diff --git a/tests/test_perception.py b/tests/test_perception.py
index 9d3293af..7e21a13d 100644
--- a/tests/test_perception.py
+++ b/tests/test_perception.py
@@ -89,3 +89,25 @@ def test_describe_cached_does_not_cache_failures() -> None:
     assert perception.describe_cached(**kw) == ""  # backend down → "" (uncached)
     assert perception.describe_cached(**kw) == "recovered"  # retried, succeeds
     assert prov.calls == 2
+
+
+def test_describe_peek_returns_none_when_absent() -> None:
+    assert perception.describe_peek(alias="omni", content_hash="missing") is None
+
+
+def test_describe_peek_returns_cached_without_recompute() -> None:
+    prov = _StubProvider(content="desc")
+    kw: dict[str, Any] = {
+        "provider": prov,
+        "client": object(),
+        "model": "m",
+        "alias": "omni",
+        "content_hash": "h",
+        "parts": _parts(),
+    }
+    perception.describe_cached(**kw)  # populate the memo
+    assert prov.calls == 1
+    # Peek serves the memoized text and never re-invokes the backend — this is
+    # what lets the wire resolver skip the PDF rasterize on a cross-send hit.
+    assert perception.describe_peek(alias="omni", content_hash="h") == "desc"
+    assert prov.calls == 1
diff --git a/tests/test_session_attachments.py b/tests/test_session_attachments.py
index d92c72cb..ee2f4307 100644
--- a/tests/test_session_attachments.py
+++ b/tests/test_session_attachments.py
@@ -650,6 +650,73 @@ class TestResolveAttachmentsCapsThreading:
         assert out["aT"]["document"]["media_type"] == "application/pdf"
 
 
+class TestResolveAttachmentsPerSendCache:
+    """The per-send wire-part memo collapses the re-fetch + re-rasterize that the
+    resolver would otherwise repeat on every agentic round-trip within one send."""
+
+    def _att(self):
+        return {
+            "attachment_id": "aT",
+            "filename": "r.pdf",
+            "mime_type": "application/pdf",
+            "kind": "pdf",
+            "content": b"%PDF",
+        }
+
+    def test_cache_collapses_repeat_resolves(self, tmp_db, mock_openai_client, monkeypatch):
+        s = _make_session(mock_openai_client)
+        fetches = {"n": 0}
+        rasters = {"n": 0}
+
+        def _fetch(ids):
+            fetches["n"] += 1
+            return [self._att()] if ids else []
+
+        monkeypatch.setattr("turnstone.core.session.get_attachments", _fetch)
+        monkeypatch.setattr(
+            "turnstone.core.pdf.rasterize_pdf",
+            lambda data: rasters.__setitem__("n", rasters["n"] + 1) or [b"pg"],
+        )
+        caps = ModelCapabilities(supports_pdf=False, supports_vision=True)
+        s._wire_part_cache = {}  # simulate being inside send()
+        first = s._resolve_attachments(["aT"], caps)
+        second = s._resolve_attachments(["aT"], caps)
+        assert first == second
+        assert isinstance(first["aT"], list)
+        # Fetched + rasterized once despite two resolver passes.
+        assert fetches["n"] == 1
+        assert rasters["n"] == 1
+
+    def test_no_cache_outside_send_rematerializes(self, tmp_db, mock_openai_client, monkeypatch):
+        s = _make_session(mock_openai_client)
+        fetches = {"n": 0}
+
+        def _fetch(ids):
+            fetches["n"] += 1
+            return [self._att()]
+
+        monkeypatch.setattr("turnstone.core.session.get_attachments", _fetch)
+        monkeypatch.setattr("turnstone.core.pdf.rasterize_pdf", lambda data: [b"pg"])
+        caps = ModelCapabilities(supports_pdf=False, supports_vision=True)
+        assert s._wire_part_cache is None  # default outside a send → no caching
+        s._resolve_attachments(["aT"], caps)
+        s._resolve_attachments(["aT"], caps)
+        assert fetches["n"] == 2
+
+    def test_cache_keyed_by_caps(self, tmp_db, mock_openai_client, monkeypatch):
+        s = _make_session(mock_openai_client)
+        monkeypatch.setattr("turnstone.core.session.get_attachments", lambda ids: [self._att()])
+        monkeypatch.setattr("turnstone.core.pdf.rasterize_pdf", lambda data: [b"pg"])
+        s._wire_part_cache = {}
+        native = s._resolve_attachments(["aT"], ModelCapabilities(supports_pdf=True))
+        rasterized = s._resolve_attachments(
+            ["aT"], ModelCapabilities(supports_pdf=False, supports_vision=True)
+        )
+        # Different caps → different materialization, not a stale same-id hit.
+        assert native["aT"]["type"] == "document"
+        assert isinstance(rasterized["aT"], list)
+
+
 class TestByReferenceMediaBudget:
     """bug-2: by-reference pdf/audio are charged a bounded budget — not zero
     (over-context), not the full multi-MB source blob (over-trim)."""
diff --git a/turnstone/core/perception.py b/turnstone/core/perception.py
index 13301dbe..a70dc645 100644
--- a/turnstone/core/perception.py
+++ b/turnstone/core/perception.py
@@ -140,3 +140,15 @@ def describe_cached(
             _cache.pop(next(iter(_cache)), None)
         _cache[key] = text
     return text
+
+
+def describe_peek(*, alias: str, content_hash: str) -> str | None:
+    """Return the memoized description for ``(alias, content_hash)`` without
+    computing, or ``None`` if absent.
+
+    Lets the wire resolver skip the expensive parts build (a PDF rasterize) when
+    the description is already memoized from an earlier send — :func:`describe_cached`
+    ignores ``parts`` on a hit, so building them first would be pure waste.
+    """
+    with _cache_lock:
+        return _cache.get(f"{alias}:{content_hash}")
diff --git a/turnstone/core/session.py b/turnstone/core/session.py
index 2ae24a78..e49c5be4 100644
--- a/turnstone/core/session.py
+++ b/turnstone/core/session.py
@@ -1057,6 +1057,14 @@ class ChatSession:
         # many times within a turn, so the injected set is touched at most once
         # per memory per turn.  Cleared alongside the search cache.
         self._touched_memory_keys: set[tuple[str, str, str]] = set()
+        # Per-send memo for the wire attachment resolver (set in send(), None
+        # outside a send).  _resolve_attachments re-runs on every agentic
+        # round-trip, so this caches the materialized part by
+        # (attachment_id, caps-signature) to avoid re-fetching + re-rasterizing +
+        # re-base64'ing the same blob once per round-trip.
+        self._wire_part_cache: (
+            dict[tuple[str, tuple[bool, bool, bool]], dict[str, Any] | list[dict[str, Any]]] | None
+        ) = None
         self._ws_id = ws_id or uuid.uuid4().hex
         self._title_generated = False
         self._read_files: set[str] = set()
@@ -2955,11 +2963,30 @@ class ChatSession:
         # right caps; default to the primary only when called without one.
         if caps is None:
             caps = self._get_capabilities()
+        # Per-send memo (see send()): the wire resolver is re-invoked on every
+        # round-trip and per fallback model, so without this a PDF in history is
+        # re-rasterized / a blob re-base64'd once per round-trip.  Key on
+        # (id, caps-signature): the same stored blob materializes differently per
+        # capability set, and a fallback to a different-caps model can resolve
+        # within one send.  ``cache`` is None outside a send → original behavior.
+        cache = self._wire_part_cache
+        caps_sig = (caps.supports_pdf, caps.supports_vision, caps.supports_audio_input)
         out: dict[str, Any] = {}
-        for att in get_attachments(ids):
-            part = self._wire_content_part(att, caps)
-            if part is not None:
-                out[str(att["attachment_id"])] = part
+        missing: list[str] = []
+        for att_id in ids:
+            hit = cache.get((att_id, caps_sig)) if cache is not None else None
+            if hit is not None:
+                out[att_id] = hit
+            else:
+                missing.append(att_id)
+        if missing:
+            for att in get_attachments(missing):
+                part = self._wire_content_part(att, caps)
+                if part is not None:
+                    aid = str(att["attachment_id"])
+                    out[aid] = part
+                    if cache is not None:
+                        cache[(aid, caps_sig)] = part
         return out
 
