diff --git a/surfsense_web/components/assistant-ui/thread.tsx b/surfsense_web/components/assistant-ui/thread.tsx
index 047ac25d8..14e474315 100644
--- a/surfsense_web/components/assistant-ui/thread.tsx
+++ b/surfsense_web/components/assistant-ui/thread.tsx
@@ -18,6 +18,7 @@ import {
 	ChevronLeftIcon,
 	ChevronRightIcon,
 	CopyIcon,
+	Dot,
 	DownloadIcon,
 	FileWarning,
 	Paperclip,
@@ -745,7 +746,15 @@ const ComposerAction: FC<ComposerActionProps> = ({
 		<div className="aui-composer-action-wrapper relative mx-2 mb-2 flex items-center justify-between">
 			<div className="flex items-center gap-1">
 				<TooltipIconButton
-					tooltip={isUploadingDocs ? "Uploading documents..." : "Upload and mention files"}
+					tooltip={
+						isUploadingDocs ? "Uploading documents..." : (
+							<div className="flex flex-col gap-0.5">
+								<span className="font-medium">Upload and mention files</span>
+								<span className="text-xs text-muted-foreground flex items-center">Max 10 files <Dot className="size-3" /> 50 MB each</span>
+								<span className="text-xs text-muted-foreground">Total upload limit: 200 MB</span>
+							</div>
+						)
+					}
 					side="bottom"
 					variant="ghost"
 					size="icon"
diff --git a/surfsense_web/components/assistant-ui/tooltip-icon-button.tsx b/surfsense_web/components/assistant-ui/tooltip-icon-button.tsx
index 154240cb4..55f7c6a2e 100644
--- a/surfsense_web/components/assistant-ui/tooltip-icon-button.tsx
+++ b/surfsense_web/components/assistant-ui/tooltip-icon-button.tsx
@@ -1,13 +1,13 @@
 "use client";
 
 import { Slottable } from "@radix-ui/react-slot";
-import { type ComponentPropsWithRef, forwardRef } from "react";
+import { type ComponentPropsWithRef, type ReactNode, forwardRef } from "react";
 import { Button } from "@/components/ui/button";
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
 import { cn } from "@/lib/utils";
 
 export type TooltipIconButtonProps = ComponentPropsWithRef<typeof Button> & {
-	tooltip: string;
+	tooltip: ReactNode;
 	side?: "top" | "bottom" | "left" | "right";
 };