diff --git a/src/CONST/index.ts b/src/CONST/index.ts
index 48819c93f275..cfb630ca73b5 100755
--- a/src/CONST/index.ts
+++ b/src/CONST/index.ts
@@ -6696,6 +6696,8 @@ const CONST = {
                     TO: this.TABLE_COLUMNS.TO,
                     CATEGORY: this.TABLE_COLUMNS.CATEGORY,
                     TAG: this.TABLE_COLUMNS.TAG,
+                    REIMBURSABLE: this.TABLE_COLUMNS.REIMBURSABLE,
+                    BILLABLE: this.TABLE_COLUMNS.BILLABLE,
                     STATUS: this.TABLE_COLUMNS.STATUS,
                     ACTION: this.TABLE_COLUMNS.ACTION,
                 },
@@ -6789,6 +6791,8 @@ const CONST = {
             TO: 'to',
             CATEGORY: 'category',
             TAG: 'tag',
+            REIMBURSABLE: 'reimbursable',
+            BILLABLE: 'billable',
             TOTAL_AMOUNT: 'amount',
             TOTAL: 'total',
             TYPE: 'type',
diff --git a/src/components/SelectionListWithSections/SearchTableHeader.tsx b/src/components/SelectionListWithSections/SearchTableHeader.tsx
index d55e102ac7ea..307a42931b8e 100644
--- a/src/components/SelectionListWithSections/SearchTableHeader.tsx
+++ b/src/components/SelectionListWithSections/SearchTableHeader.tsx
@@ -80,6 +80,16 @@ const getExpenseHeaders = (groupBy?: SearchGroupBy): SearchColumnConfig[] => [
         translationKey: 'common.tag',
         canBeMissing: true,
     },
+    {
+        columnName: CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE,
+        translationKey: 'common.reimbursable',
+        canBeMissing: true,
+    },
+    {
+        columnName: CONST.SEARCH.TABLE_COLUMNS.BILLABLE,
+        translationKey: 'common.billable',
+        canBeMissing: true,
+    },
     {
         columnName: CONST.SEARCH.TABLE_COLUMNS.WITHDRAWAL_ID,
         translationKey: 'common.withdrawalID',
diff --git a/src/components/TransactionItemRow/index.tsx b/src/components/TransactionItemRow/index.tsx
index 8b3606761416..6295983cbc78 100644
--- a/src/components/TransactionItemRow/index.tsx
+++ b/src/components/TransactionItemRow/index.tsx
@@ -311,6 +311,22 @@ function TransactionItemRow({
                     />
                 </View>
             ),
+            [CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE]: (
+                <View
+                    key={CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE}
+                    style={[StyleUtils.getReportTableColumnStyles(CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE)]}
+                >
+                    <Text>{transactionItem.reimbursable ? translate('common.yes') : translate('common.no')}</Text>
+                </View>
+            ),
+            [CONST.SEARCH.TABLE_COLUMNS.BILLABLE]: (
+                <View
+                    key={CONST.SEARCH.TABLE_COLUMNS.BILLABLE}
+                    style={[StyleUtils.getReportTableColumnStyles(CONST.SEARCH.TABLE_COLUMNS.BILLABLE)]}
+                >
+                    <Text>{transactionItem.billable ? translate('common.yes') : translate('common.no')}</Text>
+                </View>
+            ),
             [CONST.SEARCH.TABLE_COLUMNS.ACTION]: (
                 <View
                     key={CONST.SEARCH.TABLE_COLUMNS.ACTION}
@@ -433,6 +449,7 @@ function TransactionItemRow({
             ),
         }),
         [
+            translate,
             StyleUtils,
             createdAt,
             report?.submitted,
diff --git a/src/libs/SearchUIUtils.ts b/src/libs/SearchUIUtils.ts
index 2ce5e4adb71c..3b64d43f3e3c 100644
--- a/src/libs/SearchUIUtils.ts
+++ b/src/libs/SearchUIUtils.ts
@@ -145,6 +145,8 @@ const transactionColumnNamesToSortingProperty: TransactionSorting = {
     [CONST.SEARCH.TABLE_COLUMNS.MERCHANT]: 'formattedMerchant' as const,
     [CONST.SEARCH.TABLE_COLUMNS.TOTAL_AMOUNT]: 'formattedTotal' as const,
     [CONST.SEARCH.TABLE_COLUMNS.CATEGORY]: 'category' as const,
+    [CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE]: 'reimbursable' as const,
+    [CONST.SEARCH.TABLE_COLUMNS.BILLABLE]: 'billable' as const,
     [CONST.SEARCH.TABLE_COLUMNS.TYPE]: null,
     [CONST.SEARCH.TABLE_COLUMNS.ACTION]: 'action' as const,
     [CONST.SEARCH.TABLE_COLUMNS.DESCRIPTION]: 'comment' as const,
@@ -2005,6 +2007,24 @@ function compareValues(a: unknown, b: unknown, sortOrder: SortOrder, sortBy: str
     return 0;
 }
 
