[#134] Clarify dropping a shift and differentiate night rows (#138)

* Expand /oncall date parser to accept more formats

Users entering everyday forms like 7/3/26 hit a generic parse
failure because the parser only accepted four-digit years and a
bare m/d. Add two-digit-year and month-name (with optional
ordinal/year) formats, treating explicit-year inputs as fixed and
keeping the year-less roll-forward for bare m/d. Update the help
text and per-command parse hints to match.

Refs: #133

* Let drop pick a shift and flag night rows

Drop now accepts an optional [day|night|holiday] qualifier and, when a
date carries more than one shift the user holds, asks which to drop
instead of silently releasing the holiday or weekend day shift. The
static post also tags day/night rows with distinct glyphs and labels on
weekdays, so the after-hours row is unmistakable.

Refs: #134

* Refine night-row labeling and drop notifications

Weekday rows are night-only, so the moon glyph alone marks the
after-hours shift; the verbose time-range label is kept only on
weekend rows where day and night shifts coexist. Channel shift-change
notifications now label the shift on every day for parity. Thread the
caller's user_id through the regular-drop path instead of re-reading it
off the employee record, and document the user-facing changes.

Refs: #134

---------

Co-authored-by: amoussa1229 <166072409+amoussa1229@users.noreply.github.com>

CHANGELOG.md

@@ -10,6 +10,23 @@ fine and still supported.
 
 ---
 
+## v1.12.0 — June 26, 2026
+
+**Clearer shift drops and an easier-to-read schedule.** Two small quality-of-life
+improvements:
+
+- **`/oncall drop` can now say which shift to let go.** If you hold more than one
+  shift on the same day — say a holiday day slot *and* that night's after-hours
+  shift, or a weekend day *and* night shift — dropping no longer guesses for you.
+  The bot lists what you hold and asks you to add `day`, `night`, or `holiday`
+  (for example `/oncall drop saturday night`), the same way picking one up
+  already works. Asking to drop a shift you don't actually hold is turned down
+  instead of quietly dropping the wrong one.
+- **Night shifts stand out on the two-week post.** Day and night rows now carry
+  their own icons — a sun for the daytime shift and a moon for the after-hours
+  (night) shift — so the on-call row is easy to spot at a glance. Weekend rows,
+  which have both a day and a night shift, still spell out the full time range.
+
 ## v1.11.1 — June 17, 2026
 
 **Fix holiday call routing to 3CX.** The holiday router was calling the wrong 3CX

src/shared/shared/blocks.py

@@ -70,6 +70,14 @@ SHIFT_LABELS = {
     "night": "Night (5pm–8am)",
 }
 
+# Per-shift glyphs so day vs. night rows are distinguishable at a glance. On
+# weekdays only the night (after-hours) shift exists, so the moon glyph alone
+# differentiates the row; the verbose time-range label is reserved for weekends.
+SHIFT_GLYPHS = {
+    "day": ":sunny:",
+    "night": ":crescent_moon:",
+}
+
 HOLIDAY_BADGE = ":palm_tree: *Holiday*"
 
 
@@ -86,10 +94,15 @@ def _format_shift_line(
     source: str,
     is_today: bool,
     shift_type: str = "night",
+    with_label: bool = True,
 ) -> str:
     day_label = date.strftime("%a %b %-d")
-    if date.strftime("%A") in WEEKEND_DAYS and shift_type in SHIFT_LABELS:
-        day_label += f" {SHIFT_LABELS[shift_type]}"
+    glyph = SHIFT_GLYPHS.get(shift_type)
+    if glyph:
+        if with_label and shift_type in SHIFT_LABELS:
+            day_label += f" {glyph} {SHIFT_LABELS[shift_type]}"
+        else:
+            day_label += f" {glyph}"
     if is_today:
         day_label = f"*{day_label} (today)*"
 
@@ -175,9 +188,21 @@ def build_week_schedule(schedule, start_date: datetime | None = None) -> list[di
             if source == "available" and not is_past:
                 open_shifts.append((date_str, "day"))
 
