RooCodeInc
diff --git a/‎packages/types/src/global-settings.ts‎
Lines changed: 1 addition & 0 deletions b/‎packages/types/src/global-settings.ts‎
Lines changed: 1 addition & 0 deletions
diff --git a/‎src/core/webview/webviewMessageHandler.ts‎
Lines changed: 34 additions & 0 deletions b/‎src/core/webview/webviewMessageHandler.ts‎
Lines changed: 34 additions & 0 deletions
diff --git a/‎src/shared/ExtensionMessage.ts‎
Lines changed: 3 additions & 0 deletions b/‎src/shared/ExtensionMessage.ts‎
Lines changed: 3 additions & 0 deletions
diff --git a/‎src/shared/WebviewMessage.ts‎
Lines changed: 4 additions & 0 deletions b/‎src/shared/WebviewMessage.ts‎
Lines changed: 4 additions & 0 deletions
diff --git a/‎webview-ui/src/components/chat/AutoApproveMenu.tsx‎
Lines changed: 26 additions & 0 deletions b/‎webview-ui/src/components/chat/AutoApproveMenu.tsx‎
Lines changed: 26 additions & 0 deletions
diff --git a/‎webview-ui/src/components/chat/ChatView.tsx‎
Lines changed: 35 additions & 4 deletions b/‎webview-ui/src/components/chat/ChatView.tsx‎
Lines changed: 35 additions & 4 deletions
diff --git a/‎webview-ui/src/components/chat/ShareButton.tsx‎
Lines changed: 31 additions & 68 deletions b/‎webview-ui/src/components/chat/ShareButton.tsx‎
Lines changed: 31 additions & 68 deletions
@@ -41,6 +41,7 @@ export const globalSettingsSchema = z.object({
 	lastShownAnnouncementId: z.string().optional(),
 	customInstructions: z.string().optional(),
 	taskHistory: z.array(historyItemSchema).optional(),
+	dismissedUpsells: z.array(z.string()).optional(),
 
 	// Image generation settings (experimental) - flattened for simplicity
 	openRouterImageApiKey: z.string().optional(),
 
@@ -3004,5 +3004,39 @@ export const webviewMessageHandler = async (
 
 			break
 		}
+		case "dismissUpsell": {
+			if (message.upsellId) {
+				try {
+					// Get current list of dismissed upsells
+					const dismissedUpsells = getGlobalState("dismissedUpsells") || []
+
+					// Add the new upsell ID if not already present
+					let updatedList = dismissedUpsells
+					if (!dismissedUpsells.includes(message.upsellId)) {
+						updatedList = [...dismissedUpsells, message.upsellId]
+						await updateGlobalState("dismissedUpsells", updatedList)
+					}
+
+					// Send updated list back to webview (use the already computed updatedList)
+					await provider.postMessageToWebview({
+						type: "dismissedUpsells",
+						list: updatedList,
+					})
+				} catch (error) {
+					// Fail silently as per Bruno's comment - it's OK to fail silently in this case
+					provider.log(`Failed to dismiss upsell: ${error instanceof Error ? error.message : String(error)}`)
+				}
+			}
+			break
+		}
+		case "getDismissedUpsells": {
+			// Send the current list of dismissed upsells to the webview
+			const dismissedUpsells = getGlobalState("dismissedUpsells") || []
+			await provider.postMessageToWebview({
+				type: "dismissedUpsells",
+				list: dismissedUpsells,
+			})
+			break
+		}
 	}
 }
@@ -123,6 +123,7 @@ export interface ExtensionMessage {
 		| "showEditMessageDialog"
 		| "commands"
 		| "insertTextIntoTextarea"
+		| "dismissedUpsells"
 	text?: string
 	payload?: any // Add a generic payload for now, can refine later
 	action?:
@@ -199,6 +200,7 @@ export interface ExtensionMessage {
 	context?: string
 	commands?: Command[]
 	queuedMessages?: QueuedMessage[]
+	list?: string[] // For dismissedUpsells
 }
 
 export type ExtensionState = Pick<
@@ -209,6 +211,7 @@ export type ExtensionState = Pick<
 	// | "lastShownAnnouncementId"
 	| "customInstructions"
 	// | "taskHistory" // Optional in GlobalSettings, required here.
+	| "dismissedUpsells"
 	| "autoApprovalEnabled"
 	| "alwaysAllowReadOnly"
 	| "alwaysAllowReadOnlyOutsideWorkspace"
 