     def _wire_content_part(
@@ -3149,19 +3176,26 @@ class ChatSession:
             return None
         if kind == "audio" and not caps.supports_audio_input:
             return None
-        parts = self._perception_parts(att, kind)
-        if not parts:
-            return None
-        from turnstone.core.perception import describe_cached
+        from turnstone.core.perception import describe_cached, describe_peek
 
-        text = describe_cached(
-            provider=provider,
-            client=client,
-            model=model,
-            alias=alias,
-            content_hash=str(att.get("attachment_id")),
-            parts=parts,
-        )
+        # Peek the (alias, content_hash) memo BEFORE building parts: for a PDF,
+        # _perception_parts rasterizes every page, but describe_cached returns a
+        # memoized description without touching parts on a hit — so on a cross-send
+        # hit the rasterize would be pure waste.
+        content_hash = str(att.get("attachment_id"))
+        text = describe_peek(alias=alias, content_hash=content_hash)
+        if text is None:
+            parts = self._perception_parts(att, kind)
+            if not parts:
+                return None
+            text = describe_cached(
+                provider=provider,
+                client=client,
+                model=model,
+                alias=alias,
+                content_hash=content_hash,
+                parts=parts,
+            )
         if not text:
             return None
         name = str(att.get("filename") or kind)
@@ -4084,6 +4118,10 @@ class ChatSession:
         # reference so subprocesses from old generations are still killed.
         self._cancel_event = threading.Event()
         self._cancelled_partial_msg = None
+        # Fresh per-send attachment wire-part memo (see __init__): bounds the
+        # heavy rasterized-page parts to one send and picks up any mid-session
+        # capability / config change.
+        self._wire_part_cache = {}
 
         # Metacognitive nudge: check for correction/completion signals
         # before _append_user_turn so any fired nudge (plus any nudges