diff --git a/src/components/admin/store/PickupOrder/index.tsx b/src/components/admin/store/PickupOrder/index.tsx
index 81bd1e63..c23bc937 100644
--- a/src/components/admin/store/PickupOrder/index.tsx
+++ b/src/components/admin/store/PickupOrder/index.tsx
@@ -1,9 +1,11 @@
 import { Button, Typography } from '@/components/common';
 import { OrderStatusIndicator } from '@/components/store';
 import { StoreAPI } from '@/lib/api';
-import { PublicOrderItemWithQuantity, PublicOrderWithItems } from '@/lib/types/apiResponses';
+import { UUID } from '@/lib/types';
+import { PublicOrderWithItems } from '@/lib/types/apiResponses';
 import { OrderStatus } from '@/lib/types/enums';
-import { getOrderItemQuantities, reportError } from '@/lib/utils';
+import { getOrderItemQuantities, itemToString, reportError } from '@/lib/utils';
+import { useState } from 'react';
 import styles from './style.module.scss';
 
 interface PickupOrderProps {
@@ -13,27 +15,23 @@ interface PickupOrderProps {
   onOrderUpdate: (orders: PublicOrderWithItems) => void;
 }
 
-const itemToString = (item: PublicOrderItemWithQuantity): string => {
-  if (item.option.metadata !== null)
-    return `${item.option.item.itemName} (${item.option.metadata.type}: ${item.option.metadata.value})`;
-  return item.option.item.itemName;
-};
-
 const PickupOrder = ({ token, canFulfill, order, onOrderUpdate }: PickupOrderProps) => {
-  const showFulfill = canFulfill && order.status === OrderStatus.PLACED;
   const itemQuantities = getOrderItemQuantities(order.items);
+  const [unselected, setUnselected] = useState(new Set<UUID>());
+
   return (
     <tr className={styles.row}>
       <td>
         <Typography variant="h5/regular">{`${order.user.firstName} ${order.user.lastName}`}</Typography>
         <OrderStatusIndicator orderStatus={order.status} />
-        {showFulfill && itemQuantities.length > 1 ? (
+        {canFulfill ? (
           <Button
             size="small"
             onClick={async () => {
               try {
-                const newOrder = await StoreAPI.fulfillOrderPickup(token, order.uuid, order.items);
-                const itemUuids = order.items.map(item => item.uuid);
+                const items = order.items.filter(item => !unselected.has(item.uuid));
+                const newOrder = await StoreAPI.fulfillOrderPickup(token, order.uuid, items);
+                const itemUuids = items.map(item => item.uuid);
                 onOrderUpdate({
                   ...newOrder,
                   items: order.items.map(item =>
@@ -45,7 +43,7 @@ const PickupOrder = ({ token, canFulfill, order, onOrderUpdate }: PickupOrderPro
               }
             }}
           >
-            Fulfill
+            Fulfill {unselected.size > 0 ? 'Selected' : 'All'}
           </Button>
         ) : null}
       </td>
@@ -53,10 +51,33 @@ const PickupOrder = ({ token, canFulfill, order, onOrderUpdate }: PickupOrderPro
         <ul className={styles.itemList}>
           {itemQuantities.map(item => {
             return (
-              <li key={item.uuid}>
-                <Typography variant="h5/regular">{`${item.quantity} x ${itemToString(
-                  item
-                )}`}</Typography>
+              <li key={item.uuids[0]}>
+                <Typography variant="h5/regular">
+                  {`${item.quantity} x ${itemToString(item)}`}{' '}
+                  {(order.status === OrderStatus.FULFILLED ||
+                    order.status === OrderStatus.PARTIALLY_FULFILLED) &&
+                  !item.fulfilled ? (
+                    <span className={styles.notFulfilled}>Not fulfilled</span>
+                  ) : null}
+                </Typography>
+                {canFulfill
+                  ? item.uuids.map(uuid => (
+                      <input
+                        key={uuid}
+                        type="checkbox"
+                        checked={!unselected.has(uuid)}
+                        onChange={e => {
+                          const copy = new Set(unselected);
+                          if (e.currentTarget.checked) {
+                            copy.delete(uuid);
+                          } else {
+                            copy.add(uuid);
+                          }
+                          setUnselected(copy);
+                        }}
+                      />
+                    ))
+                  : null}
               </li>
             );
           })}
diff --git a/src/components/admin/store/PickupOrder/style.module.scss b/src/components/admin/store/PickupOrder/style.module.scss
index 20869336..c75d6b8b 100644
--- a/src/components/admin/store/PickupOrder/style.module.scss
+++ b/src/components/admin/store/PickupOrder/style.module.scss
@@ -1,3 +1,5 @@
+@use 'src/styles/vars.scss' as vars;
+
 .row {
   border-top: 1px solid var(--theme-accent-line-2);
 
