feat: support multiple event proposals in single AI response

- Change proposedChange to proposedChanges array in ChatMessage type
- Add unique id and individual respondedAction to each ProposedEventChange
- Implement arrow navigation UI for multiple proposals with "Event X von Y" counter
- Add updateProposalResponse() method for per-proposal confirm/reject tracking
- GPTAdapter now collects multiple tool call results into proposals array
- Add RRULE documentation to system prompt (separate events for different times)
- Fix RRULE parsing to strip RRULE: prefix if present
- Add log summarization for large args (conversationHistory, existingEvents)
- Keep proposedChanges logged in full for debugging AI issues

CLAUDE.md

@@ -205,15 +205,17 @@ src/
 - `User`: id, email, userName, passwordHash?, createdAt?, updatedAt?
 - `CalendarEvent`: id, userId, title, description?, startTime, endTime, note?, isRecurring?, recurrenceRule?
 - `ExpandedEvent`: Extends CalendarEvent with occurrenceStart, occurrenceEnd (for recurring event instances)
-- `ChatMessage`: id, conversationId, sender ('user' | 'assistant'), content, proposedChange?, respondedAction?
+- `ChatMessage`: id, conversationId, sender ('user' | 'assistant'), content, proposedChanges?
-- `ProposedEventChange`: action ('create' | 'update' | 'delete'), eventId?, event?, updates?
+- `ProposedEventChange`: id, action ('create' | 'update' | 'delete'), eventId?, event?, updates?, respondedAction?
+  - Each proposal has unique `id` (e.g., "proposal-0") for individual confirm/reject
+  - `respondedAction` tracks user response per proposal (not per message)
 - `Conversation`: id, userId, createdAt?, updatedAt? (messages loaded separately via lazy loading)
 - `CreateUserDTO`: email, userName, password (for registration)
 - `LoginDTO`: identifier (email OR userName), password
 - `CreateEventDTO`: Used for creating events AND for AI-proposed events
 - `GetMessagesOptions`: Cursor-based pagination with `before?: string` and `limit?: number`
 - `ConversationSummary`: id, lastMessage?, createdAt? (for conversation list)
-- `UpdateMessageDTO`: respondedAction? (for marking messages as confirmed/rejected)
+- `UpdateMessageDTO`: proposalId?, respondedAction? (for marking individual proposals as confirmed/rejected)
 - `RespondedAction`: 'confirm' | 'reject' (tracks user response to proposed events)
 - `Day`: "Monday" | "Tuesday" | ... | "Sunday"
 - `Month`: "January" | "February" | ... | "December"
@@ -275,6 +277,14 @@ export class GPTAdapter implements AIProvider { ... }
 
 The decorator uses a Proxy to intercept method calls lazily, preserves sync/async nature, and logs start/completion/failure with duration.
 
+**Log Summarization:**
+The `@Logged` decorator automatically summarizes large arguments to keep logs readable:
+- `conversationHistory` → `"[5 messages]"`
+- `existingEvents` → `"[3 events]"`
+- `proposedChanges` → logged in full (for debugging AI issues)
+- Long strings (>100 chars) → truncated
+- Arrays → `"[Array(n)]"`
+
 **Client Logging:**
 - `react-native-logs` with namespaced loggers (apiLogger, storeLogger)
 - ApiClient logs all requests with method, endpoint, status, duration
@@ -339,10 +349,12 @@ NODE_ENV=development        # development = pretty logs, production = JSON
   - `utils/recurrenceExpander`: expandRecurringEvents() using rrule library for RRULE parsing
   - `ChatController`: getConversations(), getConversation() with cursor-based pagination support
   - `ChatService`: getConversations(), getConversation(), processMessage() uses real AI or test responses (via USE_TEST_RESPONSES), confirmEvent()/rejectEvent() update respondedAction and persist response messages
-  - `MongoChatRepository`: Full CRUD implemented (getConversationsByUser, createConversation, getMessages with cursor pagination, createMessage, updateMessage)
+  - `MongoChatRepository`: Full CRUD implemented (getConversationsByUser, createConversation, getMessages with cursor pagination, createMessage, updateMessage, updateProposalResponse)
-  - `ChatRepository` interface: updateMessage() added for respondedAction tracking
+  - `ChatRepository` interface: updateMessage() and updateProposalResponse() for per-proposal respondedAction tracking
-  - `GPTAdapter`: Full implementation with OpenAI GPT (gpt-5-mini model), function calling for calendar operations
+  - `GPTAdapter`: Full implementation with OpenAI GPT (gpt-4o-mini model), function calling for calendar operations, collects multiple proposals per response
   - `ai/utils/`: Provider-agnostic shared utilities (systemPrompt, toolDefinitions, toolExecutor, eventFormatter)
+  - `ai/utils/systemPrompt`: Includes RRULE documentation - AI knows to create separate events when times differ by day
+  - `utils/recurrenceExpander`: Handles RRULE parsing, strips `RRULE:` prefix if present (AI may include it)
   - `logging/`: Structured logging with pino, pino-http middleware, @Logged decorator
   - All repositories and GPTAdapter decorated with @Logged for automatic method logging
   - CORS configured to allow X-User-Id header
@@ -373,6 +385,9 @@ NODE_ENV=development        # development = pretty logs, production = JSON
   - Supports events from adjacent months visible in grid
   - Uses `useFocusEffect` for automatic reload on tab focus
 - Chat screen fully functional with FlashList, message sending, and event confirm/reject
+  - **Multiple event proposals**: AI can propose multiple events in one response
+  - Arrow navigation between proposals with "Event X von Y" counter
+  - Each proposal individually confirmable/rejectable
   - Messages persisted to database via ChatService and loaded on mount
   - Tracks conversationId for message continuity across sessions
   - ChatStore with addMessages() for bulk loading, chatMessageToMessageData() helper

apps/client/src/app/(tabs)/chat.tsx

@@ -20,6 +20,7 @@ import {
 } from "../../stores";
 import { ProposedEventChange } from "@caldav/shared";
 import { ProposedEventCard } from "../../components/ProposedEventCard";
+import { Ionicons } from "@expo/vector-icons";
 
