diff --git a/drizzle/migrations/0007_create_prompt_generation_jobs.sql b/drizzle/migrations/0007_create_prompt_generation_jobs.sql
new file mode 100644
index 00000000..4c6270e2
--- /dev/null
+++ b/drizzle/migrations/0007_create_prompt_generation_jobs.sql
@@ -0,0 +1,17 @@
+-- Migration 0007: Create missing prompt_generation_jobs table
+-- This table was defined in schema.ts and migration 0002 but was never applied to production.
+
+CREATE TABLE IF NOT EXISTS "prompt_generation_jobs" (
+	"id" uuid PRIMARY KEY DEFAULT gen_random_uuid() NOT NULL,
+	"user_id" uuid NOT NULL,
+	"domain" text NOT NULL,
+	"status" text DEFAULT 'pending' NOT NULL,
+	"result_prompt" text,
+	"error_message" text,
+	"created_at" timestamp with time zone DEFAULT now() NOT NULL,
+	"updated_at" timestamp with time zone DEFAULT now() NOT NULL
+);
+--> statement-breakpoint
+ALTER TABLE "prompt_generation_jobs" ADD CONSTRAINT "prompt_generation_jobs_user_id_fkey" FOREIGN KEY ("user_id") REFERENCES "public"."users"("id") ON DELETE cascade ON UPDATE no action NOT VALID;
+--> statement-breakpoint
+ALTER TABLE "prompt_generation_jobs" VALIDATE CONSTRAINT "prompt_generation_jobs_user_id_fkey";
diff --git a/drizzle/migrations/0008_allow_data_message_role.sql b/drizzle/migrations/0008_allow_data_message_role.sql
new file mode 100644
index 00000000..26fb9585
--- /dev/null
+++ b/drizzle/migrations/0008_allow_data_message_role.sql
@@ -0,0 +1,12 @@
+-- Migration 0008: Allow 'data' as a valid message role
+-- The messages_role_check constraint currently only allows: user, assistant, system, tool
+-- Internal context messages (drawing context, calendar notes) use role 'data'
+-- This migration adds 'data' to the allowed values.
+-- NOTE: updateDrawingContext and calendar.ts have been updated to use 'tool' instead of 'data'.
+-- This migration is preventive: if any future code needs role 'data', it will be available.
+
+ALTER TABLE "messages" DROP CONSTRAINT IF EXISTS "messages_role_check";
+--> statement-breakpoint
+ALTER TABLE "messages" ADD CONSTRAINT "messages_role_check" CHECK (role = ANY (ARRAY['user'::text, 'assistant'::text, 'system'::text, 'tool'::text, 'data'::text])) NOT VALID;
+--> statement-breakpoint
+ALTER TABLE "messages" VALIDATE CONSTRAINT "messages_role_check";
diff --git a/lib/actions/calendar.ts b/lib/actions/calendar.ts
index d2e4dcf9..cf6fe21e 100644
--- a/lib/actions/calendar.ts
+++ b/lib/actions/calendar.ts
@@ -93,7 +93,7 @@ export async function saveNote(noteData: NewCalendarNote | CalendarNote): Promis
                 const calendarContextMessage: NewMessage = {
                     chatId: newNote.chatId,
                     userId: userId,
-                    role: 'data',
+                    role: 'tool',
                     content: JSON.stringify({
                         type: 'calendar_note',
                         note: newNote,
diff --git a/lib/actions/chat-db.ts b/lib/actions/chat-db.ts
index 3fcdc2f9..0498d426 100644
--- a/lib/actions/chat-db.ts
+++ b/lib/actions/chat-db.ts
@@ -120,7 +120,7 @@ export async function saveChat(chatData: NewChat, messagesData: Omit<NewMessage,
       const messagesToInsert: typeof messages.$inferInsert[] = [];
 
       for (const msg of messagesData) {
-        let id = msg.id;
+        let id = msg.id ?? crypto.randomUUID();
 
         // If we've already seen this ID in this batch, generate a unique one
         while (seenIds.has(id)) {
diff --git a/lib/actions/chat.ts b/lib/actions/chat.ts
index 9e65a6cf..303d3c19 100644
--- a/lib/actions/chat.ts
+++ b/lib/actions/chat.ts
@@ -235,7 +235,7 @@ export async function updateDrawingContext(chatId: string, contextData: { drawnF
   const newDrawingMessage: DbNewMessage = {
     userId: userId,
     chatId: chatId,
-    role: 'data',
+    role: 'tool',
     content: JSON.stringify(contextData),
     createdAt: new Date(),
   };