diff --git a/app/modules/asset/service.server.ts b/app/modules/asset/service.server.ts
index ba5980955..6a63872a2 100644
--- a/app/modules/asset/service.server.ts
+++ b/app/modules/asset/service.server.ts
@@ -838,6 +838,7 @@ export async function updateAssetMainImage({
   });
 }
 
+/** Creates a singular note */
 export async function createNote({
   content,
   type,
@@ -868,6 +869,29 @@ export async function createNote({
   });
 }
 
+/** Creates multiple notes with the same content */
+export async function createNotes({
+  content,
+  type,
+  userId,
+  assetIds,
+}: Pick<Note, "content"> & {
+  type?: Note["type"];
+  userId: User["id"];
+  assetIds: Asset["id"][];
+}) {
+  const data = assetIds.map((id) => ({
+    content,
+    type: type || "COMMENT",
+    userId,
+    assetId: id,
+  }));
+
+  return db.note.createMany({
+    data,
+  });
+}
+
 export async function deleteNote({
   id,
   userId,
diff --git a/app/modules/booking/email-helpers.ts b/app/modules/booking/email-helpers.ts
index 75dc4f44d..c26d69cfb 100644
--- a/app/modules/booking/email-helpers.ts
+++ b/app/modules/booking/email-helpers.ts
@@ -179,7 +179,7 @@ export const sendCheckinReminder = async (
       heading: `Your booking is due for checkin in ${getTimeRemainingMessage(
         new Date(booking.to!),
         new Date()
-      )} minutes.`,
+      )}.`,
       assetCount,
       hints,
     }),
diff --git a/app/modules/booking/service.server.ts b/app/modules/booking/service.server.ts
index 22de08ff5..c88ce0cea 100644
--- a/app/modules/booking/service.server.ts
+++ b/app/modules/booking/service.server.ts
@@ -21,6 +21,7 @@ import {
   sendCheckinReminder,
 } from "./email-helpers";
 import type { ClientHint, SchedulerData } from "./types";
+import { createNotes } from "../asset";
 import { getOrganizationAdminsEmails } from "../organization";
 
 /** Includes needed for booking to have all data required for emails */
@@ -271,7 +272,7 @@ export const upsertBooking = async (
                 /** We need to invoke this function separately for the admin email as the footer of emails is different */
                 html: bookingUpdatesTemplateString({
                   booking: res,
-                  heading: `Booking reservation for ${custodian}`,
+                  heading: `Booking reservation request for ${custodian}`,
                   assetCount: res.assets.length,
                   hints,
                   isAdminEmail: true,
@@ -515,9 +516,19 @@ export async function getBookings({
   return { bookings, bookingCount };
 }
 
-export const removeAssets = async (
-  booking: Pick<Booking, "id"> & { assetIds: Asset["id"][] }
-) => {
+export const removeAssets = async ({
+  booking,
+  firstName,
+  lastName,
+  userId,
+}: {
+  booking: Pick<Booking, "id"> & {
+    assetIds: Asset["id"][];
+  };
+  firstName: string;
+  lastName: string;
+  userId: string;
+}) => {
   const { assetIds, id } = booking;
   const b = await db.booking.update({
     // First, disconnect the assets from the booking
@@ -549,6 +560,15 @@ export const removeAssets = async (
     });
   }
 
+  createNotes({
+    content: `**${firstName?.trim()} ${lastName?.trim()}** removed asset from booking **[${
+      b.name
+    }](/bookings/${b.id})**.`,
+    type: "UPDATE",
+    userId,
+    assetIds,
+  });
+
   return b;
 };
 
