feat(daemon): enhance conversation session mode handling

- Added a new `mode` flag to CLI commands for project and conversation creation, allowing users to specify 'design' or 'chat' modes.
- Implemented `normalizeChatSessionModeFlag` function to validate and normalize session mode inputs.
- Updated project routes to handle session mode during conversation creation and updates.
- Enhanced web components to support session mode changes, including new props and handlers for managing session modes in conversations.
- Adjusted UI elements to reflect the current session mode, improving user experience and interaction flexibility.

This update provides a more robust framework for managing conversation modes, catering to diverse user needs and enhancing overall functionality.

apps/daemon/src/cli.ts

@@ -152,7 +152,7 @@ const PROJECT_STRING_FLAGS = new Set([
   'daemon-url', 'name', 'skill', 'design-system', 'plugin', 'metadata-json',
   'pending-prompt', 'project', 'conversation', 'message', 'path', 'as',
   'agent', 'model', 'snapshot-id', 'inputs', 'grant-caps', 'editor',
-  'title', 'against', 'seed-from',
+  'title', 'against', 'seed-from', 'mode',
 ]);
 const PROJECT_BOOLEAN_FLAGS = new Set(['help', 'h', 'json', 'follow']);
 // `od automation …` mirrors the Automations tab. Same surface, same
@@ -4319,6 +4319,14 @@ async function projectDaemonUrl(flags) {
   return cliDaemonUrl(flags);
 }
 
+function normalizeChatSessionModeFlag(value) {
+  if (value == null) return undefined;
+  const mode = String(value).trim().toLowerCase();
+  if (mode === 'design' || mode === 'chat') return mode;
+  console.error('--mode must be one of: design, chat');
+  process.exit(2);
+}
+
 function safeReadJsonFile(p) {
   try {
     const fs = (require ? require('node:fs') : null);
@@ -4335,6 +4343,7 @@ async function runProject(args) {
     console.log(`Usage:
   od project create [--name "<title>"] [--skill <id>] [--design-system <id>]
                     [--plugin <id>] [--inputs <json>] [--metadata-json <path|->]
+                    [--mode design|chat]
   od project import <baseDir> [--name "<title>"]
   od project list                         List projects.
   od project info <id>                    Print one project.
@@ -4406,6 +4415,8 @@ Common options:
         skillId:        flags.skill ?? null,
         designSystemId: flags['design-system'] ?? null,
       };
+      const conversationMode = normalizeChatSessionModeFlag(flags.mode);
+      if (conversationMode) body.conversationMode = conversationMode;
       if (flags['pending-prompt']) body.pendingPrompt = flags['pending-prompt'];
       if (flags['metadata-json']) {
         const mj = safeReadJsonFile(flags['metadata-json']);
@@ -5103,7 +5114,7 @@ function renderDiffLineContent(value) {
 async function runConversation(args) {
   if (args.length === 0 || args[0] === 'help' || args.includes('--help') || args.includes('-h')) {
     console.log(`Usage:
-  od conversation new  <projectId> [--title "<title>"] [--seed-from <cid>]
+  od conversation new  <projectId> [--title "<title>"] [--seed-from <cid>] [--mode design|chat]
                                            Create a conversation in a project.
                                            --seed-from copies another
                                            conversation's messages in (Side Chat).
@@ -5128,6 +5139,8 @@ Common options:
       }
       const body = {};
       if (typeof flags.title === 'string') body.title = flags.title;
+      const sessionMode = normalizeChatSessionModeFlag(flags.mode);
+      if (sessionMode) body.sessionMode = sessionMode;
       if (typeof flags['seed-from'] === 'string' && flags['seed-from']) {
         body.seedFromConversationId = flags['seed-from'];
       }
@@ -5139,7 +5152,8 @@ Common options:
       if (!resp.ok) return structuredHttpFailure(resp, 'project-not-found');
       const data = await resp.json();
       if (flags.json) return process.stdout.write(JSON.stringify(data, null, 2) + '\n');
-      console.log(`[conversation] created ${data.conversation?.id ?? '-'}`);
+      const conv = data.conversation;
+      console.log(`[conversation] created ${conv?.id ?? '-'} (mode ${conv?.sessionMode ?? sessionMode ?? 'design'})`);
       return;
     }
     case 'list': {
@@ -5185,7 +5199,7 @@ Common options:
 async function runChat(args) {
   if (args.length === 0 || args[0] === 'help' || args.includes('--help') || args.includes('-h')) {
     console.log(`Usage:
-  od chat new --project <id> [--seed-from <cid>] [--title "<title>"] [--json]
+  od chat new --project <id> [--seed-from <cid>] [--title "<title>"] [--mode design|chat] [--json]
                                            Create a Side Chat — a new conversation
                                            that copies in another conversation's
                                            context (--seed-from) so the new chat
@@ -5213,6 +5227,8 @@ Common options:
       }
       const body = {};
       if (typeof flags.title === 'string') body.title = flags.title;
+      const sessionMode = normalizeChatSessionModeFlag(flags.mode);
+      if (sessionMode) body.sessionMode = sessionMode;
       if (typeof flags['seed-from'] === 'string' && flags['seed-from']) {
         body.seedFromConversationId = flags['seed-from'];
       }
@@ -5228,7 +5244,7 @@ Common options:
       const seeded = body.seedFromConversationId
         ? ` (seeded from ${body.seedFromConversationId})`
         : '';
-      console.log(`[chat] created ${conv?.id ?? '-'}${conv?.title ? ` "${conv.title}"` : ''}${seeded}`);
+      console.log(`[chat] created ${conv?.id ?? '-'}${conv?.title ? ` "${conv.title}"` : ''}${seeded} (mode ${conv?.sessionMode ?? sessionMode ?? 'design'})`);
       return;
     }
     default:

