diff --git a/apps/studio/components/interfaces/Support/AIAssistantOption.tsx b/apps/studio/components/interfaces/Support/AIAssistantOption.tsx
index 7d1a3372548..f0381dbeab0 100644
--- a/apps/studio/components/interfaces/Support/AIAssistantOption.tsx
+++ b/apps/studio/components/interfaces/Support/AIAssistantOption.tsx
@@ -2,25 +2,19 @@ import { AnimatePresence, motion } from 'framer-motion'
 import { MessageSquare } from 'lucide-react'
 import Link from 'next/link'
 import { useCallback, useEffect, useState } from 'react'
-// End of third-party imports
 
 import { useSendEventMutation } from 'data/telemetry/send-event-mutation'
-import { Button } from 'ui'
+import { AiIconAnimation, Button } from 'ui'
 import { NO_ORG_MARKER, NO_PROJECT_MARKER } from './SupportForm.utils'
 
 interface AIAssistantOptionProps {
   projectRef?: string | null
   organizationSlug?: string | null
-  isCondensed?: boolean
 }
 
-export const AIAssistantOption = ({
-  projectRef,
-  organizationSlug,
-  isCondensed = false,
-}: AIAssistantOptionProps) => {
+export const AIAssistantOption = ({ projectRef, organizationSlug }: AIAssistantOptionProps) => {
   const { mutate: sendEvent } = useSendEventMutation()
-  const [isVisible, setIsVisible] = useState(isCondensed)
+  const [isVisible, setIsVisible] = useState(false)
 
   useEffect(() => {
     const timer = setTimeout(() => setIsVisible(true), 800)
@@ -46,57 +40,56 @@ export const AIAssistantOption = ({
   if (!organizationSlug || organizationSlug === NO_ORG_MARKER) return null
 
