diff --git a/packages/richtext-lexical/src/features/toolbars/fixed/client/Toolbar/index.tsx b/packages/richtext-lexical/src/features/toolbars/fixed/client/Toolbar/index.tsx
index f4d2a51561..ab16cd5b40 100644
--- a/packages/richtext-lexical/src/features/toolbars/fixed/client/Toolbar/index.tsx
+++ b/packages/richtext-lexical/src/features/toolbars/fixed/client/Toolbar/index.tsx
@@ -116,7 +116,11 @@ function ToolbarGroupComponent({
   )
 
   return (
-    <div className={`fixed-toolbar__group fixed-toolbar__group-${group.key}`} key={group.key}>
+    <div
+      className={`fixed-toolbar__group fixed-toolbar__group-${group.key}`}
+      data-toolbar-group-key={group.key}
+      key={group.key}
+    >
       {group.type === 'dropdown' && group.items.length ? (
         DropdownIcon ? (
           <ToolbarDropdown
diff --git a/packages/richtext-lexical/src/features/toolbars/inline/client/Toolbar/index.tsx b/packages/richtext-lexical/src/features/toolbars/inline/client/Toolbar/index.tsx
index 202e3347cd..599ce23a14 100644
--- a/packages/richtext-lexical/src/features/toolbars/inline/client/Toolbar/index.tsx
+++ b/packages/richtext-lexical/src/features/toolbars/inline/client/Toolbar/index.tsx
@@ -94,6 +94,7 @@ function ToolbarGroupComponent({
   return (
     <div
       className={`inline-toolbar-popup__group inline-toolbar-popup__group-${group.key}`}
+      data-toolbar-group-key={group.key}
       key={group.key}
     >
       {group.type === 'dropdown' && group.items.length ? (
diff --git a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarButton/index.tsx b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarButton/index.tsx
index c596e5e414..efd6beea2d 100644
--- a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarButton/index.tsx
+++ b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarButton/index.tsx
@@ -63,6 +63,9 @@ export const ToolbarButton = ({
   const runDeprioritized = useRunDeprioritized()
 
   useEffect(() => {
+    // Run on mount
+    void runDeprioritized(updateStates)
+
     const listener = () => runDeprioritized(updateStates)
 
     const cleanup = mergeRegister(editor.registerUpdateListener(listener))
@@ -99,7 +102,13 @@ export const ToolbarButton = ({
   }, [])
 
   return (
-    <button className={className} onClick={handleClick} onMouseDown={handleMouseDown} type="button">
+    <button
+      className={className}
+      data-button-key={item.key}
+      onClick={handleClick}
+      onMouseDown={handleMouseDown}
+      type="button"
+    >
       {children}
     </button>
   )
diff --git a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/DropDown.tsx b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/DropDown.tsx
index bfa2c34eaf..6e64ff36ea 100644
--- a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/DropDown.tsx
+++ b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/DropDown.tsx
@@ -21,6 +21,7 @@ export function DropDownItem({
   enabled,
   Icon,
   item,
+  itemKey,
   tooltip,
 }: {
   active?: boolean
@@ -29,6 +30,7 @@ export function DropDownItem({
   enabled?: boolean
   Icon: React.ReactNode
   item: ToolbarGroupItem
+  itemKey: string
   tooltip?: string
 }): React.ReactNode {
   const className = useMemo(() => {
@@ -64,6 +66,9 @@ export function DropDownItem({
       buttonStyle="none"
       className={className}
       disabled={enabled === false}
+      extraButtonProps={{
+        'data-item-key': itemKey,
+      }}
       icon={Icon}
       iconPosition="left"
       iconStyle="none"
@@ -183,6 +188,7 @@ export function DropDown({
   buttonClassName,
   children,
   disabled = false,
+  dropdownKey,
   Icon,
   itemsContainerClassNames,
   label,
@@ -192,6 +198,7 @@ export function DropDown({
   buttonClassName: string
   children: ReactNode
   disabled?: boolean
+  dropdownKey: string
   Icon?: React.FC
   itemsContainerClassNames?: string[]
   label?: string
@@ -262,6 +269,7 @@ export function DropDown({
       <button
         aria-label={buttonAriaLabel}
         className={buttonClassName + (showDropDown ? ' active' : '')}
+        data-dropdown-key={dropdownKey}
         disabled={disabled}
         onClick={(event) => {
           event.preventDefault()
diff --git a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/index.tsx b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/index.tsx
index c2cf95bfdb..9df48e31e8 100644
--- a/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/index.tsx
+++ b/packages/richtext-lexical/src/features/toolbars/shared/ToolbarDropdown/index.tsx
@@ -71,6 +71,7 @@ const ToolbarItem = ({
       enabled={enabled}
       Icon={item?.ChildComponent ? <item.ChildComponent /> : undefined}
       item={item}
+      itemKey={item.key}
       key={item.key}
       tooltip={title}
     >
@@ -166,6 +167,9 @@ export const ToolbarDropdown = ({
   }, [editor, editorConfigContext, group, items, maxActiveItems, onActiveChange])
 
