URLs. IDs are thread IDs for `hey thread read <id>`.",
+		},
+		Example: `  hey sent
+  hey sent --limit 10 --json
+  hey sent --all --json
+  hey sent --ids-only`,
+		RunE: sentCommand.run,
+		Args: cobra.NoArgs,
+	}
+
+	sentCommand.cmd.Flags().IntVar(&sentCommand.limit, "limit", 0, "Maximum number of sent messages to show")
+	sentCommand.cmd.Flags().BoolVar(&sentCommand.all, "all", false, "Fetch up to 100 results pages (override --limit)")
+	sentCommand.cmd.Flags().IntVar(&sentCommand.page, "page", 1, "Results page")
+	return sentCommand
+}
+
+func (c *sentCommand) run(cmd *cobra.Command, _ []string) error {
+	if err := requireAuth(); err != nil {
+		return err
+	}
+	if c.page < 1 {
+		return apierr.ErrUsage("--page must be at least 1")
+	}
+	if c.limit < 0 {
+		return apierr.ErrUsage("--limit must be at least 0")
+	}
+
+	startPage := ""
+	if c.page > 1 {
+		startPage = strconv.Itoa(c.page)
+	}
+	first, err := readSentPage(cmd.Context(), startPage)
+	if err != nil {
+		return err
+	}
+	collected, err := collectPages(cmd.Context(), first, pageRequest{Limit: c.limit, All: c.all, MaxPages: maxSentPages}, readSentPage)
+	if err != nil {
+		return err
+	}
+
+	messages := makeSentMessages(collected.Items)
+	nextPage := collected.Cursor
+	notice := sentListingNotice(len(messages), collected.Read, nextPage, collected.Truncated)
+	if c.limit > 0 && !c.all && len(messages) > c.limit {
+		messages = messages[:c.limit]
+		nextPage = ""
+		notice = output.TruncationNotice(len(messages), len(collected.Items))
+	}
+
+	switch writer.EffectiveFormat() {
+	case output.FormatStyled:
+		return writeSentStyled(cmd, messages, notice)
+	case output.FormatMarkdown:
+		if stderrNotice := paginationNoticeForStderr(writer.EffectiveFormat(), notice); stderrNotice != "" {
+			fmt.Fprintln(cmd.ErrOrStderr(), stderrNotice)
+		}
+		return writeOK(makeSentTableRows(messages))
+	default:
+		if stderrNotice := paginationNoticeForStderr(writer.EffectiveFormat(), notice); stderrNotice != "" {
+			fmt.Fprintln(cmd.ErrOrStderr(), stderrNotice)
+		}
+		opts := []output.ResponseOption{
+			output.WithSummary(fmt.Sprintf("%d %s", len(messages), sentMessageNoun(len(messages)))),
+			output.WithNotice(notice),
+			output.WithMeta("page", c.page),
+			output.WithMeta("pages_fetched", collected.Read),
+			output.WithBreadcrumbs(output.Breadcrumb{
+				Action:      "read",
+				Command:     "hey thread read <id>",
+				Description: "Read a sent email thread",
+			}),
+		}
+		if nextPage != "" {
+			opts = append(opts, output.WithMeta("next_page", nextPage))
+		}
+		return writeOK(messages, opts...)
+	}
+}
+
+func readSentPage(ctx context.Context, cursor string) (pageResult[generated.Topic], error) {
+	page, err := sdk.Topics().GetSentPage(ctx, cursor)
+	if err != nil {
+		return pageResult[generated.Topic]{}, apierr.FromSDK(err)
+	}
+	if page == nil {
+		return pageResult[generated.Topic]{}, nil
+	}
+	return pageResult[generated.Topic]{Items: page.Topics, Cursor: page.NextPage}, nil
+}
+
+func makeSentMessages(topics []generated.Topic) []sentMessage {
+	messages := make([]sentMessage, 0, len(topics))
+	for _, topic := range topics {
+		entry := topic.LatestEntry
+		sentAt := entry.ActiveAt
+		if sentAt.IsZero() {
+			sentAt = entry.CreatedAt
+		}
+		messages = append(messages, sentMessage{
+			ID:      topic.Id,
+			Subject: topic.Name,
+			To:      makeSentRecipients(entry.Addressed.Directly),
+			CC:      makeSentRecipients(entry.Addressed.Copied),
+			BCC:     makeSentRecipients(entry.Addressed.Blindcopied),
+			Summary: entry.Summary,
+			SentAt:  sentAt,
+			AppURL:  topic.AppUrl,
+		})
+	}
+	return messages
+}
+
+func makeSentRecipients(contacts []generated.Contact) []sentRecipient {
+	recipients := make([]sentRecipient, len(contacts))
+	for i, contact := range contacts {
+		recipients[i] = sentRecipient{Name: contact.Name, EmailAddress: contact.EmailAddress}
+	}
+	return recipients
+}
+
+func writeSentStyled(cmd *cobra.Command, messages []sentMessage, notice string) error {
+	if len(messages) == 0 {
+		fmt.Fprintln(cmd.OutOrStdout(), "No sent messages.")
+		return nil
+	}
+
+	table := newTable(cmd.OutOrStdout())
+	table.addRow([]string{"Thread", "Subject", "Recipients", "Summary", "Sent"})
+	for _, message := range messages {
+		table.addRow([]string{
+			strconv.FormatInt(message.ID, 10),
+			truncate(message.Subject, 42),
+			truncate(sentRecipientSummary(message), 32),
+			truncate(message.Summary, 52),
+			formatTimestamp(message.SentAt.Local()),
+		})
+	}
+	table.print()
+	if notice != "" {
+		fmt.Fprintf(cmd.OutOrStdout(), "\n%s\n", notice)
+	}
+	return nil
+}
+
+func makeSentTableRows(messages []sentMessage) []sentTableRow {
+	rows := make([]sentTableRow, len(messages))
+	for i, message := range messages {
+		rows[i] = sentTableRow{
+			ID:         message.ID,
+			Subject:    message.Subject,
+			Recipients: sentRecipientSummary(message),
+			Summary:    message.Summary,
+			Sent:       formatTimestamp(message.SentAt.Local()),
+			AppURL:     message.AppURL,
+		}
+	}
+	return rows
+}
+
+func sentRecipientSummary(message sentMessage) string {
+	recipients := make([]sentRecipient, 0, len(message.To)+len(message.CC)+len(message.BCC))
+	recipients = append(recipients, message.To...)
+	recipients = append(recipients, message.CC...)
+	recipients = append(recipients, message.BCC...)
+	if len(recipients) == 0 {
+		return "Me"
+	}
+
+	name := strings.TrimSpace(recipients[0].Name)
+	if name == "" {
+		name = recipients[0].EmailAddress
+	}
+	if len(recipients) == 1 {
+		return "Me → " + name
+	}
+	return fmt.Sprintf("Me → %s + %d", name, len(recipients)-1)
+}
+
+func sentListingNotice(shown, pages int, nextPage string, truncated bool) string {
+	switch {
+	case truncated:
+		return fmt.Sprintf("Sent listing stopped after %d pages. Continue with --page %s.", pages, nextPage)
+	case nextPage != "":
+		return fmt.Sprintf("Showing %d %s. Use --all to see everything.", shown, sentMessageNoun(shown))
+	default:
+		return ""
+	}
+}
+
+func sentMessageNoun(count int) string {
+	if count == 1 {
+		return "sent message"
+	}
+	return "sent messages"
+}
diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
new file mode 100644
index 00000000..38562368
--- /dev/null
+++ b/internal/cmd/sent_test.go
@@ -0,0 +1,201 @@
+package cmd
+
+import (
+	"encoding/json"
+	"fmt"
+	"io"
+	"net/http"
+	"strings"
+	"sync"
+	"testing"
+	"time"
+)
+
+const sentTopicsJSON = `{
+	"title":"Sent Mail",
+	"topics":[{
+		"id":42,
+		"name":"Quarterly planning follow-up",
+		"app_url":"https://app.hey.com/topics/42/entries/99",
+		"latest_entry":{
+			"id":99,
+			"subject":"Quarterly planning follow-up",
+			"summary":"Here are the decisions and owners from today's planning session.",
+			"created_at":"2026-09-18T09:00:00Z",
+			"active_at":"2026-09-19T14:30:00Z",
+			"addressed":{
+				"directly":[{"id":1,"name":"Sarah Chen","email_address":"sarah@example.com"}],
+				"copied":[{"id":2,"name":"Jamal Reed","email_address":"jamal@example.org"}],
+				"blindcopied":[{"id":3,"name":"Pat Quinn","email_address":"pat@example.com"}]
+			}
+		}
+	}]
+}`
+
+type sentTestRecipient struct {
+	Name         string `json:"name"`
+	EmailAddress string `json:"email_address"`
+}
+
+type sentTestRow struct {
+	ID      int64               `json:"id"`
+	Subject string              `json:"subject"`
+	To      []sentTestRecipient `json:"to"`
+	CC      []sentTestRecipient `json:"cc"`
+	BCC     []sentTestRecipient `json:"bcc"`
+	SentAt  time.Time           `json:"sent_at"`
+	AppURL  string              `json:"app_url"`
+}
+
+func decodeSentData[T any](t *testing.T, data any) T {
+	t.Helper()
+	encoded, err := json.Marshal(data)
+	if err != nil {
+		t.Fatalf("encode response data: %v", err)
+	}
+	var decoded T
+	if err := json.Unmarshal(encoded, &decoded); err != nil {
+		t.Fatalf("decode response data: %v", err)
+	}
+	return decoded
+}
+
+func TestSentCommandReturnsStableOutboundRows(t *testing.T) {
