diff --git a/application/single_app/config.py b/application/single_app/config.py
index 276949d40..028a6ea81 100644
--- a/application/single_app/config.py
+++ b/application/single_app/config.py
@@ -101,7 +101,7 @@
 EXECUTOR_TYPE = 'thread'
 EXECUTOR_MAX_WORKERS = 30
 SESSION_TYPE = 'filesystem'
-VERSION = "0.261.337"
+VERSION = "0.261.338"
 IS_DEVELOPMENT = is_development_env_enabled()
 
 # Opt-out for deployments where App Service Easy Auth is active but the platform
diff --git a/application/v2_ui/src/components/chat/MessageActions.tsx b/application/v2_ui/src/components/chat/MessageActions.tsx
index 9f4b8aa31..90ed03459 100644
--- a/application/v2_ui/src/components/chat/MessageActions.tsx
+++ b/application/v2_ui/src/components/chat/MessageActions.tsx
@@ -11,6 +11,7 @@ import {
     BookmarkPlus,
     BookOpen,
     Brain,
+    CalendarClock,
     ChevronLeft,
     ChevronRight,
     Clipboard,
@@ -70,20 +71,29 @@ export function IconButton({
     children,
     active = false,
     disabled = false,
+    expanded,
+    controls,
+    buttonRef,
 }: {
     label: string;
     onClick: () => void;
     children: React.ReactNode;
     active?: boolean;
     disabled?: boolean;
+    expanded?: boolean;
+    controls?: string;
+    buttonRef?: React.Ref<HTMLButtonElement>;
 }) {
     return (
         <button
+            ref={buttonRef}
             type="button"
             onClick={onClick}
             disabled={disabled}
             title={label}
             aria-label={label}
+            aria-expanded={expanded}
+            aria-controls={controls}
             className={clsx(
                 'rounded-md p-1.5 transition-colors disabled:cursor-not-allowed disabled:opacity-40',
                 active
@@ -407,12 +417,19 @@ export function MessageActions({
     inspector,
     onInspect,
     alignRight,
+    planReplay,
 }: {
     message: ChatMessage;
     onEdit?: () => void;
     /** Section currently open below the message, or null when the panel is closed. */
     inspector?: InspectorSection | null;
     onInspect?: (section: InspectorSection | null) => void;
+    planReplay?: {
+        expanded: boolean;
+        panelId: string;
+        buttonRef: React.Ref<HTMLButtonElement>;
+        onToggle: () => void;
+    };
     /**
      * Which side the message bubble sits on.
      *
@@ -524,10 +541,12 @@ export function MessageActions({
 
     return (
         <div
+            role="group"
+            aria-label="Message actions"
             className={clsx(
                 // Groups are separated by a wider gap than the buttons within them, so the
                 // row reads as related sets rather than one long undifferentiated strip.
-                'mt-1 flex items-center gap-3',
+                'mt-1 flex flex-wrap items-center gap-x-3 gap-y-1',
                 (alignRight ?? isUser) ? 'justify-end' : 'justify-start',
             )}
         >
@@ -600,6 +619,18 @@ export function MessageActions({
                 )}
 
                 {!isUser && ttsEnabled && <SpeakButton message={message} />}
+                {!isUser && planReplay && (
+                    <IconButton
+                        label="Repeat on a schedule"
+                        active={planReplay.expanded}
+                        expanded={planReplay.expanded}
+                        controls={planReplay.panelId}
+                        buttonRef={planReplay.buttonRef}
+                        onClick={planReplay.onToggle}
+                    >
+                        <CalendarClock size={15} aria-hidden="true" />
+                    </IconButton>
+                )}
             </div>
 
             {!isUser && feedbackEnabled && (
diff --git a/application/v2_ui/src/components/chat/MessageList.tsx b/application/v2_ui/src/components/chat/MessageList.tsx
index 22b8ae39b..a56e547e9 100644
--- a/application/v2_ui/src/components/chat/MessageList.tsx
+++ b/application/v2_ui/src/components/chat/MessageList.tsx
@@ -2,7 +2,7 @@
 import { ReasoningAdjustmentNotice } from './ReasoningAdjustmentNotice';
 // Renders the message thread, the in-flight streaming bubble and the reasoning panel.
 
