diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2c05c93fa1..44cccf4e3d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -11,12 +11,14 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Ensure correct order when conditionally rendering `Menu.Item`, `Listbox.Option` and `RadioGroup.Option` ([#1045](https://github.com/tailwindlabs/headlessui/pull/1045))
 - Improve controlled Tabs behaviour ([#1050](https://github.com/tailwindlabs/headlessui/pull/1050))
+- Improve typeahead search logic ([#1051](https://github.com/tailwindlabs/headlessui/pull/1051))
 
 ## [Unreleased - @headlessui/vue]
 
 ### Fixed
 
 - Ensure correct order when conditionally rendering `MenuItem`, `ListboxOption` and `RadioGroupOption` ([#1045](https://github.com/tailwindlabs/headlessui/pull/1045))
+- Improve typeahead search logic ([#1051](https://github.com/tailwindlabs/headlessui/pull/1051))
 
 ## [@headlessui/react@v1.4.3] - 2022-01-14
 
diff --git a/packages/@headlessui-react/src/components/listbox/listbox.test.tsx b/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
index f766f256f3..90011989f2 100644
--- a/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
+++ b/packages/@headlessui-react/src/components/listbox/listbox.test.tsx
@@ -3073,6 +3073,40 @@ describe('Keyboard interactions', () => {
         assertActiveListboxOption(options[1])
       })
     )
+
+    it(
+      'should be possible to search for the next occurence',
+      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()
+
+        // Search for bob
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for bob again
+        await type(word('b'))
+
+        // We should be on the second `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 5fc4f05012..26432b85b4 100644
--- a/packages/@headlessui-react/src/components/listbox/listbox.tsx
+++ b/packages/@headlessui-react/src/components/listbox/listbox.tsx
@@ -131,14 +131,24 @@ let reducers: {
     if (state.listboxState === ListboxStates.Closed) return state
 
     let searchQuery = state.searchQuery + action.value.toLowerCase()
-    let match = state.options.findIndex(
+
+    let reOrderedOptions =
+      state.activeOptionIndex !== null
+        ? state.options
+            .slice(state.activeOptionIndex + 1)
+            .concat(state.options.slice(0, state.activeOptionIndex + 1))
+        : state.options
+
+    let matchingOption = reOrderedOptions.find(
       option =>
         !option.dataRef.current.disabled &&
         option.dataRef.current.textValue?.startsWith(searchQuery)
     )
 
-    if (match === -1 || match === state.activeOptionIndex) return { ...state, searchQuery }
-    return { ...state, searchQuery, activeOptionIndex: match }
+    let matchIdx = matchingOption ? state.options.indexOf(matchingOption) : -1
+
+    if (matchIdx === -1 || matchIdx === state.activeOptionIndex) return { ...state, searchQuery }
+    return { ...state, searchQuery, activeOptionIndex: matchIdx }
   },
   [ActionTypes.ClearSearch](state) {
     if (state.disabled) return state
diff --git a/packages/@headlessui-react/src/components/menu/menu.test.tsx b/packages/@headlessui-react/src/components/menu/menu.test.tsx
index 0080e97884..a5a2a9b67c 100644
--- a/packages/@headlessui-react/src/components/menu/menu.test.tsx
+++ b/packages/@headlessui-react/src/components/menu/menu.test.tsx
@@ -2631,6 +2631,7 @@ describe('Keyboard interactions', () => {
         assertMenuLinkedWithMenuItem(items[2])
       })
     )
+
     it(
       'should be possible to search for a word (case insensitive)',
       suppressConsoleLogs(async () => {
@@ -2663,6 +2664,40 @@ describe('Keyboard interactions', () => {
         assertMenuLinkedWithMenuItem(items[1])
       })
     )
+
+    it(
+      'should be possible to search for the next occurence',
+      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()
+
+        // Search for bob
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertMenuLinkedWithMenuItem(items[1])
+
+        // Search for bob again
+        await type(word('b'))
+
+        // We should be on the second `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 c3299f36f0..3e871fe15a 100644
--- a/packages/@headlessui-react/src/components/menu/menu.tsx
+++ b/packages/@headlessui-react/src/components/menu/menu.tsx
@@ -100,17 +100,26 @@ let reducers: {
   },
   [ActionTypes.Search]: (state, action) => {
     let searchQuery = state.searchQuery + action.value.toLowerCase()
-    let match = state.items.findIndex(
+
+    let reOrderedItems =
+      state.activeItemIndex !== null
+        ? state.items
+            .slice(state.activeItemIndex + 1)
+            .concat(state.items.slice(0, state.activeItemIndex + 1))
+        : state.items
+
+    let matchingItem = reOrderedItems.find(
       item =>
         item.dataRef.current.textValue?.startsWith(searchQuery) && !item.dataRef.current.disabled
     )
 
