feat(email): follow-up tracking — flag sent mail awaiting a reply

docs/guides/email.mdx

@@ -11,6 +11,7 @@ The Email Triage Agent connects to your Gmail account through GAIA's connectors
 ## What it does
 
 - **Triage your inbox** — classify every message as `urgent`, `actionable`, `informational`, or `low priority`, plus separate `is_spam` and `is_phishing` flags.
+- **Follow-up tracking** — flag the emails *you* sent that never got a reply, once they're older than a configurable window (default 3 days). Read-only detection: the agent surfaces the overdue threads, it never auto-sends a chaser.
 - **Organize** — archive, label, mark read/unread, star/unstar. Reversible via the per-action undo log.
 - **Soft-delete with undo** — `trash_message` records the action; `restore_message` reverses it within a 30-second window.
 - **Draft + confirmed send** — generate replies (`draft_reply`) and forwards (`draft_forward`); `send_draft` and `send_now` require explicit user confirmation in the UI.
@@ -147,7 +148,9 @@ Senders you reply to quickly are automatically promoted to priority on the next
 
 ### Read
 
-`list_inbox`, `get_message`, `get_thread`, `search_messages`, `list_labels`, `triage_inbox`, `pre_scan_inbox`
+`list_inbox`, `get_message`, `get_thread`, `search_messages`, `list_labels`, `triage_inbox`, `pre_scan_inbox`, `find_awaiting_reply`
+
+`find_awaiting_reply` ([#1606](https://github.com/amd/gaia/issues/1606)) scans your Sent folder and returns the threads whose newest message is still yours — i.e. nobody replied — once the send is older than the window (`window_days` per call, or the agent's `followup_window_days` config, default 3). Each hit carries the message id, recipient, subject, and age in days, most overdue first. Ask the agent *"who hasn't replied to me?"* or *"what am I still waiting on?"*. One scan inspects up to the 100 most-recent sent threads; when older sends exist beyond that, the result carries `scan_truncated: true` so the agent tells you the list may be incomplete rather than passing it off as exhaustive. Detection only — sending an actual follow-up goes through the normal confirmation-gated reply tools, and only when you ask ([#555](https://github.com/amd/gaia/issues/555) tracks autonomous nudging). Gmail-only for now: the Outlook backend has no Sent-label mapping yet, so a Microsoft-only setup gets a clear error instead of a wrong answer.
 
 ### Session preferences (in-memory; wiped on agent restart)
 

hub/agents/npm/agent-email/CHANGELOG.md

@@ -5,6 +5,19 @@ follows [SemVer](https://semver.org/): the **MAJOR** of the on-the-wire
 `SCHEMA_VERSION` is what `checkVersion` enforces at startup, so a contract MAJOR
 bump is always at least a package MINOR bump with a migration note.
 
+## Unreleased
+
+- **Follow-up tracking — flag sent mail awaiting a reply** (#1606): the agent can
+  now scan the Sent folder and surface every thread whose newest message is still
+  the user's own — i.e. nobody replied — once the send is older than a configurable
+  window (`followup_window_days`, default 3 days, or per call). The new read-only
+  `find_awaiting_reply` agent tool returns message id, recipient, subject, and age,
+  most overdue first. Detection only: it never drafts or sends a nudge (autonomous
+  follow-up sending remains #555, confirmation-gated). Gmail-only for now — a
+  Microsoft-only setup gets a loud error instead of a silently wrong scan.
+  Agent-loop surface (Agent UI natural-language queries); no new REST route, so the
+  REST contract and `SCHEMA_VERSION` are unchanged.
+
 ## 0.3.0
 
 Contract bumped to `SCHEMA_VERSION` **2.1** — additive, no triage shape change, so

hub/agents/npm/agent-email/README.md

@@ -21,6 +21,8 @@ the agent runs as a frozen, self-contained REST sidecar your app launches and ow
 
 - **Triage** — classify each message (urgent / needs-response / FYI / promotional /
   personal), summarize a thread, and extract action items and phishing signals.
+- **Follow-up tracking** — flag sent threads still awaiting a reply after a
+  configurable window (read-only detection; the agent never auto-sends a chaser).
 - **Organize** — archive, label, move, mark read/unread — one message or in batches.
 - **Reply & send** — draft context-aware replies and forwards, then send.
 - **Calendar** — detect meeting requests, flag conflicts, RSVP, and create events
@@ -217,8 +219,9 @@ When you need finer control, the steps are exported individually:
 As of `SCHEMA_VERSION` 2.1 this package exposes inbox **search** (read-only),
 the **archive** / phishing-**quarantine** mailbox actions (+ their undo), and
 calendar **view / create / respond**. The remaining mailbox **actions** (label,
-move, mark read/unread) are part of the full agent but not yet exposed through
-this package — see
+move, mark read/unread) and the read-only **follow-up tracker** (flag sent mail
+awaiting a reply, `find_awaiting_reply`, #1606) are part of the full agent but
+not yet exposed through this package — see
 [`SPEC.md`](https://github.com/amd/gaia/blob/main/hub/agents/npm/agent-email/SPEC.md) for the complete surface.
 