@@ -223,6 +223,8 @@ export interface WebviewMessage {
 		| "queueMessage"
 		| "removeQueuedMessage"
 		| "editQueuedMessage"
+		| "dismissUpsell"
+		| "getDismissedUpsells"
 	text?: string
 	editedMessageContent?: string
 	tab?: "settings" | "history" | "mcp" | "modes" | "chat" | "marketplace" | "cloud"
@@ -268,6 +270,8 @@ export interface WebviewMessage {
 	visibility?: ShareVisibility // For share visibility
 	hasContent?: boolean // For checkRulesDirectoryResult
 	checkOnly?: boolean // For deleteCustomMode check
+	upsellId?: string // For dismissUpsell
+	list?: string[] // For dismissedUpsells response
 	codeIndexSettings?: {
 		// Global state settings
 		codebaseIndexEnabled: boolean
 
@@ -9,6 +9,9 @@ import { AutoApproveToggle, AutoApproveSetting, autoApproveSettingsConfig } from
 import { StandardTooltip } from "@src/components/ui"
 import { useAutoApprovalState } from "@src/hooks/useAutoApprovalState"
 import { useAutoApprovalToggles } from "@src/hooks/useAutoApprovalToggles"
+import DismissibleUpsell from "@src/components/common/DismissibleUpsell"
+import { useCloudUpsell } from "@src/hooks/useCloudUpsell"
+import { CloudUpsellDialog } from "@src/components/cloud/CloudUpsellDialog"
 
 interface AutoApproveMenuProps {
 	style?: React.CSSProperties
@@ -35,7 +38,12 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 
 	const { t } = useAppTranslation()
 
+	const { isOpen, openUpsell, closeUpsell, handleConnect } = useCloudUpsell({
+		autoOpenOnAuth: false,
+	})
+
 	const baseToggles = useAutoApprovalToggles()
+	const enabledCount = useMemo(() => Object.values(baseToggles).filter(Boolean).length, [baseToggles])
 
 	// AutoApproveMenu needs alwaysApproveResubmit in addition to the base toggles
 	const toggles = useMemo(
@@ -173,6 +181,23 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 					</div>
 
 					<AutoApproveToggle {...toggles} onToggle={onAutoApproveToggle} />
+
+					{enabledCount > 7 && (
+						<>
+							<DismissibleUpsell
+								upsellId="autoApprovePowerUserA"
+								onClick={() => openUpsell()}
+								dismissOnClick={false}
+								variant="banner">
+								<Trans
+									i18nKey="cloud:upsell.autoApprovePowerUser"
+									components={{
+										learnMoreLink: <VSCodeLink href="#" />,
+									}}
+								/>
+							</DismissibleUpsell>
+						</>
+					)}
 				</div>
 			)}
 
@@ -240,6 +265,7 @@ const AutoApproveMenu = ({ style }: AutoApproveMenuProps) => {
 					/>
 				</div>
 			</div>
+			<CloudUpsellDialog open={isOpen} onOpenChange={closeUpsell} onConnect={handleConnect} />
 		</div>
 	)
 }
 
@@ -3,10 +3,10 @@ import { useDeepCompareEffect, useEvent, useMount } from "react-use"
 import debounce from "debounce"
 import { Virtuoso, type VirtuosoHandle } from "react-virtuoso"
 import removeMd from "remove-markdown"
-import { VSCodeButton } from "@vscode/webview-ui-toolkit/react"
+import { VSCodeButton, VSCodeLink } from "@vscode/webview-ui-toolkit/react"
 import useSound from "use-sound"
 import { LRUCache } from "lru-cache"
-import { useTranslation } from "react-i18next"
+import { Trans, useTranslation } from "react-i18next"
 
 import { useDebounceEffect } from "@src/utils/useDebounceEffect"
 import { appendImages } from "@src/utils/imageUtils"
@@ -37,10 +37,10 @@ import { useExtensionState } from "@src/context/ExtensionStateContext"
 import { useSelectedModel } from "@src/components/ui/hooks/useSelectedModel"
 import RooHero from "@src/components/welcome/RooHero"
 import RooTips from "@src/components/welcome/RooTips"
-import RooCloudCTA from "@src/components/welcome/RooCloudCTA"
 import { StandardTooltip } from "@src/components/ui"
 import { useAutoApprovalState } from "@src/hooks/useAutoApprovalState"
 import { useAutoApprovalToggles } from "@src/hooks/useAutoApprovalToggles"
+import { CloudUpsellDialog } from "@src/components/cloud/CloudUpsellDialog"
 