 // TODO: better shadows for everything
 // (maybe with extra library because of differences between android and ios)
@@ -30,10 +31,9 @@ type BubbleSide = "left" | "right";
 type ChatMessageProps = {
   side: BubbleSide;
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChanges?: ProposedEventChange[];
-  respondedAction?: "confirm" | "reject";
+  onConfirm?: (proposalId: string, proposal: ProposedEventChange) => void;
-  onConfirm?: () => void;
+  onReject?: (proposalId: string) => void;
-  onReject?: () => void;
 };
 
 type ChatInputProps = {
@@ -88,10 +88,17 @@ const Chat = () => {
     action: "confirm" | "reject",
     messageId: string,
     conversationId: string,
+    proposalId: string,
     proposedChange?: ProposedEventChange,
   ) => {
-    // Mark message as responded (optimistic update)
+    // Mark proposal as responded (optimistic update)
-    updateMessage(messageId, { respondedAction: action });
+    const message = messages.find((m) => m.id === messageId);
+    if (message?.proposedChanges) {
+      const updatedProposals = message.proposedChanges.map((p) =>
+        p.id === proposalId ? { ...p, respondedAction: action as "confirm" | "reject" } : p,
+      );
+      updateMessage(messageId, { proposedChanges: updatedProposals });
+    }
 
     try {
       const response =
@@ -99,12 +106,13 @@ const Chat = () => {
           ? await ChatService.confirmEvent(
               conversationId,
               messageId,
+              proposalId,
               proposedChange.action,
               proposedChange.event,
               proposedChange.eventId,
               proposedChange.updates,
             )
-          : await ChatService.rejectEvent(conversationId, messageId);
+          : await ChatService.rejectEvent(conversationId, messageId, proposalId);
 
       const botMessage: MessageData = {
         id: response.message.id,
@@ -117,7 +125,12 @@ const Chat = () => {
     } catch (error) {
       console.error(`Failed to ${action} event:`, error);
       // Revert on error
-      updateMessage(messageId, { respondedAction: undefined });
+      if (message?.proposedChanges) {
+        const revertedProposals = message.proposedChanges.map((p) =>
+          p.id === proposalId ? { ...p, respondedAction: undefined } : p,
+        );
+        updateMessage(messageId, { proposedChanges: revertedProposals });
+      }
     }
   };
 
@@ -149,7 +162,7 @@ const Chat = () => {
         id: response.message.id,
         side: "left",
         content: response.message.content,
-        proposedChange: response.message.proposedChange,
+        proposedChanges: response.message.proposedChanges,
         conversationId: response.conversationId,
       };
       addMessage(botMessage);
@@ -173,18 +186,18 @@ const Chat = () => {
             <ChatMessage
               side={item.side}
               content={item.content}
-              proposedChange={item.proposedChange}
+              proposedChanges={item.proposedChanges}
-              respondedAction={item.respondedAction}
+              onConfirm={(proposalId, proposal) =>
-              onConfirm={() =>
                 handleEventResponse(
                   "confirm",
                   item.id,
                   item.conversationId!,
-                  item.proposedChange,
+                  proposalId,
+                  proposal,
                 )
               }
-              onReject={() =>
+              onReject={(proposalId) =>
-                handleEventResponse("reject", item.id, item.conversationId!)
+                handleEventResponse("reject", item.id, item.conversationId!, proposalId)
               }
             />
           )}
@@ -271,11 +284,12 @@ const ChatInput = ({ onSend }: ChatInputProps) => {
 const ChatMessage = ({
   side,
   content,
-  proposedChange,
+  proposedChanges,
-  respondedAction,
   onConfirm,
   onReject,
 }: ChatMessageProps) => {
+  const [currentIndex, setCurrentIndex] = useState(0);
+
   const borderColor =
     side === "left" ? currentTheme.chatBot : currentTheme.primeFg;
   const selfSide =
@@ -283,24 +297,87 @@ const ChatMessage = ({
       ? "self-start ml-2 rounded-bl-sm"
       : "self-end mr-2 rounded-br-sm";
 
+  const hasProposals = proposedChanges && proposedChanges.length > 0;
+  const hasMultiple = proposedChanges && proposedChanges.length > 1;
+  const currentProposal = proposedChanges?.[currentIndex];
+
+  const goToPrev = () => setCurrentIndex((i) => Math.max(0, i - 1));
+  const goToNext = () =>
+    setCurrentIndex((i) =>
+      Math.min((proposedChanges?.length || 1) - 1, i + 1),
+    );
+
+  const canGoPrev = currentIndex > 0;
+  const canGoNext = currentIndex < (proposedChanges?.length || 1) - 1;
+
   return (
     <View
       className={`bg-white border-2 border-solid rounded-xl my-2 ${selfSide}`}
       style={{
         borderColor: borderColor,
         maxWidth: "80%",
+        minWidth: hasProposals ? "75%" : undefined,
         elevation: 8,
       }}
     >
       <Text className="p-2">{content}</Text>
 