+	response, err := runJSONCommand(t, sentTopicsHandler(t, sentTopicsJSON), "sent")
+	if err != nil {
+		t.Fatalf("execute sent: %v", err)
+	}
+
+	rows := decodeSentData[[]sentTestRow](t, response.Data)
+	if len(rows) != 1 {
+		t.Fatalf("rows = %d, want 1", len(rows))
+	}
+	row := rows[0]
+	if row.ID != 42 || row.Subject != "Quarterly planning follow-up" {
+		t.Errorf("row identity = %#v", row)
+	}
+	if len(row.To) != 1 || row.To[0].Name != "Sarah Chen" || row.To[0].EmailAddress != "sarah@example.com" {
+		t.Errorf("to = %#v", row.To)
+	}
+	if len(row.CC) != 1 || row.CC[0].EmailAddress != "jamal@example.org" {
+		t.Errorf("cc = %#v", row.CC)
+	}
+	if len(row.BCC) != 1 || row.BCC[0].EmailAddress != "pat@example.com" {
+		t.Errorf("bcc = %#v", row.BCC)
+	}
+	if got := row.SentAt.Format(time.RFC3339); got != "2026-09-19T14:30:00Z" {
+		t.Errorf("sent_at = %q", got)
+	}
+	if row.AppURL != "https://app.hey.com/topics/42/entries/99" {
+		t.Errorf("app_url = %q", row.AppURL)
+	}
+	if response.Summary != "1 sent message" {
+		t.Errorf("summary = %q", response.Summary)
+	}
+}
+
+func TestSentCommandStyledMatchesHEYRecipientSummary(t *testing.T) {
+	stdout, err := runStyledCommand(t, sentTopicsHandler(t, sentTopicsJSON), "sent")
+	if err != nil {
+		t.Fatalf("execute sent --styled: %v", err)
+	}
+	for _, want := range []string{
+		"Quarterly planning follow-up",
+		"Me → Sarah Chen + 2",
+		"Here are the decisions and owners",
+		"2026-09-19",
+	} {
+		if !strings.Contains(stdout, want) {
+			t.Errorf("styled output missing %q:\n%s", want, stdout)
+		}
+	}
+}
+
+func TestSentCommandAllFollowsNextPageLink(t *testing.T) {
+	var mu sync.Mutex
+	var pages []string
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.URL.Path != "/topics/sent.json" {
+			http.NotFound(w, r)
+			return
+		}
+		page := r.URL.Query().Get("page")
+		mu.Lock()
+		pages = append(pages, page)
+		mu.Unlock()
+
+		w.Header().Set("Content-Type", "application/json")
+		switch page {
+		case "":
+			w.Header().Set("Link", `</topics/sent.json?page=2>; rel="next"`)
+			_, _ = io.WriteString(w, sentTopicsJSON)
+		case "2":
+			_, _ = io.WriteString(w, strings.ReplaceAll(sentTopicsJSON, `"id":42`, `"id":43`))
+		default:
+			t.Errorf("unexpected page %q", page)
+			http.Error(w, "unexpected page", http.StatusBadRequest)
+		}
+	})
+
+	response, err := runJSONCommand(t, handler, "sent", "--all")
+	if err != nil {
+		t.Fatalf("execute sent --all: %v", err)
+	}
+	rows := decodeSentData[[]sentTestRow](t, response.Data)
+	if len(rows) != 2 || rows[0].ID != 42 || rows[1].ID != 43 {
+		t.Fatalf("rows = %#v", rows)
+	}
+	mu.Lock()
+	gotPages := strings.Join(pages, ",")
+	mu.Unlock()
+	if gotPages != ",2" {
+		t.Errorf("pages = %q, want first page then 2", gotPages)
+	}
+}
+
+func TestSentCommandIDsAndCountUseThreadIDs(t *testing.T) {
+	handler := sentTopicsHandler(t, sentTopicsJSON)
+
+	ids, err := runFormattedCommand(t, handler, []string{"--ids-only"}, "sent")
+	if err != nil {
+		t.Fatalf("execute sent --ids-only: %v", err)
+	}
+	if ids != "42\n" {
+		t.Errorf("ids = %q, want thread ID", ids)
+	}
+
+	count, err := runFormattedCommand(t, handler, []string{"--count"}, "sent")
+	if err != nil {
+		t.Fatalf("execute sent --count: %v", err)
+	}
+	if count != "1\n" {
+		t.Errorf("count = %q", count)
+	}
+}
+
+func TestSentCommandRejectsInvalidPage(t *testing.T) {
+	_, err := runJSONCommand(t, http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		t.Errorf("unexpected request: %s", r.URL.String())
+	}), "sent", "--page", "0")
+	if err == nil || !strings.Contains(err.Error(), "--page must be at least 1") {
+		t.Fatalf("error = %v", err)
+	}
+}
+
+func sentTopicsHandler(t *testing.T, body string) http.Handler {
+	t.Helper()
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.Method != http.MethodGet || r.URL.Path != "/topics/sent.json" {
+			t.Errorf("request = %s %s, want GET /topics/sent.json", r.Method, r.URL.Path)
+			http.NotFound(w, r)
+			return
+		}
+		if page := r.URL.Query().Get("page"); page != "" && page != "1" {
+			t.Errorf("page = %q, want first page", page)
+		}
+		w.Header().Set("Content-Type", "application/json")
+		if _, err := fmt.Fprint(w, body); err != nil {
+			t.Errorf("write response: %v", err)
+		}
+	})
+}
diff --git a/internal/mcpserver/model/PROVENANCE.json b/internal/mcpserver/model/PROVENANCE.json
index c32e64dc..61f85986 100644
--- a/internal/mcpserver/model/PROVENANCE.json
+++ b/internal/mcpserver/model/PROVENANCE.json
@@ -1,7 +1,10 @@
 {
   "source": "github.com/basecamp/hey-sdk",
-  "commit": "41585abf862677fd40375c23cd858cc6eeac8a02",
-  "ref": "go/v0.31.1",
-  "files": ["behavior-model.json", "openapi.json"],
+  "commit": "2d40721c770f6ad2330757f064d20ccae99d25c0",
+  "ref": "go/v0.31.2-0.20260920180340-2d40721c770f",
+  "files": [
+    "behavior-model.json",
+    "openapi.json"
+  ],
   "synced_by": "scripts/sync-mcp-model.sh"
 }
diff --git a/internal/mcpserver/model/openapi.json b/internal/mcpserver/model/openapi.json
index 6e2b7c4b..9b3e5e07 100644
--- a/internal/mcpserver/model/openapi.json
+++ b/internal/mcpserver/model/openapi.json
@@ -2,7 +2,7 @@
   "openapi": "3.1.0",
   "info": {
     "title": "HEY",
-    "version": "2026-09-16",
+    "version": "2026-09-20",
     "description": "HEY API",
     "contact": {
       "name": "Basecamp",
@@ -12193,6 +12193,16 @@
             },
             "x-omitzero": true
           },
+          "active_at": {
+            "type": "string",
+            "description": "Delivery time. Present on the latest entry in Sent topics.",
+            "format": "date-time",
+            "x-go-type": "time.Time",
+            "x-go-type-import": {
+              "path": "time"
+            },
+            "x-omitzero": true
+          },
           "creator": {
             "$ref": "#/components/schemas/Contact"
           },
@@ -12214,6 +12224,9 @@
           "topic_id": {
             "type": "integer",
             "format": "int64"
+          },
+          "addressed": {
+            "$ref": "#/components/schemas/Addressed"
           }
         },
         "required": [
diff --git a/tests/smoke/sent_test.go b/tests/smoke/sent_test.go
new file mode 100644
index 00000000..18ff59d3
--- /dev/null
+++ b/tests/smoke/sent_test.go
@@ -0,0 +1,55 @@
+package smoke_test
+
+import (
+	"strconv"
+	"strings"
+	"testing"
+	"time"
+)
+
+type smokeSentRecipient struct {
+	Name         string `json:"name"`
+	EmailAddress string `json:"email_address"`
+}
+
+type smokeSentMessage struct {
+	ID      int64                `json:"id"`
+	Subject string               `json:"subject"`
+	To      []smokeSentRecipient `json:"to"`
+	CC      []smokeSentRecipient `json:"cc"`
+	BCC     []smokeSentRecipient `json:"bcc"`
+	SentAt  time.Time            `json:"sent_at"`
+	AppURL  string               `json:"app_url"`
+}
+
+func TestSentListing(t *testing.T) {
+	resp := heyJSON(t, "sent", "--all")
+	messages := dataAs[[]smokeSentMessage](t, resp)
+	for _, message := range messages {
+		if message.ID <= 0 {
+			t.Errorf("sent thread id = %d, want positive", message.ID)
+		}
+		if strings.TrimSpace(message.Subject) == "" {
+			t.Errorf("sent thread %d has no subject", message.ID)
+		}
+		if message.SentAt.IsZero() {
+			t.Errorf("sent thread %d has no sent_at", message.ID)
+		}
+		if strings.TrimSpace(message.AppURL) == "" {
+			t.Errorf("sent thread %d has no app_url", message.ID)
+		}
+		if message.To == nil || message.CC == nil || message.BCC == nil {
+			t.Errorf("sent thread %d recipient arrays = to:%v cc:%v bcc:%v, want arrays even when empty", message.ID, message.To, message.CC, message.BCC)
+		}
+	}
+
+	ids := strings.Fields(heyOK(t, "sent", "--ids-only"))
+	countText := strings.TrimSpace(heyOK(t, "sent", "--count"))
+	count, err := strconv.Atoi(countText)
+	if err != nil {
+		t.Fatalf("sent --count = %q: %v", countText, err)
+	}
+	if len(ids) != count {
+		t.Errorf("sent --ids-only returned %d ids, --count returned %d", len(ids), count)
+	}
+}

