diff --git a/sdk/typescript/src/events.ts b/sdk/typescript/src/events.ts
index abb60797..dbb65b89 100644
--- a/sdk/typescript/src/events.ts
+++ b/sdk/typescript/src/events.ts
@@ -26,7 +26,7 @@ export interface HistoryEvent {
    *   (e.g. `watch_triggered`'s `{watch_name, command, poll_count, max_polls,
    *   is_final}`) so the renderer can rebuild per-kind UI (the watch-result
    *   card); absent for kinds with no structured data
-   * - `attachments`: per-attachment metadata `{kind, filename, mime_type, size_bytes}`
+   * - `attachments`: per-attachment metadata `{kind, filename, mime_type}`
    * - `reasoning`: concatenated reasoning text for assistant turns that
    *   round-tripped a thinking-block lane (Anthropic-with-thinking today;
    *   OpenAI Responses + Gemini in later phases). Present only when the
diff --git a/tests/test_app_js.py b/tests/test_app_js.py
index b3a82537..928997fb 100644
--- a/tests/test_app_js.py
+++ b/tests/test_app_js.py
@@ -279,6 +279,34 @@ def test_replay_renders_system_turn_via_add_system_context() -> None:
     )
 
 
+def test_retry_walk_skips_operator_context_cards() -> None:
+    """Interactive twin of the coord retry-skip guard.
+    ``_attachRetryToLastAssistant`` walks back past ``.operator-context`` rows
+    before testing for ``.ts-approval`` — so a watch-result / guard-finding
+    card (or a plain system bubble) trailing a tool-only turn doesn't make retry
+    attach to a stale earlier assistant turn.  Pin the walk predicate (scoped to
+    the method) AND the shared marker on every operator row that can trail a
+    tool batch, so adding a card kind without the marker fails loudly here."""
+    body = _APP_JS.read_text(encoding="utf-8")
+    start = _pane_method_offset(body, "_attachRetryToLastAssistant")
+    end = _pane_method_offset(body, "announceToolBlock")
+    fn = body[start:end]
+    assert 'classList.contains("operator-context")' in fn, (
+        "_attachRetryToLastAssistant must walk back past .operator-context "
+        "rows so the tool-only retry skip fires even when a card trails."
+    )
+    # Every operator row that can trail a tool batch carries the shared marker.
+    for cls in (
+        '"msg system-context operator-context"',
+        '"msg watch-result operator-context"',
+        '"msg guard-finding operator-context"',
+    ):
+        assert cls in body, (
+            f"operator row className {cls} must carry the operator-context "
+            "marker or the retry walk won't skip it."
+        )
+
+
 # ---------------------------------------------------------------------------
 # Phase 8 — Chunk D: MCP error embed + settings panel UX
 # ---------------------------------------------------------------------------
diff --git a/tests/test_coordinator_page.py b/tests/test_coordinator_page.py
index aaf2b315..8c0ee7f6 100644
--- a/tests/test_coordinator_page.py
+++ b/tests/test_coordinator_page.py
@@ -335,13 +335,46 @@ def test_coord_history_renders_system_turn_via_msg_variants():
     assert 'role === "system"' in body, (
         "coord history loop must have a system-role branch for first-class operator-context turns."
     )
-    # The ``system`` _MSG_VARIANTS entry gives the bubble operator styling.
-    assert 'system: "system-context"' in body, (
-        "coordinator.js must map the system role to the .msg.system-context "
-        "variant so operator-context turns get the operator styling."
+    # The ``system`` _MSG_VARIANTS entry gives the bubble operator styling and
+    # tags it with the shared ``operator-context`` marker (so the retry-skip
+    # walk steps over it — see test_coord_retry_walk_skips_operator_context_cards).
+    assert 'system: "system-context operator-context"' in body, (
+        "coordinator.js must map the system role to the "
+        "'system-context operator-context' variant so operator-context turns "
+        "get the operator styling AND carry the retry-skip marker."
