diff --git a/app/actions/generate.ts b/app/actions/generate.ts
index 69e18d4..5dc10dc 100644
--- a/app/actions/generate.ts
+++ b/app/actions/generate.ts
@@ -163,7 +163,22 @@ export async function generateAnswer({ prompt, tool, authorId, authorEmail, atta
   const tokenCost = Number.isFinite(rawTokenCost)
     ? Math.max(1, Math.min(Math.round(rawTokenCost), 2_147_483_647))
     : 1
-  const creditsToCharge = Math.max(1, Math.min(tokenCost, creditsRemaining))
+
+  if (tokenCost > creditsRemaining) {
+    const cap = getPlanCreditCap(userProfile.subscriptionPlan)
+    const resetLabel = resetDate
+      ? new Date(resetDate).toLocaleDateString('en-US', { month: 'short', day: 'numeric' })
+      : 'in 30 days'
+    const errorMessage = `You've reached your monthly credit cap (${cap}). Upgrade your plan now, or wait until your credits reset on ${resetLabel}.`
+    return {
+      answer: errorMessage,
+      sessionId: sessionId,
+      chatId: chatId,
+      error: errorMessage
+    }
+  }
+
+  const creditsToCharge = tokenCost
 
   const currentSessionId = sessionId || crypto.randomUUID()
 
diff --git a/components/PromptShell.tsx b/components/PromptShell.tsx
index 92fef61..805c69f 100644
--- a/components/PromptShell.tsx
+++ b/components/PromptShell.tsx
@@ -558,7 +558,7 @@ export default function PromptShell({
                     researchMode: researchMode && useWebSearch // Only send researchMode if web search is enabled/active
                 })
 
-                const { answer, sessionId: newSessionId, chatId: savedChatId, error: limitError } = result
+                const { answer, sessionId: newSessionId, chatId: savedChatId, error: limitError, warning } = result
 
                 // Clear web search status
                 if (useWebSearch) {
@@ -635,6 +635,12 @@ export default function PromptShell({
                     )
                 )
 
+                if (warning) {
+                    setAttachmentMessage(warning)
+                } else {
+                    setAttachmentMessage(null)
+                }
+
                 dispatchUsageRefresh('messages')
                 if (useWebSearch) {
                     dispatchUsageRefresh('web-search')