   useEffect(() => {
+    // Run on mount in order to update states when dropdown is opened
+    void runDeprioritized(updateStates)
+
     return mergeRegister(
       editor.registerUpdateListener(async () => {
         await runDeprioritized(updateStates)
@@ -195,6 +199,7 @@ export const ToolbarDropdown = ({
         .filter(Boolean)
         .join(' ')}
       disabled={!deferredToolbarState.enabledGroup}
+      dropdownKey={groupKey}
       Icon={Icon}
       itemsContainerClassNames={[`${baseClass}-items`, ...(itemsContainerClassNames || [])]}
       key={groupKey}
diff --git a/packages/ui/src/elements/Button/index.tsx b/packages/ui/src/elements/Button/index.tsx
index a60403b64e..42554a144f 100644
--- a/packages/ui/src/elements/Button/index.tsx
+++ b/packages/ui/src/elements/Button/index.tsx
@@ -59,6 +59,7 @@ export const Button: React.FC<Props> = (props) => {
     disabled,
     el = 'button',
     enableSubMenu,
+    extraButtonProps = {},
     icon,
     iconPosition = 'right',
     iconStyle = 'without-border',
@@ -125,6 +126,7 @@ export const Button: React.FC<Props> = (props) => {
     rel: newTab ? 'noopener noreferrer' : undefined,
     target: newTab ? '_blank' : undefined,
     title: ariaLabel,
+    ...extraButtonProps,
   }
 
   let buttonElement
diff --git a/packages/ui/src/elements/Button/types.ts b/packages/ui/src/elements/Button/types.ts
index e7425857bf..0e62368e9f 100644
--- a/packages/ui/src/elements/Button/types.ts
+++ b/packages/ui/src/elements/Button/types.ts
@@ -27,6 +27,7 @@ export type Props = {
    * Setting to `true` will allow the submenu to be opened when the button is disabled
    */
   enableSubMenu?: boolean
+  extraButtonProps?: Record<string, any>
   icon?: ['chevron' | 'edit' | 'plus' | 'x'] | React.ReactNode
   iconPosition?: 'left' | 'right'
   iconStyle?: 'none' | 'with-border' | 'without-border'
diff --git a/test/lexical/collections/_LexicalFullyFeatured/e2e.spec.ts b/test/lexical/collections/_LexicalFullyFeatured/e2e.spec.ts
index fa91154386..9462407136 100644
--- a/test/lexical/collections/_LexicalFullyFeatured/e2e.spec.ts
+++ b/test/lexical/collections/_LexicalFullyFeatured/e2e.spec.ts
@@ -23,6 +23,7 @@ const { serverURL } = await initPayloadE2ENoConfig({
 })
 