     )
 
 
+def test_coord_retry_walk_skips_operator_context_cards():
+    """Retry must NOT regenerate a stale assistant turn when the last DOM row is
+    a tool batch trailed by an operator-context row.  ``_refreshRetryButton``
+    walks back past ``.operator-context`` rows before testing for
+    ``.coord-tool-batch`` — which only works if EVERY operator row carries the
+    shared marker.  Pin the walk predicate AND the marker on each structured
+    card so a new card kind (or a walk keyed on a single class) can't silently
+    re-introduce the wrong-turn retry regression."""
+    from pathlib import Path
+
+    coord_js = Path(__file__).resolve().parent.parent / (
+        "turnstone/console/static/coordinator/coordinator.js"
+    )
+    body = coord_js.read_text(encoding="utf-8")
+
+    assert 'classList.contains("operator-context")' in body, (
+        "_refreshRetryButton must walk back past .operator-context rows so the "
+        "tool-only retry skip fires even when a card trails the tool batch."
+    )
+    for builder, cls in (
+        ("appendWatchResult", '"msg watch-result operator-context"'),
+        ("appendGuardFinding", '"msg guard-finding operator-context"'),
+        ("appendIdleChildren", '"msg idle-children operator-context"'),
+    ):
+        assert cls in body, (
+            f"{builder} must tag its card with the shared operator-context "
+            f"marker ({cls}) or the retry walk won't skip it."
+        )
+
+
 def test_coordinator_js_seeds_resume_cursor_only_on_initial_connect():
     """coordinator.js must consume the /history resume cursor the same way
     ui/static/app.js does: the shared make_history_handler trims the
diff --git a/turnstone/console/static/coordinator/coordinator.js b/turnstone/console/static/coordinator/coordinator.js
index 77d20cd7..7a7e5b09 100644
--- a/turnstone/console/static/coordinator/coordinator.js
+++ b/turnstone/console/static/coordinator/coordinator.js
@@ -356,7 +356,10 @@
     // `.msg.system-context` rule (turnstone/shared_static/chat.css).  The
     // generic history-replay branch already renders unknown roles via
     // appendText("system", …); this variant gives it the operator styling.
-    system: "system-context",
+    // The `operator-context` marker is shared by every operator row (this
+    // bubble + the watch-result / guard-finding / idle-children cards) so the
+    // retry-skip walk in _refreshRetryButton can skip them all uniformly.
+    system: "system-context operator-context",
   };
 
   function appendMsg(role, html, opts) {
@@ -402,7 +405,7 @@
   // _buildWatchResultBubble.
   function appendWatchResult(meta, content) {
     const el = document.createElement("div");
-    el.className = "msg watch-result";
+    el.className = "msg watch-result operator-context";
     el.setAttribute("role", "article");
     el.setAttribute("data-ts-role", "watch");
     el.setAttribute("aria-label", "watch");
@@ -452,7 +455,7 @@
   // _buildGuardFindingBubble.
   function appendGuardFinding(meta) {
     const el = document.createElement("div");
-    el.className = "msg guard-finding";
+    el.className = "msg guard-finding operator-context";
     el.setAttribute("role", "article");
     el.setAttribute("data-ts-role", "output_guard");
     el.setAttribute("aria-label", "output guard");
@@ -494,7 +497,7 @@
   // producer); rendered via textContent so a hostile workstream name is inert.
   function appendIdleChildren(meta) {
     const el = document.createElement("div");
-    el.className = "msg idle-children";
+    el.className = "msg idle-children operator-context";
     el.setAttribute("role", "article");
     el.setAttribute("data-ts-role", "idle_children");
     el.setAttribute("aria-label", "idle children");
@@ -535,7 +538,7 @@
   // "queued message" bubble for a ``user_interjection`` system turn — shows the
   // user's raw words (``meta.message``) rather than the model-directed framing
   // baked into ``content``, with brighter emphasis for ``!!!``-important
-  // interjections.  Reuses ``appendText`` (→ ``.msg.system-context``) + a class.