 ## Running in production

hub/agents/npm/agent-email/SKILL.md

@@ -124,6 +124,12 @@ reversible inside a 30s window via the ungated `unarchive` / `unquarantine`. Eve
 non-2xx response throws `HttpError` (`status`, `url`, `bodyText`) — handle it; there is
 no silent null.
 
+The full agent (the natural-language loop behind GAIA's Agent UI) covers more than
+this typed client: organize/label actions, calendar detect/conflicts, and read-only
+**follow-up tracking** (`find_awaiting_reply` flags sent mail still awaiting a reply,
+#1606). None of those have REST routes yet — don't look for them on this client; see
+`SPEC.md` for the exact exposed surface.
+
 ## 5. From a renderer (Electron / browser)
 
 The sidecar serves **same-origin only — no CORS**. A renderer on a different origin

hub/agents/npm/agent-email/SPEC.md

@@ -282,9 +282,10 @@ phishing-**quarantine** mailbox actions plus their undo (`confirmAction` / `arch
 `unarchive` / `quarantine` / `unquarantine`), and calendar **view / create / respond**
 (`listCalendarEvents` / `previewCalendarEvent` / `createCalendarEvent` /
 `respondToCalendarEvent`). The full GAIA email agent does more on the live mailbox
-(label, move, mark spam) and calendar (detect / conflicts); those remaining actions are
-connector-gated by definition and are **not exposed through this package's REST API
-yet**.
+(label, move, mark spam), follow-up tracking (flag sent mail still awaiting a reply —
+read-only `find_awaiting_reply`, #1606), and calendar (detect / conflicts); those
+remaining capabilities are connector-gated by definition and are **not exposed through
+this package's REST API yet**.
 
 ## Browser / Electron renderer (`./client`)
 

hub/agents/python/email/gaia_agent_email/agent.py

@@ -47,6 +47,7 @@ class never passes ``use_claude=True`` / ``use_chatgpt=True`` to
 )
 from gaia_agent_email.tools.calendar_tools import CalendarToolsMixin
 from gaia_agent_email.tools.delete_tools import DeleteToolsMixin
+from gaia_agent_email.tools.followup_tools import FollowupToolsMixin
 from gaia_agent_email.tools.organize_tools import OrganizeToolsMixin
 from gaia_agent_email.tools.phishing_tools import PhishingToolsMixin
 from gaia_agent_email.tools.preference_tools import (
@@ -118,7 +119,11 @@ def __getattr__(self, name: str):
 
 ACTIONS:
 - Read tools (list_inbox, get_message, get_thread, search_messages,
-  list_labels, triage_inbox, pre_scan_inbox) — never require confirmation.
+  list_labels, triage_inbox, pre_scan_inbox, find_awaiting_reply) — never
+  require confirmation. find_awaiting_reply flags sent mail whose thread
+  never got a reply; it is DETECTION ONLY — never send a chaser from its
+  results unless the user explicitly asks, and any send stays
+  confirmation-gated.
 - Organize tools (archive_message, mark_read, mark_unread, add_star,
   remove_star, label_message, move_to_label) — reversible via the undo
   log; do not require per-action confirmation, but bulk operations
@@ -167,6 +172,7 @@ class EmailTriageAgent(
     MemoryMixin,
     DatabaseMixin,
     ReadToolsMixin,
+    FollowupToolsMixin,
     OrganizeToolsMixin,
     ReplyToolsMixin,
     SummarizeToolsMixin,
@@ -349,6 +355,7 @@ def _register_tools(self) -> None:
         _TOOL_REGISTRY.clear()
         self._reset_organize_counter()
         self._register_read_tools()
+        self._register_followup_tools()
         self._register_organize_tools()
         self._register_reply_tools()
         self._register_summarize_tools()

hub/agents/python/email/gaia_agent_email/config.py

@@ -97,6 +97,9 @@ class EmailAgentConfig:
       default), tracks ``mail_provider`` so a Microsoft-only user who set
       ``mail_provider="microsoft"`` gets the Outlook calendar too without
       separately configuring it.
+    - ``followup_window_days``: how many days a sent message may sit with no
+      inbound reply on its thread before ``find_awaiting_reply`` flags it
+      (#1606). Callers can override per call via the tool's ``window_days``.
     - ``gmail_backend`` / ``outlook_backend`` / ``calendar_backend``: eval
       seam — when set, the agent's tools use the injected backend instead of
       constructing the live one. ``gmail_backend`` is honored for
@@ -122,6 +125,7 @@ class EmailAgentConfig:
     outlook_backend: Optional[Any] = None
     calendar_backend: Optional[Any] = None
     force_llm: bool = False
+    followup_window_days: int = 3
 
     def validate(self) -> None:
         """Run startup-time invariants. Called from the agent's __init__.
@@ -140,6 +144,11 @@ def validate(self) -> None:
                     "cloud LLM endpoints are permitted (AC3). To use a "
                     "non-default Lemonade port, set LEMONADE_BASE_URL."
                 )
+        if self.followup_window_days < 1:
+            raise ConfigurationError(
+                f"EmailAgentConfig.followup_window_days must be >= 1 "
+                f"(got {self.followup_window_days})."
+            )
 
     def resolved_db_path(self) -> str:
         """Return the SQLite path with ``$HOME`` expanded.