diff --git a/src/select/__tests__/connect-options.test.ts b/src/select/__tests__/connect-options.test.ts
index ef9b9b878e..43df365cef 100644
--- a/src/select/__tests__/connect-options.test.ts
+++ b/src/select/__tests__/connect-options.test.ts
@@ -31,4 +31,34 @@ describe('connectOptionsByValue', () => {
     const result = connectOptionsByValue([{ option }], [{ value: '1' }]);
     expect(result[0]).toEqual({ option });
   });
+
+  test('should return an empty array when there are no selected options', () => {
+    expect(connectOptionsByValue([{ option: { value: '1' } }], [])).toEqual([]);
+  });
+
+  test('should preserve the order of the selected options', () => {
+    const options = [{ option: { value: '1' } }, { option: { value: '2' } }, { option: { value: '3' } }];
+    const result = connectOptionsByValue(options, [{ value: '3' }, { value: '1' }]);
+    expect(result).toEqual([{ option: { value: '3' } }, { option: { value: '1' } }]);
+  });
+
+  test('should skip parent options when matching by value', () => {
+    const child = { option: { value: '1' }, type: 'child' as const };
+    const parent = { option: { value: '1' }, type: 'parent' as const };
+    const result = connectOptionsByValue([parent, child], [{ value: '1' }]);
+    expect(result[0]).toBe(child);
+  });
+
+  test('should return the first matching option when multiple share the same value', () => {
+    const first = { option: { value: '1', label: 'first' } };
+    const second = { option: { value: '1', label: 'second' } };
+    const result = connectOptionsByValue([first, second], [{ value: '1' }]);
+    expect(result[0]).toBe(first);
+  });
+
+  test('should match options with an undefined value', () => {
+    const option = { option: { label: 'no value' } };
+    const result = connectOptionsByValue([option], [{ label: 'no value' }]);
+    expect(result[0]).toBe(option);
+  });
 });
diff --git a/src/select/utils/connect-options.ts b/src/select/utils/connect-options.ts
index 86c2750edc..fc9a4acaf1 100644
--- a/src/select/utils/connect-options.ts
+++ b/src/select/utils/connect-options.ts
@@ -6,17 +6,19 @@ export const connectOptionsByValue = (
   options: ReadonlyArray<DropdownOption>,
   selectedOptions: ReadonlyArray<OptionDefinition>
 ): ReadonlyArray<DropdownOption> => {
-  return (selectedOptions || []).map(selectedOption => {
-    for (const dropdownOption of options) {
-      if (
-        dropdownOption.type !== 'parent' &&
-        (dropdownOption.option as OptionDefinition).value === selectedOption.value
-      ) {
-        return dropdownOption;
+  if (!selectedOptions || selectedOptions.length === 0) {
+    return [];
+  }
+  const optionByValue = new Map<OptionDefinition['value'], DropdownOption>();
+  for (const dropdownOption of options) {
+    if (dropdownOption.type !== 'parent') {
+      const value = (dropdownOption.option as OptionDefinition).value;
+      if (!optionByValue.has(value)) {
+        optionByValue.set(value, dropdownOption);
       }
     }
-    return { option: selectedOption };
-  });
+  }
+  return selectedOptions.map(selectedOption => optionByValue.get(selectedOption.value) ?? { option: selectedOption });
 };
 
 export const findOptionIndex = (options: ReadonlyArray<OptionDefinition>, option: OptionDefinition) => {
diff --git a/src/select/utils/use-select.ts b/src/select/utils/use-select.ts
index 99cc16c3a1..f650a44cb2 100644
--- a/src/select/utils/use-select.ts
+++ b/src/select/utils/use-select.ts
@@ -76,6 +76,7 @@ export function useSelect({
   const hasFilter = filteringType !== 'none' && !embedded;
   const activeRef = hasFilter ? filterRef : menuRef;
   const __selectedOptions = connectOptionsByValue(options, selectedOptions);
+  const __selectedOptionsSet = new Set(__selectedOptions);
   const __selectedValuesSet = selectedOptions.reduce((selectedValuesSet: Set<string>, item: OptionDefinition) => {
     if (item.value) {
       selectedValuesSet.add(item.value);
@@ -277,17 +278,17 @@ export function useSelect({
     const isSelectAll = option.type === 'select-all';
     const highlighted = option === highlightedOption;
     const groupState = isGroup(option.option) ? getGroupState(option.option) : undefined;
-    const selected = isSelectAll ? isAllSelected : __selectedOptions.indexOf(option) > -1 || !!groupState?.selected;
+    const selected = isSelectAll ? isAllSelected : __selectedOptionsSet.has(option) || !!groupState?.selected;
     const nextOption = options[index + 1]?.option;
     const isNextSelected =
       !!nextOption && isGroup(nextOption)
         ? getGroupState(nextOption).selected
-        : __selectedOptions.indexOf(options[index + 1]) > -1;
+        : __selectedOptionsSet.has(options[index + 1]);
     const previousOption = options[index - 1]?.option;
     const isPreviousSelected =
       !!previousOption && isGroup(previousOption)
         ? getGroupState(previousOption).selected
-        : __selectedOptions.indexOf(options[index - 1]) > -1;
+        : __selectedOptionsSet.has(options[index - 1]);
     const optionProps: any = {
       key: index,
       option,
@@ -354,7 +355,7 @@ export function useSelect({
   const highlightedGroupSelected =
     !!highlightedOption && isGroup(highlightedOption.option) && getGroupState(highlightedOption.option).selected;
   const announceSelected =
-    !!highlightedOption && (__selectedOptions.indexOf(highlightedOption) > -1 || highlightedGroupSelected);
+    !!highlightedOption && (__selectedOptionsSet.has(highlightedOption) || highlightedGroupSelected);
 
   return {
     isOpen,