-      {proposedChange && onConfirm && onReject && (
+      {hasProposals && currentProposal && onConfirm && onReject && (
-        <ProposedEventCard
+        <View>
-          proposedChange={proposedChange}
+          {/* Event card with optional navigation arrows */}
-          respondedAction={respondedAction}
+          <View className="flex-row items-center">
-          onConfirm={onConfirm}
+            {/* Left arrow */}
-          onReject={onReject}
+            {hasMultiple && (
-        />
+              <Pressable
+                onPress={goToPrev}
+                disabled={!canGoPrev}
+                className="p-1"
+                style={{ opacity: canGoPrev ? 1 : 0.3 }}
+              >
+                <Ionicons
+                  name="chevron-back"
+                  size={24}
+                  color={currentTheme.primeFg}
+                />
+              </Pressable>
+            )}
+
+            {/* Event Card */}
+            <View className="flex-1">
+              <ProposedEventCard
+                proposedChange={currentProposal}
+                onConfirm={() => onConfirm(currentProposal.id, currentProposal)}
+                onReject={() => onReject(currentProposal.id)}
+              />
+            </View>
+
+            {/* Right arrow */}
+            {hasMultiple && (
+              <Pressable
+                onPress={goToNext}
+                disabled={!canGoNext}
+                className="p-1"
+                style={{ opacity: canGoNext ? 1 : 0.3 }}
+              >
+                <Ionicons
+                  name="chevron-forward"
+                  size={24}
+                  color={currentTheme.primeFg}
+                />
+              </Pressable>
+            )}
+          </View>
+
+          {/* Event counter */}
+          {hasMultiple && (
+            <Text
+              className="text-center text-sm pb-2"
+              style={{ color: currentTheme.textSecondary || "#666" }}
+            >
+              Event {currentIndex + 1} von {proposedChanges.length}
+            </Text>
+          )}
+        </View>
       )}
     </View>
   );

apps/client/src/components/Header.tsx

@@ -27,7 +27,7 @@ const Header = (props: HeaderProps) => {
         {props.children}
         <Pressable
           onPress={handleLogout}
-          className="absolute right-1 top-0 p-2"
+          className="absolute left-1 bottom-0 p-2"
           hitSlop={8}
         >
           <Ionicons name="log-out-outline" size={24} color={currentTheme.primeFg} />

apps/client/src/components/ProposedEventCard.tsx

@@ -5,7 +5,6 @@ import { EventCardBase } from "./EventCardBase";
 
 type ProposedEventCardProps = {
   proposedChange: ProposedEventChange;
-  respondedAction?: "confirm" | "reject";
   onConfirm: () => void;
   onReject: () => void;
 };
@@ -59,12 +58,12 @@ const ConfirmRejectButtons = ({
 
 export const ProposedEventCard = ({
   proposedChange,
-  respondedAction,
   onConfirm,
   onReject,
 }: ProposedEventCardProps) => {
   const event = proposedChange.event;
-  const isDisabled = !!respondedAction;
+  // respondedAction is now part of the proposedChange
+  const isDisabled = !!proposedChange.respondedAction;
 
   if (!event) {
     return null;
@@ -82,7 +81,7 @@ export const ProposedEventCard = ({
       >
         <ConfirmRejectButtons
           isDisabled={isDisabled}
-          respondedAction={respondedAction}
+          respondedAction={proposedChange.respondedAction}
           onConfirm={onConfirm}
           onReject={onReject}
         />

apps/client/src/services/ChatService.ts

@@ -11,12 +11,17 @@ import {
 import { ApiClient } from "./ApiClient";
 
 interface ConfirmEventRequest {
+  proposalId: string;
   action: EventAction;
   event?: CreateEventDTO;
   eventId?: string;
   updates?: UpdateEventDTO;
 }
 
+interface RejectEventRequest {
+  proposalId: string;
+}
+
 export const ChatService = {
   sendMessage: async (data: SendMessageDTO): Promise<ChatResponse> => {
     return ApiClient.post<ChatResponse>("/chat/message", data);
@@ -25,12 +30,19 @@ export const ChatService = {
   confirmEvent: async (
     conversationId: string,
     messageId: string,
+    proposalId: string,
     action: EventAction,
     event?: CreateEventDTO,
     eventId?: string,
     updates?: UpdateEventDTO,
   ): Promise<ChatResponse> => {
-    const body: ConfirmEventRequest = { action, event, eventId, updates };
+    const body: ConfirmEventRequest = {
+      proposalId,
+      action,
+      event,
+      eventId,
+      updates,
+    };
     return ApiClient.post<ChatResponse>(
       `/chat/confirm/${conversationId}/${messageId}`,
       body,
@@ -40,9 +52,12 @@ export const ChatService = {
   rejectEvent: async (
     conversationId: string,
     messageId: string,
+    proposalId: string,
   ): Promise<ChatResponse> => {
+    const body: RejectEventRequest = { proposalId };
     return ApiClient.post<ChatResponse>(
       `/chat/reject/${conversationId}/${messageId}`,
+      body,
     );
   },
 

apps/client/src/stores/ChatStore.ts

@@ -7,8 +7,7 @@ export type MessageData = {
   id: string;
   side: BubbleSide;
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChanges?: ProposedEventChange[];
-  respondedAction?: "confirm" | "reject";
   conversationId?: string;
 };
 
@@ -46,8 +45,7 @@ export function chatMessageToMessageData(msg: ChatMessage): MessageData {
     id: msg.id,
     side: msg.sender === "assistant" ? "left" : "right",
     content: msg.content,
-    proposedChange: msg.proposedChange,
+    proposedChanges: msg.proposedChanges,
-    respondedAction: msg.respondedAction,
     conversationId: msg.conversationId,
   };
 }

apps/server/src/ai/GPTAdapter.ts

@@ -61,7 +61,8 @@ export class GPTAdapter implements AIProvider {
     // Add current user message
     messages.push({ role: "user", content: message });
 