 describe('Lexical Fully Featured', () => {
+  let lexical: LexicalHelpers
   beforeAll(async ({ browser }, testInfo) => {
     testInfo.setTimeout(TEST_TIMEOUT_LONG)
     process.env.SEED_IN_CONFIG_ONINIT = 'false' // Makes it so the payload config onInit seed is not run. Otherwise, the seed would be run unnecessarily twice for the initial test run - once for beforeEach and once for onInit
@@ -37,14 +38,13 @@ describe('Lexical Fully Featured', () => {
       uploadsDir: [path.resolve(dirname, './collections/Upload/uploads')],
     })
     const url = new AdminUrlUtil(serverURL, lexicalFullyFeaturedSlug)
-    const lexical = new LexicalHelpers(page)
+    lexical = new LexicalHelpers(page)
     await page.goto(url.create)
     await lexical.editor.first().focus()
   })
   test('prevent extra paragraph when inserting decorator blocks like blocks or upload node', async ({
     page,
   }) => {
-    const lexical = new LexicalHelpers(page)
     await lexical.slashCommand('block')
     await lexical.slashCommand('relationship')
     await lexical.drawer.locator('.list-drawer__header').getByText('Create New').click()
@@ -68,7 +68,6 @@ describe('Lexical Fully Featured', () => {
   test('ControlOrMeta+A inside input should select all the text inside the input', async ({
     page,
   }) => {
-    const lexical = new LexicalHelpers(page)
     await lexical.editor.first().focus()
     await page.keyboard.type('Hello')
     await page.keyboard.press('Enter')
@@ -85,15 +84,50 @@ describe('Lexical Fully Featured', () => {
   test('text state feature', async ({ page }) => {
     await page.keyboard.type('Hello')
     await page.keyboard.press('ControlOrMeta+A')
-    await page.locator('.toolbar-popup__dropdown-textState').first().click()
-    await page.getByRole('button', { name: 'Red' }).first().click()
+
+    await lexical.clickInlineToolbarButton({
+      dropdownKey: 'textState',
+      buttonKey: 'bg-red',
+    })
+
     const colored = page.locator('span').filter({ hasText: 'Hello' })
     await expect(colored).toHaveCSS('background-color', 'oklch(0.704 0.191 22.216)')
-    await expect(colored).toHaveAttribute('data-color', 'bg-red')
-    await page.locator('.toolbar-popup__dropdown-textState').first().click()
-    await page.getByRole('button', { name: 'Default style' }).click()
+    await expect(colored).toHaveAttribute('data-background-color', 'bg-red')
+    await lexical.clickInlineToolbarButton({
+      dropdownKey: 'textState',
+      buttonKey: 'clear-style',
+    })
+
     await expect(colored).toBeVisible()
     await expect(colored).not.toHaveCSS('background-color', 'oklch(0.704 0.191 22.216)')
-    await expect(colored).not.toHaveAttribute('data-color', 'bg-red')
+    await expect(colored).not.toHaveAttribute('data-background-color', 'bg-red')
+  })
+
+  test('ensure inline toolbar items are updated when selecting word by double-clicking', async ({
+    page,
+  }) => {
+    await page.keyboard.type('Hello')
+    await page.getByText('Hello').first().dblclick()
+
+    const { dropdownItems } = await lexical.clickInlineToolbarButton({
+      dropdownKey: 'textState',
+    })
+
+    const someButton = dropdownItems!.locator(`[data-item-key="bg-red"]`)
+    await expect(someButton).toHaveAttribute('aria-disabled', 'false')
+  })
+
+  test('ensure fixed toolbar items are updated when selecting word by double-clicking', async ({
+    page,
+  }) => {
+    await page.keyboard.type('Hello')
+    await page.getByText('Hello').first().dblclick()
+
+    const { dropdownItems } = await lexical.clickFixedToolbarButton({
+      dropdownKey: 'textState',
+    })
+
+    const someButton = dropdownItems!.locator(`[data-item-key="bg-red"]`)
+    await expect(someButton).toHaveAttribute('aria-disabled', 'false')
   })
 })
diff --git a/test/lexical/collections/utils.ts b/test/lexical/collections/utils.ts
index 560c21379b..867acafeed 100644
--- a/test/lexical/collections/utils.ts
+++ b/test/lexical/collections/utils.ts
@@ -1,4 +1,4 @@
-import type { Page } from 'playwright'
+import type { Locator, Page } from 'playwright'
 
 import { expect } from '@playwright/test'
 
@@ -29,6 +29,64 @@ export class LexicalHelpers {
     await this.page.keyboard.type(text)
   }
 
+  async clickFixedToolbarButton({
+    buttonKey,
+    dropdownKey,
+  }: {
+    buttonKey?: string
+    dropdownKey?: string
+  }): Promise<{
+    dropdownItems?: Locator
+  }> {
+    if (dropdownKey) {
+      await this.fixedToolbar.locator(`[data-dropdown-key="${dropdownKey}"]`).click()
+
+      const dropdownItems = this.page.locator(`.toolbar-popup__dropdown-items`)
+      await expect(dropdownItems).toBeVisible()
+
+      if (buttonKey) {
+        await dropdownItems.locator(`[data-item-key="${buttonKey}"]`).click()
+      }
+      return {
+        dropdownItems,
+      }
+    }
+
+    if (buttonKey) {
+      await this.fixedToolbar.locator(`[data-item-key="${buttonKey}"]`).click()
+    }
+    return {}
+  }
+
+  async clickInlineToolbarButton({
+    buttonKey,
+    dropdownKey,
+  }: {
+    buttonKey?: string
+    dropdownKey?: string
+  }): Promise<{
+    dropdownItems?: Locator
+  }> {
+    if (dropdownKey) {
+      await this.inlineToolbar.locator(`[data-dropdown-key="${dropdownKey}"]`).click()
+
+      const dropdownItems = this.page.locator(`.toolbar-popup__dropdown-items`)
+      await expect(dropdownItems).toBeVisible()
+
+      if (buttonKey) {
+        await dropdownItems.locator(`[data-item-key="${buttonKey}"]`).click()
+      }
+      return {
+        dropdownItems,
+      }
+    }
+
+    if (buttonKey) {
+      await this.inlineToolbar.locator(`[data-item-key="${buttonKey}"]`).click()
+    }
+    return {}
+  }
+
   async save(container: 'document' | 'drawer') {
     if (container === 'drawer') {
       await this.drawer.getByText('Save').click()
@@ -64,6 +122,14 @@ export class LexicalHelpers {
     return this.page.locator('[data-lexical-editor="true"]')
   }
 
+  get fixedToolbar() {
+    return this.page.locator('.fixed-toolbar')
+  }
+
+  get inlineToolbar() {
+    return this.page.locator('.inline-toolbar-popup')
+  }
+
   get paragraph() {
     return this.editor.locator('p')
   }