From 1ed1d4370cfb1c485d527dc9c885495e6a909863 Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 14:10:50 -0400
Subject: [PATCH 2/8] Test sent listing limits

---
 internal/cmd/sent_test.go | 43 +++++++++++++++++++++++++++++++++++++++
 1 file changed, 43 insertions(+)

diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
index 38562368..0c74432d 100644
--- a/internal/cmd/sent_test.go
+++ b/internal/cmd/sent_test.go
@@ -153,6 +153,41 @@ func TestSentCommandAllFollowsNextPageLink(t *testing.T) {
 	}
 }
 
+func TestSentCommandLimitReadsEnoughPagesAndTrims(t *testing.T) {
+	var pages []string
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		page := r.URL.Query().Get("page")
+		pages = append(pages, page)
+		w.Header().Set("Content-Type", "application/json")
+		switch page {
+		case "":
+			w.Header().Set("Link", `</topics/sent.json?page=2>; rel="next"`)
+			_, _ = io.WriteString(w, sentTopicsPage(42))
+		case "2":
+			w.Header().Set("Link", `</topics/sent.json?page=3>; rel="next"`)
+			_, _ = io.WriteString(w, sentTopicsPage(43, 44))
+		default:
+			t.Errorf("unexpected page %q", page)
+			http.Error(w, "unexpected page", http.StatusBadRequest)
+		}
+	})
+
+	response, err := runJSONCommand(t, handler, "sent", "--limit", "2")
+	if err != nil {
+		t.Fatalf("execute sent --limit 2: %v", err)
+	}
+	rows := decodeSentData[[]sentTestRow](t, response.Data)
+	if len(rows) != 2 || rows[0].ID != 42 || rows[1].ID != 43 {
+		t.Fatalf("rows = %#v", rows)
+	}
+	if got := strings.Join(pages, ","); got != ",2" {
+		t.Errorf("pages = %q, want first page then 2", got)
+	}
+	if response.Notice != "Showing 2 of 3 results. Use --all to see everything." {
+		t.Errorf("notice = %q", response.Notice)
+	}
+}
+
 func TestSentCommandIDsAndCountUseThreadIDs(t *testing.T) {
 	handler := sentTopicsHandler(t, sentTopicsJSON)
 