-    let proposedChange: ProposedEventChange | undefined;
+    const proposedChanges: ProposedEventChange[] = [];
+    let proposalIndex = 0;
 
     // Tool calling loop
     while (true) {
@@ -81,7 +82,8 @@ export class GPTAdapter implements AIProvider {
         return {
           content:
             assistantMessage.content || "Ich konnte keine Antwort generieren.",
-          proposedChange,
+          proposedChanges:
+            proposedChanges.length > 0 ? proposedChanges : undefined,
         };
       }
 
@@ -95,9 +97,12 @@ export class GPTAdapter implements AIProvider {
 
         const result = executeToolCall(name, args, context);
 
-        // If the tool returned a proposedChange, capture it
+        // If the tool returned a proposedChange, add it to the array with unique ID
         if (result.proposedChange) {
-          proposedChange = result.proposedChange;
+          proposedChanges.push({
+            id: `proposal-${proposalIndex++}`,
+            ...result.proposedChange,
+          });
         }
 
         // Add assistant message with tool call

apps/server/src/ai/utils/systemPrompt.ts

@@ -28,10 +28,33 @@ Wichtige Regeln:
 - Wenn der Benutzer einen Termin erstellen will, nutze proposeCreateEvent
 - Wenn der Benutzer einen Termin ändern will, nutze proposeUpdateEvent mit der Event-ID
 - Wenn der Benutzer einen Termin löschen will, nutze proposeDeleteEvent mit der Event-ID
-- Du kannst NUR EINEN Event-Vorschlag pro Antwort machen
+- Du kannst mehrere Event-Vorschläge in einer Antwort machen (z.B. für mehrere Termine auf einmal)
 - Wenn der Benutzer nach seinen Terminen fragt, nutze die unten stehende Liste
 - Nutze searchEvents um nach Terminen zu suchen, wenn du die genaue ID brauchst
 
+WICHTIG - Tool-Verwendung:
+- Du MUSST die proposeCreateEvent/proposeUpdateEvent/proposeDeleteEvent Tools verwenden, um Termine vorzuschlagen!
+- Sage NIEMALS einfach nur "ich habe einen Termin erstellt" ohne das Tool zu verwenden
+- Die Tools erzeugen Karten, die dem Benutzer angezeigt werden - ohne Tool-Aufruf sieht er nichts
+
+WICHTIG - Wiederkehrende Termine (RRULE):
+- Ein wiederkehrendes Event hat EINE FESTE Start- und Endzeit
+- RRULE bestimmt NUR an welchen Tagen das Event wiederholt wird, NICHT unterschiedliche Uhrzeiten pro Tag!
+- Wenn der Benutzer UNTERSCHIEDLICHE ZEITEN an verschiedenen Tagen will, MUSST du SEPARATE Events erstellen
+- Beispiel: "Arbeit Mo+Do 9-17:30, Fr 9-13" → ZWEI Events:
+  1. "Arbeit" Mo+Do 9:00-17:30 (RRULE mit BYDAY=MO,TH)
+  2. "Arbeit" Fr 9:00-13:00 (RRULE mit BYDAY=FR)
+- Nutze NIEMALS BYHOUR/BYMINUTE in RRULE - diese überschreiben die Startzeit nicht wie erwartet!
+- Gültige RRULE-Optionen: FREQ (DAILY/WEEKLY/MONTHLY/YEARLY), BYDAY (MO,TU,WE,TH,FR,SA,SU), INTERVAL, COUNT, UNTIL
+
+WICHTIG - Antwortformat:
+- Halte deine Textantworten SEHR KURZ (1-2 Sätze maximal)
+- Die Event-Details (Titel, Datum, Uhrzeit, Beschreibung) werden dem Benutzer automatisch in separaten Karten angezeigt
+- Wiederhole NIEMALS die Event-Details im Text! Der Benutzer sieht sie bereits in den Karten
+- Gute Beispiele: "Alles klar!" oder "Hier sind deine Termine:"
+- Schlechte Beispiele: Lange Listen mit allen Terminen und ihren Details im Text
+- Bei Rückfragen oder wenn keine Termine erstellt werden, kannst du ausführlicher antworten
+
 Existierende Termine des Benutzers:
 ${eventsText}`;
 }

apps/server/src/ai/utils/toolExecutor.ts

@@ -7,12 +7,17 @@ import {
 import { AIContext } from "../../services/interfaces";
 import { formatDate, formatTime, formatDateTime } from "./eventFormatter";
 
+/**
+ * Proposed change without ID - ID is added by GPTAdapter when collecting proposals
+ */
+type ToolProposedChange = Omit<ProposedEventChange, "id" | "respondedAction">;
+
 /**
  * Result of executing a tool call.
  */
 export interface ToolResult {
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChange?: ToolProposedChange;
 }
 
 /**

apps/server/src/controllers/ChatController.ts

@@ -31,7 +31,8 @@ export class ChatController {
     try {
       const userId = req.user!.userId;
       const { conversationId, messageId } = req.params;
-      const { action, event, eventId, updates } = req.body as {
+      const { proposalId, action, event, eventId, updates } = req.body as {
+        proposalId: string;
         action: EventAction;
         event?: CreateEventDTO;
         eventId?: string;
@@ -41,6 +42,7 @@ export class ChatController {
         userId,
         conversationId,
         messageId,
+        proposalId,
         action,
         event,
         eventId,
@@ -57,10 +59,12 @@ export class ChatController {
     try {
       const userId = req.user!.userId;
       const { conversationId, messageId } = req.params;
+      const { proposalId } = req.body as { proposalId: string };
       const response = await this.chatService.rejectEvent(
         userId,
         conversationId,
         messageId,
+        proposalId,
       );
       res.json(response);
     } catch (error) {

apps/server/src/logging/Logged.ts

@@ -1,5 +1,57 @@
 import { createLogger } from "./logger";
 