-import { memo, useCallback, useEffect, useMemo, useRef, useState } from 'react';
+import { memo, useCallback, useEffect, useId, useMemo, useRef, useState } from 'react';
 import { clsx } from 'clsx';
 import {
     BookOpen,
@@ -821,6 +821,9 @@ function MessageBubbleInner({
     const [editing, setEditing] = useState(false);
     const [draft, setDraft] = useState(message.content);
     const [inspector, setInspector] = useState<InspectorSection | null>(null);
+    const replayPanelId = useId();
+    const replayButtonRef = useRef<HTMLButtonElement>(null);
+    const [expandedReplayRun, setExpandedReplayRun] = useState<string | null>(null);
     const bodyRef = useRef<HTMLDivElement>(null);
     const editMessage = useChatStore((state) => state.editMessage);
     const applyMask = useChatStore((state) => state.applyMask);
@@ -905,6 +908,18 @@ function MessageBubbleInner({
     const markAnalysisUnavailable = useCallback(() => setUnavailableAnalysisKey(analysisKey), [analysisKey]);
     const analysisUnavailable = hasSavedAnalysis && (!savedAnalysis || savedAnalysis.available === false ||
         savedAnalysis.conversation_id !== activeConversationId || unavailableAnalysisKey === analysisKey);
+    const canRepeatPlan = message.role === 'assistant' && !analysisUnavailable
+        && planReplayAvailable && Boolean(orchestration.run_id) && orchestration.outcome === 'completed'
+        && !masks.fullyMasked && masks.ranges.length === 0 && personalConversation
+        && message.conversation_id === activeConversationId
+        && !orchestrationProposedWorkflow(message.metadata?.orchestration)
+        && !orchestrationStartedWorkflow(message.metadata?.orchestration)
+        && !orchestrationHandedOffWorkflow(message.metadata?.orchestration);
+    const replayRunKey = `${message.conversation_id}:${orchestration.run_id}`;
+    const replayExpanded = canRepeatPlan && expandedReplayRun === replayRunKey;
+    useEffect(() => {
+        setExpandedReplayRun(null);
+    }, [canRepeatPlan, replayRunKey]);
     const artifactsReplaceText = !hasSavedAnalysis && suppressesAssistantText(artifacts);
     useEffect(() => {
         const store = useChatStore.getState();
@@ -1206,14 +1221,6 @@ function MessageBubbleInner({
                             <WorkflowHandoffCards conversationId={message.conversation_id} runId={orchestration.run_id}
                                 liveRunStatus={liveRunStatus} />
                         ) : null}
-                        {planReplayAvailable && orchestration.run_id && orchestration.outcome === 'completed'
-                            && masks.ranges.length === 0 && personalConversation
-                            && message.conversation_id === activeConversationId
-                            && !orchestrationProposedWorkflow(message.metadata?.orchestration)
-                            && !orchestrationStartedWorkflow(message.metadata?.orchestration)
-                            && !orchestrationHandedOffWorkflow(message.metadata?.orchestration) ? (
-                            <PlanReplaySaveCard conversationId={message.conversation_id} runId={orchestration.run_id} />
-                        ) : null}
                         {/* Inside the bubble, because a generated file belongs to the reply
                             that produced it rather than sitting loose in the thread. */}
                         {hasSavedAnalysis && (masks.ranges.length > 0 ? (
@@ -1265,7 +1272,7 @@ function MessageBubbleInner({
             <div
                 className={clsx(
                     'transition-opacity group-hover/message:opacity-100 focus-within:opacity-100',
-                    inspector ? 'opacity-100' : 'opacity-0',
+                    inspector || replayExpanded ? 'opacity-100' : 'opacity-0',
                 )}
             >
                 {!analysisUnavailable && <MessageActions
@@ -1274,9 +1281,29 @@ function MessageBubbleInner({
                     inspector={inspector}
                     onInspect={setInspector}
                     alignRight={alignRight}
+                    planReplay={canRepeatPlan ? {
+                        expanded: replayExpanded,
+                        panelId: replayPanelId,
+                        buttonRef: replayButtonRef,
+                        onToggle: () => setExpandedReplayRun(replayExpanded ? null : replayRunKey),
+                    } : undefined}
                 />}
             </div>
 
+            {canRepeatPlan && orchestration.run_id && (
+                <PlanReplaySaveCard
+                    key={replayRunKey}
+                    conversationId={message.conversation_id}
+                    runId={orchestration.run_id}
+                    panelId={replayPanelId}
+                    expanded={replayExpanded}
+                    onCollapse={() => {
+                        setExpandedReplayRun(null);
+                        replayButtonRef.current?.focus();
+                    }}
+                />
+            )}
+
             {inspector && (
                 <MessageInspector
                     message={message}
diff --git a/application/v2_ui/src/components/chat/PlanReplaySaveCard.tsx b/application/v2_ui/src/components/chat/PlanReplaySaveCard.tsx
index ce7279a9c..1b7929b76 100644
--- a/application/v2_ui/src/components/chat/PlanReplaySaveCard.tsx
+++ b/application/v2_ui/src/components/chat/PlanReplaySaveCard.tsx
@@ -1,7 +1,7 @@
 // PlanReplaySaveCard.tsx
 // Lets the requester save one completed chat orchestration plan as a read-only personal workflow.
 
-import { useCallback, useId, useState, type ReactNode } from 'react';
+import { useCallback, useEffect, useState, type ReactNode } from 'react';
 import { Link } from 'react-router-dom';
 import { CalendarClock, ChevronDown, RefreshCw } from 'lucide-react';
 import { GlassButton } from '../ui/primitives';
@@ -65,12 +65,16 @@ function defaultName(request: string): string {
 export function PlanReplaySaveCard({
     runId,
     conversationId,
+    panelId,
+    expanded,
+    onCollapse,
 }: {
     runId: string;
     conversationId: string;
+    panelId: string;
+    expanded: boolean;
+    onCollapse: () => void;
 }) {
-    const panelId = useId();
-    const [expanded, setExpanded] = useState(false);
     const [loading, setLoading] = useState(false);
     const [preview, setPreview] = useState<PlanReplayPreview | null>(null);
     const [options, setOptions] = useState<WorkflowEditorOptions | null>(null);
@@ -85,7 +89,6 @@ export function PlanReplaySaveCard({
     const [saved, setSaved] = useState<{ id: string; name: string; created: boolean; enabled: boolean } | null>(null);
 
     const load = useCallback(async () => {
-        setExpanded(true);
         setLoading(true);
         setError('');
         setErrorCode('');
@@ -108,6 +111,10 @@ export function PlanReplaySaveCard({
         }
     }, [conversationId, runId]);
 
+    useEffect(() => {
+        if (expanded) void load();
+    }, [expanded, load]);
+
     const save = async () => {
         if (!preview || saving) return;
         setSaving(true);
@@ -139,16 +146,7 @@ export function PlanReplaySaveCard({
         }
     };
 