-        # After-hours (night) shift
+        # After-hours (night) shift. Weekdays are night-only, so the moon glyph
+        # carries the meaning; only weekends (where both shifts coexist) repeat
+        # the full time-range label.
         ext, name, source = schedule.resolve_shift(date_str, day_name)
-        lines.append(_format_shift_line(date, ext, name, source, is_today))
+        lines.append(
+            _format_shift_line(
+                date,
+                ext,
+                name,
+                source,
+                is_today,
+                "night",
+                with_label=day_name in WEEKEND_DAYS,
+            )
+        )
         if source == "available" and not is_past:
             open_shifts.append((date_str, "night"))
 
@@ -245,11 +270,10 @@ def build_shift_change_message(
     """Build a channel notification for a shift change."""
     dt = datetime.strptime(date_str, "%Y-%m-%d")
     day_label = dt.strftime("%A, %b %-d")
-    type_label = (
-        f" ({SHIFT_LABELS.get(shift_type, shift_type)})"
-        if dt.strftime("%A") in WEEKEND_DAYS
-        else ""
-    )
+    # Label the shift on every day, not just weekends: a single-line notification
+    # has room to spell out the after-hours (night) shift the static post conveys
+    # with the moon glyph.
+    type_label = f" ({SHIFT_LABELS.get(shift_type, shift_type)})"
 
     if action == "picked_up":
         text = f":white_check_mark: <@{user_id}> picked up the *{day_label}*{type_label} shift (Ext {ext})"
@@ -430,7 +454,7 @@ def build_help_blocks(is_admin: bool = False) -> list[dict]:
         "`/oncall` — Show the two-week schedule\n"
         "`/oncall next` — Show the following two weeks\n"
         "`/oncall pick <date>` — Pick up a shift\n"
-        "`/oncall drop <date>` — Drop your shift (marks it open; locked within 24h of start — swap instead)\n"
+        "`/oncall drop <date> [day|night|holiday]` — Drop your shift (marks it open; locked within 24h of start — swap instead)\n"
         "`/oncall swap <date> @person` — Swap your shift with someone\n"
         "`/oncall register <extension>` — Link your Slack account to your extension\n"
         "`/oncall pay` — Show last week's pay summary\n"

src/slack-bot/CHANGELOG.md

@@ -10,6 +10,23 @@ fine and still supported.
 
 ---
 
+## v1.12.0 — June 26, 2026
+
+**Clearer shift drops and an easier-to-read schedule.** Two small quality-of-life
+improvements:
+
+- **`/oncall drop` can now say which shift to let go.** If you hold more than one
+  shift on the same day — say a holiday day slot *and* that night's after-hours
+  shift, or a weekend day *and* night shift — dropping no longer guesses for you.
+  The bot lists what you hold and asks you to add `day`, `night`, or `holiday`
+  (for example `/oncall drop saturday night`), the same way picking one up
+  already works. Asking to drop a shift you don't actually hold is turned down
+  instead of quietly dropping the wrong one.
+- **Night shifts stand out on the two-week post.** Day and night rows now carry
+  their own icons — a sun for the daytime shift and a moon for the after-hours
+  (night) shift — so the on-call row is easy to spot at a glance. Weekend rows,
+  which have both a day and a night shift, still spell out the full time range.
+
 ## v1.11.1 — June 17, 2026
 
 **Fix holiday call routing to 3CX.** The holiday router was calling the wrong 3CX

src/slack-bot/app.py

@@ -364,6 +364,34 @@ def _find_employee_shift(schedule, date_str, day_name, employee_ext):
     return None
 
 
+_DROP_SHIFT_LABELS = {
+    "holiday": "holiday",
+    "day": "day (8am–5pm)",
+    "night": "night (5pm–8am)",
+}
+
+
+def _droppable_shifts(schedule, date_str, day_name, employee_ext) -> list[str]:
+    """Return the shift types the employee holds on a date and could drop.
+
+    Possible values, in display priority: ``holiday``, ``day``, ``night``. A
+    holiday day-slot supersedes a regular weekend day shift on its date.
+    """
+    held = []
+    holiday_ctx = schedule.get_shift_context(date_str, day_name, "day")
+    if holiday_ctx["kind"] == "holiday":
+        if any(a["extension"] == employee_ext for a in holiday_ctx["assignees"]):
+            held.append("holiday")
+    elif day_name in WEEKEND_DAYS:
+        ext, _name, _source = schedule.resolve_shift(date_str, day_name, "day")
+        if ext == employee_ext:
+            held.append("day")
+    ext, _name, _source = schedule.resolve_shift(date_str, day_name, "night")
+    if ext == employee_ext:
+        held.append("night")
+    return held
+
+
 def _refresh_schedule_post(schedule, schedule_channel, client):
     """Update the pinned schedule message in-place after a shift change."""
     channel = schedule_channel
@@ -920,9 +948,11 @@ def _pick_holiday(
 def _handle_drop(
     respond, schedule, user_id, text, channel_id, client, schedule_channel
 ):
-    parts = text.split(maxsplit=1)
+    parts = text.split()
     if len(parts) < 2:
-        respond(text="Usage: `/oncall drop <date>`  (e.g. `/oncall drop friday`)")
+        respond(
+            text="Usage: `/oncall drop <date> [day|night|holiday]`  (e.g. `/oncall drop friday`)"
+        )
         return
 