@@ -182,6 +217,14 @@ func TestSentCommandRejectsInvalidPage(t *testing.T) {
 	}
 }
 
+func sentTopicsPage(ids ...int64) string {
+	rows := make([]string, len(ids))
+	for i, id := range ids {
+		rows[i] = fmt.Sprintf(`{"id":%d,"name":"Planning follow-up %d","app_url":"https://app.hey.com/topics/%d/entries/99","latest_entry":{"id":99,"summary":"Decisions and owners.","active_at":"2026-09-19T14:30:00Z","addressed":{"directly":[],"copied":[],"blindcopied":[]}}}`, id, id, id)
+	}
+	return `{"title":"Sent Mail","topics":[` + strings.Join(rows, ",") + `]}`
+}
+
 func sentTopicsHandler(t *testing.T, body string) http.Handler {
 	t.Helper()
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {

From c102fc792aa5f847179d40bebf3a69571626f58c Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 14:13:45 -0400
Subject: [PATCH 3/8] Keep sent pagination notices consistent

---
 internal/cmd/sent.go | 13 ++++++-------
 1 file changed, 6 insertions(+), 7 deletions(-)

diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
index 9dde3fba..ca0257f4 100644
--- a/internal/cmd/sent.go
+++ b/internal/cmd/sent.go
@@ -109,18 +109,17 @@ func (c *sentCommand) run(cmd *cobra.Command, _ []string) error {
 		notice = output.TruncationNotice(len(messages), len(collected.Items))
 	}
 
-	switch writer.EffectiveFormat() {
+	format := writer.EffectiveFormat()
+	if stderrNotice := paginationNoticeForStderr(format, notice); stderrNotice != "" {
+		fmt.Fprintln(cmd.ErrOrStderr(), stderrNotice)
+	}
+
+	switch format {
 	case output.FormatStyled:
 		return writeSentStyled(cmd, messages, notice)
 	case output.FormatMarkdown:
-		if stderrNotice := paginationNoticeForStderr(writer.EffectiveFormat(), notice); stderrNotice != "" {
-			fmt.Fprintln(cmd.ErrOrStderr(), stderrNotice)
-		}
 		return writeOK(makeSentTableRows(messages))
 	default:
-		if stderrNotice := paginationNoticeForStderr(writer.EffectiveFormat(), notice); stderrNotice != "" {
-			fmt.Fprintln(cmd.ErrOrStderr(), stderrNotice)
-		}
 		opts := []output.ResponseOption{
 			output.WithSummary(fmt.Sprintf("%d %s", len(messages), sentMessageNoun(len(messages)))),
 			output.WithNotice(notice),

From dfa55c886fa3f59a9ee0da28cc8ea251529ea391 Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 14:36:35 -0400
Subject: [PATCH 4/8] Harden sent pagination and delivery metadata

---
 docs/cli.md               |  2 +-
 internal/cmd/sent.go      | 36 +++++++++++++-------------
 internal/cmd/sent_test.go | 53 +++++++++++++++++++++++++++++++++------
 nix/package.nix           |  2 +-
 4 files changed, 67 insertions(+), 26 deletions(-)

diff --git a/docs/cli.md b/docs/cli.md
index aca42303..2d4212ca 100644
--- a/docs/cli.md
+++ b/docs/cli.md
@@ -272,7 +272,7 @@ Drafts are the review-before-send lane: `hey compose --draft` (and `hey reply --
 
 `hey share <thread_id>` gets a sharing link for a thread. Anyone with the link can see the entire thread and future emails or replies sent to it. `hey unshare <thread_id>` turns off the sharing link.
 
-`hey sent` lists the latest message you sent in each thread, newest first. Its `id` is the thread ID accepted by `hey thread read`; `sent_at` is when HEY delivered that message, not when an earlier draft was created. JSON separates exact recipients into `to`, `cc`, and `bcc` arrays and includes the subject, summary, and `app_url`. Styled and Markdown output use HEY's compact `Me → first recipient + N` summary. One page arrives by default; `--limit` reads enough pages for the requested count, `--all` follows HEY's next-page links for up to 100 pages, and `--page` continues from a reported page.
+`hey sent` lists the latest message you sent in each thread, newest first. Its `id` is the thread ID accepted by `hey thread read`; `sent_at` is when HEY delivered that message, not when an earlier draft was created. If an older server omits the delivery time, JSON reports `sent_at` as `null` and human output says `Unavailable`. JSON separates exact recipients into `to`, `cc`, and `bcc` arrays and includes the subject, summary, and `app_url`. Styled and Markdown output use HEY's compact `Me → first recipient + N` summary. One page arrives by default; `--limit` reads enough pages for the requested count, `--all` follows HEY's next-page links for up to 100 pages, and `--page` continues from a reported page cursor.
 
 Search accepts free text plus `--required`, `--any`, `--none`, `--exact`, `--from`, `--to`, `--subject`, `--date`, `--in`, `--label`, and `--attachment`. `--in`, `--date`, `--label` and `--attachment` take one of the values `hey search filters` lists — the attachment kinds are `any`, `images`, `pdfs`, `calendar_invites`, `documents`, `spreadsheets`, `presentations`, `media` and `zip_files`, so it is `--attachment pdfs` rather than `pdf`, and an unrecognized `--in`, `--date` or `--attachment` is refused with the values it accepts before anything is sent. Use `--page` for one page or `--all` to fetch up to 100 pages; capped searches report the next page for continuation. Search results include `topic_id` for reading the thread and the matching message summaries. Results with an active box item also include `id` for organization actions.
 
diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
index ca0257f4..3893da98 100644
--- a/internal/cmd/sent.go
+++ b/internal/cmd/sent.go
@@ -13,6 +13,7 @@ import (
 
 	"github.com/basecamp/hey-cli/internal/apierr"
 	"github.com/basecamp/hey-cli/internal/output"
+	"github.com/basecamp/hey-cli/internal/terminal"
 )
 
 // maxSentPages bounds one invocation even if the server returns a bad pagination loop.
@@ -22,7 +23,7 @@ type sentCommand struct {
 	cmd   *cobra.Command
 	limit int
 	all   bool
-	page  int
+	page  string
 }
 
 type sentRecipient struct {
@@ -37,7 +38,7 @@ type sentMessage struct {
 	CC      []sentRecipient `json:"cc"`
 	BCC     []sentRecipient `json:"bcc"`
 	Summary string          `json:"summary,omitempty"`
-	SentAt  time.Time       `json:"sent_at"`
+	SentAt  *time.Time      `json:"sent_at"`
 	AppURL  string          `json:"app_url"`
 }
 