-    if (!expanded) {
-        return (
-            <div className="mt-3">
-                <GlassButton type="button" size="sm" variant="subtle" aria-expanded="false"
-                    aria-controls={panelId} onClick={() => void load()}>
-                    <CalendarClock size={14} aria-hidden="true" /> Repeat on a schedule
-                </GlassButton>
-            </div>
-        );
-    }
+    if (!expanded) return null;
 
     return (
         <section id={panelId} aria-label="Save chat plan as workflow"
@@ -163,7 +161,7 @@ export function PlanReplaySaveCard({
                     </p>
                 </div>
                 <GlassButton type="button" size="sm" variant="ghost" aria-expanded="true"
-                    aria-controls={panelId} onClick={() => setExpanded(false)}>
+                    aria-controls={panelId} onClick={onCollapse}>
                     <ChevronDown size={14} aria-hidden="true" /> Collapse
                 </GlassButton>
             </div>
diff --git a/docs/explanation/features/WORKFLOW_PLAN_REPLAY.md b/docs/explanation/features/WORKFLOW_PLAN_REPLAY.md
index eb84360bb..89f8a01f1 100644
--- a/docs/explanation/features/WORKFLOW_PLAN_REPLAY.md
+++ b/docs/explanation/features/WORKFLOW_PLAN_REPLAY.md
@@ -6,6 +6,8 @@ Application version tracking: `application\single_app\config.py`.
 
 Shared schedule policy implemented in version: **0.261.317**.
 
+Calendar message action implemented in version: **0.261.338**.
+
 Related issue: part of #1550, under #1543. Builds on
 [Chat orchestration workflow proposals](CHAT_ORCHESTRATION_WORKFLOW_PROPOSALS.md),
 [Chat orchestration workflow runs](CHAT_ORCHESTRATION_WORKFLOW_RUNS.md),
@@ -289,8 +291,15 @@ withholds `plan_replay` along with the rest of the result.
 
 ## Creation path
 
-Creation path **B**: a **Repeat on a schedule** button under a finished
-orchestrated answer opens a **Save this chat plan** card.
+Creation path **B**: a **Repeat on a schedule** calendar icon in a finished
+orchestrated answer's message action bar opens a **Save this chat plan** card.
+The icon shares the existing Copy/Retry controls' hover and keyboard-focus
+reveal behavior, with an accessible name, tooltip, and expanded-state
+announcement. There is no standalone scheduling button inside the answer.
+The card expands below the message, outside the fading action bar, and stays
+visible until collapsed. Collapse restores focus to the calendar icon; the
+icon can also close an open card. Moving the control does not change the
+workflow defaults or create anything automatically.
 
 Why B rather than asking the planner: the plan being saved is one the user
 already saw run, so the card can show exactly that plan. The planner never
@@ -444,7 +453,7 @@ settings instead.
 
 ### When the setting is turned off or a capability is removed
 
-Nothing is deleted or rewritten. The **Repeat on a schedule** button
+Nothing is deleted or rewritten. The **Repeat on a schedule** calendar icon
 disappears, the routes refuse with `replay_disabled`, and every existing replay
 workflow fails its next run with the fixed `replay_disabled` reason before
 running any step. With the default alert, the creator sees that reason in the
@@ -477,7 +486,7 @@ builds and run-history redaction against a golden captured from base
 | `functions_orchestration_registry.py` | The setting's name. |
 | `functions_saved_analysis.py` | Redaction withholds `plan_replay`. |
 | `static/js/workspace/workspace_workflows.js` | The Classic page routes replay workflows to V2. |
-| `v2_ui/src/components/chat/PlanReplaySaveCard.tsx`, `MessageList.tsx` | The card and when it shows. |
+| `v2_ui/src/components/chat/PlanReplaySaveCard.tsx`, `MessageList.tsx`, `MessageActions.tsx` | The on-demand card, calendar message action, and shared availability conditions. |
 | `v2_ui/src/lib/workflowPlanReplay.ts` | API client, parsing and disclosure text. |
 | `v2_ui/src/components/workflows/WorkflowEditorDialog.tsx`, `WorkflowRunHistory.tsx`, `lib/workflowEditor.ts`, `lib/workflowEditorSections.ts` | Read-only editor section and the run inspector block. |
 
@@ -492,7 +501,8 @@ builds and run-history redaction against a golden captured from base
 | `functional_tests/test_workflow_plan_replay_boundaries.py` | Import order and boundaries, scheduler exclusion. |
 | `functional_tests/route_tests/test_route_blueprint_policy_inventory.py`, `test_route_unauthenticated_policy_contract.py` | Route policy for the two new routes. |
 | `functional_tests/test_v2_workflow_plan_replay_client.mjs` | V2 client parsing, disclosure text, time-zone fallback, editor payloads, and the alert notice naming the server's rule. |
-| `ui_tests/test_v2_workflow_plan_replay_card.py` | The card, refusals, the alert notice and save in a browser, with hostile step titles and workflow names. |
+| `functional_tests/test_v2_message_actions.py` | Calendar action wiring, controlled panel, and lazy-preview contract alongside existing message actions. |
+| `ui_tests/test_v2_workflow_plan_replay_card.py` | Calendar placement, hover/keyboard reveal, desktop/mobile layout, eligibility, collapse/reopen, run/masking changes, errors, refusals, the alert notice and save in a browser, with hostile step titles and workflow names. |
 | `ui_tests/test_workflow_classic_advanced_guard.py` | The Classic page routes replay workflows to V2. |
 
