diff --git a/eslint-suppressions.json b/eslint-suppressions.json
index 60ed887058a..a9975b4476e 100644
--- a/eslint-suppressions.json
+++ b/eslint-suppressions.json
@@ -2610,11 +2610,6 @@
       "count": 1
     }
   },
-  "web/app/components/base/zendesk/utils.ts": {
-    "ts/no-explicit-any": {
-      "count": 4
-    }
-  },
   "web/app/components/billing/header-billing-btn/index.tsx": {
     "jsx-a11y/click-events-have-key-events": {
       "count": 1
diff --git a/web/app/components/base/zendesk/__tests__/utils.spec.ts b/web/app/components/base/zendesk/__tests__/utils.spec.ts
index 7697be3e3fd..da110ff8ecf 100644
--- a/web/app/components/base/zendesk/__tests__/utils.spec.ts
+++ b/web/app/components/base/zendesk/__tests__/utils.spec.ts
@@ -10,6 +10,7 @@ describe('zendesk/utils', () => {
   })
 
   afterEach(() => {
+    vi.useRealTimers()
     // Clean up window.zE after each test
     window.zE = mockZE
   })
@@ -120,4 +121,40 @@ describe('zendesk/utils', () => {
       expect(window.zE).not.toHaveBeenCalled()
     })
   })
+
+  describe('openZendeskWindow', () => {
+    it('should show and open messenger when zE exists', async () => {
+      vi.doMock('@/config', () => ({ IS_CE_EDITION: false }))
+      const { openZendeskWindow } = await import('../utils')
+
+      openZendeskWindow()
+
+      expect(window.zE).toHaveBeenCalledWith('messenger', 'show')
+      expect(window.zE).toHaveBeenCalledWith('messenger', 'open')
+    })
+
+    it('should retry opening until zE is ready', async () => {
+      vi.useFakeTimers()
+      vi.doMock('@/config', () => ({ IS_CE_EDITION: false }))
+      const { openZendeskWindow } = await import('../utils')
+
+      window.zE = undefined
+      openZendeskWindow({ interval: 10, retries: 2 })
+      window.zE = mockZE
+      vi.advanceTimersByTime(10)
+
+      expect(window.zE).toHaveBeenCalledWith('messenger', 'show')
+      expect(window.zE).toHaveBeenCalledWith('messenger', 'open')
+      vi.useRealTimers()
+    })
+
+    it('should not call window.zE when IS_CE_EDITION is true', async () => {
+      vi.doMock('@/config', () => ({ IS_CE_EDITION: true }))
+      const { openZendeskWindow } = await import('../utils')
+
+      openZendeskWindow()
+
+      expect(window.zE).not.toHaveBeenCalled()
+    })
+  })
 })
diff --git a/web/app/components/base/zendesk/utils.ts b/web/app/components/base/zendesk/utils.ts
index 35f3da74113..825cd887569 100644
--- a/web/app/components/base/zendesk/utils.ts
+++ b/web/app/components/base/zendesk/utils.ts
@@ -2,7 +2,7 @@ import { IS_CE_EDITION } from '@/config'
 
 type ConversationField = {
   id: string
-  value: any
+  value: unknown
 }
 
 declare global {
@@ -11,13 +11,13 @@ declare global {
     zE?: (
       command: string,
       value: string,
-      payload?: ConversationField[] | string | string[] | (() => any),
-      callback?: () => any,
+      payload?: ConversationField[] | string | string[] | (() => unknown),
+      callback?: () => unknown,
     ) => void
   }
 }
 
