diff --git a/src/components/input/Select.tsx b/src/components/input/Select.tsx
index 15c2e2df4..fadda06b3 100644
--- a/src/components/input/Select.tsx
+++ b/src/components/input/Select.tsx
@@ -5,6 +5,7 @@ import {
   useContext,
   useId,
   useLayoutEffect,
+  useMemo,
   useRef,
   useState,
 } from 'preact/hooks';
@@ -77,9 +78,23 @@ function SelectOption<T>({
   }
 
   const { selectValue, value: currentValue, multiple } = selectContext;
-  const selected =
-    !disabled &&
-    ((multiple && currentValue.includes(value)) || currentValue === value);
+  const selected = useMemo(() => {
+    if (disabled) {
+      return false;
+    }
+
+    if (!multiple) {
+      return currentValue === value;
+    }
+
+    // In multi-select, the option should be marked as selected for values
+    // which are explicitly part of the array, or for `undefined` values if the
+    // array is empty
+    return (
+      currentValue.includes(value) ||
+      (currentValue.length === 0 && value === undefined)
+    );
+  }, [currentValue, disabled, multiple, value]);
 
   const selectOneValue = useCallback(() => {
     const options: SelectValueOptions = { closeListbox: true };
@@ -96,10 +111,14 @@ function SelectOption<T>({
       return;
     }
 
-    const options: SelectValueOptions = { closeListbox: false };
+    const options: SelectValueOptions = {
+      // Close listbox only if selected value is a "clear" option. Clear options
+      // are those with `undefined` value
+      closeListbox: value === undefined,
+    };
 
-    // In multi-select, clear selection for nullish values
-    if (!value) {
+    // In multi-select, clear selection for `undefined` values
+    if (value === undefined) {
       selectValue([], options);
       return;
     }
diff --git a/src/components/input/test/Select-test.js b/src/components/input/test/Select-test.js
index 760b1c8f5..e5ee3fa51 100644
--- a/src/components/input/test/Select-test.js
+++ b/src/components/input/test/Select-test.js
@@ -37,7 +37,12 @@ describe('Select', () => {
     const wrapper = mount(
       <Component value={undefined} onChange={sinon.stub()} {...props}>
         <Component.Option value={undefined}>
-          <span data-testid="option-reset">Reset</span>
+          {({ selected }) => (
+            <span data-testid="option-reset">
+              Reset
+              {selected && <span data-testid="selected-option" />}
+            </span>
+          )}
         </Component.Option>
         {items.map(item => (
           <Component.Option
@@ -136,6 +141,11 @@ describe('Select', () => {
     checkbox.getDOMNode().dispatchEvent(new KeyboardEvent('keydown', { key }));
   }
 
+  const isOptionSelected = (wrapper, id) =>
+    wrapper
+      .find(`[data-testid="option-${id}"]`)
+      .exists('[data-testid="selected-option"]');
+
   it('changes selected value when an option is clicked', () => {
     const onChange = sinon.stub();
     const wrapper = createComponent({ onChange });
@@ -186,16 +196,12 @@ describe('Select', () => {
 
   it('marks the right item as selected', () => {
     const wrapper = createComponent({ value: items[2] });
-    const isOptionSelected = id =>
-      wrapper
-        .find(`[data-testid="option-${id}"]`)
-        .exists('[data-testid="selected-option"]');
 
-    assert.isFalse(isOptionSelected(1));
-    assert.isFalse(isOptionSelected(2));
-    assert.isTrue(isOptionSelected(3));
-    assert.isFalse(isOptionSelected(4));
-    assert.isFalse(isOptionSelected(5));
+    assert.isFalse(isOptionSelected(wrapper, 1));
+    assert.isFalse(isOptionSelected(wrapper, 2));
+    assert.isTrue(isOptionSelected(wrapper, 3));
+    assert.isFalse(isOptionSelected(wrapper, 4));
+    assert.isFalse(isOptionSelected(wrapper, 5));
   });
 
   it('marks the right item as disabled', () => {
@@ -478,6 +484,16 @@ describe('Select', () => {
       });
     });
 
+    [
+      { value: [], isResetSelected: true },
+      { value: [items[0], items[2]], isResetSelected: false },
+    ].forEach(({ value, isResetSelected }) => {
+      it('marks reset option as selected when value is empty', () => {
+        const wrapper = createComponent({ value }, { Component: MultiSelect });
+        assert.equal(isOptionSelected(wrapper, 'reset'), isResetSelected);
+      });
+    });
+
     ['Enter', ' '].forEach(key => {
       it(`does not change selected value when ${key} is pressed in an option's checkbox`, () => {
         const onChange = sinon.stub();