diff --git a/apps/web/components/add-document/connections.tsx b/apps/web/components/add-document/connections.tsx
index 221a73296..f37af299c 100644
--- a/apps/web/components/add-document/connections.tsx
+++ b/apps/web/components/add-document/connections.tsx
@@ -328,11 +328,11 @@ export function ConnectContent({ selectedProject }: ConnectContentProps) {
 	const projects = (queryClient.getQueryData<Project[]>(["projects"]) ||
 		[]) as Project[]
 
-	const handleUpgrade = async () => {
+	const handleUpgrade = async (planId: "api_pro" | "api_max" = "api_pro") => {
 		setIsUpgrading(true)
 		try {
 			const result = await autumn.attach({
-				planId: "api_pro",
+				planId,
 				successUrl: window.location.href,
 			})
 			if (result?.paymentUrl) {
@@ -614,11 +614,21 @@ export function ConnectContent({ selectedProject }: ConnectContentProps) {
 												</span>
 											)}
 											<Button
-												onClick={() => setGranolaModalOpen(true)}
-												disabled={!isMaxUser}
+												onClick={() => {
+													if (!isMaxUser) {
+														handleUpgrade("api_max")
+														return
+													}
+													setGranolaModalOpen(true)
+												}}
+												disabled={isUpgrading || autumn.isLoading}
 												className="bg-[#4BA0FA] text-black hover:bg-[#4BA0FA]/90 text-[14px] font-medium px-3 py-1.5 h-8"
 											>
-												Connect
+												{!isMaxUser
+													? isUpgrading || autumn.isLoading
+														? "Upgrading..."
+														: "Upgrade"
+													: "Connect"}
 											</Button>
 										</>
 									) : (
@@ -783,8 +793,14 @@ export function ConnectContent({ selectedProject }: ConnectContentProps) {
 											</div>
 										</DropdownMenuItem>
 										<DropdownMenuItem
-											disabled={!isMaxUser}
-											onClick={() => setGranolaModalOpen(true)}
+											disabled={isUpgrading || autumn.isLoading}
+											onClick={() => {
+												if (!isMaxUser) {
+													handleUpgrade("api_max")
+													return
+												}
+												setGranolaModalOpen(true)
+											}}
 											className="flex items-start gap-2.5 px-3 py-2.5 rounded-md cursor-pointer text-white opacity-60 hover:opacity-100 hover:bg-[#293952]/40 focus:bg-[#293952]/40 focus:opacity-100 data-disabled:opacity-40 data-disabled:cursor-not-allowed data-disabled:hover:bg-transparent"
 										>
 											<Granola className="size-5 mt-0.5 shrink-0" />
@@ -798,7 +814,9 @@ export function ConnectContent({ selectedProject }: ConnectContentProps) {
 													)}
 												</span>
 												<span className="text-[11px] text-[#737373] leading-tight">
-													Meeting notes & transcripts
+													{isMaxUser
+														? "Meeting notes & transcripts"
+														: "Upgrade to Max"}
 												</span>
 											</div>
 										</DropdownMenuItem>
diff --git a/apps/web/components/chat/index.tsx b/apps/web/components/chat/index.tsx
index a19daa1e3..a2d8e3057 100644
--- a/apps/web/components/chat/index.tsx
+++ b/apps/web/components/chat/index.tsx
@@ -201,6 +201,7 @@ export function ChatSidebar({
 	const [attachmentDrafts, setAttachmentDrafts] = useState<
 		ChatAttachmentDraft[]
 	>([])
+	const [isChatDraggingFiles, setIsChatDraggingFiles] = useState(false)
 	const [selectedModel, setSelectedModel] = useState<ModelId>(
 		initialSelectedModel ?? "grok-4.3",
 	)
@@ -246,6 +247,7 @@ export function ChatSidebar({
 		null,
 	)
 	const messagesContainerRef = useRef<HTMLDivElement>(null)
+	const chatDragDepthRef = useRef(0)
 	const isScrolledToBottomRef = useRef(true)
 	const userJustSentRef = useRef(false)
 	const sentQueuedMessageRef = useRef<string | null>(null)
@@ -725,6 +727,77 @@ export function ChatSidebar({
 		[attachmentDrafts, currentChatId, uploadAttachmentDraft],
 	)
 