+/**
+ * Summarize args for logging to avoid huge log entries.
+ * - Arrays: show length only
+ * - Long strings: truncate
+ * - Objects with conversationHistory/existingEvents: summarize
+ */
+// eslint-disable-next-line @typescript-eslint/no-explicit-any
+function summarizeArgs(args: any[]): any[] {
+  return args.map((arg) => summarizeValue(arg));
+}
+
+// eslint-disable-next-line @typescript-eslint/no-explicit-any
+function summarizeValue(value: any, depth = 0): any {
+  if (depth > 2) return "[...]";
+
+  if (value === null || value === undefined) return value;
+
+  if (Array.isArray(value)) {
+    return `[Array(${value.length})]`;
+  }
+
+  if (typeof value === "string" && value.length > 100) {
+    return value.substring(0, 100) + "...";
+  }
+
+  if (typeof value === "object") {
+    // Summarize known large fields
+    const summarized: Record<string, unknown> = {};
+    for (const [key, val] of Object.entries(value)) {
+      if (key === "conversationHistory" && Array.isArray(val)) {
+        summarized[key] = `[${val.length} messages]`;
+      } else if (key === "existingEvents" && Array.isArray(val)) {
+        summarized[key] = `[${val.length} events]`;
+      } else if (key === "proposedChanges" && Array.isArray(val)) {
+        // Log full proposedChanges for debugging AI issues
+        summarized[key] = val.map((p) => summarizeValue(p, depth + 1));
+      } else if (Array.isArray(val)) {
+        summarized[key] = `[Array(${val.length})]`;
+      } else if (typeof val === "object" && val !== null) {
+        summarized[key] = summarizeValue(val, depth + 1);
+      } else if (typeof val === "string" && val.length > 100) {
+        summarized[key] = val.substring(0, 100) + "...";
+      } else {
+        summarized[key] = val;
+      }
+    }
+    return summarized;
+  }
+
+  return value;
+}
+
 export function Logged(name: string) {
   const log = createLogger(name);
 
@@ -27,8 +79,8 @@ export function Logged(name: string) {
               const start = performance.now();
               const method = String(propKey);
 
-              // Pino's redact handles sanitization - just pass args directly
+              // Summarize args to avoid huge log entries
-              log.debug({ method, args: methodArgs }, `${method} started`);
+              log.debug({ method, args: summarizeArgs(methodArgs) }, `${method} started`);
 
               const logCompletion = (err?: unknown) => {
                 const duration = Math.round(performance.now() - start);

apps/server/src/repositories/mongo/MongoChatRepository.ts

@@ -53,7 +53,7 @@ export class MongoChatRepository implements ChatRepository {
       conversationId: conversationId,
       sender: message.sender,
       content: message.content,
-      proposedChange: message.proposedChange,
+      proposedChanges: message.proposedChanges,
     });
     return repoMessage.toJSON() as unknown as ChatMessage;
   }
@@ -69,4 +69,17 @@ export class MongoChatRepository implements ChatRepository {
     );
     return doc ? (doc.toJSON() as unknown as ChatMessage) : null;
   }
+
+  async updateProposalResponse(
+    messageId: string,
+    proposalId: string,
+    respondedAction: "confirm" | "reject",
+  ): Promise<ChatMessage | null> {
+    const doc = await ChatMessageModel.findOneAndUpdate(
+      { _id: messageId, "proposedChanges.id": proposalId },
+      { $set: { "proposedChanges.$.respondedAction": respondedAction } },
+      { new: true },
+    );
+    return doc ? (doc.toJSON() as unknown as ChatMessage) : null;
+  }
 }

apps/server/src/repositories/mongo/models/ChatModel.ts

@@ -44,6 +44,7 @@ const UpdatesSchema = new Schema<UpdateEventDTO>(
 
 const ProposedChangeSchema = new Schema<ProposedEventChange>(
   {
+    id: { type: String, required: true },
     action: {
       type: String,
       enum: ["create", "update", "delete"],
@@ -52,6 +53,10 @@ const ProposedChangeSchema = new Schema<ProposedEventChange>(
     eventId: { type: String },
     event: { type: EventSchema },
     updates: { type: UpdatesSchema },
+    respondedAction: {
+      type: String,
+      enum: ["confirm", "reject"],
+    },
   },
   { _id: false },
 );
@@ -77,12 +82,9 @@ const ChatMessageSchema = new Schema<
       type: String,
       required: true,
     },
-    proposedChange: {
+    proposedChanges: {
-      type: ProposedChangeSchema,
+      type: [ProposedChangeSchema],
-    },
+      default: undefined,
-    respondedAction: {
-      type: String,
-      enum: ["confirm", "reject"],
     },
   },
   {

apps/server/src/services/ChatService.ts

@@ -14,7 +14,7 @@ import {
 import { ChatRepository, EventRepository, AIProvider } from "./interfaces";
 import { getWeeksOverview, getMonthOverview } from "../utils/eventFormatters";
 
-type TestResponse = { content: string; proposedChange?: ProposedEventChange };
+type TestResponse = { content: string; proposedChanges?: ProposedEventChange[] };
 