apps/daemon/src/project-routes.ts

@@ -323,13 +323,14 @@ export function registerProjectRoutes(app: Express, ctx: RegisterProjectRoutesDe
       });
       // Seed a default conversation so the UI always has somewhere to write.
       const cid = randomId();
+      const initialSessionMode = normalizeChatSessionMode(
+        req.body?.conversationMode ?? req.body?.sessionMode,
+      );
       insertConversation(db, {
         id: cid,
         projectId: id,
         title: null,
-        sessionMode: normalizeChatSessionMode(
-          req.body?.conversationMode ?? req.body?.sessionMode,
-        ),
+        sessionMode: initialSessionMode,
         createdAt: now,
         updatedAt: now,
       });
@@ -341,7 +342,7 @@ export function registerProjectRoutes(app: Express, ctx: RegisterProjectRoutesDe
             && req.body.appliedPluginSnapshotId.trim().length > 0;
       let resolveBody =
         explicitPlugin ? (req.body as Record<string, unknown>) : null;
-      if (!resolveBody) {
+      if (!resolveBody && initialSessionMode === 'design') {
         const fallbackPluginId = defaultScenarioPluginIdForProjectMetadata(projectMetadata);
         if (fallbackPluginId && getInstalledPlugin(db, fallbackPluginId)) {
           resolveBody = { ...(req.body || {}), pluginId: fallbackPluginId };