 ## Limits and follow-ups
diff --git a/docs/explanation/fixes/PLAN_REPLAY_MESSAGE_ACTION_FIX.md b/docs/explanation/fixes/PLAN_REPLAY_MESSAGE_ACTION_FIX.md
new file mode 100644
index 000000000..b707c1585
--- /dev/null
+++ b/docs/explanation/fixes/PLAN_REPLAY_MESSAGE_ACTION_FIX.md
@@ -0,0 +1,96 @@
+# Plan replay calendar message action fix
+
+Fixed in version: **0.261.338**.
+
+Application version tracking: `application\single_app\config.py`.
+
+## Issue and root cause
+
+Every eligible completed orchestration answer displayed a persistent
+**Repeat on a schedule** text button inside its message bubble.
+`MessageList.tsx` mounted `PlanReplaySaveCard.tsx` in the answer body, and the
+card's collapsed state rendered that button instead of using the existing
+message action bar. Scheduling remained useful, but its entry point distracted
+from answers even when the reader did not want to create a workflow.
+
+## Changes
+
+`MessageActions.tsx` now renders a calendar icon beside the other message
+actions, using the shared `IconButton`, the existing local Lucide icon, and the
+incumbent theme. It retains the **Repeat on a schedule** accessible name and
+tooltip, and announces whether its associated panel is expanded. Action groups
+wrap on narrow screens rather than overflowing as the extra icon appears.
+
+`MessageList.tsx` shares one availability condition between the icon and panel.
+The existing feature switches, private active conversation restriction,
+completed-run requirement, masking restrictions, and workflow proposal/start/
+hand-off exclusions still apply. The open state belongs to the message's run;
+a changed run or newly ineligible answer closes the panel without reusing the
+previous run's preview.
+
+`PlanReplaySaveCard.tsx` is now a controlled inline panel without a second
+collapsed trigger. Choosing the calendar loads the preview and opens the
+existing form below the answer, outside the hover-fading action bar.
+**Collapse** returns focus to the calendar. Reopening the same eligible plan
+preserves its name and description while reloading the preview, as before.
+
+No routes, administrative settings, replay execution rules, schedule defaults,
+or save payloads changed. Merely displaying or hovering over an answer does
+not fetch a preview or create a workflow.
+
+## Regression coverage
+
+`functional_tests/test_v2_message_actions.py` checks the icon wiring and
+controlled, lazy-loaded panel contract. The real-component browser suite in
+`ui_tests/test_v2_workflow_plan_replay_card.py` covers placement beside Copy,
+hover and keyboard reveal, expansion and collapse, preserved form state,
+desktop/light and mobile/dark layouts, prerequisite flags, answer eligibility,
+masking and run changes, visible preview failures, paused saving, refusals,
+and inert hostile content.
+
+Related client contracts remain covered by
+`functional_tests/test_v2_workflow_plan_replay_client.mjs`.
+
+## Validation
+
+The V2 production build passed, including TypeScript compilation. Browser
+coverage passed all **27 tests**, including desktop/light and mobile/dark
+interaction. The plan-replay client suite passed all **9 tests**. Documentation
+inventory/coverage passed all **7 checks**, and site quality passed all
+**6 checks**. Regenerating the inventory produced no content change.
+
+The message-action functional suite passed **7 tests** when excluding
+`test_retry_and_edit_are_two_step_flows`. The full selected run exposed that
+existing test's stale source assertion: it expects `'chat_request':
+chat_request`, while the current route returns `'chat_request': body`.
+Executing the unchanged test from `HEAD` reproduced the same failure. The
+unrelated assertion and production retry behavior were left unchanged.
+
+Commands used from the worktree root:
+
+```powershell
+npm --prefix .\application\v2_ui run build -- --outDir ..\..\ui_tests\artifacts\orchestration-plan-editor
+.\.venv\Scripts\python.exe -m pytest .\ui_tests\test_v2_workflow_plan_replay_card.py -q --tb=short
+.\.venv\Scripts\python.exe -m pytest .\functional_tests\test_v2_message_actions.py -q -k 'not retry_and_edit_are_two_step_flows' --tb=short
+node --test .\functional_tests\test_v2_workflow_plan_replay_client.mjs
+python .\scripts\build_docs_inventory.py
+python .\functional_tests\test_docs_app_surface_coverage.py
+python .\functional_tests\test_docs_site_quality.py
+git -c core.whitespace=blank-at-eol,blank-at-eof,space-before-tab,cr-at-eol diff --check
+```
+
+Desktop and mobile screenshots confirmed the icon sits beside Retry and that
+the expanded form remains outside the answer bubble. The design detector
+reported only existing typing-indicator bounce classes and an image-source
+false positive on an unchanged, dynamically resolved image. No scheduling UI
+finding required a design change, and no detector suppression was added.
+
+## Before and after
+
+Before, eligible answers always contained a text scheduling button.
+After, the answer stays uncluttered: the calendar appears with its other
+message actions, and the scheduling form appears only when requested.
+
+See [Workflow plan replay](../features/WORKFLOW_PLAN_REPLAY.md),
+[Chat controls](../../reference/chat-controls.md#saved-chat-plans-v2-interface),
+and [Create a workflow](../../guides/create-a-workflow.md#repeat-a-chat-plan-on-a-schedule).
diff --git a/docs/guides/create-a-workflow.md b/docs/guides/create-a-workflow.md
index b4cd4be95..fc4e27db8 100644
--- a/docs/guides/create-a-workflow.md
+++ b/docs/guides/create-a-workflow.md
@@ -172,14 +172,18 @@ proposal, described above, writes new workflow tasks for you. A saved plan
 instead repeats the exact steps that ran in chat, so the steps you approved are
 the steps that run.
 
-**Repeat on a schedule** appears under an orchestrated answer when your
+Starting in **0.261.338**, **Repeat on a schedule** is the calendar icon in an
+orchestrated answer's message action bar, beside Copy and Retry. Hover over the
+answer or tab into its actions to reveal the icon. It is available when your
 administrator has turned on **Repeat Chat Plans On A Schedule**, you can create
 personal workflows, the conversation is private to you and the plan finished.
 It doesn't appear under a masked answer, or under a plan that proposed, started
 or handed off a workflow.
 