   return (
-    <AnimatePresence initial={false}>
+    <AnimatePresence>
       {isVisible && (
-        <motion.div
+        <motion.aside
           initial={{ height: 0, opacity: 0 }}
           animate={{ height: 'auto', opacity: 1 }}
           exit={{ height: 0, opacity: 0 }}
-          className="w-full overflow-hidden border rounded-md relative"
+          className="w-full overflow-hidden border rounded-md relative bg-200"
         >
-          <div className={`flex flex-col xl:flex-row ${isCondensed ? 'py-4 px-5' : 'py-8 px-10'}`}>
+          <div className="flex items-center p-6">
             <div className="flex flex-col gap-3 z-[2] flex-shrink-0 w-full">
               <div>
-                <p className="text-sm text-foreground">Try the AI Assistant</p>
+                <h5 className="text-sm font-medium text-foreground">Try Supabase Assistant</h5>
                 <p className="text-sm text-foreground-lighter">
-                  Ask the AI assistant to help you with your support issue
+                  Ask our AI assistant to help you with your support issue.
                 </p>
               </div>
               <div>
                 <Link href={aiLink} onClick={onAiAssistantClicked}>
-                  <Button size="tiny" type="default">
-                    Ask AI assistant
+                  <Button size="tiny" type="default" icon={<AiIconAnimation size={14} />}>
+                    Ask the Assistant
                   </Button>
                 </Link>
               </div>
             </div>
-            {!isCondensed && (
-              <div className="absolute z-[1] scale-75 -right-24 top-0">
-                <div className="relative grow flex flex-col gap-3 w-[400px]">
-                  <div className="flex items-start gap-3 pl-12">
-                    <div className="w-8 h-8 rounded-full bg-background-surface-300 flex items-center justify-center">
-                      <MessageSquare size={16} className="text-foreground-lighter" />
-                    </div>
-                    <div className="flex-1 bg-background-surface-200 rounded-lg p-4 max-w-[280px]">
-                      <p className="text-sm text-foreground-lighter">
-                        Hi! I'm your AI assistant. How can I help you today?
-                      </p>
-                    </div>
+            {/* Decorative background */}
+            <div className="absolute z-[1] scale-75 -right-40 md:-right-24 -top-6 md:top-0">
+              <div className="relative grow flex flex-col gap-3 w-[400px]">
+                <div className="flex items-start gap-3 pl-12">
+                  <div className="w-8 h-8 rounded-full bg-background-surface-300 flex items-center justify-center">
+                    <MessageSquare size={16} className="text-foreground-lighter" />
                   </div>
-                  <div className="flex items-start justify-end gap-3 pr-10">
-                    <div className="bg-background-surface-200 rounded-lg p-4 max-w-[280px]">
-                      <p className="text-sm text-foreground-lighter">
-                        I can help you with database queries, API endpoints, or any other technical
-                        questions you might have.
-                      </p>
-                    </div>
+                  <div className="flex-1 bg-background-surface-200 rounded-lg p-4 max-w-[280px]">
+                    <p className="text-sm text-foreground-lighter">
+                      Hi! I'm your AI assistant. How can I help you today?
+                    </p>
+                  </div>
+                </div>
+                <div className="flex items-start justify-end gap-3 pr-10">
+                  <div className="bg-background-surface-200 rounded-lg p-4 max-w-[280px]">
+                    <p className="text-sm text-foreground-lighter">
+                      I can help you with database queries, API endpoints, or any other technical
+                      questions you might have.
+                    </p>
                   </div>
                 </div>
-                <div className="absolute -inset-2 bg-gradient-to-l from-transparent via-background-200 via-[95%] to-background-200 to-[100%] z-[1]" />
               </div>
-            )}
+              <div className="absolute -inset-2 bg-gradient-to-l from-transparent via-background-200 via-[90%] to-background-200 to-[100%] z-[1]" />
+            </div>
           </div>
-        </motion.div>
+        </motion.aside>
       )}
     </AnimatePresence>
   )
diff --git a/apps/studio/components/interfaces/Support/DiscordCTACard.tsx b/apps/studio/components/interfaces/Support/DiscordCTACard.tsx
new file mode 100644
index 00000000000..376db759eca
--- /dev/null
+++ b/apps/studio/components/interfaces/Support/DiscordCTACard.tsx
@@ -0,0 +1,81 @@
+import { useOrganizationsQuery } from 'data/organizations/organizations-query'
+import { AnimatePresence, motion } from 'framer-motion'
+import Link from 'next/link'
+import router from 'next/router'
+import { useEffect, useState } from 'react'
+import SVG from 'react-inlinesvg'
+import { Button } from 'ui'
+import { NO_ORG_MARKER } from './SupportForm.utils'
+
+interface DiscordCTACardProps {
+  organizationSlug?: string | null
+}
+
+export const DiscordCTACard = ({ organizationSlug }: DiscordCTACardProps) => {
+  const { data: organizations } = useOrganizationsQuery()
+  const [isVisible, setIsVisible] = useState(false)
+
+  const selectedOrg = organizations?.find((org) => org.slug === organizationSlug)
+  const isFreePlan = selectedOrg?.plan.id === 'free'
+
+  useEffect(() => {
+    const timer = setTimeout(() => setIsVisible(true), 800)
+    return () => clearTimeout(timer)
+  }, [])
+
+  return (
+    <AnimatePresence>
+      {isVisible && isFreePlan && organizationSlug !== NO_ORG_MARKER && (
+        <motion.aside
+          initial={{ height: 0, opacity: 0 }}
+          animate={{ height: 'auto', opacity: 1 }}
+          exit={{ height: 0, opacity: 0 }}
+          className="w-full overflow-hidden border border-transparent rounded-md relative"
+          style={{
+            background: '#404EED',
+            borderColor: 'color-mix(in srgb, #404EED 95%, #000000)',
+          }}
+        >
+          <div className="flex items-center p-6">
+            {/* Decorative background */}
+            <div
+              className="absolute inset-0 opacity-20 md:opacity-30"
+              style={{
+                backgroundImage: `url(${router.basePath}/img/support/discord-bg-small.jpg)`,
+                backgroundSize: '75%',
+                backgroundPosition: '112% 50%',
+                backgroundRepeat: 'no-repeat',
+                maskImage: 'linear-gradient(to left, rgba(0,0,0,1) 10%, rgba(0,0,0,0) 100%)',
+                WebkitMaskImage: 'linear-gradient(to left, rgba(0,0,0,1) 10%, rgba(0,0,0,0) 100%)',
+              }}
+            />
+            {/* Content */}
+            <div className="relative z-10">
+              <div className="flex flex-col gap-3">
+                <div>
+                  <h5 className="text-sm font-medium text-white">Ask the Discord community</h5>
+                  <p className="text-sm text-white/75">
+                    Many code-related questions are answered within minutes.
+                  </p>
+                </div>
+
+                <Link href="https://discord.supabase.com" target="_blank" rel="noreferrer">
+                  <Button
+                    size="tiny"
+                    type="secondary"
+                    icon={
+                      <SVG src={`${router.basePath}/img/discord-icon.svg`} className="h-4 w-4" />
+                    }
+                    className="bg-white hover:bg-white/90" // Force white button on all color schemes
+                  >
+                    <span style={{ color: '#404EED' }}>Ask on Discord</span>
+                  </Button>
+                </Link>
+              </div>
+            </div>
+          </div>
+        </motion.aside>
+      )}
+    </AnimatePresence>
+  )
+}
diff --git a/apps/studio/components/interfaces/Support/SupportFormPage.tsx b/apps/studio/components/interfaces/Support/SupportFormPage.tsx
index 4043ef900a1..2034a4067e5 100644
--- a/apps/studio/components/interfaces/Support/SupportFormPage.tsx
+++ b/apps/studio/components/interfaces/Support/SupportFormPage.tsx
@@ -10,12 +10,14 @@ import { toast } from 'sonner'
 import CopyButton from 'components/ui/CopyButton'
 import InformationBox from 'components/ui/InformationBox'
 import { InlineLink, InlineLinkClassName } from 'components/ui/InlineLink'
+import { useOrganizationsQuery } from 'data/organizations/organizations-query'
 import { usePlatformStatusQuery } from 'data/platform/platform-status-query'
 import { useSendEventMutation } from 'data/telemetry/send-event-mutation'
 import { useStateTransition } from 'hooks/misc/useStateTransition'
 import { BASE_PATH, DOCS_URL } from 'lib/constants'
 import { Button, cn, Tooltip, TooltipContent, TooltipTrigger } from 'ui'
 import { AIAssistantOption } from './AIAssistantOption'
+import { DiscordCTACard } from './DiscordCTACard'
 import { HighlightProjectRefProvider, useHighlightProjectRefContext } from './HighlightContext'
 import { Success } from './Success'
 import type { ExtendedSupportCategories } from './Support.constants'
@@ -65,9 +67,12 @@ export function SupportFormPage() {
 }
 