apps/web/src/components/FileWorkspace.tsx

@@ -6,6 +6,7 @@ import {
   type DragEvent as ReactDragEvent,
 } from 'react';
 import type { TrackingProjectKind } from '@open-design/contracts/analytics';
+import type { ChatSessionMode } from '@open-design/contracts';
 import { useAnalytics } from '../analytics/provider';
 import {
   trackFileManagerClick,
@@ -136,6 +137,7 @@ interface Props {
   onSelectConversation?: (id: string) => void;
   onDeleteConversation?: (id: string) => void;
   onRenameConversation?: (id: string, title: string) => void;
+  onConversationSessionModeChange?: (id: string, mode: ChatSessionMode) => void;
   onNewConversation?: () => void;
   /** Create a context-seeded conversation and resolve its id (backs the launcher). */
   onCreateSideChat?: (seedFromConversationId: string | null) => Promise<string | null>;
@@ -265,6 +267,7 @@ export function FileWorkspace({
   onSelectConversation,
   onDeleteConversation,
   onRenameConversation,
+  onConversationSessionModeChange,
   onNewConversation,
   onCreateSideChat,
 }: Props) {
@@ -1246,6 +1249,7 @@ export function FileWorkspace({
             onSelectConversation={onSelectConversation ?? (() => {})}
             onDeleteConversation={onDeleteConversation ?? (() => {})}
             onRenameConversation={onRenameConversation}
+            onSessionModeChange={onConversationSessionModeChange}
             onNewConversation={onNewConversation}
             onRequestOpenFile={openFile}
           />

apps/web/src/components/ProjectView.tsx

@@ -107,7 +107,7 @@ import {
   type SaveMessageOptions,
   waitGeneratedPluginShareTask,
 } from '../state/projects';
-import type { AppliedPluginSnapshot } from '@open-design/contracts';
+import type { AppliedPluginSnapshot, ChatSessionMode } from '@open-design/contracts';
 import type {
   AgentEvent,
   AgentInfo,
@@ -115,7 +115,6 @@ import type {
   Artifact,
   ChatAttachment,
   ChatCommentAttachment,
-  ChatSessionMode,
   ChatMessage,
   ChatMessageFeedbackChange,
   Conversation,
@@ -1434,7 +1433,9 @@ export function ProjectView({
     return project.id;
   }, [project.id]);
 
-  const composedSystemPrompt = useCallback(async (): Promise<string> => {
+  const composedSystemPrompt = useCallback(async (
+    sessionModeOverride: ChatSessionMode = activeSessionMode,
+  ): Promise<string> => {
     let skillBody: string | undefined;
     let skillName: string | undefined;
     let skillMode: SkillSummary['mode'] | undefined;
@@ -1537,6 +1538,7 @@ export function ProjectView({
       audioVoiceOptions,
       audioVoiceOptionsError: audioVoiceOptionsLookupError,
       streamFormat: config.mode === 'api' ? 'plain' : undefined,
+      sessionMode: sessionModeOverride,
       locale,
       userInstructions: config.customInstructions,
       projectInstructions: project.customInstructions,
@@ -1551,6 +1553,7 @@ export function ProjectView({
     designSystems,
     config.mode,
     config.customInstructions,
+    activeSessionMode,
     locale,
   ]);
 
@@ -2267,6 +2270,7 @@ export function ProjectView({
     ) => {
       if (!activeConversationId) return;
       if (messagesConversationIdRef.current !== activeConversationId) return;
+      const runSessionMode = meta?.sessionMode ?? activeSessionMode;
       const retryTarget = meta?.retryOfAssistantId
         ? resolveRetryTarget(messages, meta.retryOfAssistantId)
         : null;
@@ -2285,7 +2289,7 @@ export function ProjectView({
           prompt,
           attachments,
           commentAttachments,
-          ...(meta === undefined ? {} : { meta }),
+          meta: { ...(meta ?? {}), sessionMode: runSessionMode },
           createdAt: Date.now(),
         });
         if (commentAttachments.length > 0) {
@@ -2770,6 +2774,7 @@ export function ProjectView({
           designSystemId: project.designSystemId ?? null,
           attachments: runAttachments.map((a) => a.path),
           commentAttachments: runCommentAttachments,
+          sessionMode: runSessionMode,
           research: meta?.research,
           mediaExecution: mediaExecutionPolicyForProjectMetadata(project.metadata),
           model: choice?.model ?? null,
@@ -2863,7 +2868,7 @@ export function ProjectView({
             // on the next event.
           }
         }
-        const systemPrompt = await composedSystemPrompt();
+        const systemPrompt = await composedSystemPrompt(runSessionMode);
         const apiHistory = await historyWithApiAttachmentContext(
           historyWithCommentAttachmentContext(nextHistory, userMsg.id),
           userMsg.id,
@@ -2911,6 +2916,7 @@ export function ProjectView({
     [
       attachedComments,
       activeConversationId,
+      activeSessionMode,
       currentConversationBusy,
       enqueueChatSend,
       messages,
@@ -3638,6 +3644,33 @@ export function ProjectView({
     [project.id],
   );
 