@@ -13,6 +15,10 @@
       display: flex;
       flex-wrap: wrap;
       gap: 10px;
+
+      .notFulfilled {
+        color: vars.$red;
+      }
     }
   }
 }
diff --git a/src/components/admin/store/PickupOrder/style.module.scss.d.ts b/src/components/admin/store/PickupOrder/style.module.scss.d.ts
index 7e31b756..85e9c3bb 100644
--- a/src/components/admin/store/PickupOrder/style.module.scss.d.ts
+++ b/src/components/admin/store/PickupOrder/style.module.scss.d.ts
@@ -1,5 +1,6 @@
 export type Styles = {
   itemList: string;
+  notFulfilled: string;
   row: string;
 };
 
diff --git a/src/components/admin/store/PickupOrdersPrepareDisplay/index.tsx b/src/components/admin/store/PickupOrdersPrepareDisplay/index.tsx
index b1352574..ea6268c7 100644
--- a/src/components/admin/store/PickupOrdersPrepareDisplay/index.tsx
+++ b/src/components/admin/store/PickupOrdersPrepareDisplay/index.tsx
@@ -1,7 +1,8 @@
 import PickupOrder from '@/components/admin/store/PickupOrder';
 import { Typography } from '@/components/common';
-import { PublicOrderItemWithQuantity, PublicOrderWithItems } from '@/lib/types/apiResponses';
-import { getOrderItemQuantities } from '@/lib/utils';
+import { PublicOrderWithItems } from '@/lib/types/apiResponses';
+import { OrderStatus } from '@/lib/types/enums';
+import { OrderItemQuantity, getOrderItemQuantities, itemToString } from '@/lib/utils';
 import { useMemo } from 'react';
 import styles from './style.module.scss';
 
@@ -12,19 +13,13 @@ interface PickupOrdersDisplayPrepareProps {
   onOrderUpdate: (orders: PublicOrderWithItems[]) => void;
 }
 
-const itemToString = (item: PublicOrderItemWithQuantity): string => {
-  if (item.option.metadata !== null)
-    return `${item.option.item.itemName} (${item.option.metadata.type}: ${item.option.metadata.value})`;
-  return item.option.item.itemName;
-};
-
 const PickupOrdersPrepareDisplay = ({
   token,
   canFulfill,
   orders,
   onOrderUpdate,
 }: PickupOrdersDisplayPrepareProps) => {
-  const itemBreakdown: PublicOrderItemWithQuantity[] = useMemo(() => {
+  const itemBreakdown: OrderItemQuantity[] = useMemo(() => {
     // Concatenate all items together into one large order to display the item breakdown.
     const allItems = orders.flatMap(a => a.items);
     return getOrderItemQuantities(allItems);
@@ -48,7 +43,7 @@ const PickupOrdersPrepareDisplay = ({
           <tbody>
             {itemBreakdown.map(item => {
               return (
-                <tr key={item.uuid}>
+                <tr key={item.uuids[0]}>
                   <td>
                     <Typography variant="h5/regular">{item.quantity}</Typography>
                   </td>
@@ -77,7 +72,7 @@ const PickupOrdersPrepareDisplay = ({
           <tbody>
             {orders.map(order => (
               <PickupOrder
-                canFulfill={canFulfill}
+                canFulfill={canFulfill && order.status === OrderStatus.PLACED}
                 order={order}
                 onOrderUpdate={newOrder =>
                   onOrderUpdate(
diff --git a/src/components/admin/store/PickupOrdersPrepareDisplay/style.module.scss b/src/components/admin/store/PickupOrdersPrepareDisplay/style.module.scss
index e57b1d91..c9cc255d 100644
--- a/src/components/admin/store/PickupOrdersPrepareDisplay/style.module.scss
+++ b/src/components/admin/store/PickupOrdersPrepareDisplay/style.module.scss
@@ -22,4 +22,12 @@
     padding: 1rem 1.5rem;
     text-align: left;
   }
+
+  td {
+    padding: 1.5rem;
+  }
+
+  tbody tr {
+    border-top: 1px solid var(--theme-accent-line-2);
+  }
 }
diff --git a/src/lib/utils.ts b/src/lib/utils.ts
index 6eb99ef0..d54b9856 100644
--- a/src/lib/utils.ts
+++ b/src/lib/utils.ts
@@ -1,7 +1,7 @@
 import defaultProfilePictures from '@/lib/constants/profilePictures';
 import ranks from '@/lib/constants/ranks';
 import showToast from '@/lib/showToast';
-import type { URL } from '@/lib/types';
+import type { URL, UUID } from '@/lib/types';
 import type {
   ApiResponse,
   CustomErrorBody,
@@ -388,25 +388,34 @@ export const isOrderPickupEvent = (
   event: PublicOrderPickupEvent | PublicEvent
 ): event is PublicOrderPickupEvent => 'status' in event;
 
+export type OrderItemQuantity = Omit<PublicOrderItemWithQuantity, 'uuid'> & { uuids: UUID[] };
+
 /**
  * Condenses a list of ordered items into unique items with quantities.
  */
-export const getOrderItemQuantities = (items: PublicOrderItem[]): PublicOrderItemWithQuantity[] => {
-  const itemMap = new Map<string, PublicOrderItemWithQuantity>();
+export const getOrderItemQuantities = (items: PublicOrderItem[]): OrderItemQuantity[] => {
+  const itemMap = new Map<string, OrderItemQuantity>();
 
   items.forEach(item => {
     const hash = `${item.option.uuid} ${item.fulfilled}`;
     const existingItem = itemMap.get(hash);
     if (existingItem) {
       existingItem.quantity += 1;
+      existingItem.uuids.push(item.uuid);
     } else {
-      itemMap.set(hash, { ...item, quantity: 1 });
+      itemMap.set(hash, { ...item, quantity: 1, uuids: [item.uuid] });
     }
   });
 
   return Array.from(itemMap.values());
 };
 
+export const itemToString = (item: Pick<PublicOrderItem, 'option'>): string => {
+  if (item.option.metadata !== null)
+    return `${item.option.item.itemName} (${item.option.metadata.type}: ${item.option.metadata.value})`;
+  return item.option.item.itemName;
+};
+
 export function isEnum<T extends Record<string, string>>(
   Enum: T,
   value: string