-export const setZendeskConversationFields = (fields: ConversationField[], callback?: () => any) => {
+export const setZendeskConversationFields = (fields: ConversationField[], callback?: () => unknown) => {
   if (!IS_CE_EDITION && window.zE)
     window.zE('messenger:set', 'conversationFields', fields, callback)
 }
@@ -31,3 +31,35 @@ export const toggleZendeskWindow = (open: boolean) => {
   if (!IS_CE_EDITION && window.zE)
     window.zE('messenger', open ? 'open' : 'close')
 }
+
+type OpenZendeskWindowOptions = {
+  interval?: number
+  retries?: number
+}
+
+const openZendeskWindowOnce = () => {
+  if (IS_CE_EDITION || !window.zE)
+    return false
+
+  window.zE('messenger', 'show')
+  window.zE('messenger', 'open')
+  return true
+}
+
+export const openZendeskWindow = ({
+  interval = 100,
+  retries = 20,
+}: OpenZendeskWindowOptions = {}) => {
+  if (IS_CE_EDITION)
+    return
+
+  if (openZendeskWindowOnce())
+    return
+
+  let attempts = 0
+  const timer = window.setInterval(() => {
+    attempts += 1
+    if (openZendeskWindowOnce() || attempts >= retries)
+      window.clearInterval(timer)
+  }, interval)
+}
diff --git a/web/app/components/main-nav/__tests__/index.spec.tsx b/web/app/components/main-nav/__tests__/index.spec.tsx
index d03bcc87ffe..d0ef0b0b67c 100644
--- a/web/app/components/main-nav/__tests__/index.spec.tsx
+++ b/web/app/components/main-nav/__tests__/index.spec.tsx
@@ -194,6 +194,8 @@ vi.mock('@/config', async (importOriginal) => {
   return {
     ...actual,
     IS_CLOUD_EDITION: true,
+    SUPPORT_EMAIL_ADDRESS: '',
+    ZENDESK_WIDGET_KEY: '',
   }
 })
 
@@ -944,6 +946,20 @@ describe('MainNav', () => {
     })
   })
 
+  it('closes the help menu from the support upgrade action', async () => {
+    renderMainNav()
+
+    fireEvent.click(screen.getByRole('button', { name: 'common.mainNav.help.openMenu' }))
+    expect(await screen.findByText('common.userProfile.contactUs')).toBeInTheDocument()
+
+    fireEvent.click(screen.getByRole('button', { name: 'billing.upgradeBtn.encourageShort' }))
+
+    await waitFor(() => {
+      expect(screen.queryByText('common.userProfile.forum')).not.toBeInTheDocument()
+    })
+    expect(mockSetShowPricingModal).toHaveBeenCalled()
+  })
+
   it('hides the help menu when branding is enabled', () => {
     renderMainNav({ branding: { enabled: true } })
 
diff --git a/web/app/components/main-nav/components/__tests__/support-menu.spec.tsx b/web/app/components/main-nav/components/__tests__/support-menu.spec.tsx
index 8d06d44ef0f..f37580748ad 100644
--- a/web/app/components/main-nav/components/__tests__/support-menu.spec.tsx
+++ b/web/app/components/main-nav/components/__tests__/support-menu.spec.tsx
@@ -1,30 +1,203 @@
+import type { Mock } from 'vitest'
 import { DropdownMenu, DropdownMenuContent, DropdownMenuTrigger } from '@langgenius/dify-ui/dropdown-menu'
-import { render, screen } from '@testing-library/react'
+import { fireEvent, render, screen } from '@testing-library/react'
+import { openZendeskWindow } from '@/app/components/base/zendesk/utils'
+import { Plan } from '@/app/components/billing/type'
+import { mailToSupport } from '@/app/components/header/utils/util'
+import { useAppContext } from '@/context/app-context'
+import { useModalContext } from '@/context/modal-context'
+import { useProviderContext } from '@/context/provider-context'
 import SupportMenu from '../support-menu'
 