+	const hasDraggedFiles = useCallback(
+		(event: React.DragEvent) =>
+			Array.from(event.dataTransfer.types).includes("Files"),
+		[],
+	)
+
+	const resetChatFileDrag = useCallback(() => {
+		chatDragDepthRef.current = 0
+		setIsChatDraggingFiles(false)
+	}, [])
+
+	const handleChatDragEnter = useCallback(
+		(event: React.DragEvent) => {
+			if (!hasDraggedFiles(event)) return
+			event.preventDefault()
+			event.stopPropagation()
+
+			chatDragDepthRef.current += 1
+			if (status !== "submitted" && status !== "streaming") {
+				setIsChatDraggingFiles(true)
+			}
+		},
+		[hasDraggedFiles, status],
+	)
+
+	const handleChatDragOver = useCallback(
+		(event: React.DragEvent) => {
+			if (!hasDraggedFiles(event)) return
+			event.preventDefault()
+			event.stopPropagation()
+			event.dataTransfer.dropEffect =
+				status === "submitted" || status === "streaming" ? "none" : "copy"
+		},
+		[hasDraggedFiles, status],
+	)
+
+	const handleChatDragLeave = useCallback(
+		(event: React.DragEvent) => {
+			if (!hasDraggedFiles(event)) return
+			event.preventDefault()
+			event.stopPropagation()
+
+			chatDragDepthRef.current = Math.max(0, chatDragDepthRef.current - 1)
+			if (chatDragDepthRef.current === 0) {
+				setIsChatDraggingFiles(false)
+			}
+		},
+		[hasDraggedFiles],
+	)
+
+	const handleChatDrop = useCallback(
+		(event: React.DragEvent) => {
+			if (!hasDraggedFiles(event)) return
+			event.preventDefault()
+			event.stopPropagation()
+
+			resetChatFileDrag()
+			const files = event.dataTransfer.files
+			if (status !== "submitted" && status !== "streaming" && files.length) {
+				handleAddAttachmentFiles(files)
+			}
+		},
+		[handleAddAttachmentFiles, hasDraggedFiles, resetChatFileDrag, status],
+	)
+
+	useEffect(() => {
+		if (status === "submitted" || status === "streaming") {
+			resetChatFileDrag()
+		}
+	}, [resetChatFileDrag, status])
+
 	useEffect(() => {
 		if (pendingThreadLoad && currentChatId === pendingThreadLoad.id) {
 			setMessages(pendingThreadLoad.messages)
@@ -1765,6 +1838,27 @@ export function ChatSidebar({
 		</div>
 	) : null
 