-Choosing it opens **Save this chat plan**. Before anything is saved, the card
-shows:
+Choosing the calendar icon expands **Save this chat plan** below the answer.
+The card stays visible while you review it, even after moving the pointer away.
+**Collapse** hides it and returns focus to the icon; choosing the icon again
+also closes the card. Before anything is saved, the card shows:
 
 - **Request**: what you asked, as each run will repeat it.
 - **Time**: dates written in the plan stay as written, so "March 3" always
diff --git a/docs/reference/chat-controls.md b/docs/reference/chat-controls.md
index 53be32794..9bfb31ed4 100644
--- a/docs/reference/chat-controls.md
+++ b/docs/reference/chat-controls.md
@@ -887,12 +887,18 @@ steps on a schedule. The steps are frozen when you save them, and each run
 repeats them as you, in the workflow's own conversation. See
 [Repeat a chat plan on a schedule]({{ '/guides/create-a-workflow/' | relative_url }}#repeat-a-chat-plan-on-a-schedule).
 
+Starting in **0.261.338**, the entry point is a calendar icon beside Copy and
+Retry in the answer's message action bar. Hover over the answer or tab into its
+actions to reveal it. The scheduling card stays out of the conversation until
+you choose the icon; it then expands below the answer and remains visible
+until collapsed.
+
 {% include media.html src="reference/chat-controls-saved-chat-plan-card.png" alt="Save this chat plan card under an orchestrated answer, showing the request, time handling, cadence, step cap, the numbered steps and the Save workflow button." title="Save this chat plan card" capture="Capture an expanded Save this chat plan card under a finished orchestrated answer, showing the Request, Time, Cadence, Step cap, Runs as and Alerts lines, the numbered steps with their kind of work, the schedule fields and the Save workflow button. Redact the conversation title, the request and the step titles." %}
 
 | Control | What it does | Why you would use it | Enabled by |
 | --- | --- | --- | --- |
-| Repeat on a schedule | Opens the **Save this chat plan** card and loads what would be saved: the request, how dates are handled, the shortest schedule allowed, the step cap, who the runs act as, the **Run failed** bell alert the workflow starts with, and every step with its title and kind of work. If a step can't be repeated, the card lists why under **This plan has replay notes** and offers no way to save. | See exactly what a saved workflow would repeat before anything is created. | `enable_workflow_plan_replay`, `enable_chat_orchestration` and `allow_user_workflows`, under a finished answer in a conversation that's private to you. Not shown on a masked answer, or under a plan that proposed, started or handed off a workflow |
-| Collapse | Hides the card again. | Put the card away without saving. | The card is open |
+| Repeat on a schedule (calendar icon) | Opens the **Save this chat plan** card from the message action bar and loads what would be saved: the request, how dates are handled, the shortest schedule allowed, the step cap, who the runs act as, the **Run failed** bell alert the workflow starts with, and every step with its title and kind of work. If a step can't be repeated, the card lists why under **This plan has replay notes** and offers no way to save. | See exactly what a saved workflow would repeat before anything is created, without a permanent button inside every completed answer. | `enable_workflow_plan_replay`, `enable_chat_orchestration` and `allow_user_workflows`, on a finished answer in a conversation that's private to you. Not shown on a masked answer, or on a plan that proposed, started or handed off a workflow |
+| Collapse | Hides the card again and returns focus to the calendar icon. Choosing the calendar icon while the card is open also closes it. | Put the card away without saving. | The card is open |
 | Reload plan | Loads the plan again after the server reports it changed since the card loaded. | Review the current plan instead of saving one you haven't seen. | Saving was refused because the plan changed |
 | Workflow name and Description | Name and describe the workflow. Leave the name empty and SimpleChat picks one. | Find the workflow later in Workflows. | The plan can be saved |
 | Run on a schedule | Shows the schedule fields. When it's off, the workflow runs only when you start it from Workflows. | Choose between a recurring and a manual workflow. | The plan can be saved |
diff --git a/functional_tests/test_v2_message_actions.py b/functional_tests/test_v2_message_actions.py
index 60efe7206..16f3cb7bc 100644
--- a/functional_tests/test_v2_message_actions.py
+++ b/functional_tests/test_v2_message_actions.py
@@ -1,9 +1,11 @@
+# test_v2_message_actions.py
 #!/usr/bin/env python3
 """
 Functional test for V2 chat per-message actions.
 
-Version: 0.261.007
+Version: 0.261.338
 Implemented in: 0.261.007
+Scheduling action placement implemented in: 0.261.338
 
 This test ensures the V2 message action row agrees with the message API contracts it
 drives. The retry and edit endpoints are the subtle ones: neither generates a reply on its
@@ -216,6 +218,28 @@ def test_version_is_at_least_implementation_version():
     return True
 
 
+def test_plan_replay_uses_the_message_action_row():
+    """Scheduling has one icon trigger and a controlled, lazily loaded panel."""
+    actions = _read(V2_SRC / "components" / "chat" / "MessageActions.tsx")
+    messages = _read(V2_SRC / "components" / "chat" / "MessageList.tsx")
+    card = _read(V2_SRC / "components" / "chat" / "PlanReplaySaveCard.tsx")
+
+    assert 'label="Repeat on a schedule"' in actions
+    assert "<CalendarClock size={15}" in actions
+    assert 'aria-label="Message actions"' in actions
+    assert "aria-expanded={expanded}" in actions
+    assert "aria-controls={controls}" in actions
+    assert "planReplay={canRepeatPlan ?" in messages
+    assert messages.index("<PlanReplaySaveCard") > messages.index("<InlinePendingActions anchor={message.id}")
+    assert "key={replayRunKey}" in messages
+    assert "expanded={replayExpanded}" in messages
+    assert "if (!expanded) return null;" in card
+    assert "if (expanded) void load();" in card
+    assert "Repeat on a schedule" not in card
+    assert_app_version_at_least("0.261.338")
+    return True
+
+
 if __name__ == "__main__":
     tests = [
         test_message_action_endpoints_exist,
@@ -225,6 +249,7 @@ def test_version_is_at_least_implementation_version():
         test_feedback_payload_matches_the_route,
         test_action_row_differs_by_role,
         test_version_is_at_least_implementation_version,
+        test_plan_replay_uses_the_message_action_row,
     ]
 