@@ -575,6 +595,11 @@ export const deleteBooking = async (
     include: {
       ...commonInclude,
       ...bookingIncludeForEmails,
+      assets: {
+        select: {
+          id: true,
+        },
+      },
     },
   });
 
diff --git a/app/modules/user/service.server.ts b/app/modules/user/service.server.ts
index 8f677f9da..d0247fbc2 100644
--- a/app/modules/user/service.server.ts
+++ b/app/modules/user/service.server.ts
@@ -36,7 +36,14 @@ export async function getUserByEmail(email: User["email"]) {
 }
 
 export async function getUserByID(id: User["id"]) {
-  return db.user.findUnique({ where: { id } });
+  try {
+    return db.user.findUnique({ where: { id } });
+  } catch (cause) {
+    throw new ShelfStackError({
+      message: "Failed to get user",
+      cause,
+    });
+  }
 }
 
 export async function getUserByIDWithOrg(id: User["id"]) {
diff --git a/app/routes/_layout+/bookings.$bookingId.add-assets.tsx b/app/routes/_layout+/bookings.$bookingId.add-assets.tsx
index 623cd586d..229a29f19 100644
--- a/app/routes/_layout+/bookings.$bookingId.add-assets.tsx
+++ b/app/routes/_layout+/bookings.$bookingId.add-assets.tsx
@@ -26,8 +26,9 @@ import { AddAssetForm } from "~/components/location/add-asset-form";
 import { Button } from "~/components/shared";
 
 import { Td } from "~/components/table";
-import { getPaginatedAndFilterableAssets } from "~/modules/asset";
+import { createNote, getPaginatedAndFilterableAssets } from "~/modules/asset";
 import { getBooking, removeAssets, upsertBooking } from "~/modules/booking";
+import { getUserByID } from "~/modules/user";
 import { getRequiredParam, isFormProcessing } from "~/utils";
 import { getClientHint } from "~/utils/client-hints";
 import { ShelfStackError } from "~/utils/error";
@@ -92,7 +93,7 @@ export const loader = async ({ request, params }: LoaderFunctionArgs) => {
 };
 
 export const action = async ({ request, params }: ActionFunctionArgs) => {
-  await requirePermision(
+  const { authSession } = await requirePermision(
     request,
     PermissionEntity.booking,
     PermissionAction.update
@@ -102,18 +103,39 @@ export const action = async ({ request, params }: ActionFunctionArgs) => {
   const formData = await request.formData();
   const assetId = formData.get("assetId") as string;
   const isChecked = formData.get("isChecked") === "yes";
+  const user = await getUserByID(authSession.userId);
+  if (!user) {
+    throw new ShelfStackError({ message: "User not found" });
+  }
+
   if (isChecked) {
-    await upsertBooking(
+    const b = await upsertBooking(
       {
         id: bookingId,
         assetIds: [assetId],
       },
       getClientHint(request)
     );
+    /** We check the ids again after updating, and if they were sent, that means assets are being added
+     * So we create notes for the assets that were added
+     */
+    await createNote({
+      content: `**${user?.firstName?.trim()} ${user?.lastName?.trim()}** added asset to booking **[${
+        b.name
+      }](/bookings/${b.id})**.`,
+      type: "UPDATE",
+      userId: authSession.userId,
+      assetId,
+    });
   } else {
     await removeAssets({
-      id: bookingId,
-      assetIds: [assetId],
+      booking: {
+        id: bookingId,
+        assetIds: [assetId],
+      },
+      firstName: user.firstName ? user.firstName : "",
+      lastName: user.lastName ? user.lastName : "",
+      userId: authSession.userId,
     });
   }
 
diff --git a/app/routes/_layout+/bookings.$bookingId.tsx b/app/routes/_layout+/bookings.$bookingId.tsx
index 12fec54ea..f080d964b 100644
--- a/app/routes/_layout+/bookings.$bookingId.tsx
+++ b/app/routes/_layout+/bookings.$bookingId.tsx
@@ -18,6 +18,7 @@ import Header from "~/components/layout/header";
 import type { HeaderData } from "~/components/layout/header/types";
 import { Badge } from "~/components/shared";
 import { db } from "~/database";
+import { createNotes } from "~/modules/asset";
 import { commitAuthSession } from "~/modules/auth";
 import {
   deleteBooking,
@@ -215,6 +216,7 @@ export async function action({ request, params }: ActionFunctionArgs) {
   );
   const id = getRequiredParam(params, "bookingId");
   const isSelfService = role === OrganizationRoles.SELF_SERVICE;
+  const user = await getUserByID(authSession.userId);
 
   switch (intent) {
     case "save":
@@ -316,7 +318,20 @@ export async function action({ request, params }: ActionFunctionArgs) {
         }
       }
 