+const { mockConfig, mockOpenZendeskWindow, mockMailToSupport, mockSetShowPricingModal } = vi.hoisted(() => ({
+  mockConfig: {
+    isCloudEdition: true,
+    supportEmailAddress: '',
+    zendeskWidgetKey: 'zendesk-key',
+  },
+  mockOpenZendeskWindow: vi.fn(),
+  mockMailToSupport: vi.fn(),
+  mockSetShowPricingModal: vi.fn(),
+}))
+
+vi.mock('@/app/components/base/zendesk/utils', () => ({
+  openZendeskWindow: mockOpenZendeskWindow,
+}))
+
+vi.mock('@/app/components/header/utils/util', () => ({
+  mailToSupport: mockMailToSupport,
+}))
+
+vi.mock('@/config', async (importOriginal) => {
+  const actual = await importOriginal<typeof import('@/config')>()
+  return {
+    ...actual,
+    get IS_CLOUD_EDITION() {
+      return mockConfig.isCloudEdition
+    },
+    get SUPPORT_EMAIL_ADDRESS() {
+      return mockConfig.supportEmailAddress
+    },
+    get ZENDESK_WIDGET_KEY() {
+      return mockConfig.zendeskWidgetKey
+    },
+  }
+})
+
+vi.mock('@/context/app-context', () => ({
+  useAppContext: vi.fn(),
+}))
+
+vi.mock('@/context/modal-context', () => ({
+  useModalContext: vi.fn(),
+}))
+
+vi.mock('@/context/provider-context', () => ({
+  useProviderContext: vi.fn(),
+}))
+
 describe('SupportMenu', () => {
   beforeEach(() => {
     vi.clearAllMocks()
+    mockConfig.isCloudEdition = true
+    mockConfig.supportEmailAddress = ''
+    mockConfig.zendeskWidgetKey = 'zendesk-key'
+    ;(useAppContext as Mock).mockReturnValue({
+      langGeniusVersionInfo: { current_version: '1.0.0' },
+      userProfile: { email: 'user@example.com' },
+    })
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: true,
+      plan: { type: Plan.team },
+    })
+    ;(useModalContext as Mock).mockReturnValue({
+      setShowPricingModal: mockSetShowPricingModal,
+    })
+    ;(mailToSupport as Mock).mockReturnValue('mailto:support@example.com')
   })
 
-  const renderSupportMenu = () => {
+  const renderSupportMenu = (onContactUsClick = vi.fn()) => {
     return render(
       <DropdownMenu open={true} onOpenChange={() => { }}>
         <DropdownMenuTrigger>open</DropdownMenuTrigger>
         <DropdownMenuContent>
-          <SupportMenu />
+          <SupportMenu onContactUsClick={onContactUsClick} />
         </DropdownMenuContent>
       </DropdownMenu>,
     )
   }
 
-  it('renders support entries as flat main nav help menu items', () => {
+  it('renders contact us before community support entries when Zendesk is configured', () => {
+    const onContactUsClick = vi.fn()
+    renderSupportMenu(onContactUsClick)
+
+    expect(screen.getByText('common.userProfile.contactUs')).toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.forum')).toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.community')).toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.contactUs').compareDocumentPosition(screen.getByText('common.userProfile.forum'))).toBe(Node.DOCUMENT_POSITION_FOLLOWING)
+    expect(screen.getByRole('menuitem', { name: 'common.userProfile.forum' })).toHaveClass('mx-0', 'px-3')
+
+    fireEvent.click(screen.getByRole('menuitem', { name: 'common.userProfile.contactUs' }))
+
+    expect(openZendeskWindow).toHaveBeenCalled()
+    expect(onContactUsClick).toHaveBeenCalled()
+  })
+
+  it('renders contact us with upgrade badge for Cloud sandbox plan without dedicated support', () => {
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: true,
+      plan: { type: Plan.sandbox },
+    })
+
+    const onContactUsClick = vi.fn()
+    renderSupportMenu(onContactUsClick)
+
+    expect(screen.getByText('common.userProfile.contactUs')).toHaveClass('text-text-disabled')
+    expect(screen.getByText('billing.upgradeBtn.encourageShort')).toHaveClass('system-xs-semibold-uppercase', 'text-saas-dify-blue-accessible')
+    expect(screen.queryByText('common.userProfile.emailSupport')).not.toBeInTheDocument()
+
+    fireEvent.click(screen.getByRole('menuitem', { name: 'common.userProfile.contactUs billing.upgradeBtn.encourageShort' }))
+
+    expect(mockSetShowPricingModal).not.toHaveBeenCalled()
+    expect(onContactUsClick).not.toHaveBeenCalled()
+
+    fireEvent.click(screen.getByRole('button', { name: 'billing.upgradeBtn.encourageShort' }))
+
+    expect(mockSetShowPricingModal).toHaveBeenCalled()
+    expect(openZendeskWindow).not.toHaveBeenCalled()
+    expect(onContactUsClick).toHaveBeenCalled()
+  })
+
+  it('hides upgrade contact for Cloud sandbox plan when billing is disabled', () => {
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: false,
+      plan: { type: Plan.sandbox },
+    })
+
     renderSupportMenu()
 
