diff --git a/apps/infoalloggi/src/server/controllers/event_queue.controller.ts b/apps/infoalloggi/src/server/controllers/event_queue.controller.ts
index fd93ec9..148ce35 100644
--- a/apps/infoalloggi/src/server/controllers/event_queue.controller.ts
+++ b/apps/infoalloggi/src/server/controllers/event_queue.controller.ts
@@ -1,17 +1,49 @@
 import type { Override } from "TypeHelpers.type";
 import { TRPCError } from "@trpc/server";
 import { add, set } from "date-fns";
+import type { Attachment } from "nodemailer/lib/mailer";
+import type { AnnunciId } from "~/schemas/public/Annunci";
 import type { NewEventQueue } from "~/schemas/public/EventQueue";
+import type { OrdiniOrdineId } from "~/schemas/public/Ordini";
+import type { TestiEStringheStingaId } from "~/schemas/public/TestiEStringhe";
 import {
 	type MinimalSMSData,
 	SendMessage,
 } from "~/server/controllers/skebby.controller";
 import { db } from "~/server/db";
 import { NewMail, type NewMailProps } from "~/server/services/mailer";
+import {
+	genPdfCondizioniBase64,
+	genPdfRicevutaCortesiaBase64,
+	genPdfSchedaAnnuncioBase64,
+} from "../services/puppeteer.service";
 
+type GeneratedAttachmentTypes =
+	| { type: "scheda_annuncio"; annuncioId: AnnunciId }
+	| { type: "ricevuta_cortesia"; ordineId: OrdiniOrdineId }
+	| { type: "condizioni"; stringId: TestiEStringheStingaId };
+
+type CustomAttachment = Attachment & { generate?: GeneratedAttachmentTypes };
 type Email_EventData = {
 	tipo: "email";
-	data: NewMailProps;
+	data: NewMailProps & {
+		mail: {
+			attachments?: CustomAttachment[];
+		};
+	};
+};
+
+const generatePdfContent = async (params: GeneratedAttachmentTypes) => {
+	switch (params.type) {
+		case "ricevuta_cortesia":
+			return await genPdfRicevutaCortesiaBase64(params.ordineId);
+		case "condizioni":
+			return await genPdfCondizioniBase64(params.stringId);
+		case "scheda_annuncio":
+			return await genPdfSchedaAnnuncioBase64(params.annuncioId);
+		default:
+			throw new Error(`Unknown PDF type: `);
+	}
 };
 
 type SMS_EventData = {
@@ -67,6 +99,36 @@ const getEventsFromQueue = async () => {
 	}
 };
 
+const processEmailEvent = async (event: Email_EventData) => {
+	const { template, mail, userId } = event.data;
+
+	// Generate attachments on-demand
+	if (mail.attachments && mail.attachments.length > 0) {
+		mail.attachments = await Promise.all(
+			mail.attachments.map(async (attachment: CustomAttachment) => {
+				// If attachment has generate metadata, generate it now
+				if (attachment.generate) {
+					const content = await generatePdfContent(attachment.generate);
+					return {
+						filename: attachment.filename,
+						content,
+						encoding: attachment.encoding,
+						contentType: attachment.contentType,
+					};
+				}
+				// If already has content, return as-is
+				return attachment;
+			}),
+		);
+	}
+
+	await NewMail({
+		template,
+		mail,
+		userId,
+	});
+};
+
 export const processEvents = async () => {
 	const events = await getEventsFromQueue();
 	if (events.length === 0) {
@@ -77,9 +139,7 @@ export const processEvents = async () => {
 
 		switch (data.tipo) {
 			case "email": {
-				await NewMail({
-					...data.data,
-				});
+				await processEmailEvent(data);
 				break;
 			}
 
diff --git a/apps/infoalloggi/src/server/controllers/stripe.controller.ts b/apps/infoalloggi/src/server/controllers/stripe.controller.ts
index be27bd0..d15c8e0 100644
--- a/apps/infoalloggi/src/server/controllers/stripe.controller.ts
+++ b/apps/infoalloggi/src/server/controllers/stripe.controller.ts
@@ -183,17 +183,25 @@ export const whIntentSucceededHandler = async ({
 										{
 											filename: `condizioni_contrattuali_${ordine.created_at.toISOString()}.pdf`,
 											//ATTENTION: hardcoded condizioni key
-											content: await genPdfCondizioniBase64(
-												"CONDIZIONI_CERCHI" as TestiEStringheStingaId,
-											),
+											// content: await genPdfCondizioniBase64(
+											// 	"CONDIZIONI_CERCHI" as TestiEStringheStingaId,
+											// ),
+											generate: {
+												type: "condizioni",
+												stringId: "CONDIZIONI_CERCHI" as TestiEStringheStingaId,
+											},
 											encoding: "base64",
 											contentType: "application/pdf",
 										},
 										{
 											filename: `ricevuta_cortesia_${ordine.ordine_id}.pdf`,
-											content: await genPdfRicevutaCortesiaBase64(
-												ordine.ordine_id,
-											),
+											// content: await genPdfRicevutaCortesiaBase64(
+											// 	ordine.ordine_id,
+											// ),
+											generate: {
+												type: "ricevuta_cortesia",
+												ordineId: ordine.ordine_id,
+											},
 											encoding: "base64",
 											contentType: "application/pdf",
 										},
@@ -231,9 +239,13 @@ export const whIntentSucceededHandler = async ({
 									attachments: [
 										{
 											filename: `ricevuta_cortesia_${ordine.ordine_id}.pdf`,
-											content: await genPdfRicevutaCortesiaBase64(
-												ordine.ordine_id,
-											),
+											generate: {
+												type: "ricevuta_cortesia",
+												ordineId: ordine.ordine_id,
+											},
+											// content: await genPdfRicevutaCortesiaBase64(
+											// 	ordine.ordine_id,
+											// ),
 											encoding: "base64",
 											contentType: "application/pdf",
 										},
@@ -267,9 +279,13 @@ export const whIntentSucceededHandler = async ({
 									attachments: [
 										{
 											filename: `ricevuta_cortesia_${ordine.ordine_id}.pdf`,
-											content: await genPdfRicevutaCortesiaBase64(
-												ordine.ordine_id,
-											),
+											// content: await genPdfRicevutaCortesiaBase64(
+											// 	ordine.ordine_id,
+											// ),
+											generate: {
+												type: "ricevuta_cortesia",
+												ordineId: ordine.ordine_id,
+											},
 											encoding: "base64",
 											contentType: "application/pdf",
 										},
@@ -297,9 +313,13 @@ export const whIntentSucceededHandler = async ({
 									attachments: [
 										{
 											filename: `ricevuta_cortesia_${ordine.ordine_id}.pdf`,
-											content: await genPdfRicevutaCortesiaBase64(
-												ordine.ordine_id,
-											),
+											// content: await genPdfRicevutaCortesiaBase64(
+											// 	ordine.ordine_id,
+											// ),
+											generate: {
+												type: "ricevuta_cortesia",
+												ordineId: ordine.ordine_id,
+											},
 											encoding: "base64",
 											contentType: "application/pdf",
 										},