diff --git a/src/controllers/api/inventoryController.ts b/src/controllers/api/inventoryController.ts
index cb855f16..c1933a80 100644
--- a/src/controllers/api/inventoryController.ts
+++ b/src/controllers/api/inventoryController.ts
@@ -9,6 +9,7 @@ import { IPolarity, ArtifactPolarity, EquipmentFeatures } from "@/src/types/inve
 import { ExportCustoms, ExportFlavour, ExportResources, ExportVirtuals } from "warframe-public-export-plus";
 import { applyCheatsToInfestedFoundry, handleSubsumeCompletion } from "@/src/services/infestedFoundryService";
 import {
+    addEmailItem,
     addMiscItems,
     allDailyAffiliationKeys,
     cleanupInventory,
@@ -110,7 +111,58 @@ export const inventoryController: RequestHandler = async (request, response) =>
         }
 
         if (inventory.CalendarProgress) {
+            const previousYearIteration = inventory.CalendarProgress.Iteration;
             getCalendarProgress(inventory); // handle year rollover; the client expects to receive an inventory with an up-to-date CalendarProgress
+
+            // also handle sending of kiss cinematic at year rollover
+            if (
+                inventory.CalendarProgress.Iteration != previousYearIteration &&
+                inventory.DialogueHistory &&
+                inventory.DialogueHistory.Dialogues
+            ) {
+                let kalymos = false;
+                for (const { dialogueName, kissEmail } of [
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/ArthurDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/ArthurKissEmailItem"
+                    },
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/EleanorDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/EleanorKissEmailItem"
+                    },
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/LettieDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/LettieKissEmailItem"
+                    },
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/JabirDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/AmirKissEmailItem"
+                    },
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/AoiDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/AoiKissEmailItem"
+                    },
+                    {
+                        dialogueName: "/Lotus/Types/Gameplay/1999Wf/Dialogue/QuincyDialogue_rom.dialogue",
+                        kissEmail: "/Lotus/Types/Items/EmailItems/QuincyKissEmailItem"
+                    }
+                ]) {
+                    const dialogue = inventory.DialogueHistory.Dialogues.find(x => x.DialogueName == dialogueName);
+                    if (dialogue) {
+                        if (dialogue.Rank == 7) {
+                            await addEmailItem(inventory, kissEmail);
+                            kalymos = false;
+                            break;
+                        }
+                        if (dialogue.Rank == 6) {
+                            kalymos = true;
+                        }
+                    }
+                }
+                if (kalymos) {
+                    await addEmailItem(inventory, "/Lotus/Types/Items/EmailItems/KalymosKissEmailItem");
+                }
+            }
         }
 
         cleanupInventory(inventory);
diff --git a/src/models/inboxModel.ts b/src/models/inboxModel.ts
index 139e8b44..793d37d8 100644
--- a/src/models/inboxModel.ts
+++ b/src/models/inboxModel.ts
@@ -23,7 +23,9 @@ export interface IMessageDatabase extends IMessage {
 export interface IMessage {
     sndr: string;
     msg: string;
+    cinematic?: string;
     sub: string;
+    customData?: string;
     icon?: string;
     highPriority?: boolean;
     lowPrioNewPlayers?: boolean;
@@ -102,7 +104,9 @@ const messageSchema = new Schema<IMessageDatabase>(
         ownerId: Schema.Types.ObjectId,
         sndr: String,
         msg: String,
+        cinematic: String,
         sub: String,
+        customData: String,
         icon: String,
         highPriority: Boolean,
         lowPrioNewPlayers: Boolean,
diff --git a/src/services/inventoryService.ts b/src/services/inventoryService.ts
index df9ac473..3bfb3244 100644
--- a/src/services/inventoryService.ts
+++ b/src/services/inventoryService.ts
@@ -83,7 +83,7 @@ import { addQuestKey, completeQuest } from "@/src/services/questService";
 import { handleBundleAcqusition } from "./purchaseService";
 import libraryDailyTasks from "@/static/fixed_responses/libraryDailyTasks.json";
 import { getRandomElement, getRandomInt, getRandomWeightedReward, SRng } from "./rngService";
-import { createMessage } from "./inboxService";
+import { createMessage, IMessageCreationTemplate } from "./inboxService";
 import { getMaxStanding, getMinStanding } from "@/src/helpers/syndicateStandingHelper";
 import { getNightwaveSyndicateTag, getWorldState } from "./worldStateService";
 import { ICalendarSeason } from "@/src/types/worldStateTypes";
@@ -1563,7 +1563,22 @@ export const addEmailItem = async (
     const meta = ExportEmailItems[typeName];
     const emailItem = inventory.EmailItems.find(x => x.ItemType == typeName);
     if (!emailItem || !meta.sendOnlyOnce) {
-        await createMessage(inventory.accountOwnerId, [convertInboxMessage(meta.message)]);
+        const msg: IMessageCreationTemplate = convertInboxMessage(meta.message);
+        if (msg.cinematic == "/Lotus/Levels/1999/PlayerHomeBalconyCinematics.level") {
+            msg.customData = JSON.stringify({
+                Tag: msg.customData + "KissCin",
+                CinLoadout: {
+                    Skins: inventory.AdultOperatorLoadOuts[0].Skins,
+                    Upgrades: inventory.AdultOperatorLoadOuts[0].Upgrades,
+                    attcol: inventory.AdultOperatorLoadOuts[0].attcol,
+                    cloth: inventory.AdultOperatorLoadOuts[0].cloth,
+                    eyecol: inventory.AdultOperatorLoadOuts[0].eyecol,
+                    pricol: inventory.AdultOperatorLoadOuts[0].pricol,
+                    syancol: inventory.AdultOperatorLoadOuts[0].syancol
+                }
+            });
+        }
+        await createMessage(inventory.accountOwnerId, [msg]);
 
         if (emailItem) {
             emailItem.ItemCount += 1;
diff --git a/src/services/itemDataService.ts b/src/services/itemDataService.ts
index c44691f5..e028e8c0 100644
--- a/src/services/itemDataService.ts
+++ b/src/services/itemDataService.ts
@@ -251,7 +251,9 @@ export const convertInboxMessage = (message: IInboxMessage): IMessage => {
     return {
         sndr: message.sender,
         msg: message.body,
+        cinematic: message.cinematic,
         sub: message.title,
+        customData: message.customData,
         att: message.attachments.length > 0 ? message.attachments : undefined,
         countedAtt: message.countedAttachments.length > 0 ? message.countedAttachments : undefined,
         icon: message.icon ?? "",