 // Test response index (cycles through responses)
 let responseIndex = 0;
@@ -22,7 +22,134 @@ let responseIndex = 0;
 // Static test responses (event proposals)
 const staticResponses: TestResponse[] = [
   // {{{
-  // Response 0: Help response (text only)
+  // === MULTI-EVENT TEST RESPONSES ===
+  // Response 0: 3 Meetings an verschiedenen Tagen
+  {
+    content:
+      "Alles klar! Ich erstelle dir 3 Team-Meetings für diese Woche:",
+    proposedChanges: [
+      {
+        id: "multi-1-a",
+        action: "create",
+        event: {
+          title: "Team-Meeting Montag",
+          startTime: getDay("Monday", 1, 10, 0),
+          endTime: getDay("Monday", 1, 11, 0),
+          description: "Wöchentliches Standup",
+        },
+      },
+      {
+        id: "multi-1-b",
+        action: "create",
+        event: {
+          title: "Team-Meeting Mittwoch",
+          startTime: getDay("Wednesday", 1, 10, 0),
+          endTime: getDay("Wednesday", 1, 11, 0),
+          description: "Sprint Planning",
+        },
+      },
+      {
+        id: "multi-1-c",
+        action: "create",
+        event: {
+          title: "Team-Meeting Freitag",
+          startTime: getDay("Friday", 1, 10, 0),
+          endTime: getDay("Friday", 1, 11, 0),
+          description: "Retrospektive",
+        },
+      },
+    ],
+  },
+  // Response 1: 5 Termine für einen Projekttag
+  {
+    content:
+      "Ich habe deinen kompletten Projekttag am Dienstag geplant:",
+    proposedChanges: [
+      {
+        id: "multi-2-a",
+        action: "create",
+        event: {
+          title: "Kickoff-Meeting",
+          startTime: getDay("Tuesday", 1, 9, 0),
+          endTime: getDay("Tuesday", 1, 10, 0),
+          description: "Projektstart mit dem Team",
+        },
+      },
+      {
+        id: "multi-2-b",
+        action: "create",
+        event: {
+          title: "Design Review",
+          startTime: getDay("Tuesday", 1, 10, 30),
+          endTime: getDay("Tuesday", 1, 11, 30),
+          description: "UI/UX Besprechung",
+        },
+      },
+      {
+        id: "multi-2-c",
+        action: "create",
+        event: {
+          title: "Mittagspause",
+          startTime: getDay("Tuesday", 1, 12, 0),
+          endTime: getDay("Tuesday", 1, 13, 0),
+          description: "Team-Lunch",
+        },
+      },
+      {
+        id: "multi-2-d",
+        action: "create",
+        event: {
+          title: "Tech Review",
+          startTime: getDay("Tuesday", 1, 14, 0),
+          endTime: getDay("Tuesday", 1, 15, 30),
+          description: "Architektur-Diskussion",
+        },
+      },
+      {
+        id: "multi-2-e",
+        action: "create",
+        event: {
+          title: "Wrap-up",
+          startTime: getDay("Tuesday", 1, 16, 0),
+          endTime: getDay("Tuesday", 1, 16, 30),
+          description: "Zusammenfassung und nächste Schritte",
+        },
+      },
+    ],
+  },
+  // Response 2: 2 wiederkehrende Termine
+  {
+    content:
+      "Ich erstelle dir zwei wiederkehrende Fitness-Termine:",
+    proposedChanges: [
+      {
+        id: "multi-3-a",
+        action: "create",
+        event: {
+          title: "Yoga",
+          startTime: getDay("Monday", 1, 7, 0),
+          endTime: getDay("Monday", 1, 8, 0),
+          description: "Morgen-Yoga",
+          isRecurring: true,
+          recurrenceRule: "FREQ=WEEKLY;BYDAY=MO,WE,FR",
+        },
+      },
+      {
+        id: "multi-3-b",
+        action: "create",
+        event: {
+          title: "Laufen",
+          startTime: getDay("Tuesday", 1, 18, 0),
+          endTime: getDay("Tuesday", 1, 19, 0),
+          description: "Abendlauf im Park",
+          isRecurring: true,
+          recurrenceRule: "FREQ=WEEKLY;BYDAY=TU,TH",
+        },
+      },
+    ],
+  },
+  // === ORIGINAL RESPONSES ===
+  // Response 3: Help response (text only)
   {
     content:
       "Ich bin dein Kalender-Assistent! Du kannst mir einfach sagen, welche Termine du erstellen, ändern oder löschen möchtest. Zum Beispiel:\n\n" +
@@ -35,30 +162,36 @@ const staticResponses: TestResponse[] = [
   {
     content:
       "Alles klar! Ich erstelle dir einen Termin für das Meeting mit Jens am nächsten Freitag um 14:00 Uhr:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-1",
-        title: "Meeting mit Jens",
+        action: "create",
-        startTime: getDay("Friday", 1, 14, 0),
+        event: {
-        endTime: getDay("Friday", 1, 15, 0),
+          title: "Meeting mit Jens",
-        description: "Arbeitstreffen",
+          startTime: getDay("Friday", 1, 14, 0),
+          endTime: getDay("Friday", 1, 15, 0),
+          description: "Arbeitstreffen",
+        },
       },
-    },
+    ],
   },
   // Response 2: Recurring event - every Saturday 10:00
   {
     content:
       "Verstanden! Ich erstelle einen wiederkehrenden Termin: Jeden Samstag um 10:00 Uhr Badezimmer putzen:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-2",
-        title: "Badezimmer putzen",
+        action: "create",
-        startTime: getDay("Saturday", 1, 10, 0),
+        event: {
-        endTime: getDay("Saturday", 1, 11, 0),
+          title: "Badezimmer putzen",
-        isRecurring: true,
+          startTime: getDay("Saturday", 1, 10, 0),
-        recurrenceRule: "FREQ=WEEKLY;BYDAY=SA",
+          endTime: getDay("Saturday", 1, 11, 0),
+          isRecurring: true,
+          recurrenceRule: "FREQ=WEEKLY;BYDAY=SA",
+        },
       },
-    },
+    ],
   },
   // Response 3: 2-week overview (DYNAMIC - placeholder)
   { content: "" },
@@ -68,45 +201,54 @@ const staticResponses: TestResponse[] = [
   {
     content:
       "Ich habe dir einen Arzttermin eingetragen. Denk daran, deine Versichertenkarte mitzunehmen!",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-5",
-        title: "Arzttermin Dr. Müller",
+        action: "create",
-        startTime: getDay("Wednesday", 1, 9, 30),
+        event: {
-        endTime: getDay("Wednesday", 1, 10, 30),
+          title: "Arzttermin Dr. Müller",
-        description: "Routineuntersuchung - Versichertenkarte nicht vergessen",
+          startTime: getDay("Wednesday", 1, 9, 30),
+          endTime: getDay("Wednesday", 1, 10, 30),
+          description: "Routineuntersuchung - Versichertenkarte nicht vergessen",
+        },
       },
-    },
