diff --git a/packages/@headlessui-react/src/components/listbox/listbox.test.tsx b/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
index eea9fc118c..2a48fca509 100644
--- a/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
+++ b/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
@@ -3108,6 +3108,79 @@ describe('Keyboard interactions', () => {
         assertActiveListboxOption(options[3])
       })
     )
+
+    it(
+      'should stay on the same item while keystrokes still match',
+      suppressConsoleLogs(async () => {
+        render(
+          <Listbox value={undefined} onChange={console.log}>
+            <Listbox.Button>Trigger</Listbox.Button>
+            <Listbox.Options>
+              <Listbox.Option value="a">alice</Listbox.Option>
+              <Listbox.Option value="b">bob</Listbox.Option>
+              <Listbox.Option value="c">charlie</Listbox.Option>
+              <Listbox.Option value="d">bob</Listbox.Option>
+            </Listbox.Options>
+          </Listbox>
+        )
+
+        // Open listbox
+        await click(getListboxButton())
+
+        let options = getListboxOptions()
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "b" in "bob"
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "b" in "bob" again
+        await type(word('b'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "bo" in "bob"
+        await type(word('bo'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "bo" in "bob" again
+        await type(word('bo'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "bob" in "bob"
+        await type(word('bob'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "bob" in "bob" again
+        await type(word('bob'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+      })
+    )
   })
 })
 
diff --git a/packages/@headlessui-react/src/components/listbox/listbox.tsx b/packages/@headlessui-react/src/components/listbox/listbox.tsx
index da2741cef6..1931534f6d 100644
--- a/packages/@headlessui-react/src/components/listbox/listbox.tsx
+++ b/packages/@headlessui-react/src/components/listbox/listbox.tsx
@@ -130,13 +130,16 @@ let reducers: {
     if (state.disabled) return state
     if (state.listboxState === ListboxStates.Closed) return state
 
+    let wasAlreadySearching = state.searchQuery !== ''
+    let offset = wasAlreadySearching ? 0 : 1
+
     let searchQuery = state.searchQuery + action.value.toLowerCase()
 
     let reOrderedOptions =
       state.activeOptionIndex !== null
         ? state.options
-            .slice(state.activeOptionIndex + 1)
-            .concat(state.options.slice(0, state.activeOptionIndex + 1))
+            .slice(state.activeOptionIndex + offset)
+            .concat(state.options.slice(0, state.activeOptionIndex + offset))
         : state.options
 
     let matchingOption = reOrderedOptions.find(
diff --git a/packages/@headlessui-react/src/components/menu/menu.test.tsx b/packages/@headlessui-react/src/components/menu/menu.test.tsx
index 1fc853d9b6..f8c36f60b1 100644
--- a/packages/@headlessui-react/src/components/menu/menu.test.tsx
+++ b/packages/@headlessui-react/src/components/menu/menu.test.tsx
@@ -2698,6 +2698,79 @@ describe('Keyboard interactions', () => {
         assertMenuLinkedWithMenuItem(items[3])
       })
     )
+
+    it(
+      'should stay on the same item while keystrokes still match',
+      suppressConsoleLogs(async () => {
+        render(
+          <Menu>
+            <Menu.Button>Trigger</Menu.Button>
+            <Menu.Items>
+              <Menu.Item as="a">alice</Menu.Item>
+              <Menu.Item as="a">bob</Menu.Item>
+              <Menu.Item as="a">charlie</Menu.Item>
+              <Menu.Item as="a">bob</Menu.Item>
+            </Menu.Items>
+          </Menu>
+        )
+
+        // Open menu
+        await click(getMenuButton())
+
+        let items = getMenuItems()
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "b" in "bob"
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "b" in "bob" again
+        await type(word('b'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "bo" in "bob"
+        await type(word('bo'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "bo" in "bob" again
+        await type(word('bo'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "bob" in "bob"
+        await type(word('bob'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "bob" in "bob" again
+        await type(word('bob'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+      })
+    )
   })
 })
 
diff --git a/packages/@headlessui-react/src/components/menu/menu.tsx b/packages/@headlessui-react/src/components/menu/menu.tsx
index 962549fdf6..04f34b39b9 100644
--- a/packages/@headlessui-react/src/components/menu/menu.tsx
+++ b/packages/@headlessui-react/src/components/menu/menu.tsx
@@ -99,13 +99,15 @@ let reducers: {
     return { ...state, searchQuery: '', activeItemIndex }
   },
   [ActionTypes.Search]: (state, action) => {
+    let wasAlreadySearching = state.searchQuery !== ''
+    let offset = wasAlreadySearching ? 0 : 1
     let searchQuery = state.searchQuery + action.value.toLowerCase()
 
     let reOrderedItems =
       state.activeItemIndex !== null
         ? state.items
-            .slice(state.activeItemIndex + 1)
-            .concat(state.items.slice(0, state.activeItemIndex + 1))
+            .slice(state.activeItemIndex + offset)
+            .concat(state.items.slice(0, state.activeItemIndex + offset))
         : state.items
 