+  const handleConversationSessionModeChange = useCallback(
+    async (id: string, sessionMode: ChatSessionMode) => {
+      setConversations((curr) =>
+        curr.map((conversation) =>
+          conversation.id === id ? { ...conversation, sessionMode } : conversation,
+        ),
+      );
+      const updated = await patchConversation(project.id, id, { sessionMode });
+      if (updated) {
+        setConversations((curr) =>
+          curr.map((conversation) =>
+            conversation.id === id ? { ...conversation, ...updated } : conversation,
+          ),
+        );
+      }
+    },
+    [project.id],
+  );
+
+  const handleActiveConversationSessionModeChange = useCallback(
+    (sessionMode: ChatSessionMode) => {
+      if (!activeConversationId) return;
+      void handleConversationSessionModeChange(activeConversationId, sessionMode);
+    },
+    [activeConversationId, handleConversationSessionModeChange],
+  );
+
   // Side Chat launcher: create a NEW conversation seeded with the current
   // chat's context (the daemon copies the source conversation's messages) and
   // resolve its id. The new conversation is a normal conversation, so it shows
@@ -4480,6 +4513,8 @@ export function ProjectView({
               queuedItems={currentConversationQueuedItems}
               error={conversationLoadError ?? error ?? audioVoiceOptionsError}
               projectId={project.id}
+              sessionMode={activeSessionMode}
+              onSessionModeChange={handleActiveConversationSessionModeChange}
               projectKindForTracking={projectKindToTracking(project.metadata?.kind)}
               projectFiles={projectFiles}
               hasActiveDesignSystem={!!project.designSystemId}
@@ -4615,6 +4650,7 @@ export function ProjectView({
           onSelectConversation={handleSelectConversation}
           onDeleteConversation={handleDeleteConversation}
           onRenameConversation={handleRenameConversation}
+          onConversationSessionModeChange={handleConversationSessionModeChange}
           onNewConversation={handleNewConversation}
           onCreateSideChat={handleCreateSideChat}
         />

apps/web/src/components/workspace/SideChatTab.tsx

@@ -7,6 +7,7 @@ import type {
   Conversation,
   ProjectFile,
 } from '../../types';
+import type { ChatSessionMode } from '@open-design/contracts';
 import { useConversationChat } from './useConversationChat';
 import styles from './SideChatTab.module.css';
 
@@ -28,6 +29,7 @@ interface Props {
   onSelectConversation: (id: string) => void;
   onDeleteConversation: (id: string) => void;
   onRenameConversation?: (id: string, title: string) => void;
+  onSessionModeChange?: (id: string, mode: ChatSessionMode) => void;
   onNewConversation?: () => void;
   /** Forward produced-file / tool-card open requests to the workspace. */
   onRequestOpenFile?: (name: string) => void;
@@ -49,14 +51,19 @@ export function SideChatTab({
   onSelectConversation,
   onDeleteConversation,
   onRenameConversation,
+  onSessionModeChange,
   onNewConversation,
   onRequestOpenFile,
 }: Props) {
   const t = useT();
+  const sessionMode =
+    conversations.find((conversation) => conversation.id === conversationId)?.sessionMode
+    ?? 'design';
   const chat = useConversationChat(projectId, conversationId, {
     config,
     agentsById,
     locale,
+    sessionMode,
   });
 