+    ],
   },
   // Response 6: Birthday - yearly recurring
   {
     content:
       "Geburtstage vergisst man leicht - aber nicht mit mir! Ich habe Mamas Geburtstag eingetragen:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-6",
-        title: "Mamas Geburtstag",
+        action: "create",
-        startTime: getDay("Thursday", 2, 0, 0),
+        event: {
-        endTime: getDay("Thursday", 2, 23, 59),
+          title: "Mamas Geburtstag",
-        isRecurring: true,
+          startTime: getDay("Thursday", 2, 0, 0),
-        recurrenceRule: "FREQ=YEARLY",
+          endTime: getDay("Thursday", 2, 23, 59),
+          isRecurring: true,
+          recurrenceRule: "FREQ=YEARLY",
+        },
       },
-    },
+    ],
   },
   // Response 7: Gym - recurring for 2 months (8 weeks)
   {
     content:
       "Perfekt! Ich habe dein Probetraining eingetragen - jeden Dienstag für die nächsten 2 Monate:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-7",
-        title: "Fitnessstudio Probetraining",
+        action: "create",
-        startTime: getDay("Tuesday", 1, 18, 0),
+        event: {
-        endTime: getDay("Tuesday", 1, 19, 30),
+          title: "Fitnessstudio Probetraining",
-        isRecurring: true,
+          startTime: getDay("Tuesday", 1, 18, 0),
-        recurrenceRule: "FREQ=WEEKLY;BYDAY=TU;COUNT=8",
+          endTime: getDay("Tuesday", 1, 19, 30),
+          isRecurring: true,
+          recurrenceRule: "FREQ=WEEKLY;BYDAY=TU;COUNT=8",
+        },
       },
-    },
+    ],
   },
   // Response 8: 1-week overview (DYNAMIC - placeholder)
   { content: "" },
@@ -114,44 +256,53 @@ const staticResponses: TestResponse[] = [
   {
     content:
       "Alles klar! Ich habe das Telefonat mit deiner Mutter eingetragen:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-9",
-        title: "Telefonat mit Mama",
+        action: "create",
-        startTime: getDay("Wednesday", 1, 11, 0),
+        event: {
-        endTime: getDay("Wednesday", 1, 11, 30),
+          title: "Telefonat mit Mama",
+          startTime: getDay("Wednesday", 1, 11, 0),
+          endTime: getDay("Wednesday", 1, 11, 30),
+        },
       },
-    },
+    ],
   },
   // Response 10: Update "Telefonat mit Mama" +3 days (DYNAMIC - placeholder)
   { content: "" },
   // Response 11: Birthday party - evening event
   {
     content: "Super! Die Geburtstagsfeier ist eingetragen. Viel Spaß!",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-11",
-        title: "Geburtstagsfeier Lisa",
+        action: "create",
-        startTime: getDay("Saturday", 2, 19, 0),
+        event: {
-        endTime: getDay("Saturday", 2, 23, 0),
+          title: "Geburtstagsfeier Lisa",
-        description: "Geschenk: Buch über Fotografie",
+          startTime: getDay("Saturday", 2, 19, 0),
+          endTime: getDay("Saturday", 2, 23, 0),
+          description: "Geschenk: Buch über Fotografie",
+        },
       },
-    },
+    ],
   },
   // Response 12: Language course - limited to 8 weeks (Thu + Sat)
   {
     content:
       "Dein Spanischkurs ist eingetragen! Er läuft jeden Donnerstag und Samstag für die nächsten 8 Wochen:",
-    proposedChange: {
+    proposedChanges: [
-      action: "create",
+      {
-      event: {
+        id: "test-12",
-        title: "Spanischkurs VHS",
+        action: "create",
-        startTime: getDay("Thursday", 1, 19, 0),
+        event: {
-        endTime: getDay("Thursday", 1, 20, 30),
+          title: "Spanischkurs VHS",
-        isRecurring: true,
+          startTime: getDay("Thursday", 1, 19, 0),
-        recurrenceRule: "FREQ=WEEKLY;BYDAY=TH,SA;COUNT=8",
+          endTime: getDay("Thursday", 1, 20, 30),
+          isRecurring: true,
+          recurrenceRule: "FREQ=WEEKLY;BYDAY=TH,SA;COUNT=8",
+        },
       },
-    },
+    ],
   },
   // Response 13: Monthly overview (DYNAMIC - placeholder)
   { content: "" },
@@ -177,17 +328,20 @@ async function getTestResponse(
     if (jensEvent) {
       return {
         content: "Soll ich diesen Termin wirklich löschen?",
-        proposedChange: {
+        proposedChanges: [
-          action: "delete",
+          {
-          eventId: jensEvent.id,
+            id: "test-4",
-          event: {
+            action: "delete",
-            title: jensEvent.title,
+            eventId: jensEvent.id,
-            startTime: jensEvent.startTime,
+            event: {
-            endTime: jensEvent.endTime,
+              title: jensEvent.title,
-            description: jensEvent.description,
+              startTime: jensEvent.startTime,
-            isRecurring: jensEvent.isRecurring,
+              endTime: jensEvent.endTime,
+              description: jensEvent.description,
+              isRecurring: jensEvent.isRecurring,
+            },
           },
-        },
+        ],
       };
     }
     return { content: "Ich konnte keinen Termin 'Meeting mit Jens' finden." };
@@ -210,18 +364,21 @@ async function getTestResponse(
       return {
         content:
           "Alles klar, ich verschiebe das Telefonat mit Mama auf Samstag um 13:00 Uhr:",
-        proposedChange: {
+        proposedChanges: [
-          action: "update",
+          {
-          eventId: mamaEvent.id,
+            id: "test-10",
-          updates: { startTime: newStart, endTime: newEnd },
+            action: "update",
-          // Include event with new times for display
+            eventId: mamaEvent.id,
-          event: {
+            updates: { startTime: newStart, endTime: newEnd },
-            title: mamaEvent.title,
+            // Include event with new times for display
-            startTime: newStart,
+            event: {
-            endTime: newEnd,
+              title: mamaEvent.title,
-            description: mamaEvent.description,
+              startTime: newStart,
+              endTime: newEnd,
+              description: mamaEvent.description,
+            },
           },
-        },
+        ],
       };
     }
     return { content: "Ich konnte keinen Termin 'Telefonat mit Mama' finden." };
@@ -290,7 +447,7 @@ export class ChatService {
     const answerMessage = await this.chatRepo.createMessage(conversationId, {
       sender: "assistant",
       content: response.content,
-      proposedChange: response.proposedChange,
+      proposedChanges: response.proposedChanges,
     });
 
