diff --git a/apps/studio/components/ui/AIAssistantPanel/AIAssistant.tsx b/apps/studio/components/ui/AIAssistantPanel/AIAssistant.tsx
index ad60d7afc75..a17ae6e39eb 100644
--- a/apps/studio/components/ui/AIAssistantPanel/AIAssistant.tsx
+++ b/apps/studio/components/ui/AIAssistantPanel/AIAssistant.tsx
@@ -1,6 +1,6 @@
 import type { UIMessage as MessageType } from '@ai-sdk/react'
 import { useChat } from '@ai-sdk/react'
-import { DefaultChatTransport } from 'ai'
+import { DefaultChatTransport, lastAssistantMessageIsCompleteWithToolCalls } from 'ai'
 import { AnimatePresence, motion } from 'framer-motion'
 import { Eraser, Info, Pencil, X } from 'lucide-react'
 import { useRouter } from 'next/router'
@@ -106,6 +106,21 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
 
   const { mutate: sendEvent } = useSendEventMutation()
 
+  const updateMessage = useCallback(
+    ({
+      messageId,
+      resultId,
+      results,
+    }: {
+      messageId: string
+      resultId?: string
+      results: any[]
+    }) => {
+      snap.updateMessage({ id: messageId, resultId, results })
+    },
+    [snap]
+  )
+
   // Handle completion of the assistant's response
   const handleChatFinish = useCallback(
     ({ message }: { message: MessageType }) => {
@@ -119,6 +134,17 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
     [snap]
   )
 
+  // Sanitize messages to remove Valtio proxy wrappers that can't be cloned
+  const sanitizedMessages = useMemo(() => {
+    if (!snap.activeChat?.messages) return undefined
+
+    return snap.activeChat.messages.map((msg: any) => {
+      // Convert proxy objects to plain objects
+      const plainMessage = JSON.parse(JSON.stringify(msg))
+      return plainMessage
+    })
+  }, [snap.activeChat?.messages])
+
   // TODO(refactor): This useChat hook should be moved down into each chat session.
   // That way we won't have to disable switching chats while the chat is loading,
   // and don't run the risk of messages getting mixed up between chats.
@@ -133,25 +159,31 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
     regenerate,
   } = useChat({
     id: snap.activeChatId,
-    // [Alaister] typecast is needed here because valtio returns readonly arrays
-    // and useChat expects a mutable array
-    messages: snap.activeChat?.messages as unknown as MessageType[] | undefined,
+    sendAutomaticallyWhen: lastAssistantMessageIsCompleteWithToolCalls,
+    messages: sanitizedMessages,
     async onToolCall({ toolCall }) {
+      if (toolCall.dynamic) {
+        return
+      }
+
       if (toolCall.toolName === 'rename_chat') {
         const { newName } = toolCall.input as { newName: string }
+
         if (snap.activeChatId && newName?.trim()) {
           snap.renameChat(snap.activeChatId, newName.trim())
+
           addToolResult({
             tool: toolCall.toolName,
             toolCallId: toolCall.toolCallId,
             output: 'Chat renamed',
           })
+        } else {
+          addToolResult({
+            tool: toolCall.toolName,
+            toolCallId: toolCall.toolCallId,
+            output: 'Failed to rename chat: Invalid chat or name',
+          })
         }
-        addToolResult({
-          tool: toolCall.toolName,
-          toolCallId: toolCall.toolCallId,
-          output: 'Failed to rename chat: Invalid chat or name',
-        })
       }
     },
     transport: new DefaultChatTransport({
@@ -160,7 +192,7 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
         // [Joshen] Specifically limiting the chat history that get's sent to reduce the
         // size of the context that goes into the model. This should always be an odd number
         // as much as possible so that the first message is always the user's
-        const MAX_CHAT_HISTORY = 5
+        const MAX_CHAT_HISTORY = 7
 
         const slicedMessages = messages.slice(-MAX_CHAT_HISTORY)
 
@@ -198,21 +230,6 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
 
   const isChatLoading = chatStatus === 'submitted' || chatStatus === 'streaming'
 
-  const updateMessage = useCallback(
-    ({
-      messageId,
-      resultId,
-      results,
-    }: {
-      messageId: string
-      resultId?: string
-      results: any[]
-    }) => {
-      snap.updateMessage({ id: messageId, resultId, results })
-    },
-    [snap]
-  )
-
   const deleteMessageFromHere = useCallback(
     (messageId: string) => {
       // Find the message index in current chatMessages
@@ -299,7 +316,6 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
   )
 
   const hasMessages = chatMessages.length > 0
-  const isShowingOnboarding = !hasMessages && isApiKeySet
 