     let matchingItem = reOrderedItems.find(
diff --git a/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx b/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
index c3cd561fef..4b4c187cfe 100644
--- a/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
+++ b/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
@@ -3231,6 +3231,82 @@ describe('Keyboard interactions', () => {
         assertActiveListboxOption(options[3])
       })
     )
+
+    it(
+      'should stay on the same item while keystrokes still match',
+      suppressConsoleLogs(async () => {
+        renderTemplate({
+          template: html`
+            <Listbox v-model="value">
+              <ListboxButton>Trigger</ListboxButton>
+              <ListboxOptions>
+                <ListboxOption value="a">alice</ListboxOption>
+                <ListboxOption value="b">bob</ListboxOption>
+                <ListboxOption value="c">charlie</ListboxOption>
+                <ListboxOption value="b">bob</ListboxOption>
+              </ListboxOptions>
+            </Listbox>
+          `,
+          setup: () => ({ value: ref(null) }),
+        })
+
+        // Open listbox
+        await click(getListboxButton())
+
+        let options = getListboxOptions()
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "b" in "bob"
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "b" in "bob" again
+        await type(word('b'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "bo" in "bob"
+        await type(word('bo'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "bo" in "bob" again
+        await type(word('bo'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+
+        // ---
+
+        // Reset: Go to first option
+        await press(Keys.Home)
+
+        // Search for "bob" in "bob"
+        await type(word('bob'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for "bob" in "bob" again
+        await type(word('bob'))
+
+        // We should be on the next `bob`
+        assertActiveListboxOption(options[3])
+      })
+    )
   })
 })
 
diff --git a/packages/@headlessui-vue/src/components/listbox/listbox.ts b/packages/@headlessui-vue/src/components/listbox/listbox.ts
index 812192da8f..1032dade3c 100644
--- a/packages/@headlessui-vue/src/components/listbox/listbox.ts
+++ b/packages/@headlessui-vue/src/components/listbox/listbox.ts
@@ -143,13 +143,16 @@ export let Listbox = defineComponent({
         if (props.disabled) return
         if (listboxState.value === ListboxStates.Closed) return
 
+        let wasAlreadySearching = searchQuery.value !== ''
+        let offset = wasAlreadySearching ? 0 : 1
+
         searchQuery.value += value.toLowerCase()
 
         let reOrderedOptions =
           activeOptionIndex.value !== null
             ? options.value
-                .slice(activeOptionIndex.value + 1)
-                .concat(options.value.slice(0, activeOptionIndex.value + 1))
+                .slice(activeOptionIndex.value + offset)
+                .concat(options.value.slice(0, activeOptionIndex.value + offset))
             : options.value
 
         let matchingOption = reOrderedOptions.find(
diff --git a/packages/@headlessui-vue/src/components/menu/menu.test.tsx b/packages/@headlessui-vue/src/components/menu/menu.test.tsx
index 4d033b457d..3f5b4e7c75 100644
--- a/packages/@headlessui-vue/src/components/menu/menu.test.tsx
+++ b/packages/@headlessui-vue/src/components/menu/menu.test.tsx
@@ -2792,6 +2792,79 @@ describe('Keyboard interactions', () => {
       // We should be on the second `bob`
       assertMenuLinkedWithMenuItem(items[3])
     })
+
+    it(
+      'should stay on the same item while keystrokes still match',
+      suppressConsoleLogs(async () => {
+        renderTemplate(jsx`
+          <Menu>
+            <MenuButton>Trigger</MenuButton>
+            <MenuItems>
+              <MenuItem as="a">alice</MenuItem>
+              <MenuItem as="a">bob</MenuItem>
+              <MenuItem as="a">charlie</MenuItem>
+              <MenuItem as="a">bob</MenuItem>
+            </MenuItems>
+          </Menu>
+        `)
+
+        // Open menu
+        await click(getMenuButton())
+
+        let items = getMenuItems()
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "b" in "bob"
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "b" in "bob" again
+        await type(word('b'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "bo" in "bob"
+        await type(word('bo'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "bo" in "bob" again
+        await type(word('bo'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+
+        // ---
+
+        // Reset: Go to first item
+        await press(Keys.Home)
+
+        // Search for "bob" in "bob"
+        await type(word('bob'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for "bob" in "bob" again
+        await type(word('bob'))
+
+        // We should be on the next `bob`
+        assertMenuLinkedWithMenuItem(items[3])
+      })
+    )
   })
 })
 
diff --git a/packages/@headlessui-vue/src/components/menu/menu.ts b/packages/@headlessui-vue/src/components/menu/menu.ts
index f154625ca2..7fc505d27e 100644
--- a/packages/@headlessui-vue/src/components/menu/menu.ts
+++ b/packages/@headlessui-vue/src/components/menu/menu.ts
@@ -106,13 +106,15 @@ export let Menu = defineComponent({
         activeItemIndex.value = nextActiveItemIndex
       },
       search(value: string) {
+        let wasAlreadySearching = searchQuery.value !== ''
+        let offset = wasAlreadySearching ? 0 : 1
         searchQuery.value += value.toLowerCase()
 
         let reOrderedItems =
           activeItemIndex.value !== null
             ? items.value
-                .slice(activeItemIndex.value + 1)
-                .concat(items.value.slice(0, activeItemIndex.value + 1))
+                .slice(activeItemIndex.value + offset)
+                .concat(items.value.slice(0, activeItemIndex.value + offset))
             : items.value
 
         let matchingItem = reOrderedItems.find(