     return { message: answerMessage, conversationId: conversationId };
@@ -300,15 +457,14 @@ export class ChatService {
     userId: string,
     conversationId: string,
     messageId: string,
+    proposalId: string,
     action: EventAction,
     event?: CreateEventDTO,
     eventId?: string,
     updates?: UpdateEventDTO,
   ): Promise<ChatResponse> {
-    // Update original message with respondedAction
+    // Update specific proposal with respondedAction
-    await this.chatRepo.updateMessage(messageId, {
+    await this.chatRepo.updateProposalResponse(messageId, proposalId, "confirm");
-      respondedAction: "confirm",
-    });
 
     // Perform the actual event operation
     let content: string;
@@ -343,9 +499,10 @@ export class ChatService {
     userId: string,
     conversationId: string,
     messageId: string,
+    proposalId: string,
   ): Promise<ChatResponse> {
-    // Update original message with respondedAction
+    // Update specific proposal with respondedAction
-    await this.chatRepo.updateMessage(messageId, { respondedAction: "reject" });
+    await this.chatRepo.updateProposalResponse(messageId, proposalId, "reject");
 
     // Save response message to DB
     const message = await this.chatRepo.createMessage(conversationId, {

apps/server/src/services/interfaces/AIProvider.ts

@@ -13,7 +13,7 @@ export interface AIContext {
 
 export interface AIResponse {
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChanges?: ProposedEventChange[];
 }
 
 export interface AIProvider {

apps/server/src/services/interfaces/ChatRepository.ts

@@ -26,4 +26,10 @@ export interface ChatRepository {
     messageId: string,
     updates: UpdateMessageDTO,
   ): Promise<ChatMessage | null>;
+
+  updateProposalResponse(
+    messageId: string,
+    proposalId: string,
+    respondedAction: "confirm" | "reject",
+  ): Promise<ChatMessage | null>;
 }

apps/server/src/utils/recurrenceExpander.ts

@@ -58,8 +58,10 @@ export function expandRecurringEvents(
 
     // Recurring event: parse RRULE and expand
     try {
+      // Strip RRULE: prefix if present (AI may include it)
+      const ruleString = event.recurrenceRule.replace(/^RRULE:/i, "");
       const rule = rrulestr(
-        `DTSTART:${formatRRuleDateString(startTime)}\nRRULE:${event.recurrenceRule}`,
+        `DTSTART:${formatRRuleDateString(startTime)}\nRRULE:${ruleString}`,
       );
 
       // Get occurrences within the range (using fake UTC dates)

packages/shared/src/models/ChatMessage.ts

@@ -7,10 +7,12 @@ export type EventAction = "create" | "update" | "delete";
 export type RespondedAction = "confirm" | "reject";
 
 export interface ProposedEventChange {
+  id: string; // Unique ID for each proposal
   action: EventAction;
   eventId?: string; // Required for update/delete
   event?: CreateEventDTO; // Required for create
   updates?: UpdateEventDTO; // Required for update
+  respondedAction?: RespondedAction; // User's response to this specific proposal
 }
 
 export interface ChatMessage {
@@ -18,8 +20,7 @@ export interface ChatMessage {
   conversationId: string;
   sender: MessageSender;
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChanges?: ProposedEventChange[]; // Array of event proposals
-  respondedAction?: RespondedAction;
   createdAt?: Date;
 }
 
@@ -38,7 +39,7 @@ export interface SendMessageDTO {
 export interface CreateMessageDTO {
   sender: MessageSender;
   content: string;
-  proposedChange?: ProposedEventChange;
+  proposedChanges?: ProposedEventChange[];
 }
 
 export interface GetMessagesOptions {
@@ -47,6 +48,7 @@ export interface GetMessagesOptions {
 }
 
 export interface UpdateMessageDTO {
+  proposalId?: string; // Identifies which proposal to update
   respondedAction?: RespondedAction;
 }