+	const chatDropOverlay = isChatDraggingFiles ? (
+		<div
+			className={cn(
+				"pointer-events-none absolute inset-0 z-[80] grid place-items-center border border-dashed border-[#4B5563] bg-black/72 text-sm font-medium text-fg-primary backdrop-blur-sm",
+				isMobile || isPageDesktop ? "rounded-none" : "rounded-2xl",
+			)}
+			aria-hidden="true"
+		>
+			<div className="rounded-lg border border-white/10 bg-black/50 px-4 py-2 shadow-[0_12px_32px_rgba(0,0,0,0.35)]">
+				Drop files to attach
+			</div>
+		</div>
+	) : null
+	const chatDropTargetProps = {
+		onDragEnter: handleChatDragEnter,
+		onDragOver: handleChatDragOver,
+		onDragLeave: handleChatDragLeave,
+		onDrop: handleChatDrop,
+		onDragEnd: resetChatFileDrag,
+	}
+
 	const shell = (
 		<>
 			{showHeaderRow ? (
@@ -1983,6 +2077,7 @@ export function ChatSidebar({
 					onRetryAttachment={handleRetryAttachment}
 					canSend={canSendMessage}
 					attachmentAccept={CHAT_ATTACHMENT_ACCEPT}
+					disableFileDropZone
 					sendDisabled={isResponding && isQueueFull}
 					sendDisabledTooltip={`Queue is full (${CHAT_QUEUE_LIMIT} max)`}
 					activeStatus={
@@ -2063,7 +2158,9 @@ export function ChatSidebar({
 				layout === "page" ? { opacity: 0, y: 12 } : { x: "100px", opacity: 0 }
 			}
 			transition={{ duration: 0.3, ease: "easeOut", bounce: 0 }}
+			{...(!isPageDesktop ? chatDropTargetProps : {})}
 		>
+			{!isPageDesktop && chatDropOverlay}
 			{chatHistorySheet}
 			{isPageDesktop ? (
 				<div className="flex h-full min-h-0 w-full flex-1 flex-row">
@@ -2073,7 +2170,11 @@ export function ChatSidebar({
 							chatProject === AUTO_CHAT_SPACE_ID ? null : [chatProject]
 						}
 					/>
-					<div className="flex h-full min-h-0 w-full min-w-0 max-w-[min(720px,100%)] shrink-0 basis-[min(720px,50vw)] flex-col">
+					<div
+						{...chatDropTargetProps}
+						className="relative flex h-full min-h-0 w-full min-w-0 max-w-[min(720px,100%)] shrink-0 basis-[min(720px,50vw)] flex-col"
+					>
+						{chatDropOverlay}
 						{pageDesktopToolbarRow}
 						<div className="relative mx-auto flex h-full min-h-0 w-full min-w-0 max-w-[min(720px,100%)] flex-1 flex-col px-3 sm:px-4 md:px-0">
 							{shell}
diff --git a/apps/web/components/chat/input/index.tsx b/apps/web/components/chat/input/index.tsx
index d655d6572..0926af531 100644
--- a/apps/web/components/chat/input/index.tsx
+++ b/apps/web/components/chat/input/index.tsx
@@ -59,6 +59,7 @@ interface ChatInputProps {
 	onRetryAttachment?: (id: string) => void
 	canSend?: boolean
 	attachmentAccept?: string
+	disableFileDropZone?: boolean
 }
 
 export default function ChatInput({
@@ -84,6 +85,7 @@ export default function ChatInput({
 	onRetryAttachment,
 	canSend,
 	attachmentAccept = CHAT_ATTACHMENT_ACCEPT,
+	disableFileDropZone = false,
 }: ChatInputProps) {
 	const [isMultiline, setIsMultiline] = useState(false)
 	const [isExpanded, setIsExpanded] = useState(false)
@@ -200,11 +202,20 @@ export default function ChatInput({
 		</>
 	) : null
 
-	const dropOverlay = isDraggingFiles ? (
-		<div className="pointer-events-none absolute inset-1 z-10 grid place-items-center rounded-lg border border-dashed border-[#4B5563] bg-black/70 text-sm font-medium text-fg-primary backdrop-blur-sm">
-			Drop files to attach
-		</div>
-	) : null
+	const dropOverlay =
+		!disableFileDropZone && isDraggingFiles ? (
+			<div className="pointer-events-none absolute inset-1 z-10 grid place-items-center rounded-lg border border-dashed border-[#4B5563] bg-black/70 text-sm font-medium text-fg-primary backdrop-blur-sm">
+				Drop files to attach
+			</div>
+		) : null
+	const dropZoneProps = disableFileDropZone
+		? {}
+		: {
+				onDragEnter: handleDragEnter,
+				onDragOver: handleDragOver,
+				onDragLeave: handleDragLeave,
+				onDrop: handleDrop,
+			}
 