   const sendMessageToAssistant = (finalContent: string) => {
     if (editingMessageId) {
@@ -391,18 +407,17 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
       ]}
     >
       <div className={cn('flex flex-col h-full', className)}>
-        <Conversation className={cn('flex-1')}>
-          <AIAssistantHeader
-            isChatLoading={isChatLoading}
-            onNewChat={snap.newChat}
-            onCloseAssistant={snap.closeAssistant}
-            showMetadataWarning={showMetadataWarning}
-            updatedOptInSinceMCP={updatedOptInSinceMCP}
-            isHipaaProjectDisallowed={isHipaaProjectDisallowed as boolean}
-            aiOptInLevel={aiOptInLevel}
-          />
-
-          {hasMessages && (
+        <AIAssistantHeader
+          isChatLoading={isChatLoading}
+          onNewChat={snap.newChat}
+          onCloseAssistant={snap.closeAssistant}
+          showMetadataWarning={showMetadataWarning}
+          updatedOptInSinceMCP={updatedOptInSinceMCP}
+          isHipaaProjectDisallowed={isHipaaProjectDisallowed as boolean}
+          aiOptInLevel={aiOptInLevel}
+        />
+        {hasMessages ? (
+          <Conversation className={cn('flex-1')}>
             <ConversationContent className="w-full px-7 py-8 mb-10">
               {renderedMessages}
               {error && (
@@ -442,14 +457,24 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
                 <motion.span
                   animate={{ opacity: [1, 0] }}
                   transition={{ duration: 1, repeat: Infinity, ease: 'linear' }}
-                  className="inline-block w-1.5 h-4 bg-foreground-lighter"
+                  className="inline-block w-1.5 h-4 bg-foreground-lighter mt-4"
                 />
               )}
             </ConversationContent>
-          )}
-
-          <ConversationScrollButton />
-        </Conversation>
+            <ConversationScrollButton />
+          </Conversation>
+        ) : (
+          <AIOnboarding
+            sqlSnippets={snap.sqlSnippets as SqlSnippet[] | undefined}
+            suggestions={
+              snap.suggestions as
+                | { title?: string; prompts?: { label: string; description: string }[] }
+                | undefined
+            }
+            onValueChange={(val) => setValue(val)}
+            onFocusInput={() => inputRef.current?.focus()}
+          />
+        )}
 
         <AnimatePresence>
           {editingMessageId && (
@@ -519,19 +544,6 @@ export const AIAssistant = ({ className }: AIAssistantProps) => {
             />
           )}
 
-          {isShowingOnboarding && (
-            <AIOnboarding
-              sqlSnippets={snap.sqlSnippets as SqlSnippet[] | undefined}
-              suggestions={
-                snap.suggestions as
-                  | { title?: string; prompts?: { label: string; description: string }[] }
-                  | undefined
-              }
-              onValueChange={(val) => setValue(val)}
-              onFocusInput={() => inputRef.current?.focus()}
-            />
-          )}
-
           <AssistantChatForm
             textAreaRef={inputRef}
             className={cn(
diff --git a/apps/studio/components/ui/AIAssistantPanel/AIOnboarding.tsx b/apps/studio/components/ui/AIAssistantPanel/AIOnboarding.tsx
index 225dc189bca..e8e8f69a419 100644
--- a/apps/studio/components/ui/AIAssistantPanel/AIOnboarding.tsx
+++ b/apps/studio/components/ui/AIAssistantPanel/AIOnboarding.tsx
@@ -1,7 +1,12 @@
 import { motion } from 'framer-motion'
-import { FileText } from 'lucide-react'
+import { partition } from 'lodash'
+import { BarChart, FileText, Shield } from 'lucide-react'
 
-import { Button } from 'ui'
+import { Button, Skeleton } from 'ui'
+import { useParams } from 'common'
+import { LINTER_LEVELS } from 'components/interfaces/Linter/Linter.constants'
+import { createLintSummaryPrompt } from 'components/interfaces/Linter/Linter.utils'
+import { useProjectLintsQuery } from 'data/lint/lint-query'
 import { type SqlSnippet } from './AIAssistant.types'
 import { codeSnippetPrompts, defaultPrompts } from './AIAssistant.prompts'
 
@@ -31,37 +36,140 @@ export const AIOnboarding = ({
       ? codeSnippetPrompts
       : defaultPrompts
 