-      await deleteBooking({ id }, getClientHint(request));
+      const deletedBooking = await deleteBooking(
+        { id },
+        getClientHint(request)
+      );
+
+      createNotes({
+        content: `**${user?.firstName?.trim()} ${user?.lastName?.trim()}** deleted booking **${
+          deletedBooking.name
+        }**.`,
+        type: "UPDATE",
+        userId: authSession.userId,
+        assetIds: deletedBooking.assets.map((a) => a.id),
+      });
+
       sendNotification({
         title: "Booking deleted",
         message: "Your booking has been deleted successfully",
@@ -331,8 +346,12 @@ export async function action({ request, params }: ActionFunctionArgs) {
       });
     case "removeAsset":
       const assetId = formData.get("assetId");
-      // @ts-ignore @TODO we need to fix this. Not sure how
-      var booking = await removeAssets({ id, assetIds: [assetId as string] });
+      var b = await removeAssets({
+        booking: { id, assetIds: [assetId as string] },
+        firstName: user?.firstName || "",
+        lastName: user?.lastName || "",
+        userId: authSession.userId,
+      });
       sendNotification({
         title: "Asset removed",
         message: "Your asset has been removed from the booking",
@@ -340,7 +359,7 @@ export async function action({ request, params }: ActionFunctionArgs) {
         senderId: authSession.userId,
       });
       return json(
-        { booking },
+        { booking: b },
         {
           status: 200,
           headers: [
@@ -354,6 +373,16 @@ export async function action({ request, params }: ActionFunctionArgs) {
         { id, status: BookingStatus.ONGOING },
         getClientHint(request)
       );
+
+      createNotes({
+        content: `**${user?.firstName?.trim()} ${user?.lastName?.trim()}** checked out asset with **[${
+          booking.name
+        }](/bookings/${booking.id})**.`,
+        type: "UPDATE",
+        userId: authSession.userId,
+        assetIds: booking.assets.map((a) => a.id),
+      });
+
       sendNotification({
         title: "Booking checked-out",
         message: "Your booking has been checked-out successfully",
@@ -377,6 +406,15 @@ export async function action({ request, params }: ActionFunctionArgs) {
         },
         getClientHint(request)
       );
+      /** Create check-in notes for all assets */
+      createNotes({
+        content: `**${user?.firstName?.trim()} ${user?.lastName?.trim()}** checked in asset with **[${
+          booking.name
+        }](/bookings/${booking.id})**.`,
+        type: "UPDATE",
+        userId: authSession.userId,
+        assetIds: booking.assets.map((a) => a.id),
+      });
       sendNotification({
         title: "Booking checked-in",
         message: "Your booking has been checked-in successfully",
@@ -413,10 +451,19 @@ export async function action({ request, params }: ActionFunctionArgs) {
         }
       );
     case "cancel":
-      await upsertBooking(
+      const cancelledBooking = await upsertBooking(
         { id, status: BookingStatus.CANCELLED },
         getClientHint(request)
       );
+
+      createNotes({
+        content: `**${user?.firstName?.trim()} ${user?.lastName?.trim()}** cancelled booking **[${
+          cancelledBooking.name
+        }](/bookings/${cancelledBooking.id})**.`,
+        type: "UPDATE",
+        userId: authSession.userId,
+        assetIds: cancelledBooking.assets.map((a) => a.id),
+      });
       sendNotification({
         title: "Booking canceled",
         message: "Your booking has been canceled successfully",