diff --git a/drb-c2-core/app/routers/discord_checks.py b/drb-c2-core/app/routers/discord_checks.py
index 39f5131..f3160bc 100644
--- a/drb-c2-core/app/routers/discord_checks.py
+++ b/drb-c2-core/app/routers/discord_checks.py
@@ -87,6 +87,16 @@ def _channel_state(rows: list[dict], enabled: bool) -> str:
     return "no_bot"
 
 
+def _checked_at(snaps: dict) -> str:
+    """When Discord was last actually asked: the OLDEST cached snapshot behind
+    this answer (a denied result is cached for 10 min), so the picker's
+    "Permissions checked N ago" never calls a stale answer fresh (server-26#225
+    S4). No snapshot (check off, no member bots) = now."""
+    times = [s.fetched_at for s in snaps.values() if s is not None and getattr(s, "fetched_at", None)]
+    ts = min(times) if times else time.time()
+    return datetime.fromtimestamp(ts, timezone.utc).isoformat()
+
+
 async def voice_check(*, guild_id: str, org_id: Optional[str], node_id: Optional[str],
                       channels: list[dict], channel_id: Optional[str], refresh: bool,
                       with_token_ids: bool) -> dict:
@@ -171,7 +181,7 @@ async def voice_check(*, guild_id: str, org_id: Optional[str], node_id: Optional
         "guild_id": guild_id,
         "node_id": node_id,
         "enabled": enabled,
-        "checked_at": datetime.now(timezone.utc).isoformat(),
+        "checked_at": _checked_at(snaps),
         "refreshed": refresh,
         "channels": out_channels,
         "invite": invite,
diff --git a/drb-c2-core/tests/test_voice_check_age.py b/drb-c2-core/tests/test_voice_check_age.py
new file mode 100644
index 0000000..e373028
--- /dev/null
+++ b/drb-c2-core/tests/test_voice_check_age.py
@@ -0,0 +1,37 @@
+"""
+voice-check's ``checked_at`` is when Discord was last asked — the oldest
+cached snapshot behind the answer — not the time of the HTTP response, so the
+picker's "Permissions checked N ago" footer never calls a 10-minute-old
+denied result fresh (server-26#225 S4).
+"""
+import time
+from datetime import datetime
+
+from app.internal import discord_rest
+from app.routers import discord_checks as checks
+from tests.test_discord_perm_check import GUILD, OWNER, _snap, _token, fs, run  # noqa: F401  (fs = fixture)
+
+
+def _age(out) -> float:
+    return time.time() - datetime.fromisoformat(out["checked_at"]).timestamp()
+
+
+def test_checked_at_is_the_oldest_snapshot_not_now(fs, monkeypatch):
+    _token(fs, "t1"); _token(fs, "t2")
+    ages = {"t1": 30, "t2": 420}
+
+    async def _old(token_doc, guild_id, *, refresh=False):
+        s = _snap(token_doc["token_id"])
+        s.fetched_at = time.time() - (0 if refresh else ages[token_doc["token_id"]])
+        return s
+    monkeypatch.setattr(discord_rest, "guild_snapshot", _old)
+
+    out = run(checks.node_voice_check("n1", GUILD, refresh=0, channel_id=None, decoded=OWNER))
+    assert 415 <= _age(out) <= 430
+    out = run(checks.node_voice_check("n1", GUILD, refresh=1, channel_id=None, decoded=OWNER))
+    assert _age(out) < 5
+
+
+def test_checked_at_without_snapshots_is_now(fs):
+    out = run(checks.node_voice_check("n1", GUILD, refresh=0, channel_id=None, decoded=OWNER))  # no bots
+    assert _age(out) < 5