 function SupportFormPageContent() {
+  const { data: organizations } = useOrganizationsQuery()
   const [state, dispatch] = useReducer(supportFormReducer, undefined, createInitialSupportFormState)
 
   const { form, initialError, projectRef, orgSlug } = useSupportForm(dispatch)
+  const selectedOrg = organizations?.find((org) => org.slug === orgSlug)
+  const isFreePlan = selectedOrg?.plan.id === 'free'
 
   const sendTelemetry = useSupportFormTelemetry()
   useStateTransition(state, 'submitting', 'success', (_, curr) => {
@@ -88,7 +93,12 @@ function SupportFormPageContent() {
   return (
     <SupportFormWrapper>
       <SupportFormHeader />
-      <AIAssistantOption projectRef={projectRef} organizationSlug={orgSlug} />
+
+      <div className="flex flex-col gap-y-4">
+        <AIAssistantOption projectRef={projectRef} organizationSlug={orgSlug} />
+        <DiscordCTACard organizationSlug={orgSlug} />
+      </div>
+
       <SupportFormBody
         form={form}
         state={state}
diff --git a/apps/studio/components/interfaces/Support/SupportLink.tsx b/apps/studio/components/interfaces/Support/SupportLink.tsx
index 1d377e00f67..5effa0e792b 100644
--- a/apps/studio/components/interfaces/Support/SupportLink.tsx
+++ b/apps/studio/components/interfaces/Support/SupportLink.tsx
@@ -14,7 +14,14 @@ export const SupportLink = ({
   const href = createSupportFormUrl(queryParams ?? {})
 
   return (
-    <Link {...props} href={href} onClick={takeBreadcrumbSnapshot}>
+    <Link
+      {...props}
+      href={href}
+      onClick={(event) => {
+        takeBreadcrumbSnapshot()
+        props.onClick?.(event)
+      }}
+    >
       {children}
     </Link>
   )
diff --git a/apps/studio/components/interfaces/Support/__tests__/SupportFormPage.test.tsx b/apps/studio/components/interfaces/Support/__tests__/SupportFormPage.test.tsx
index 6dcb98600a1..2d2e3d9ddb4 100644
--- a/apps/studio/components/interfaces/Support/__tests__/SupportFormPage.test.tsx
+++ b/apps/studio/components/interfaces/Support/__tests__/SupportFormPage.test.tsx
@@ -1036,7 +1036,7 @@ describe('SupportFormPage', () => {
     renderSupportFormPage()
 
     await waitFor(() => {
-      expect(screen.getByText('Try the AI Assistant')).toBeInTheDocument()
+      expect(screen.getByText('Try Supabase Assistant')).toBeInTheDocument()
     })
   })
 
diff --git a/apps/studio/components/layouts/ProjectLayout/LayoutHeader/HelpPopover.tsx b/apps/studio/components/layouts/ProjectLayout/LayoutHeader/HelpPopover.tsx
index a2565cdd617..6b0f47d34af 100644
--- a/apps/studio/components/layouts/ProjectLayout/LayoutHeader/HelpPopover.tsx
+++ b/apps/studio/components/layouts/ProjectLayout/LayoutHeader/HelpPopover.tsx
@@ -134,17 +134,22 @@ export const HelpPopover = () => {
               {IS_PLATFORM && (
                 <>
                   <ButtonGroupItem
+                    asChild
                     size="tiny"
                     icon={<Activity strokeWidth={1.5} size={14} />}
-                    asChild
                   >
                     <a href="https://status.supabase.com/" target="_blank" rel="noreferrer">
                       Supabase status
                     </a>
                   </ButtonGroupItem>
 
-                  <ButtonGroupItem size="tiny" icon={<Mail strokeWidth={1.5} size={14} />}>
-                    <SupportLink queryParams={supportLinkQueryParams}>Contact support</SupportLink>
+                  <ButtonGroupItem asChild size="tiny" icon={<Mail strokeWidth={1.5} size={14} />}>
+                    <SupportLink
+                      queryParams={supportLinkQueryParams}
+                      onClick={() => setIsOpen(false)}
+                    >
+                      Contact support
+                    </SupportLink>
                   </ButtonGroupItem>
                 </>
               )}