     employee = schedule.get_employee_by_slack_id(user_id)
@@ -930,10 +960,24 @@ def _handle_drop(
         respond(text="You're not registered. Use `/oncall register <extension>` first.")
         return
 
-    date = parse_date(parts[1])
+    # An optional trailing qualifier picks the shift to drop; the date itself may
+    # be multiple words (e.g. `jul 3`), so strip the qualifier off the end first.
+    tokens = parts[1:]
+    explicit_shift = None
+    if tokens[-1] in ("day", "night", "holiday"):
+        explicit_shift = tokens[-1]
+        tokens = tokens[:-1]
+    if not tokens:
+        respond(
+            text="Usage: `/oncall drop <date> [day|night|holiday]`  (e.g. `/oncall drop friday`)"
+        )
+        return
+
+    date_text = " ".join(tokens)
+    date = parse_date(date_text)
     if not date:
         respond(
-            text=f"Couldn't parse date: `{parts[1]}`. Try: today, tomorrow, friday, 4/5, 7/3/26, jul 3, 2026-04-05"
+            text=f"Couldn't parse date: `{date_text}`. Try: today, tomorrow, friday, 4/5, 7/3/26, jul 3, 2026-04-05"
         )
         return
 
@@ -943,13 +987,43 @@ def _handle_drop(
         return
 
     day_name = date.strftime("%A")
+    held = _droppable_shifts(schedule, date_str, day_name, employee["extension"])
+    date_label = date.strftime("%A, %b %-d")
 
-    # A holiday slot the employee holds is dropped (released) ahead of regular
-    # day/night shifts — holidays take priority on their date.
-    holiday_ctx = schedule.get_shift_context(date_str, day_name, "day")
-    if holiday_ctx["kind"] == "holiday" and any(
-        a["extension"] == employee["extension"] for a in holiday_ctx["assignees"]
-    ):
+    if explicit_shift:
+        if explicit_shift not in held:
+            if held:
+                options = ", ".join(_DROP_SHIFT_LABELS[s] for s in held)
+                respond(
+                    text=(
+                        f"You don't hold the {_DROP_SHIFT_LABELS[explicit_shift]} "
+                        f"shift on *{date_label}*. You hold: {options}."
+                    )
+                )
+            else:
+                ext, name, _source = schedule.resolve_shift(date_str, day_name)
+                respond(
+                    text=f"That's not your shift — it belongs to {name} (Ext {ext})."
+                )
+            return
+        target = explicit_shift
+    elif not held:
+        ext, name, _source = schedule.resolve_shift(date_str, day_name)
+        respond(text=f"That's not your shift — it belongs to {name} (Ext {ext}).")
+        return
+    elif len(held) > 1:
+        options = ", ".join(_DROP_SHIFT_LABELS[s] for s in held)
+        respond(
+            text=(
+                f"You hold more than one shift on *{date_label}*: {options}. "
+                f"Tell me which to drop: `/oncall drop {date_text} [{'|'.join(held)}]`."
+            )
+        )
+        return
+    else:
+        target = held[0]
+
+    if target == "holiday":
         _drop_holiday(
             respond,
             schedule,
@@ -962,15 +1036,33 @@ def _handle_drop(
         )
         return
 
-    found = _find_employee_shift(schedule, date_str, day_name, employee["extension"])
+    _drop_regular(
+        respond,
+        schedule,
+        user_id,
+        date,
+        date_str,
+        day_name,
+        target,
+        channel_id,
+        client,
+        schedule_channel,
+    )
 