+/**
+ * @private
+ * Gets the value to use for sorting a transaction by a given property.
+ * Handles special cases like comments and boolean fields (reimbursable, billable).
+ */
+function getTransactionSortValue(transaction: TransactionListItemType, sortingProperty: string): unknown {
+    if (sortingProperty === 'comment') {
+        return transaction.comment?.comment;
+    }
+
+    if (sortingProperty === 'reimbursable' || sortingProperty === 'billable') {
+        const boolValue = transaction[sortingProperty as keyof TransactionListItemType];
+        return boolValue ? CONST.SEARCH.BOOLEAN.YES : CONST.SEARCH.BOOLEAN.NO;
+    }
+
+    return transaction[sortingProperty as keyof TransactionListItemType];
+}
+
 /**
  * @private
  * Sorts transaction sections based on a specified column and sort order.
@@ -2042,10 +2062,23 @@ function getSortedTransactionData(
     }
 
     return data.sort((a, b) => {
-        const aValue = sortingProperty === 'comment' ? a.comment?.comment : a[sortingProperty as keyof TransactionListItemType];
-        const bValue = sortingProperty === 'comment' ? b.comment?.comment : b[sortingProperty as keyof TransactionListItemType];
+        const aValue = getTransactionSortValue(a, sortingProperty);
+        const bValue = getTransactionSortValue(b, sortingProperty);
 
-        return compareValues(aValue, bValue, sortOrder, sortingProperty, localeCompare);
+        const primaryComparison = compareValues(aValue, bValue, sortOrder, sortingProperty, localeCompare);
+
+        if (primaryComparison !== 0) {
+            return primaryComparison;
+        }
+
+        // If we have a tie in the primary comparison, we add a tie breaker on date and/or transactionID as a last resort to make the sort deterministic
+        const createdComparison = compareValues(a.created, b.created, sortOrder, 'created', localeCompare);
+
+        if (createdComparison !== 0) {
+            return createdComparison;
+        }
+
+        return compareValues(a.transactionID, b.transactionID, sortOrder, 'transactionID', localeCompare);
     });
 }
 
@@ -2246,6 +2279,10 @@ function getSearchColumnTranslationKey(columnId: SearchCustomColumnIds): Transla
             return 'common.receipt';
         case CONST.SEARCH.TABLE_COLUMNS.TAG:
             return 'common.tag';
+        case CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE:
+            return 'common.reimbursable';
+        case CONST.SEARCH.TABLE_COLUMNS.BILLABLE:
+            return 'common.billable';
         case CONST.SEARCH.TABLE_COLUMNS.ACTION:
             return 'common.action';
         case CONST.SEARCH.TABLE_COLUMNS.TITLE:
@@ -2711,6 +2748,8 @@ function getColumnsToShow(
               [CONST.SEARCH.TABLE_COLUMNS.TO]: false,
               [CONST.SEARCH.TABLE_COLUMNS.CATEGORY]: false,
               [CONST.SEARCH.TABLE_COLUMNS.TAG]: false,
+              [CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE]: false,
+              [CONST.SEARCH.TABLE_COLUMNS.BILLABLE]: false,
               [CONST.SEARCH.TABLE_COLUMNS.TAX_AMOUNT]: false,
               [CONST.SEARCH.TABLE_COLUMNS.TOTAL_AMOUNT]: true,
               [CONST.SEARCH.TABLE_COLUMNS.STATUS]: false,
@@ -2920,6 +2959,8 @@ function getTableMinWidth(columns: SearchColumnType[]) {
             minWidth += 72;
         } else if (column === CONST.SEARCH.TABLE_COLUMNS.TYPE) {
             minWidth += 20;
+        } else if (column === CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE || column === CONST.SEARCH.TABLE_COLUMNS.BILLABLE) {
+            minWidth += 92;
         } else {
             minWidth += 200;
         }
diff --git a/src/styles/utils/index.ts b/src/styles/utils/index.ts
index d1cb7ea5711c..ad0a69a8b65f 100644
--- a/src/styles/utils/index.ts
+++ b/src/styles/utils/index.ts
@@ -1771,6 +1771,10 @@ const createStyleUtils = (theme: ThemeColors, styles: ThemeStyles) => ({
             case CONST.SEARCH.TABLE_COLUMNS.TYPE:
                 columnWidth = {...getWidthStyle(variables.w20), ...styles.alignItemsCenter};
                 break;
+            case CONST.SEARCH.TABLE_COLUMNS.REIMBURSABLE:
+            case CONST.SEARCH.TABLE_COLUMNS.BILLABLE:
+                columnWidth = {...getWidthStyle(variables.w92)};
+                break;
             case CONST.SEARCH.TABLE_COLUMNS.ACTION:
                 columnWidth = {...getWidthStyle(variables.w80), ...styles.alignItemsCenter};
                 break;
diff --git a/src/types/onyx/SearchResults.ts b/src/types/onyx/SearchResults.ts
index 8e273aa050bf..b4c1b566c49c 100644
--- a/src/types/onyx/SearchResults.ts
+++ b/src/types/onyx/SearchResults.ts
@@ -170,6 +170,12 @@ type SearchTransaction = {
     /** The group currency if the transaction is grouped. Defaults to the active policy currency if group has no target currency */
     groupCurrency?: string;
 
+    /** Reimbursable status of the transaction */
+    reimbursable?: boolean;
+
+    /** Billable status of the transaction */
+    billable?: boolean;
+
     /** The card transaction's posted date */
     posted?: string;
 };