+  // interjections.  Reuses ``appendText`` and adds ``.important`` for ``!!!`` ones.
   function appendInterjection(meta, content) {
     const important = meta && meta.priority === "important";
     const text =
@@ -543,7 +546,6 @@
     const el = appendText("system", text, {
       label: important ? "queued message · important" : "queued message",
     });
-    el.classList.add("interjection");
     if (important) el.classList.add("important");
     return el;
   }
@@ -4439,13 +4441,16 @@
     const old = messagesEl.querySelectorAll(".msg.assistant .msg-actions");
     for (let i = 0; i < old.length; i++) old[i].parentNode.removeChild(old[i]);
     // Skip retry when the most recent semantic turn is tool-only (last DOM
-    // child is a .coord-tool-batch construct); walk back past .system-context
-    // operator bubbles first so the guard still fires when the tool turn
-    // carried a nudge / guard finding. (Coord's batch class is
+    // child is a .coord-tool-batch construct); walk back past operator-context
+    // rows first — the plain system bubble AND the structured watch-result /
+    // guard-finding / idle-children cards all carry .operator-context — so the
+    // guard still fires when the tool turn carried a nudge / guard finding.
+    // Keying on the shared marker (not any single card class) keeps the skip
+    // correct as new card kinds are added. (Coord's batch class is
     // .coord-tool-batch — the interactive pane uses .ts-approval, which does
     // not exist in coord's DOM.)
     let lastChild = messagesEl.lastElementChild;
-    while (lastChild && lastChild.classList.contains("system-context")) {
+    while (lastChild && lastChild.classList.contains("operator-context")) {
       lastChild = lastChild.previousElementSibling;
     }
     if (lastChild && lastChild.classList.contains("coord-tool-batch")) {
diff --git a/turnstone/core/session_routes.py b/turnstone/core/session_routes.py
index df391398..983ae18c 100644
--- a/turnstone/core/session_routes.py
+++ b/turnstone/core/session_routes.py
@@ -3731,6 +3731,8 @@ def make_attachment_handlers(cfg: SessionEndpointConfig) -> AttachmentHandlers:
         return JSONResponse({"attachments": rows})
 
     async def get_content(request: Request) -> Response:
+        import asyncio
+
         from starlette.responses import Response as _Response
 
         from turnstone.core.attachment_buffer import get_attachment_buffer
@@ -3762,8 +3764,14 @@ def make_attachment_handlers(cfg: SessionEndpointConfig) -> AttachmentHandlers:
             stored_mime = staged.mime_type or "application/octet-stream"
             filename = staged.filename or "attachment"
         else:
-            row = get_attachment(attachment_id)
-            if not row or not attachment_referenced_in_ws(attachment_id, ws_id):
+            # Both committed-blob gates are sync DB I/O — the ref check is an
+            # unbounded ws-scoped LIKE scan (O(turns-in-ws)) run on every
+            # committed-image request, so keep it off the event loop.  Matches
+            # the asyncio.to_thread convention used throughout this module.
+            row = await asyncio.to_thread(get_attachment, attachment_id)
+            if not row or not await asyncio.to_thread(
+                attachment_referenced_in_ws, attachment_id, ws_id
+            ):
                 return JSONResponse({"error": "Not found"}, status_code=404)
             body = row.get("content") or b""
             kind = row.get("kind") or ""
diff --git a/turnstone/sdk/events.py b/turnstone/sdk/events.py
index ee78c7fd..ed6e5640 100644
--- a/turnstone/sdk/events.py
+++ b/turnstone/sdk/events.py
@@ -67,6 +67,8 @@ class HistoryEvent(ServerEvent):
       poll_count, max_polls, is_final}``) so the renderer can rebuild
       per-kind UI (the watch-result card); absent when the kind carries no
       structured data
+    * ``attachments`` — per-attachment metadata ``{kind, filename,
+      mime_type}`` (turns that carried image / document refs)
     * ``reasoning`` — concatenated reasoning text for assistant turns
       that round-tripped a thinking-block lane (Anthropic-with-thinking
       today; OpenAI Responses + Gemini in later phases). Present only
diff --git a/turnstone/shared_static/chat.css b/turnstone/shared_static/chat.css
index a2f2dea8..c4fafea9 100644
--- a/turnstone/shared_static/chat.css
+++ b/turnstone/shared_static/chat.css