@@ -72,7 +73,7 @@ One page arrives by default. --limit reads pages until it has enough messages, a
 
 	sentCommand.cmd.Flags().IntVar(&sentCommand.limit, "limit", 0, "Maximum number of sent messages to show")
 	sentCommand.cmd.Flags().BoolVar(&sentCommand.all, "all", false, "Fetch up to 100 results pages (override --limit)")
-	sentCommand.cmd.Flags().IntVar(&sentCommand.page, "page", 1, "Results page")
+	sentCommand.cmd.Flags().StringVar(&sentCommand.page, "page", "", "Results page cursor")
 	return sentCommand
 }
 
@@ -80,18 +81,11 @@ func (c *sentCommand) run(cmd *cobra.Command, _ []string) error {
 	if err := requireAuth(); err != nil {
 		return err
 	}
-	if c.page < 1 {
-		return apierr.ErrUsage("--page must be at least 1")
-	}
 	if c.limit < 0 {
 		return apierr.ErrUsage("--limit must be at least 0")
 	}
 
-	startPage := ""
-	if c.page > 1 {
-		startPage = strconv.Itoa(c.page)
-	}
-	first, err := readSentPage(cmd.Context(), startPage)
+	first, err := readSentPage(cmd.Context(), c.page)
 	if err != nil {
 		return err
 	}
@@ -153,9 +147,10 @@ func makeSentMessages(topics []generated.Topic) []sentMessage {
 	messages := make([]sentMessage, 0, len(topics))
 	for _, topic := range topics {
 		entry := topic.LatestEntry
-		sentAt := entry.ActiveAt
-		if sentAt.IsZero() {
-			sentAt = entry.CreatedAt
+		var sentAt *time.Time
+		if !entry.ActiveAt.IsZero() {
+			activeAt := entry.ActiveAt
+			sentAt = &activeAt
 		}
 		messages = append(messages, sentMessage{
 			ID:      topic.Id,
@@ -193,7 +188,7 @@ func writeSentStyled(cmd *cobra.Command, messages []sentMessage, notice string)
 			truncate(message.Subject, 42),
 			truncate(sentRecipientSummary(message), 32),
 			truncate(message.Summary, 52),
-			formatTimestamp(message.SentAt.Local()),
+			formatSentTimestamp(message.SentAt),
 		})
 	}
 	table.print()
@@ -211,7 +206,7 @@ func makeSentTableRows(messages []sentMessage) []sentTableRow {
 			Subject:    message.Subject,
 			Recipients: sentRecipientSummary(message),
 			Summary:    message.Summary,
-			Sent:       formatTimestamp(message.SentAt.Local()),
+			Sent:       formatSentTimestamp(message.SentAt),
 			AppURL:     message.AppURL,
 		}
 	}
@@ -237,10 +232,17 @@ func sentRecipientSummary(message sentMessage) string {
 	return fmt.Sprintf("Me → %s + %d", name, len(recipients)-1)
 }
 
+func formatSentTimestamp(sentAt *time.Time) string {
+	if sentAt == nil {
+		return "Unavailable"
+	}
+	return formatTimestamp(sentAt.Local())
+}
+
 func sentListingNotice(shown, pages int, nextPage string, truncated bool) string {
 	switch {
 	case truncated:
-		return fmt.Sprintf("Sent listing stopped after %d pages. Continue with --page %s.", pages, nextPage)
+		return fmt.Sprintf("Sent listing stopped after %d pages. Continue with --page %s.", pages, terminal.SanitizeLine(nextPage))
 	case nextPage != "":
 		return fmt.Sprintf("Showing %d %s. Use --all to see everything.", shown, sentMessageNoun(shown))
 	default:
diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
index 0c74432d..a50a3bd7 100644
--- a/internal/cmd/sent_test.go
+++ b/internal/cmd/sent_test.go
@@ -43,7 +43,7 @@ type sentTestRow struct {
 	To      []sentTestRecipient `json:"to"`
 	CC      []sentTestRecipient `json:"cc"`
 	BCC     []sentTestRecipient `json:"bcc"`
-	SentAt  time.Time           `json:"sent_at"`
+	SentAt  *time.Time          `json:"sent_at"`
 	AppURL  string              `json:"app_url"`
 }
 
@@ -83,6 +83,9 @@ func TestSentCommandReturnsStableOutboundRows(t *testing.T) {
 	if len(row.BCC) != 1 || row.BCC[0].EmailAddress != "pat@example.com" {
 		t.Errorf("bcc = %#v", row.BCC)
 	}
+	if row.SentAt == nil {
+		t.Fatal("sent_at is nil")
+	}
 	if got := row.SentAt.Format(time.RFC3339); got != "2026-09-19T14:30:00Z" {
 		t.Errorf("sent_at = %q", got)
 	}
@@ -208,12 +211,48 @@ func TestSentCommandIDsAndCountUseThreadIDs(t *testing.T) {
 	}
 }
 
-func TestSentCommandRejectsInvalidPage(t *testing.T) {
-	_, err := runJSONCommand(t, http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-		t.Errorf("unexpected request: %s", r.URL.String())
-	}), "sent", "--page", "0")
-	if err == nil || !strings.Contains(err.Error(), "--page must be at least 1") {
-		t.Fatalf("error = %v", err)
+func TestSentCommandPreservesOpaquePageCursor(t *testing.T) {
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if page := r.URL.Query().Get("page"); page != "cursor-2" {
+			t.Errorf("page = %q, want cursor-2", page)
+		}
+		w.Header().Set("Content-Type", "application/json")
+		w.Header().Set("Link", `</topics/sent.json?page=cursor-3>; rel="next"`)
+		_, _ = io.WriteString(w, sentTopicsJSON)
+	})
+
+	response, err := runJSONCommand(t, handler, "sent", "--page", "cursor-2")
+	if err != nil {
+		t.Fatalf("execute sent --page cursor-2: %v", err)
+	}
+	if got := response.Meta["page"]; got != "cursor-2" {
+		t.Errorf("page metadata = %#v", got)
+	}
+	if got := response.Meta["next_page"]; got != "cursor-3" {
+		t.Errorf("next_page metadata = %#v", got)
+	}
+}
+
+func TestSentCommandDoesNotUseCreationTimeAsDeliveryTime(t *testing.T) {
+	body := strings.Replace(sentTopicsJSON, `"active_at":"2026-09-19T14:30:00Z",`, "", 1)
+	response, err := runJSONCommand(t, sentTopicsHandler(t, body), "sent")
+	if err != nil {
+		t.Fatalf("execute sent: %v", err)
+	}
+
+	rows := decodeSentData[[]sentTestRow](t, response.Data)
+	if rows[0].SentAt != nil {
+		t.Errorf("sent_at = %v, want null", rows[0].SentAt)
+	}
+}
+
+func TestSentListingNoticeSanitizesCursor(t *testing.T) {
+	notice := sentListingNotice(100, 100, "cursor-\x1b[31mnext", true)
+	if strings.ContainsRune(notice, '\x1b') {
+		t.Errorf("notice contains escape byte: %q", notice)
+	}
+	if !strings.Contains(notice, "cursor-next") {
+		t.Errorf("notice = %q", notice)
 	}
 }
 
diff --git a/nix/package.nix b/nix/package.nix
index 1fd2d6e6..5c76094f 100644
--- a/nix/package.nix
+++ b/nix/package.nix
@@ -18,7 +18,7 @@ buildGoModule.override { inherit go; } (finalAttrs: {
 