   return (
@@ -73,6 +80,8 @@ export function SideChatTab({
           streaming={chat.streaming}
           error={chat.error}
           projectId={projectId}
+          sessionMode={sessionMode}
+          onSessionModeChange={(mode) => onSessionModeChange?.(conversationId, mode)}
           projectFiles={projectFiles}
           projectFileNames={projectFileNames}
           onEnsureProject={async () => projectId}

apps/web/src/components/workspace/useConversationChat.ts

@@ -18,6 +18,7 @@ import type {
   ChatCommentAttachment,
   ChatMessage,
 } from '../../types';
+import type { ChatSessionMode } from '@open-design/contracts';
 
 // ---------------------------------------------------------------------------
 // useConversationChat — drives a secondary ChatPane bound to a single
@@ -51,6 +52,7 @@ export interface ConversationChatContext {
   agentsById: Map<string, AgentInfo>;
   /** UI locale forwarded to the daemon so prompts compose in-language. */
   locale: string;
+  sessionMode: ChatSessionMode;
 }
 
 export interface UseConversationChatResult {
@@ -137,7 +139,12 @@ export function useConversationChat(
       commentAttachments: ChatCommentAttachment[],
       retryOfAssistantId?: string,
     ) => {
-      const { config: cfg, agentsById: agents, locale: loc } = ctxRef.current;
+      const {
+        config: cfg,
+        agentsById: agents,
+        locale: loc,
+        sessionMode,
+      } = ctxRef.current;
       if (cfg.mode !== 'daemon') {
         setError('Side Chat needs a local agent. Pick one in the top bar.');
         return;
@@ -277,6 +284,7 @@ export function useConversationChat(
         model: choice?.model ?? null,
         reasoning: choice?.reasoning ?? null,
         locale: loc,
+        sessionMode,
         onRunCreated: (runId) => {
           updateAssistant(assistantId, (prev) => ({
             ...prev,

apps/web/src/providers/daemon.ts

@@ -17,6 +17,7 @@ import type {
   ChatRunStatus,
   ChatRunStatusResponse,
   ChatRequest,
+  ChatSessionMode,
   ChatSseEvent,
   ChatSseStartPayload,
   DaemonAgentPayload,
@@ -204,6 +205,7 @@ export interface DaemonStreamOptions {
   // workspace.
   projectId?: string | null;
   conversationId?: string | null;
+  sessionMode?: ChatSessionMode;
   assistantMessageId?: string | null;
   clientRequestId?: string | null;
   skillId?: string | null;
@@ -300,6 +302,7 @@ export async function streamViaDaemon({
   handlers,
   projectId,
   conversationId,
+  sessionMode,
   assistantMessageId,
   clientRequestId,
   skillId,
@@ -333,6 +336,7 @@ export async function streamViaDaemon({
     currentPrompt: latestUserPromptFromHistory(history),
     projectId: projectId ?? null,
     conversationId: conversationId ?? null,
+    sessionMode,
     assistantMessageId: assistantMessageId ?? null,
     clientRequestId: clientRequestId ?? null,
     skillId: skillId ?? null,

apps/web/src/styles/chat.css

@@ -629,6 +629,14 @@
   overflow: hidden;
   text-overflow: ellipsis;
 }
+@media (max-width: 700px) {
+  .session-mode-toggle__option {
+    padding: 0 6px;
+  }
+  .session-mode-toggle__label {
+    display: none;
+  }
+}
 .composer-import {
   background: transparent;
   border: 1px solid var(--border);

packages/contracts/src/api/projects.ts

@@ -193,7 +193,7 @@ export interface Conversation {
   id: string;
   projectId: string;
   title: string | null;
-  sessionMode: ChatSessionMode;
+  sessionMode?: ChatSessionMode;
   createdAt: number;
   updatedAt: number;
   latestRun?: {