 import TelemetryBanner from "../common/TelemetryBanner"
 import VersionIndicator from "../common/VersionIndicator"
@@ -56,6 +56,9 @@ import SystemPromptWarning from "./SystemPromptWarning"
 import ProfileViolationWarning from "./ProfileViolationWarning"
 import { CheckpointWarning } from "./CheckpointWarning"
 import { QueuedMessages } from "./QueuedMessages"
+import DismissibleUpsell from "../common/DismissibleUpsell"
+import { useCloudUpsell } from "@src/hooks/useCloudUpsell"
+import { Cloud } from "lucide-react"
 
 export interface ChatViewProps {
 	isHidden: boolean
@@ -208,6 +211,15 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		clineAskRef.current = clineAsk
 	}, [clineAsk])
 
+	const {
+		isOpen: isUpsellOpen,
+		openUpsell,
+		closeUpsell,
+		handleConnect,
+	} = useCloudUpsell({
+		autoOpenOnAuth: false,
+	})
+
 	// Keep inputValueRef in sync with inputValue state
 	useEffect(() => {
 		inputValueRef.current = inputValue
@@ -1831,7 +1843,25 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 						{telemetrySetting === "unset" && <TelemetryBanner />}
 
 						<div className="mb-2.5">
-							{cloudIsAuthenticated || taskHistory.length < 4 ? <RooTips /> : <RooCloudCTA />}
+							{cloudIsAuthenticated || taskHistory.length < 4 ? (
+								<RooTips />
+							) : (
+								<>
+									<DismissibleUpsell
+										upsellId="taskList"
+										icon={<Cloud className="size-4 mt-0.5 shrink-0" />}
+										onClick={() => openUpsell()}
+										dismissOnClick={false}
+										className="bg-vscode-editor-background p-4 !text-base">
+										<Trans
+											i18nKey="cloud:upsell.taskList"
+											components={{
+												learnMoreLink: <VSCodeLink href="#" />,
+											}}
+										/>
+									</DismissibleUpsell>
+								</>
+							)}
 						</div>
 						{/* Show the task history preview if expanded and tasks exist */}
 						{taskHistory.length > 0 && isExpanded && <HistoryPreview />}
@@ -2013,6 +2043,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 			)}
 
 			<div id="roo-portal" />
+			<CloudUpsellDialog open={isUpsellOpen} onOpenChange={closeUpsell} onConnect={handleConnect} />
 		</div>
 	)
 }
 
@@ -1,4 +1,4 @@
-import { useState, useEffect, useRef } from "react"
+import { useState, useEffect } from "react"
 import { useTranslation } from "react-i18next"
 import { SquareArrowOutUpRightIcon } from "lucide-react"
 
@@ -7,6 +7,8 @@ import { type HistoryItem, type ShareVisibility, TelemetryEventName } from "@roo
 import { vscode } from "@/utils/vscode"
 import { telemetryClient } from "@/utils/TelemetryClient"
 import { useExtensionState } from "@/context/ExtensionStateContext"
+import { useCloudUpsell } from "@/hooks/useCloudUpsell"
+import { CloudUpsellDialog } from "@/components/cloud/CloudUpsellDialog"
 import {
 	Button,
 	Popover,
@@ -16,10 +18,6 @@ import {
 	CommandList,
 	CommandItem,
 	CommandGroup,
-	Dialog,
-	DialogContent,
-	DialogHeader,
-	DialogTitle,
 	StandardTooltip,
 } from "@/components/ui"
 
@@ -31,29 +29,34 @@ interface ShareButtonProps {
 
 export const ShareButton = ({ item, disabled = false, showLabel = false }: ShareButtonProps) => {
 	const [shareDropdownOpen, setShareDropdownOpen] = useState(false)
-	const [connectModalOpen, setConnectModalOpen] = useState(false)
 	const [shareSuccess, setShareSuccess] = useState<{ visibility: ShareVisibility; url: string } | null>(null)
+	const [wasConnectInitiatedFromShare, setWasConnectInitiatedFromShare] = useState(false)
 	const { t } = useTranslation()
-	const { sharingEnabled, cloudIsAuthenticated, cloudUserInfo } = useExtensionState()
-	const wasUnauthenticatedRef = useRef(false)
-	const initiatedAuthFromThisButtonRef = useRef(false)
+	const { cloudUserInfo } = useExtensionState()
+
+	// Use enhanced cloud upsell hook with auto-open on auth success
+	const {
+		isOpen: connectModalOpen,
+		openUpsell,
+		closeUpsell,
+		handleConnect,
+		isAuthenticated: cloudIsAuthenticated,
+		sharingEnabled,
+	} = useCloudUpsell({
+		onAuthSuccess: () => {
+			// Auto-open share dropdown after successful authentication
+			setShareDropdownOpen(true)
+			setWasConnectInitiatedFromShare(false)
+		},
+	})
 