-    if not found:
-        ext, name, _source = schedule.resolve_shift(date_str, day_name)
-        respond(text=f"That's not your shift — it belongs to {name} (Ext {ext}).")
-        return
-
-    ext, name, source, shift_type = found
 
+def _drop_regular(
+    respond,
+    schedule,
+    user_id,
+    date,
+    date_str,
+    day_name,
+    shift_type,
+    channel_id,
+    client,
+    schedule_channel,
+):
+    """Release a regular (weekend day or night) shift, honouring the 24h lock."""
     if _within_drop_lock(date_str, shift_type):
         respond(
             text=(
@@ -981,6 +1073,8 @@ def _handle_drop(
         )
         return
 
+    ext, name, _source = schedule.resolve_shift(date_str, day_name, shift_type)
+
     # No 3CX repoint here: a same-day shift is always inside the 24h lock above,
     # so a drop that reaches this point is never today's active shift.
     schedule.mark_open(date_str, shift_type)
@@ -995,7 +1089,12 @@ def _handle_drop(
     )
 
     blocks = build_shift_change_message(
-        user_id, date_str, "dropped", ext, name, shift_type=shift_type
+        user_id,
+        date_str,
+        "dropped",
+        ext,
+        name,
+        shift_type=shift_type,
     )
     try:
         client.chat_postMessage(

tests/shared/test_blocks.py

@@ -51,6 +51,37 @@ class TestBuildWeekSchedule:
         assert "pickup_2026-06-03" not in _all_action_ids(blocks)
         assert "Alice (Ext 114)" in blocks[1]["text"]["text"]
 
+    @freeze_time("2026-06-01 12:00:00")
+    def test_weekday_night_row_shows_glyph_without_time_label(self, schedule, seed):
+        # Weekdays are night-only, so the moon glyph alone differentiates the row;
+        # the verbose time-range label is reserved for weekends where both shifts
+        # coexist (and would otherwise repeat on ~10 weekday rows).
+        seed.weekly("Wednesday", "114", "Alice")
+        text = build_week_schedule(schedule)[1]["text"]["text"]
+        wednesday_line = next(
+            line for line in text.splitlines() if "Alice (Ext 114)" in line
+        )
+        assert ":crescent_moon:" in wednesday_line
+        assert "Night (5pm" not in wednesday_line
+
+    @freeze_time("2026-06-01 12:00:00")
+    def test_weekend_night_row_keeps_glyph_and_time_label(self, schedule, seed):
+        # Weekends carry both shifts, so the night row keeps the full label.
+        seed.weekly("Saturday", "200", "Alice")
+        text = build_week_schedule(schedule)[1]["text"]["text"]
+        saturday_line = next(
+            line for line in text.splitlines() if "Alice (Ext 200)" in line
+        )
+        assert ":crescent_moon:" in saturday_line
+        assert "Night (5pm" in saturday_line
+
+    @freeze_time("2026-06-01 12:00:00")
+    def test_weekend_day_row_shows_day_glyph_and_label(self, schedule, seed):
+        seed.weekly("Saturday", "200", "Alice", shift_type="day")
+        text = build_week_schedule(schedule)[1]["text"]["text"]
+        assert ":sunny:" in text
+        assert "Day (8am" in text
+
     @freeze_time("2026-06-01 12:00:00")
     def test_holiday_on_weekday_renders_badge_and_open_slots(self, schedule, seed):
         # A holiday can land on a weekday (here a Thursday) and shows the badge,
@@ -108,8 +139,8 @@ class TestBuildShiftChangeMessage:
         )
         text = blocks[0]["text"]["text"]
         assert "<@U1>" in text and "picked up" in text and "Ext 114" in text
-        # Weekday → no (Day/Night) label
-        assert "(Night" not in text
+        # Weekday is night-only → the notification still labels the after-hours shift
+        assert "Night (5pm" in text
 
     def test_dropped_shows_available(self):
         blocks = build_shift_change_message(