   # To update: run `make update-nix-hash` (Docker). It rewrites this quoted
   # value in place, so keep it a string literal rather than lib.fakeHash.
-  vendorHash = "sha256-ZfLot6LMYS4yL+5A4Jb9qzNVRobgUuVqXkuWfnX751k=";
+  vendorHash = "sha256-za+/pNZGLU2zXIRO9DjvW4KAXUvwi8k9WSWAKUZw1zk=";
 
   subPackages = [ "cmd/hey" ];
 

From 1f7a2c251dbf49042ee97d78d51316cd06518888 Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 15:04:01 -0400
Subject: [PATCH 5/8] Complete sent output edge-case coverage

---
 internal/cmd/sent.go      |  3 +++
 internal/cmd/sent_test.go | 35 +++++++++++++++++++++++++++++++++++
 tests/smoke/sent_test.go  |  6 +++---
 3 files changed, 41 insertions(+), 3 deletions(-)

diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
index 3893da98..1702b016 100644
--- a/internal/cmd/sent.go
+++ b/internal/cmd/sent.go
@@ -177,6 +177,9 @@ func makeSentRecipients(contacts []generated.Contact) []sentRecipient {
 func writeSentStyled(cmd *cobra.Command, messages []sentMessage, notice string) error {
 	if len(messages) == 0 {
 		fmt.Fprintln(cmd.OutOrStdout(), "No sent messages.")
+		if notice != "" {
+			fmt.Fprintf(cmd.OutOrStdout(), "\n%s\n", notice)
+		}
 		return nil
 	}
 
diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
index a50a3bd7..48b2ba37 100644
--- a/internal/cmd/sent_test.go
+++ b/internal/cmd/sent_test.go
@@ -114,6 +114,41 @@ func TestSentCommandStyledMatchesHEYRecipientSummary(t *testing.T) {
 	}
 }
 
+func TestSentCommandMarkdownReportsRecipientsURLAndUnavailableDeliveryTime(t *testing.T) {
+	body := strings.Replace(sentTopicsJSON, `"active_at":"2026-09-19T14:30:00Z",`, "", 1)
+	markdown, err := runFormattedCommand(t, sentTopicsHandler(t, body), []string{"--markdown"}, "sent")
+	if err != nil {
+		t.Fatalf("execute sent --markdown: %v", err)
+	}
+	for _, want := range []string{
+		"Me → Sarah Chen + 2",
+		"https://app.hey.com/topics/42/entries/99",
+		"Unavailable",
+	} {
+		if !strings.Contains(markdown, want) {
+			t.Errorf("Markdown output missing %q:\n%s", want, markdown)
+		}
+	}
+}
+
+func TestSentCommandStyledShowsContinuationAfterAnEmptyPage(t *testing.T) {
+	handler := http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.Header().Set("Link", `</topics/sent.json?page=cursor-2>; rel="next"`)
+		_, _ = io.WriteString(w, `{"title":"Sent Mail","topics":[]}`)
+	})
+
+	stdout, err := runStyledCommand(t, handler, "sent")
+	if err != nil {
+		t.Fatalf("execute sent --styled: %v", err)
+	}
+	for _, want := range []string{"No sent messages.", "Use --all to see everything."} {
+		if !strings.Contains(stdout, want) {
+			t.Errorf("styled output missing %q:\n%s", want, stdout)
+		}
+	}
+}
+
 func TestSentCommandAllFollowsNextPageLink(t *testing.T) {
 	var mu sync.Mutex
 	var pages []string
diff --git a/tests/smoke/sent_test.go b/tests/smoke/sent_test.go
index 18ff59d3..d32ec2ec 100644
--- a/tests/smoke/sent_test.go
+++ b/tests/smoke/sent_test.go
@@ -18,7 +18,7 @@ type smokeSentMessage struct {
 	To      []smokeSentRecipient `json:"to"`
 	CC      []smokeSentRecipient `json:"cc"`
 	BCC     []smokeSentRecipient `json:"bcc"`
-	SentAt  time.Time            `json:"sent_at"`
+	SentAt  *time.Time           `json:"sent_at"`
 	AppURL  string               `json:"app_url"`
 }
 
@@ -32,8 +32,8 @@ func TestSentListing(t *testing.T) {
 		if strings.TrimSpace(message.Subject) == "" {
 			t.Errorf("sent thread %d has no subject", message.ID)
 		}
-		if message.SentAt.IsZero() {
-			t.Errorf("sent thread %d has no sent_at", message.ID)
+		if message.SentAt != nil && message.SentAt.IsZero() {
+			t.Errorf("sent thread %d has an invalid sent_at", message.ID)
 		}
 		if strings.TrimSpace(message.AppURL) == "" {
 			t.Errorf("sent thread %d has no app_url", message.ID)

From bc05bbfe54ba1d72302d764a4768827309ee6d76 Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 15:21:05 -0400
Subject: [PATCH 6/8] Stabilize sent output and pagination notices

---
 internal/cmd/sent.go      | 10 +++++++---
 internal/cmd/sent_test.go | 23 ++++++++++++++++++++++-
 2 files changed, 29 insertions(+), 4 deletions(-)

diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
index 1702b016..5b1b8b99 100644
--- a/internal/cmd/sent.go
+++ b/internal/cmd/sent.go
@@ -37,7 +37,7 @@ type sentMessage struct {
 	To      []sentRecipient `json:"to"`
 	CC      []sentRecipient `json:"cc"`
 	BCC     []sentRecipient `json:"bcc"`
-	Summary string          `json:"summary,omitempty"`
+	Summary string          `json:"summary"`
 	SentAt  *time.Time      `json:"sent_at"`
 	AppURL  string          `json:"app_url"`
 }
@@ -46,7 +46,7 @@ type sentTableRow struct {
 	ID         int64  `json:"id"`
 	Subject    string `json:"subject"`
 	Recipients string `json:"recipients"`
-	Summary    string `json:"summary,omitempty"`
+	Summary    string `json:"summary"`
 	Sent       string `json:"sent"`
 	AppURL     string `json:"app_url"`
 }
@@ -100,7 +100,11 @@ func (c *sentCommand) run(cmd *cobra.Command, _ []string) error {
 	if c.limit > 0 && !c.all && len(messages) > c.limit {
 		messages = messages[:c.limit]
 		nextPage = ""
-		notice = output.TruncationNotice(len(messages), len(collected.Items))
+		if collected.Cursor != "" {
+			notice = sentListingNotice(len(messages), collected.Read, collected.Cursor, false)
+		} else {
+			notice = output.TruncationNotice(len(messages), len(collected.Items))
+		}
 	}
 
 	format := writer.EffectiveFormat()
diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
index 48b2ba37..48017f72 100644
--- a/internal/cmd/sent_test.go
+++ b/internal/cmd/sent_test.go
@@ -131,6 +131,27 @@ func TestSentCommandMarkdownReportsRecipientsURLAndUnavailableDeliveryTime(t *te
 	}
 }
 