+  const { ref: projectRef } = useParams()
+  const {
+    data: lints,
+    isLoading: isLoadingLints,
+    isFetching: isFetchingLints,
+  } = useProjectLintsQuery({ projectRef })
+  const isLintsLoading = isLoadingLints || isFetchingLints
+
+  const errorLints = lints?.filter((lint) => lint.level === LINTER_LEVELS.ERROR) ?? []
+  const [securityErrorLints, performanceErrorLints] = partition(
+    errorLints,
+    (lint) => lint.categories?.[0] === 'SECURITY'
+  )
+
   return (
-    <div className="w-full mb-6">
-      <div className="px-4 mb-4">
-        <h2 className="heading-section text-foreground mb-1">How can I assist you?</h2>
-        <p className="text-foreground-light text-sm">
-          Generate SQL, RLS policies and edge functions, debug issues or check on your project
-          health.
-        </p>
-      </div>
-      <div>
-        {prompts.map((item, index) => (
-          <motion.div
-            key={index}
-            initial={{ y: 5, opacity: 0 }}
-            animate={{ y: 0, opacity: 1 }}
-            transition={{ duration: 0.3, delay: index * 0.05 }}
-          >
-            <Button
-              size="small"
-              type="text"
-              className="w-full justify-start"
-              icon={<FileText strokeWidth={1.5} size={14} className="text-foreground-light" />}
-              onClick={() => {
-                onValueChange(item.prompt)
-                onFocusInput?.()
-              }}
-            >
-              {item.title}
-            </Button>
-          </motion.div>
-        ))}
+    <div className="flex-1 overflow-y-auto">
+      <div className="w-full flex-1 max-h-full min-h-full px-4 flex flex-col gap-0">
+        <div className="mt-auto w-full space-y-6 py-8 ">
+          <h2 className="heading-section text-foreground mx-4">How can I assist you?</h2>
+          {suggestions?.prompts?.length ? (
+            <>
+              <h3 className="heading-meta text-foreground-light mb-3 mx-4">Suggestions</h3>
+              {prompts.map((item, index) => (
+                <motion.div
+                  key={index}
+                  initial={{ y: 5, opacity: 0 }}
+                  animate={{ y: 0, opacity: 1 }}
+                  transition={{ duration: 0.3, delay: index * 0.05 }}
+                >
+                  <Button
+                    size="small"
+                    type="text"
+                    className="w-full justify-start border-b hover:border-b-0 hover:rounded-md rounded-none"
+                    icon={
+                      <FileText strokeWidth={1.5} size={14} className="text-foreground-light" />
+                    }
+                    onClick={() => {
+                      onValueChange(item.prompt)
+                      onFocusInput?.()
+                    }}
+                  >
+                    {item.title}
+                  </Button>
+                </motion.div>
+              ))}
+            </>
+          ) : (
+            <>
+              {isLintsLoading ? (
+                <div className="px-4 flex flex-col gap-2">
+                  {Array.from({ length: 6 }).map((_, index) => (
+                    <Skeleton className="h-4 w-full" />
+                  ))}
+                </div>
+              ) : (
+                <>
+                  {performanceErrorLints.length > 0 && (
+                    <div className="mb-4">
+                      <h3 className="heading-meta text-foreground-light mb-3 mx-4">
+                        Improve Performance
+                      </h3>
+                      {performanceErrorLints.map((lint, index) => {
+                        return (
+                          <Button
+                            size="small"
+                            type="text"
+                            className="w-full justify-start"
+                            icon={
+                              <BarChart
+                                strokeWidth={1.5}
+                                size={14}
+                                className="text-foreground-light"
+                              />
+                            }
+                            onClick={() => {
+                              onValueChange(createLintSummaryPrompt(lint))
+                              onFocusInput?.()
+                            }}
+                          >
+                            {lint.detail ? lint.detail.replace('\\`', '') : lint.title}
+                          </Button>
+                        )
+                      })}
+                    </div>
+                  )}
+
+                  {securityErrorLints.length > 0 && (
+                    <div className="mb-4">
+                      <h3 className="heading-meta text-foreground-light mb-3 mx-4">
+                        Improve Security
+                      </h3>
+                      {securityErrorLints.map((lint, index) => {
+                        return (
+                          <Button
+                            size="small"
+                            type="text"
+                            className="w-full justify-start"
+                            icon={<Shield strokeWidth={1.5} size={14} className="text-warning" />}
+                            onClick={() => {
+                              onValueChange(createLintSummaryPrompt(lint))
+                              onFocusInput?.()
+                            }}
+                          >
+                            {lint.detail ? lint.detail.replace(/\\`/g, '') : lint.title}
+                          </Button>
+                        )
+                      })}
+                    </div>
+                  )}
+
+                  <div>
+                    <h3 className="heading-meta text-foreground-light mb-3 mx-4">Ideas</h3>
+                    {prompts.map((item, index) => (
+                      <Button
+                        size="small"
+                        type="text"
+                        className="w-full justify-start"
+                        icon={
+                          <FileText strokeWidth={1.5} size={14} className="text-foreground-light" />
+                        }
+                        onClick={() => {
+                          onValueChange(item.prompt)
+                          onFocusInput?.()
+                        }}
+                      >
+                        {item.title}
+                      </Button>
+                    ))}
+                  </div>
+                </>
+              )}
+            </>
+          )}
+        </div>
       </div>
     </div>
   )