diff --git a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workspace-header/workspace-header.tsx b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workspace-header/workspace-header.tsx
index abd4a77a566..3de09fe074e 100644
--- a/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workspace-header/workspace-header.tsx
+++ b/apps/sim/app/workspace/[workspaceId]/w/components/sidebar/components/workspace-header/workspace-header.tsx
@@ -1,6 +1,6 @@
 'use client'
 
-import { memo, useEffect, useRef, useState } from 'react'
+import { memo, type ReactElement, useEffect, useRef, useState } from 'react'
 import {
   ChevronDown,
   Chip,
@@ -14,6 +14,7 @@ import {
   Plus,
   Send,
   Skeleton,
+  Tooltip,
 } from '@sim/emcn'
 import { ManageWorkspace, PanelLeft } from '@sim/emcn/icons'
 import { createLogger } from '@sim/logger'
@@ -33,6 +34,27 @@ import { useSettingsNavigation } from '@/hooks/use-settings-navigation'
 
 const logger = createLogger('WorkspaceHeader')
 
+interface DisabledReasonTooltipProps {
+  reason: string | null
+  children: ReactElement
+}
+
+/**
+ * Wraps a menu item in a tooltip explaining why the action is unavailable.
+ * Renders the child as-is when there is no reason to show.
+ */
+function DisabledReasonTooltip({ reason, children }: DisabledReasonTooltipProps) {
+  if (!reason) return children
+  return (
+    <Tooltip.Root>
+      <Tooltip.Trigger asChild>{children}</Tooltip.Trigger>
+      <Tooltip.Content>
+        <p>{reason}</p>
+      </Tooltip.Content>
+    </Tooltip.Root>
+  )
+}
+
 interface WorkspaceHeaderProps {
   /** The active workspace object */
   activeWorkspace?: { name: string } | null
@@ -548,62 +570,67 @@ function WorkspaceHeaderImpl({
                 <DropdownMenuSeparator className='mx-0' />
 
                 <div className='flex flex-col gap-0.5'>
+                  <DisabledReasonTooltip reason={createWorkspaceDisabledReason}>
+                    <Chip
+                      leftIcon={Plus}
+                      onClick={(e) => {
+                        e.stopPropagation()
+                        if (!canCreateWorkspace) return
+                        setIsWorkspaceMenuOpen(false)
+                        setIsCreateModalOpen(true)
+                      }}
+                      disabled={isCreatingWorkspace}
+                      aria-disabled={!canCreateWorkspace || undefined}
+                      fullWidth
+                      flush
+                      className={cn(
+                        'select-none',
+                        !canCreateWorkspace &&
+                          'cursor-not-allowed opacity-60 hover-hover:bg-transparent'
+                      )}
+                    >
+                      New workspace
+                    </Chip>
+                  </DisabledReasonTooltip>
+                </div>
+
+                <DropdownMenuSeparator className='mx-0' />
+                <DisabledReasonTooltip reason={inviteDisabledReason}>
                   <Chip
-                    leftIcon={Plus}
-                    onClick={(e) => {
-                      e.stopPropagation()
+                    leftIcon={Send}
+                    onClick={() => {
                       setIsWorkspaceMenuOpen(false)
-                      if (!canCreateWorkspace) {
+                      if (isInvitationsDisabled) {
                         if (isBillingEnabled) navigateToSettings({ section: 'billing' })
                         return
                       }
-                      setIsCreateModalOpen(true)
+                      setIsInviteModalOpen(true)
                     }}
-                    disabled={isCreatingWorkspace}
-                    title={createWorkspaceDisabledReason ?? undefined}
                     fullWidth
                     flush
-                    className='w-full select-none disabled:pointer-events-none disabled:opacity-50'
+                    className='select-none'
                   >
-                    New workspace
+                    Invite teammates
                   </Chip>
-                </div>
-
-                <DropdownMenuSeparator className='mx-0' />
-                <Chip
-                  leftIcon={Send}
-                  onClick={() => {
-                    setIsWorkspaceMenuOpen(false)
-                    if (isInvitationsDisabled) {
-                      if (isBillingEnabled) navigateToSettings({ section: 'billing' })
-                      return
-                    }
-                    setIsInviteModalOpen(true)
-                  }}
-                  title={inviteDisabledReason ?? undefined}
-                  fullWidth
-                  flush
-                  className='w-full select-none'
-                >
-                  Invite teammates
-                </Chip>
-                <Chip
-                  leftIcon={ManageWorkspace}
-                  onClick={() => {
-                    setIsWorkspaceMenuOpen(false)
-                    if (isInvitationsDisabled) {
-                      if (isBillingEnabled) navigateToSettings({ section: 'billing' })
-                      return
-                    }
-                    navigateToSettings({ section: 'teammates' })
-                  }}
-                  title={inviteDisabledReason ?? undefined}
-                  fullWidth
-                  flush
-                  className='w-full select-none'
-                >
-                  Manage workspace
-                </Chip>
+                </DisabledReasonTooltip>
+                <DisabledReasonTooltip reason={inviteDisabledReason}>
+                  <Chip
+                    leftIcon={ManageWorkspace}
+                    onClick={() => {
+                      setIsWorkspaceMenuOpen(false)
+                      if (isInvitationsDisabled) {
+                        if (isBillingEnabled) navigateToSettings({ section: 'billing' })
+                        return
+                      }
+                      navigateToSettings({ section: 'teammates' })
+                    }}
+                    fullWidth
+                    flush
+                    className='select-none'
+                  >
+                    Manage workspace
+                  </Chip>
+                </DisabledReasonTooltip>
               </>
             )}
           </DropdownMenuContent>