 	return (
 		<motion.div
@@ -328,10 +339,7 @@ export default function ChatInput({
 			{stackedToolbar ? (
 				<fieldset
 					aria-label="Chat input with file drop zone"
-					onDragEnter={handleDragEnter}
-					onDragOver={handleDragOver}
-					onDragLeave={handleDragLeave}
-					onDrop={handleDrop}
+					{...dropZoneProps}
 					className="relative z-30 m-0 flex min-w-0 flex-col gap-2 rounded-xl border-0 bg-surface-card/60 p-2 shadow-[0_16px_48px_rgba(0,0,0,0.34)] backdrop-blur-md transition-all duration-200 focus-within:ring-1 focus-within:ring-fg-primary/10"
 				>
 					{dropOverlay}
@@ -368,10 +376,7 @@ export default function ChatInput({
 			) : (
 				<fieldset
 					aria-label="Chat input with file drop zone"
-					onDragEnter={handleDragEnter}
-					onDragOver={handleDragOver}
-					onDragLeave={handleDragLeave}
-					onDrop={handleDrop}
+					{...dropZoneProps}
 					className={cn(
 						"relative m-0 flex min-w-0 flex-col gap-2 rounded-xl border-0 bg-surface-card/60 p-2 shadow-[0_16px_48px_rgba(0,0,0,0.34)] backdrop-blur-md transition-all duration-200 focus-within:ring-1 focus-within:ring-fg-primary/10",
 						isMultiline && "flex-col",
diff --git a/apps/web/components/integrations-view.tsx b/apps/web/components/integrations-view.tsx
index 6379aa89b..57c6aeb76 100644
--- a/apps/web/components/integrations-view.tsx
+++ b/apps/web/components/integrations-view.tsx
@@ -2425,10 +2425,11 @@ export function IntegrationsView({
 		}
 	}
 
-	const handleUpgrade = async (planId: "api_pro" | "api_max" = "api_pro") => {
+	const handleUpgrade = async (planId?: unknown) => {
+		const checkoutPlanId = planId === "api_max" ? "api_max" : "api_pro"
 		try {
 			const result = await autumn.attach({
-				planId,
+				planId: checkoutPlanId,
 				successUrl: `${window.location.origin}/?view=integrations`,
 			})
 			if (result?.paymentUrl) {
@@ -2741,7 +2742,7 @@ export function IntegrationsView({
 				}
 				if (claudeCodeConnected) return
 				if (claudeCodeNeedsPro) {
-					handleUpgrade()
+					handleUpgrade("api_pro")
 					return
 				}
 				createPluginKeyMutation.mutate("claude_code")
@@ -2818,7 +2819,7 @@ export function IntegrationsView({
 							title="Connect another agent"
 							onClick={() => {
 								if (needsProUpgrade) {
-									handleUpgrade()
+									handleUpgrade("api_pro")
 									return
 								}
 								trackCard(item)
@@ -2843,6 +2844,11 @@ export function IntegrationsView({
 						<FinishSetupButton
 							onClick={() => {
 								trackCard(item)
+								if (!PLUGIN_CATALOG[item.pluginId]?.usesOAuth) {
+									if (connectingPlugin) return
+									createPluginKeyMutation.mutate(item.pluginId)
+									return
+								}
 								setFinishSetupPluginId(item.pluginId)
 							}}
 						/>
@@ -2850,7 +2856,7 @@ export function IntegrationsView({
 				}
 				if (needsProUpgrade) {
 					return (
-						<PillButton onClick={() => handleUpgrade()}>
+						<PillButton onClick={() => handleUpgrade("api_pro")}>
 							<Zap className="size-3.5 text-[#4BA0FA]" /> Upgrade
 						</PillButton>
 					)
@@ -3020,7 +3026,7 @@ export function IntegrationsView({
 						<PillButton
 							onClick={() => {
 								if (needsProUpgrade) {
-									handleUpgrade()
+									handleUpgrade("api_pro")
 									return
 								}
 								trackCard(item)
@@ -3465,7 +3471,7 @@ export function IntegrationsView({
 					</div>
 					<div className="flex shrink-0 items-center justify-between gap-2">
 						{connectedDialogNeedsPro ? (
-							<PillButton onClick={() => handleUpgrade()}>
+							<PillButton onClick={() => handleUpgrade("api_pro")}>
 								<Zap className="size-3.5 text-[#4BA0FA]" /> Upgrade to connect
 								more
 							</PillButton>