+func TestSentCommandPreservesEmptySummaryFields(t *testing.T) {
+	body := strings.Replace(sentTopicsJSON, `"summary":"Here are the decisions and owners from today's planning session."`, `"summary":""`, 1)
+
+	response, err := runJSONCommand(t, sentTopicsHandler(t, body), "sent")
+	if err != nil {
+		t.Fatalf("execute sent --json: %v", err)
+	}
+	rows := decodeSentData[[]map[string]any](t, response.Data)
+	if summary, ok := rows[0]["summary"]; !ok || summary != "" {
+		t.Errorf("summary = %#v, present = %v", summary, ok)
+	}
+
+	markdown, err := runFormattedCommand(t, sentTopicsHandler(t, body), []string{"--markdown"}, "sent")
+	if err != nil {
+		t.Fatalf("execute sent --markdown: %v", err)
+	}
+	if !strings.Contains(markdown, " summary |") {
+		t.Errorf("Markdown output has no summary column:\n%s", markdown)
+	}
+}
+
 func TestSentCommandStyledShowsContinuationAfterAnEmptyPage(t *testing.T) {
 	handler := http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
 		w.Header().Set("Content-Type", "application/json")
@@ -221,7 +242,7 @@ func TestSentCommandLimitReadsEnoughPagesAndTrims(t *testing.T) {
 	if got := strings.Join(pages, ","); got != ",2" {
 		t.Errorf("pages = %q, want first page then 2", got)
 	}
-	if response.Notice != "Showing 2 of 3 results. Use --all to see everything." {
+	if response.Notice != "Showing 2 sent messages. Use --all to see everything." {
 		t.Errorf("notice = %q", response.Notice)
 	}
 }

From 75fe8f3076d2051eafa8b1c852a87db10fd03695 Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 15:27:10 -0400
Subject: [PATCH 7/8] Document sent API coverage

---
 API-COVERAGE.md | 1 +
 1 file changed, 1 insertion(+)

diff --git a/API-COVERAGE.md b/API-COVERAGE.md
index 1480e1db..ecd10d6a 100644
--- a/API-COVERAGE.md
+++ b/API-COVERAGE.md
@@ -55,6 +55,7 @@ which is what `Entries().ListDraftsPage` and `hey draft list --page` exist for.
 | `/contacts/{id}/note.json` | DELETE | SDK `Contacts().DeleteNote` | `hey contact note delete`, Contacts TUI | covered |
 | `/calendars.json` | GET | SDK `Calendars().List` | `hey calendar list` | covered |
 | `/calendars/{id}/recordings.json` | GET | SDK `Calendars().GetRecordings` | `hey event list`, `hey event edit <id>` (reading the event back; with `--occurrence`, the occurrence's day and then the series' first day for its `Calendar::Countdown`), `hey todo list`, `hey journal list` | covered |
+| `/topics/sent.json` | GET | SDK `Topics().GetSentPage` | `hey sent` | covered |
 | `/topics/{id}/entries.json` | GET | SDK `Topics().GetEntries` | `hey thread read <id>`, `hey attachment list <topic-id>` | covered, but see the paging note below |
 | `/topics/{id}/publication` | POST | SDK `Publications().Create` | `hey share <thread-id>` | covered |
 | `/topics/{id}/publication.json` | GET | SDK `Publications().Create` readback | `hey share <thread-id>` | covered |

From 8624becc51c8d2f4ca013ca3049d15f28d76b5ee Mon Sep 17 00:00:00 2001
From: Rob Zolkos <rob@zolkos.com>
Date: Sun, 20 Sep 2026 16:55:17 -0400
Subject: [PATCH 8/8] Handle sent pagination and timestamp fallbacks

---
 docs/cli.md               |  2 +-
 internal/cmd/sent.go      | 14 +++++++----
 internal/cmd/sent_test.go | 50 +++++++++++++++++++++++++++++++++++----
 3 files changed, 56 insertions(+), 10 deletions(-)

diff --git a/docs/cli.md b/docs/cli.md
index 2d4212ca..b61cfff7 100644
--- a/docs/cli.md
+++ b/docs/cli.md
@@ -272,7 +272,7 @@ Drafts are the review-before-send lane: `hey compose --draft` (and `hey reply --
 
 `hey share <thread_id>` gets a sharing link for a thread. Anyone with the link can see the entire thread and future emails or replies sent to it. `hey unshare <thread_id>` turns off the sharing link.
 
-`hey sent` lists the latest message you sent in each thread, newest first. Its `id` is the thread ID accepted by `hey thread read`; `sent_at` is when HEY delivered that message, not when an earlier draft was created. If an older server omits the delivery time, JSON reports `sent_at` as `null` and human output says `Unavailable`. JSON separates exact recipients into `to`, `cc`, and `bcc` arrays and includes the subject, summary, and `app_url`. Styled and Markdown output use HEY's compact `Me → first recipient + N` summary. One page arrives by default; `--limit` reads enough pages for the requested count, `--all` follows HEY's next-page links for up to 100 pages, and `--page` continues from a reported page cursor.
+`hey sent` lists the latest message you sent in each thread, newest first. Its `id` is the thread ID accepted by `hey thread read`; `sent_at` uses HEY's delivery time when present and otherwise its creation time, matching the web view. If a server omits both times, JSON reports `sent_at` as `null` and human output says `Unavailable`. JSON separates exact recipients into `to`, `cc`, and `bcc` arrays and includes the subject, summary, and `app_url`. Styled and Markdown output use HEY's compact `Me → first recipient + N` summary. One page arrives by default; `--limit` reads enough pages for the requested count, `--all` follows HEY's next-page links for up to 100 pages, and `--page` continues from a reported page cursor.
 
 Search accepts free text plus `--required`, `--any`, `--none`, `--exact`, `--from`, `--to`, `--subject`, `--date`, `--in`, `--label`, and `--attachment`. `--in`, `--date`, `--label` and `--attachment` take one of the values `hey search filters` lists — the attachment kinds are `any`, `images`, `pdfs`, `calendar_invites`, `documents`, `spreadsheets`, `presentations`, `media` and `zip_files`, so it is `--attachment pdfs` rather than `pdf`, and an unrecognized `--in`, `--date` or `--attachment` is refused with the values it accepts before anything is sent. Use `--page` for one page or `--all` to fetch up to 100 pages; capped searches report the next page for continuation. Search results include `topic_id` for reading the thread and the matching message summaries. Results with an active box item also include `id` for organization actions.
 