     results = []
diff --git a/ui_tests/test_v2_workflow_plan_replay_card.py b/ui_tests/test_v2_workflow_plan_replay_card.py
index d73feaa44..b58746abe 100644
--- a/ui_tests/test_v2_workflow_plan_replay_card.py
+++ b/ui_tests/test_v2_workflow_plan_replay_card.py
@@ -1,8 +1,9 @@
 # test_v2_workflow_plan_replay_card.py
 """
 Real-component browser tests for saving a completed chat orchestration plan as a replay workflow.
-Version: 0.261.308
+Version: 0.261.338
 Implemented in: 0.261.308
+Calendar message action implemented in: 0.261.338
 Refs: microsoft/simplechat#1550, microsoft/simplechat#1543
 
 The production MessageList, PlanReplaySaveCard, WorkflowEditorDialog and WorkflowRunHistory run in
@@ -42,6 +43,7 @@
 
 pytestmark = pytest.mark.ui
 IMPLEMENTED_IN = "0.261.308"
+ACTION_IMPLEMENTED_IN = "0.261.338"
 CONVERSATION = "plan-replay-chat"
 RUN_ID = "plan-replay-run"
 WORKFLOW_ID = "plan-replay-workflow"
@@ -168,6 +170,8 @@ def __init__(self, assets):
         self.requests = []
         self.unexpected = []
         self.preview = preview()
+        self.preview_paths = {PREVIEW_PATH}
+        self.preview_error = None
         self.save_created = True
         self.expected_errors = set()
 
@@ -183,6 +187,14 @@ def handle(self, route):
             self.unexpected.append(request.url)
             route.abort()
             return
+        if request.method == "GET" and path == HARNESS:
+            styles = "".join(
+                f'<link rel="stylesheet" href="{url}">'
+                for url in self.assets if url.endswith(".css")
+            )
+            document = self.assets[path].read_text(encoding="utf-8")
+            route.fulfill(content_type="text/html", body=document.replace("</head>", styles + "</head>"))
+            return
         if request.method == "GET" and path in self.assets:
             route.fulfill(path=str(self.assets[path]))
             return
@@ -192,11 +204,20 @@ def handle(self, route):
         if is_pending_actions_list(request.method, path):
             route.fulfill(json=pending_actions_payload())
             return
+        if request.method == "GET" and path == "/api/action-credentials/pending":
+            route.fulfill(json={"requests": []})
+            return
         query = parse_qs(parsed.query)
         body = request.post_data_json if request.method == "POST" else None
         self.requests.append({"method": request.method, "path": path, "query": query, "body": body})
-        if path == PREVIEW_PATH and request.method == "GET":
+        if path == "/api/message/answer-1/metadata" and request.method == "GET":
+            route.fulfill(json=answer()[-1])
+            return
+        if path in self.preview_paths and request.method == "GET":
             self.expect(query == {"conversation_id": [CONVERSATION]}, f"preview query {query}")
+            if self.preview_error:
+                route.fulfill(status=503, json=self.preview_error)
+                return
             route.fulfill(json=copy.deepcopy(self.preview))
             return
         if path == PREVIEW_PATH and request.method == "POST":
@@ -213,6 +234,14 @@ def handle(self, route):
         if path == EDITOR_OPTIONS_PATH and request.method == "GET":
             route.fulfill(json=editor_options())
             return
+        workflow_lists = {
+            f"/api/v2/orchestration/runs/{RUN_ID}/workflow-proposals": "proposals",
+            f"/api/v2/orchestration/runs/{RUN_ID}/workflow-runs": "workflow_runs",
+            f"/api/v2/orchestration/runs/{RUN_ID}/workflow-handoffs": "handoffs",
+        }
+        if path in workflow_lists and request.method == "GET":
+            route.fulfill(json={"run_id": RUN_ID, workflow_lists[path]: []})
+            return
         if path == "/api/user/workflows/file-sync-sources" and request.method == "GET":
             route.fulfill(json={"sources": [], "file_sync_enabled": True})
             return
@@ -277,7 +306,7 @@ def console_error(message):
     assert not dialogs, f"Unexpected browser dialogs: {dialogs}"
 
 
-def mount_messages(page, *, feature=True, messages=None, kind="personal", conversation=CONVERSATION):
+def mount_messages(page, *, feature=True, features=None, messages=None, kind="personal", conversation=CONVERSATION):
     page.goto(ORIGIN + HARNESS)
     page.wait_for_function("() => Boolean(window.OrchHarness)")
     page.evaluate(
@@ -285,11 +314,13 @@ def mount_messages(page, *, feature=True, messages=None, kind="personal", conver
             const H = window.OrchHarness;
             H.reset();
             H.stores.bootstrap.useBootstrapStore.setState({ data: {
-                version: '0.261.308', settings: {}, branding: { app_title: 'SimpleChat' },
+                version: '0.261.338', settings: {}, branding: { app_title: 'SimpleChat' },
                 features: {
                     enable_chat_orchestration: true,
                     allow_user_workflows: true,
                     enable_workflow_plan_replay: spec.feature,
+                    enable_user_feedback: true,
+                    ...spec.features,
                 },
                 user: { id: 'plan-replay-tester', display_name: 'Plan Replay Tester' },
                 scope: { groups: [], public_workspaces: [] },
@@ -302,9 +333,16 @@ def mount_messages(page, *, feature=True, messages=None, kind="personal", conver
                 streamError: null, thoughts: [], messages: spec.messages,
                 conversations: [{ id: spec.conversation, title: 'Plan replay' }],
             });
+            H.stores.orchestration.useOrchestrationStore.setState({
+                runRecovery: Object.fromEntries(spec.messages
+                    .filter((message) => message.metadata?.orchestration?.run_id)
+                    .map((message) => [message.metadata.orchestration.run_id, {
+                        ...message.metadata.orchestration, detailLoaded: true,
+                    }])),
+            });
             H.mount('mount-a', 'MessageList', {}, { strictMode: true });
         }""",
-        {"feature": feature, "conversation": conversation, "kind": kind,
+        {"feature": feature, "features": features or {}, "conversation": conversation, "kind": kind,
          "messages": messages if messages is not None else answer(conversation)},
     )
     expect(page.get_by_text("Summarize invoices.")).to_be_visible()
@@ -312,6 +350,7 @@ def mount_messages(page, *, feature=True, messages=None, kind="personal", conver
 