     expect(screen.queryByText('common.userProfile.contactUs')).not.toBeInTheDocument()
+    expect(screen.queryByText('billing.upgradeBtn.encourageShort')).not.toBeInTheDocument()
+    expect(screen.queryByText('common.userProfile.emailSupport')).not.toBeInTheDocument()
     expect(screen.getByText('common.userProfile.forum')).toBeInTheDocument()
-    expect(screen.getByText('common.userProfile.community')).toBeInTheDocument()
-    expect(screen.getByRole('menuitem', { name: 'common.userProfile.forum' })).toHaveClass('mx-0', 'px-3')
+  })
+
+  it('keeps Zendesk contact us for Cloud sandbox plan with support email and Zendesk configured', () => {
+    mockConfig.supportEmailAddress = 'support@example.com'
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: true,
+      plan: { type: Plan.sandbox },
+    })
+
+    renderSupportMenu()
+
+    expect(screen.getByText('common.userProfile.contactUs')).toBeInTheDocument()
+    expect(screen.queryByText('billing.upgradeBtn.encourageShort')).not.toBeInTheDocument()
+    fireEvent.click(screen.getByRole('menuitem', { name: 'common.userProfile.contactUs' }))
+
+    expect(openZendeskWindow).toHaveBeenCalled()
+    expect(mockSetShowPricingModal).not.toHaveBeenCalled()
+  })
+
+  it('keeps email support for Cloud sandbox plan with support email and no Zendesk configured', () => {
+    mockConfig.supportEmailAddress = 'support@example.com'
+    mockConfig.zendeskWidgetKey = ''
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: true,
+      plan: { type: Plan.sandbox },
+    })
+
+    renderSupportMenu()
+
+    expect(screen.queryByText('common.userProfile.contactUs')).not.toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.emailSupport')).toBeInTheDocument()
+    expect(screen.queryByText('billing.upgradeBtn.encourageShort')).not.toBeInTheDocument()
+    expect(mailToSupport).toHaveBeenCalledWith('user@example.com', Plan.sandbox, '1.0.0', 'support@example.com')
+  })
+
+  it('hides dedicated support channels for non-Cloud sandbox plan without support email', () => {
+    mockConfig.isCloudEdition = false
+    ;(useProviderContext as Mock).mockReturnValue({
+      enableBilling: true,
+      plan: { type: Plan.sandbox },
+    })
+
+    renderSupportMenu()
+
+    expect(screen.queryByText('common.userProfile.contactUs')).not.toBeInTheDocument()
+    expect(screen.queryByText('common.userProfile.emailSupport')).not.toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.forum')).toBeInTheDocument()
+  })
+
+  it('renders email support when Zendesk is not configured for a dedicated support channel', () => {
+    mockConfig.zendeskWidgetKey = ''
+
+    renderSupportMenu()
+
+    expect(screen.queryByText('common.userProfile.contactUs')).not.toBeInTheDocument()
+    expect(screen.getByText('common.userProfile.emailSupport')).toBeInTheDocument()
+    expect(mailToSupport).toHaveBeenCalledWith('user@example.com', Plan.team, '1.0.0', '')
+    expect(screen.getByRole('menuitem', { name: 'common.userProfile.emailSupport' })).toHaveAttribute('href', 'mailto:support@example.com')
   })
 
   it('has correct forum and community links', () => {
diff --git a/web/app/components/main-nav/components/help-menu.tsx b/web/app/components/main-nav/components/help-menu.tsx
index 2f74454fd2e..647ef49bdb2 100644
--- a/web/app/components/main-nav/components/help-menu.tsx
+++ b/web/app/components/main-nav/components/help-menu.tsx
@@ -124,7 +124,7 @@ const HelpMenu = ({
             </DropdownMenuGroup>
             <DropdownMenuSeparator className="my-0!" />
             <DropdownMenuGroup className="p-1">
-              <SupportMenu />
+              <SupportMenu onContactUsClick={() => setOpen(false)} />
             </DropdownMenuGroup>
             <DropdownMenuSeparator className="my-0!" />
             <DropdownMenuGroup className="p-1">
diff --git a/web/app/components/main-nav/components/support-menu.tsx b/web/app/components/main-nav/components/support-menu.tsx
index cd904a300d3..e55b90ca43e 100644
--- a/web/app/components/main-nav/components/support-menu.tsx
+++ b/web/app/components/main-nav/components/support-menu.tsx
@@ -1,12 +1,87 @@
-import { DropdownMenuLinkItem } from '@langgenius/dify-ui/dropdown-menu'
+import { DropdownMenuItem, DropdownMenuLinkItem } from '@langgenius/dify-ui/dropdown-menu'
 import { useTranslation } from 'react-i18next'
+import { openZendeskWindow } from '@/app/components/base/zendesk/utils'
+import { Plan } from '@/app/components/billing/type'
 import { ExternalLinkIndicator, MenuItemContent } from '@/app/components/header/account-dropdown/menu-item-content'
+import { mailToSupport } from '@/app/components/header/utils/util'
+import { IS_CLOUD_EDITION, SUPPORT_EMAIL_ADDRESS, ZENDESK_WIDGET_KEY } from '@/config'
+import { useAppContext } from '@/context/app-context'
+import { useModalContext } from '@/context/modal-context'
+import { useProviderContext } from '@/context/provider-context'
 