tests/slack_bot/test_handle_drop.py

@@ -140,3 +140,117 @@ def test_drop_bad_date(slackbot_app, schedule, seed, respond, client, text_of):
 def test_drop_usage(slackbot_app, schedule, respond, client, text_of):
     slackbot_app._handle_drop(respond, schedule, "U_ALICE", "drop", "C1", client, None)
     assert "Usage" in text_of(respond)
+
+
+# ── shift disambiguation (#134) ──────────────────────────────────────────────
+
+
+@freeze_time(MON_0800)
+def test_ambiguous_holiday_and_night_prompts(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    # Thursday 2026-06-04: Alice holds both a holiday slot and the night shift.
+    seed.roster("114", "Alice", slack_user_id="U_ALICE")
+    seed.holiday(
+        "2026-06-04",
+        slots=2,
+        label="Test Holiday",
+        assignees={"114": {"name": "Alice", "claimed_at": "x"}},
+    )
+    seed.weekly("Thursday", "114", "Alice")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop 2026-06-04", "C1", client, None
+    )
+    msg = text_of(respond)
+    assert "more than one" in msg.lower()
+    assert "holiday" in msg.lower() and "night" in msg.lower()
+    # Nothing was dropped.
+    assert "114" in schedule.get_holiday("2026-06-04")["assignees"]
+    assert schedule.get_override("2026-06-04") is None
+    client.chat_postMessage.assert_not_called()
+
+
+@freeze_time(MON_0800)
+def test_explicit_night_drops_night_not_holiday(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    seed.roster("114", "Alice", slack_user_id="U_ALICE")
+    seed.holiday(
+        "2026-06-04",
+        slots=2,
+        label="Test Holiday",
+        assignees={"114": {"name": "Alice", "claimed_at": "x"}},
+    )
+    seed.weekly("Thursday", "114", "Alice")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop 2026-06-04 night", "C1", client, None
+    )
+    assert "dropped" in text_of(respond)
+    assert schedule.get_override("2026-06-04")["extension"] == "OPEN"  # night opened
+    assert "114" in schedule.get_holiday("2026-06-04")["assignees"]  # holiday kept
+
+
+@freeze_time(MON_0800)
+def test_explicit_holiday_drops_holiday_not_night(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    seed.roster("114", "Alice", slack_user_id="U_ALICE")
+    seed.holiday(
+        "2026-06-04",
+        slots=2,
+        label="Test Holiday",
+        assignees={"114": {"name": "Alice", "claimed_at": "x"}},
+    )
+    seed.weekly("Thursday", "114", "Alice")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop 2026-06-04 holiday", "C1", client, None
+    )
+    assert "dropped your slot" in text_of(respond).lower()
+    assert "114" not in schedule.get_holiday("2026-06-04")["assignees"]
+    assert schedule.get_override("2026-06-04") is None  # night untouched
+
+
+@freeze_time(MON_0800)
+def test_ambiguous_weekend_day_and_night_prompts(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    # Saturday 2026-06-06: Alice holds both the day and night shift.
+    seed.roster("200", "Alice", slack_user_id="U_ALICE")
+    seed.weekly("Saturday", "200", "Alice", shift_type="day")
+    seed.weekly("Saturday", "200", "Alice", shift_type="night")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop saturday", "C1", client, None
+    )
+    assert "more than one" in text_of(respond).lower()
+    assert schedule.get_override("2026-06-06", "day") is None
+    assert schedule.get_override("2026-06-06") is None
+
+
+@freeze_time(MON_0800)
+def test_explicit_weekend_night_drops_night(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    seed.roster("200", "Alice", slack_user_id="U_ALICE")
+    seed.weekly("Saturday", "200", "Alice", shift_type="day")
+    seed.weekly("Saturday", "200", "Alice", shift_type="night")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop saturday night", "C1", client, None
+    )
+    assert "dropped" in text_of(respond)
+    assert schedule.get_override("2026-06-06")["extension"] == "OPEN"  # night opened
+    assert schedule.get_override("2026-06-06", "day") is None  # day untouched
+
+
+@freeze_time(MON_0800)
+def test_explicit_qualifier_not_held_is_rejected(
+    slackbot_app, schedule, seed, respond, client, text_of
+):
+    # Alice holds only the (weekday) night shift; asking to drop the day shift
+    # is rejected rather than silently dropping the night shift.
+    seed.roster("114", "Alice", slack_user_id="U_ALICE")
+    seed.weekly("Tuesday", "114", "Alice")
+    slackbot_app._handle_drop(
+        respond, schedule, "U_ALICE", "drop tomorrow day", "C1", client, None
+    )
+    assert "don't hold" in text_of(respond).lower()
+    assert schedule.get_override("2026-06-02") is None