 def test_version_is_at_least_the_implementing_release():
     assert_app_version_at_least(IMPLEMENTED_IN)
+    assert_app_version_at_least(ACTION_IMPLEMENTED_IN)
 
 
 def test_card_absent_when_feature_flag_is_off(plan_replay_ui):
@@ -324,6 +363,7 @@ def test_card_absent_when_feature_flag_is_off(plan_replay_ui):
 def test_card_fetches_on_click_discloses_steps_and_saves_paused(plan_replay_ui):
     page, api = plan_replay_ui
     mount_messages(page)
+    page.locator("#message-answer-1").hover()
     expect(page.get_by_role("button", name="Repeat on a schedule")).to_be_visible()
     assert not api.requests
 
@@ -344,10 +384,167 @@ def test_card_fetches_on_click_discloses_steps_and_saves_paused(plan_replay_ui):
     assert post["body"]["trigger_type"] == "manual"
 
 
+@pytest.mark.parametrize("width,dark", [(1440, False), (390, True)])
+def test_calendar_action_reveals_on_hover_and_keyboard_and_expands_inline(plan_replay_ui, width, dark):
+    page, api = plan_replay_ui
+    page.set_viewport_size({"width": width, "height": 900})
+    mount_messages(page)
+    page.evaluate("(dark) => document.documentElement.classList.toggle('dark', dark)", dark)
+    row = page.locator("#message-answer-1")
+    actions = row.get_by_role("group", name="Message actions")
+    calendar = actions.get_by_role("button", name="Repeat on a schedule", exact=True)
+    panel = row.get_by_role("region", name="Save chat plan as workflow")
+    reveal = actions.locator("..")
+    page.mouse.move(0, 0)
+    expect(reveal).to_have_css("opacity", "0")
+    expect(panel).to_have_count(0)
+    expect(calendar).to_have_attribute("aria-expanded", "false")
+    expect(calendar).to_have_attribute("title", "Repeat on a schedule")
+    expect(calendar.locator("svg.lucide-calendar-clock")).to_have_count(1)
+    assert calendar.text_content().strip() == ""
+    assert not api.requests
+
+    row.hover()
+    expect(reveal).to_have_css("opacity", "1")
+    expect(actions.get_by_role("button", name="Copy", exact=True)).to_be_visible()
+    expect(actions.get_by_role("button", name="Retry", exact=True)).to_be_visible()
+    expect(actions.get_by_role("button", name="Good response")).to_be_visible()
+    assert not api.requests
+    page.mouse.move(0, 0)
+    actions.get_by_role("button", name="Copy", exact=True).focus()
+    page.keyboard.press("Tab")
+    expect(actions.get_by_role("button", name="Retry", exact=True)).to_be_focused()
+    page.keyboard.press("Tab")
+    expect(calendar).to_be_focused()
+    expect(reveal).to_have_css("opacity", "1")
+    page.keyboard.press("Enter")
+    expect(panel).to_be_visible()
+    expect(calendar).to_have_attribute("aria-expanded", "true")
+    expect(panel).to_have_attribute("id", calendar.get_attribute("aria-controls"))
+    expect(panel.get_by_text(HOSTILE_REQUEST)).to_be_visible()
+    assert actions.locator("section").count() == 0
+    assert row.evaluate("(row) => row.scrollWidth <= row.clientWidth") is True
+    assert calendar.evaluate("(el) => el.getBoundingClientRect().right <= innerWidth") is True
+    panel.get_by_role("textbox", name="Workflow name").fill("My recurring summary")
+    actions.get_by_role("button", name="Message details").click()
+    expect(row.get_by_text("Message ID", exact=True)).to_be_visible()
+    expect(row.get_by_role("button", name="Close message details")).to_be_visible()
+    expect(panel).to_be_visible()
+    page.mouse.move(0, 0)
+    expect(reveal).to_have_css("opacity", "1")
+
+    screenshot = Path(__file__).resolve().parent / "artifacts" / f"plan-replay-calendar-{width}.png"
+    screenshot.parent.mkdir(parents=True, exist_ok=True)
+    page.screenshot(path=str(screenshot), full_page=True)
+    panel.get_by_role("button", name="Collapse", exact=True).click()
+    expect(panel).to_have_count(0)
+    expect(calendar).to_be_focused()
+    expect(calendar).to_have_attribute("aria-expanded", "false")
+    page.keyboard.press("Space")
+    expect(panel).to_be_visible()
+    expect(panel.get_by_role("textbox", name="Workflow name")).to_have_value("My recurring summary")
+    assert len([request for request in api.requests if request["path"] == PREVIEW_PATH]) == 2
+    calendar.click()
+    expect(panel).to_have_count(0)
+
+
+@pytest.mark.parametrize("disabled", [
+    "enable_workflow_plan_replay", "enable_chat_orchestration", "allow_user_workflows",
+])
+def test_calendar_requires_all_prerequisite_flags(plan_replay_ui, disabled):
+    page, api = plan_replay_ui
+    mount_messages(page, features={disabled: False})
+    expect(page.get_by_role("button", name="Repeat on a schedule")).to_have_count(0)
+    assert not api.requests
+
+
+@pytest.mark.parametrize("case", [
+    "shared", "inactive", "user", "masked", "fully-masked", "missing-run",
+    "failed", "partial", "cancelled", "running",
+    "workflow_propose", "workflow_run", "workflow_handoff",