-    if (match === -1 || match === state.activeItemIndex) return { ...state, searchQuery }
-    return { ...state, searchQuery, activeItemIndex: match }
+    let matchIdx = matchingItem ? state.items.indexOf(matchingItem) : -1
+    if (matchIdx === -1 || matchIdx === state.activeItemIndex) return { ...state, searchQuery }
+    return { ...state, searchQuery, activeItemIndex: matchIdx }
   },
   [ActionTypes.ClearSearch](state) {
     if (state.searchQuery === '') return state
-    return { ...state, searchQuery: '' }
+    return { ...state, searchQuery: '', searchActiveItemIndex: null }
   },
   [ActionTypes.RegisterItem]: (state, action) => {
     let orderMap = Array.from(
diff --git a/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx b/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
index 73a6a55d20..c0a437e995 100644
--- a/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
+++ b/packages/@headlessui-vue/src/components/listbox/listbox.test.tsx
@@ -3316,6 +3316,43 @@ describe('Keyboard interactions', () => {
         assertActiveListboxOption(options[1])
       })
     )
+
+    it(
+      'should be possible to search for the next occurence',
+      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()
+
+        // Search for bob
+        await type(word('b'))
+
+        // We should be on the first `bob`
+        assertActiveListboxOption(options[1])
+
+        // Search for bob again
+        await type(word('b'))
+
+        // We should be on the second `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 5ec48a4f6a..cbc244d0de 100644
--- a/packages/@headlessui-vue/src/components/listbox/listbox.ts
+++ b/packages/@headlessui-vue/src/components/listbox/listbox.ts
@@ -145,13 +145,22 @@ export let Listbox = defineComponent({
 
         searchQuery.value += value.toLowerCase()
 
-        let match = options.value.findIndex(
+        let reOrderedOptions =
+          activeOptionIndex.value !== null
+            ? options.value
+                .slice(activeOptionIndex.value + 1)
+                .concat(options.value.slice(0, activeOptionIndex.value + 1))
+            : options.value
+
+        let matchingOption = reOrderedOptions.find(
           option =>
-            !option.dataRef.disabled && option.dataRef.textValue.startsWith(searchQuery.value)
+            option.dataRef.textValue.startsWith(searchQuery.value) && !option.dataRef.disabled
         )
 
-        if (match === -1 || match === activeOptionIndex.value) return
-        activeOptionIndex.value = match
+        let matchIdx = matchingOption ? options.value.indexOf(matchingOption) : -1
+        if (matchIdx === -1 || matchIdx === activeOptionIndex.value) return
+
+        activeOptionIndex.value = matchIdx
       },
       clearSearch() {
         if (props.disabled) return
diff --git a/packages/@headlessui-vue/src/components/menu/menu.test.tsx b/packages/@headlessui-vue/src/components/menu/menu.test.tsx
index 478cd7e5f4..fe34508d35 100644
--- a/packages/@headlessui-vue/src/components/menu/menu.test.tsx
+++ b/packages/@headlessui-vue/src/components/menu/menu.test.tsx
@@ -2753,6 +2753,37 @@ describe('Keyboard interactions', () => {
       // We should be on `bob`
       assertMenuLinkedWithMenuItem(items[1])
     })
+
+    it('should be possible to search for the next occurence', 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()
+
+      // Search for bob
+      await type(word('b'))
+
+      // We should be on the first `bob`
+      assertMenuLinkedWithMenuItem(items[1])
+
+      // Search for bob again
+      await type(word('b'))
+
+      // We should be on the second `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 42fc04ac16..1b25dcbc09 100644
--- a/packages/@headlessui-vue/src/components/menu/menu.ts
+++ b/packages/@headlessui-vue/src/components/menu/menu.ts
@@ -108,13 +108,21 @@ export let Menu = defineComponent({
       search(value: string) {
         searchQuery.value += value.toLowerCase()
 
-        let match = items.value.findIndex(
+        let reOrderedItems =
+          activeItemIndex.value !== null
+            ? items.value
+                .slice(activeItemIndex.value + 1)
+                .concat(items.value.slice(0, activeItemIndex.value + 1))
+            : items.value
+
+        let matchingItem = reOrderedItems.find(
           item => item.dataRef.textValue.startsWith(searchQuery.value) && !item.dataRef.disabled
         )
 
-        if (match === -1 || match === activeItemIndex.value) return
+        let matchIdx = matchingItem ? items.value.indexOf(matchingItem) : -1
+        if (matchIdx === -1 || matchIdx === activeItemIndex.value) return
 
-        activeItemIndex.value = match
+        activeItemIndex.value = matchIdx
       },
       clearSearch() {
         searchQuery.value = ''