diff --git a/internal/cmd/sent.go b/internal/cmd/sent.go
index 5b1b8b99..6bcf7690 100644
--- a/internal/cmd/sent.go
+++ b/internal/cmd/sent.go
@@ -96,12 +96,12 @@ func (c *sentCommand) run(cmd *cobra.Command, _ []string) error {
 
 	messages := makeSentMessages(collected.Items)
 	nextPage := collected.Cursor
-	notice := sentListingNotice(len(messages), collected.Read, nextPage, collected.Truncated)
+	notice := sentListingNotice(len(messages), collected.Read, nextPage, collected.Truncated, c.all)
 	if c.limit > 0 && !c.all && len(messages) > c.limit {
 		messages = messages[:c.limit]
 		nextPage = ""
 		if collected.Cursor != "" {
-			notice = sentListingNotice(len(messages), collected.Read, collected.Cursor, false)
+			notice = sentListingNotice(len(messages), collected.Read, collected.Cursor, false, false)
 		} else {
 			notice = output.TruncationNotice(len(messages), len(collected.Items))
 		}
@@ -152,9 +152,13 @@ func makeSentMessages(topics []generated.Topic) []sentMessage {
 	for _, topic := range topics {
 		entry := topic.LatestEntry
 		var sentAt *time.Time
-		if !entry.ActiveAt.IsZero() {
+		switch {
+		case !entry.ActiveAt.IsZero():
 			activeAt := entry.ActiveAt
 			sentAt = &activeAt
+		case !entry.CreatedAt.IsZero():
+			createdAt := entry.CreatedAt
+			sentAt = &createdAt
 		}
 		messages = append(messages, sentMessage{
 			ID:      topic.Id,
@@ -246,10 +250,12 @@ func formatSentTimestamp(sentAt *time.Time) string {
 	return formatTimestamp(sentAt.Local())
 }
 
-func sentListingNotice(shown, pages int, nextPage string, truncated bool) string {
+func sentListingNotice(shown, pages int, nextPage string, truncated, all bool) string {
 	switch {
 	case truncated:
 		return fmt.Sprintf("Sent listing stopped after %d pages. Continue with --page %s.", pages, terminal.SanitizeLine(nextPage))
+	case all && nextPage != "":
+		return fmt.Sprintf("Showing %d %s. Continue with --page %s.", shown, sentMessageNoun(shown), terminal.SanitizeLine(nextPage))
 	case nextPage != "":
 		return fmt.Sprintf("Showing %d %s. Use --all to see everything.", shown, sentMessageNoun(shown))
 	default:
diff --git a/internal/cmd/sent_test.go b/internal/cmd/sent_test.go
index 48017f72..b9ab436d 100644
--- a/internal/cmd/sent_test.go
+++ b/internal/cmd/sent_test.go
@@ -102,11 +102,12 @@ func TestSentCommandStyledMatchesHEYRecipientSummary(t *testing.T) {
 	if err != nil {
 		t.Fatalf("execute sent --styled: %v", err)
 	}
+	wantDate := time.Date(2026, time.September, 19, 14, 30, 0, 0, time.UTC).Local().Format("2006-01-02")
 	for _, want := range []string{
 		"Quarterly planning follow-up",
 		"Me → Sarah Chen + 2",
 		"Here are the decisions and owners",
-		"2026-09-19",
+		wantDate,
 	} {
 		if !strings.Contains(stdout, want) {
 			t.Errorf("styled output missing %q:\n%s", want, stdout)
@@ -116,6 +117,7 @@ func TestSentCommandStyledMatchesHEYRecipientSummary(t *testing.T) {
 
 func TestSentCommandMarkdownReportsRecipientsURLAndUnavailableDeliveryTime(t *testing.T) {
 	body := strings.Replace(sentTopicsJSON, `"active_at":"2026-09-19T14:30:00Z",`, "", 1)
+	body = strings.Replace(body, `"created_at":"2026-09-18T09:00:00Z",`, "", 1)
 	markdown, err := runFormattedCommand(t, sentTopicsHandler(t, body), []string{"--markdown"}, "sent")
 	if err != nil {
 		t.Fatalf("execute sent --markdown: %v", err)
@@ -170,6 +172,41 @@ func TestSentCommandStyledShowsContinuationAfterAnEmptyPage(t *testing.T) {
 	}
 }
 
+func TestSentCommandAllContinuesAfterAnEmptyPageWithACursor(t *testing.T) {
+	var pages []string
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		page := r.URL.Query().Get("page")
+		pages = append(pages, page)
+		w.Header().Set("Content-Type", "application/json")
+
+		switch page {
+		case "":
+			w.Header().Set("Link", `</topics/sent.json?page=cursor-2>; rel="next"`)
+			_, _ = io.WriteString(w, sentTopicsJSON)
+		case "cursor-2":
+			w.Header().Set("Link", `</topics/sent.json?page=cursor-3>; rel="next"`)
+			_, _ = io.WriteString(w, `{"title":"Sent Mail","topics":[]}`)
+		default:
+			t.Errorf("unexpected page %q", page)
+			http.Error(w, "unexpected page", http.StatusBadRequest)
+		}
+	})
+
+	response, err := runJSONCommand(t, handler, "sent", "--all")
+	if err != nil {
+		t.Fatalf("execute sent --all: %v", err)
+	}
+	if got := strings.Join(pages, ","); got != ",cursor-2" {
+		t.Errorf("pages = %q, want first page then cursor-2", got)
+	}
+	if response.Notice != "Showing 1 sent message. Continue with --page cursor-3." {
+		t.Errorf("notice = %q", response.Notice)
+	}
+	if got := response.Meta["next_page"]; got != "cursor-3" {
+		t.Errorf("next_page = %#v", got)
+	}
+}
+
 func TestSentCommandAllFollowsNextPageLink(t *testing.T) {
 	var mu sync.Mutex
 	var pages []string
@@ -289,7 +326,7 @@ func TestSentCommandPreservesOpaquePageCursor(t *testing.T) {
 	}
 }
 
-func TestSentCommandDoesNotUseCreationTimeAsDeliveryTime(t *testing.T) {
+func TestSentCommandFallsBackToCreationTimeWhenDeliveryTimeIsMissing(t *testing.T) {
 	body := strings.Replace(sentTopicsJSON, `"active_at":"2026-09-19T14:30:00Z",`, "", 1)
 	response, err := runJSONCommand(t, sentTopicsHandler(t, body), "sent")
 	if err != nil {
@@ -297,13 +334,16 @@ func TestSentCommandDoesNotUseCreationTimeAsDeliveryTime(t *testing.T) {
 	}
 
 	rows := decodeSentData[[]sentTestRow](t, response.Data)
-	if rows[0].SentAt != nil {
-		t.Errorf("sent_at = %v, want null", rows[0].SentAt)
+	if rows[0].SentAt == nil {
+		t.Fatal("sent_at is nil")
+	}
+	if got := rows[0].SentAt.Format(time.RFC3339); got != "2026-09-18T09:00:00Z" {
+		t.Errorf("sent_at = %q", got)
 	}
 }
 
 func TestSentListingNoticeSanitizesCursor(t *testing.T) {
-	notice := sentListingNotice(100, 100, "cursor-\x1b[31mnext", true)
+	notice := sentListingNotice(100, 100, "cursor-\x1b[31mnext", true, false)
 	if strings.ContainsRune(notice, '\x1b') {
 		t.Errorf("notice contains escape byte: %q", notice)
 	}