-	// Track authentication state changes to auto-open popover after login
+	// Auto-open popover when user becomes authenticated after clicking Connect from share button
 	useEffect(() => {
-		if (!cloudIsAuthenticated || !sharingEnabled) {
-			wasUnauthenticatedRef.current = true
-		} else if (wasUnauthenticatedRef.current && cloudIsAuthenticated && sharingEnabled) {
-			// Only open dropdown if auth was initiated from this button
-			if (initiatedAuthFromThisButtonRef.current) {
-				// User just authenticated from this share button, send telemetry, close modal, and open the popover
-				telemetryClient.capture(TelemetryEventName.ACCOUNT_CONNECT_SUCCESS)
-				setConnectModalOpen(false)
-				setShareDropdownOpen(true)
-				initiatedAuthFromThisButtonRef.current = false // Reset the flag
-			}
-			wasUnauthenticatedRef.current = false
+		if (wasConnectInitiatedFromShare && cloudIsAuthenticated) {
+			setShareDropdownOpen(true)
+			setWasConnectInitiatedFromShare(false)
 		}
-	}, [cloudIsAuthenticated, sharingEnabled])
+	}, [wasConnectInitiatedFromShare, cloudIsAuthenticated])
 
 	// Listen for share success messages from the extension
 	useEffect(() => {
@@ -95,14 +98,9 @@ export const ShareButton = ({ item, disabled = false, showLabel = false }: Share
 	}
 
 	const handleConnectToCloud = () => {
-		// Send telemetry for connect to cloud action
-		telemetryClient.capture(TelemetryEventName.SHARE_CONNECT_TO_CLOUD_CLICKED)
-
-		// Mark that authentication was initiated from this button
-		initiatedAuthFromThisButtonRef.current = true
-		vscode.postMessage({ type: "rooCloudSignIn" })
+		setWasConnectInitiatedFromShare(true)
+		handleConnect()
 		setShareDropdownOpen(false)
-		setConnectModalOpen(false)
 	}
 
 	const handleShareButtonClick = () => {
@@ -111,7 +109,8 @@ export const ShareButton = ({ item, disabled = false, showLabel = false }: Share
 
 		if (!cloudIsAuthenticated) {
 			// Show modal for unauthenticated users
-			setConnectModalOpen(true)
+			openUpsell()
+			telemetryClient.capture(TelemetryEventName.SHARE_CONNECT_TO_CLOUD_CLICKED)
 		} else {
 			// Show popover for authenticated users
 			setShareDropdownOpen(true)
@@ -241,43 +240,7 @@ export const ShareButton = ({ item, disabled = false, showLabel = false }: Share
 			)}
 
 			{/* Connect to Cloud Modal */}
-			<Dialog open={connectModalOpen} onOpenChange={setConnectModalOpen}>
-				<DialogContent className="max-w-sm">
-					<DialogHeader className="text-center">
-						<DialogTitle className="text-lg font-medium text-vscode-foreground">
-							{t("cloud:cloudBenefitsTitle")}
-						</DialogTitle>
-					</DialogHeader>
-
-					<div className="flex flex-col space-y-6">
-						<div>
-							<p className="text-md text-vscode-descriptionForeground mb-4">
-								{t("cloud:cloudBenefitsSubtitle")}
-							</p>
-							<ul className="text-sm text-vscode-descriptionForeground space-y-2">
-								<li className="flex items-start">
-									<span className="mr-2 text-vscode-foreground">•</span>
-									{t("cloud:cloudBenefitSharing")}
-								</li>
-								<li className="flex items-start">
-									<span className="mr-2 text-vscode-foreground">•</span>
-									{t("cloud:cloudBenefitHistory")}
-								</li>
-								<li className="flex items-start">
-									<span className="mr-2 text-vscode-foreground">•</span>
-									{t("cloud:cloudBenefitMetrics")}
-								</li>
-							</ul>
-						</div>
-
-						<div className="flex flex-col gap-4">
-							<Button onClick={handleConnectToCloud} className="w-full">
-								{t("cloud:connect")}
-							</Button>
-						</div>
-					</div>
-				</DialogContent>
-			</Dialog>
+			<CloudUpsellDialog open={connectModalOpen} onOpenChange={closeUpsell} onConnect={handleConnectToCloud} />
 		</>
 	)
 }