@@ -1005,7 +1005,9 @@
    trajectory) — the consolidation of the metacognition reminder /
    user-interjection / output-guard bubbles into one turn type that FOLLOWS
    the turn it advises.  Shared so the interactive UI and the console coord
-   viewer render it identically.  Yellow accent reads as "operator metadata"
+   viewer render the bubble identically (the visible kind label is
+   interactive-only — see ``.msg-system-context-label`` below).  Yellow accent
+   reads as "operator metadata"
    against the amber user colour and the cyan tool cards; deliberately quieter
    so it doesn't compete for attention.  The ``watch_triggered`` kind carries
    structured per-kind meta and branches into the richer ``.msg.watch-result``
@@ -1017,6 +1019,12 @@
   padding: 6px 10px;
   white-space: pre-wrap;
 }
+/* The visible kind label is built ONLY by the interactive pane
+   (app.js ``addSystemContext`` → a ``.msg-system-context-label`` span).  The
+   coord viewer (coordinator.js ``appendMsg``) renders the kind via
+   border-colour + ``data-ts-role``/``aria-label`` with no visible label for
+   ANY role, so this rule (and its ``.important`` variant below) is inert on the
+   coord pane by design — not dead CSS. */
 .msg.system-context .msg-system-context-label {
   color: var(--yellow);
   font-weight: 600;
diff --git a/turnstone/ui/static/app.js b/turnstone/ui/static/app.js
index 9fa4b032..a5ac5e05 100644
--- a/turnstone/ui/static/app.js
+++ b/turnstone/ui/static/app.js
@@ -273,7 +273,8 @@ class Pane {
       source === "user_interjection" && meta && typeof meta === "object";
     const important = isInterjection && meta.priority === "important";
     const el = document.createElement("div");
-    el.className = "msg system-context" + (important ? " important" : "");
+    el.className =
+      "msg system-context operator-context" + (important ? " important" : "");
     const body = document.createElement("div");
     body.className = "msg-body";
     const labelEl = document.createElement("span");
@@ -2211,14 +2212,16 @@ class Pane {
     // .msg.assistant selector already excludes them — no extra guard needed.
     //
     // Skip retry attachment when the most recent semantic turn is
-    // tool-only — last DOM child is a .ts-approval block.  Walk back
-    // past .system-context bubbles (operator-context system turns that
-    // FOLLOW the tool batch they advise) so the guard fires correctly
-    // even when the tool turn carried a nudge / guard finding.  Without
-    // this skip, retry lands on a stale prior assistant content bubble
-    // belonging to an earlier turn.
+    // tool-only — last DOM child is a .ts-approval block.  Walk back past
+    // operator-context rows (the plain system bubble AND the structured
+    // watch-result / guard-finding cards — every operator row carries
+    // .operator-context) which FOLLOW the tool batch they advise, so the
+    // guard fires even when the tool turn carried a nudge / guard finding.
+    // Keying on the shared marker (not any single card class) keeps the skip
+    // correct as new card kinds are added.  Without it, retry lands on a
+    // stale prior assistant content bubble belonging to an earlier turn.
     let lastChild = this.messagesEl.lastElementChild;
-    while (lastChild && lastChild.classList.contains("system-context")) {
+    while (lastChild && lastChild.classList.contains("operator-context")) {
       lastChild = lastChild.previousElementSibling;
     }
     if (lastChild && lastChild.classList.contains("ts-approval")) {
@@ -2758,7 +2761,7 @@ class Pane {
 // buildWatchResultBubble.
 function _buildWatchResultBubble(meta, content) {
   const el = document.createElement("div");
-  el.className = "msg watch-result";
+  el.className = "msg watch-result operator-context";
   el.setAttribute("role", "article");
   el.setAttribute("data-ts-role", "watch");
   el.setAttribute("aria-label", "watch");
@@ -2805,7 +2808,7 @@ function _buildWatchResultBubble(meta, content) {
 // tool chip omits to stay terse.  All text via textContent.
 function _buildGuardFindingBubble(meta) {
   const el = document.createElement("div");
-  el.className = "msg guard-finding";
+  el.className = "msg guard-finding operator-context";
   el.setAttribute("role", "article");
   el.setAttribute("data-ts-role", "output_guard");
   el.setAttribute("aria-label", "output guard");