-export default function SupportMenu() {
+type SupportMenuProps = {
+  onContactUsClick?: () => void
+}
+
+export default function SupportMenu({ onContactUsClick }: SupportMenuProps) {
   const { t } = useTranslation()
+  const { enableBilling, plan } = useProviderContext()
+  const { userProfile, langGeniusVersionInfo } = useAppContext()
+  const { setShowPricingModal } = useModalContext()
+  const hasDedicatedChannel = plan.type !== Plan.sandbox || Boolean(SUPPORT_EMAIL_ADDRESS.trim())
+  const shouldShowUpgradeContact = IS_CLOUD_EDITION && enableBilling && plan.type === Plan.sandbox && !hasDedicatedChannel
+  const hasZendeskWidget = Boolean(ZENDESK_WIDGET_KEY.trim())
 
   return (
     <>
+      {shouldShowUpgradeContact && (
+        <DropdownMenuItem
+          className="mx-0 h-8 cursor-default gap-1 px-3 py-1"
+          onClick={(event) => {
+            event.preventDefault()
+          }}
+        >
+          <MenuItemContent
+            iconClassName="i-ri-chat-smile-2-line text-text-disabled"
+            label={(
+              <span className="text-text-disabled">
+                {t('userProfile.contactUs', { ns: 'common' })}
+              </span>
+            )}
+            trailing={(
+              <button
+                type="button"
+                className="max-w-30 shrink-0 truncate px-1 system-xs-semibold-uppercase text-saas-dify-blue-accessible transition-colors hover:text-saas-dify-blue-static-hover focus-visible:ring-2 focus-visible:ring-state-accent-solid focus-visible:outline-hidden focus-visible:ring-inset"
+                onClick={(event) => {
+                  event.stopPropagation()
+                  setShowPricingModal()
+                  onContactUsClick?.()
+                }}
+              >
+                {t('upgradeBtn.encourageShort', { ns: 'billing' })}
+              </button>
+            )}
+          />
+        </DropdownMenuItem>
+      )}
+      {!shouldShowUpgradeContact && hasDedicatedChannel && hasZendeskWidget && (
+        <DropdownMenuItem
+          className="mx-0 h-8 gap-1 px-3 py-1"
+          onClick={() => {
+            openZendeskWindow()
+            onContactUsClick?.()
+          }}
+        >
+          <MenuItemContent
+            iconClassName="i-ri-chat-smile-2-line"
+            label={t('userProfile.contactUs', { ns: 'common' })}
+          />
+        </DropdownMenuItem>
+      )}
+      {!shouldShowUpgradeContact && hasDedicatedChannel && !hasZendeskWidget && (
+        <DropdownMenuLinkItem
+          className="mx-0 h-8 gap-1 px-3 py-1"
+          href={mailToSupport(userProfile.email, plan.type, langGeniusVersionInfo?.current_version, SUPPORT_EMAIL_ADDRESS)}
+          rel="noopener noreferrer"
+          target="_blank"
+        >
+          <MenuItemContent
+            iconClassName="i-ri-mail-send-line"
+            label={t('userProfile.emailSupport', { ns: 'common' })}
+            trailing={<ExternalLinkIndicator />}
+          />
+        </DropdownMenuLinkItem>
+      )}
       <DropdownMenuLinkItem
         className="mx-0 h-8 gap-1 px-3 py-1"
         href="https://forum.dify.ai/"