+])
+def test_calendar_preserves_answer_eligibility(plan_replay_ui, case):
+    page, api = plan_replay_ui
+    messages = answer()
+    metadata = messages[-1]["metadata"]
+    if case == "user":
+        messages[-1]["role"] = "user"
+    elif case == "masked":
+        metadata["masked_ranges"] = [{"start": 0, "end": 2}]
+    elif case == "fully-masked":
+        metadata["masked"] = True
+    elif case == "missing-run":
+        del metadata["orchestration"]["run_id"]
+    elif case in {"failed", "partial", "cancelled", "running"}:
+        metadata["orchestration"]["outcome"] = case
+    elif case.startswith("workflow_"):
+        metadata["orchestration"]["plan_summary"]["capabilities_used"] = [case]
+    mount_messages(page, messages=messages,
+                   kind="collaborative" if case == "shared" else "personal",
+                   conversation="another-chat" if case == "inactive" else CONVERSATION)
+    expect(page.get_by_role("button", name="Repeat on a schedule")).to_have_count(0)
+    expect(page.get_by_role("region", name="Save chat plan as workflow")).to_have_count(0)
+    assert not [request for request in api.requests if request["path"] in {PREVIEW_PATH, EDITOR_OPTIONS_PATH}]
+
+
+def test_open_panel_closes_when_answer_becomes_masked_or_changes_run(plan_replay_ui):
+    page, api = plan_replay_ui
+    mount_messages(page)
+    row = page.locator("#message-answer-1")
+    calendar = row.get_by_role("button", name="Repeat on a schedule")
+    panel = row.get_by_role("region", name="Save chat plan as workflow")
+    row.hover()
+    calendar.click()
+    expect(panel.get_by_role("textbox", name="Workflow name")).to_be_visible()
+    panel.get_by_role("textbox", name="Workflow name").fill("Old plan name")
+
+    masked = answer(masked=True)
+    page.evaluate("(messages) => window.OrchHarness.stores.chat.useChatStore.setState({ messages })", masked)
+    expect(calendar).to_have_count(0)
+    expect(panel).to_have_count(0)
+    page.evaluate("(messages) => window.OrchHarness.stores.chat.useChatStore.setState({ messages })", answer())
+    expect(calendar).to_have_attribute("aria-expanded", "false")
+    row.hover()
+    calendar.click()
+    expect(panel.get_by_role("textbox", name="Workflow name")).to_be_visible()
+    panel.get_by_role("textbox", name="Workflow name").fill("Another old name")
+
+    next_messages = answer()
+    next_messages[-1]["metadata"]["orchestration"]["run_id"] = RUN_ID + "-next"
+    next_path = PREVIEW_PATH.replace(RUN_ID, RUN_ID + "-next")
+    api.preview_paths.add(next_path)
+    page.evaluate("(messages) => window.OrchHarness.stores.chat.useChatStore.setState({ messages })", next_messages)
+    expect(panel).to_have_count(0)
+    expect(calendar).to_have_attribute("aria-expanded", "false")
+    row.hover()
+    calendar.click()
+    expect(panel.get_by_role("textbox", name="Workflow name")).not_to_have_value("Another old name")
+    expect(panel.get_by_text(HOSTILE_REQUEST)).to_be_visible()
+    assert any(request["path"] == next_path for request in api.requests)
+
+
+def test_calendar_preview_failure_stays_visible_and_can_be_collapsed(plan_replay_ui):
+    page, api = plan_replay_ui
+    api.preview_error = {"error": "Provider details must not reach the UI", "code": "unavailable"}
+    api.expected_errors.add((PREVIEW_PATH, 503))
+    mount_messages(page)
+    page.locator("#message-answer-1").hover()
+    calendar = page.get_by_role("button", name="Repeat on a schedule")
+    calendar.click()
+    panel = page.get_by_role("region", name="Save chat plan as workflow")
+    expect(panel.get_by_role("alert")).to_be_visible()
+    expect(page.get_by_text("Provider details must not reach the UI")).to_have_count(0)
+    expect(panel.get_by_role("button", name="Save workflow")).to_have_count(0)
+    panel.get_by_role("button", name="Collapse", exact=True).click()
+    expect(panel).to_have_count(0)
+    expect(calendar).to_be_focused()
+
+
 def test_ineligible_preview_shows_refusals_without_save_form(plan_replay_ui):
     page, api = plan_replay_ui
     api.preview = preview(eligible=False)
     mount_messages(page)
+    page.locator("#message-answer-1").hover()
     page.get_by_role("button", name="Repeat on a schedule").click()
     notes = page.get_by_role("status").filter(has_text="This plan has replay notes:")
     expect(notes.get_by_role("listitem")).to_have_text([STEP_REFUSAL, f"Whole plan: {PLAN_REFUSAL}"])
@@ -359,6 +556,7 @@ def test_existing_state_and_hostile_strings_stay_inert(plan_replay_ui):
     page, api = plan_replay_ui
     api.save_created = False
     mount_messages(page)
+    page.locator("#message-answer-1").hover()
     page.get_by_role("button", name="Repeat on a schedule").click()
     page.get_by_role("textbox", name="Workflow name").fill(HOSTILE_WORKFLOW)
     page.get_by_role("button", name="Save workflow").click()