diff --git a/webview-ui/src/components/chat/ShareButton.tsx b/webview-ui/src/components/chat/ShareButton.tsx
index 20442ba76b..7c90e72039 100644
--- a/webview-ui/src/components/chat/ShareButton.tsx
+++ b/webview-ui/src/components/chat/ShareButton.tsx
@@ -35,20 +35,32 @@ export const ShareButton = ({ item, disabled = false }: ShareButtonProps) => {
 	const { t } = useTranslation()
 	const { sharingEnabled, cloudIsAuthenticated, cloudUserInfo } = useExtensionState()
 	const wasUnauthenticatedRef = useRef(false)
+	const initiatedAuthFromThisButtonRef = useRef(false)
 
 	// Track authentication state changes to auto-open popover after login
 	useEffect(() => {
 		if (!cloudIsAuthenticated || !sharingEnabled) {
 			wasUnauthenticatedRef.current = true
 		} else if (wasUnauthenticatedRef.current && cloudIsAuthenticated && sharingEnabled) {
-			// User just authenticated, send telemetry, close modal, and open the popover
-			telemetryClient.capture(TelemetryEventName.ACCOUNT_CONNECT_SUCCESS)
-			setConnectModalOpen(false)
-			setShareDropdownOpen(true)
+			// 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
 		}
 	}, [cloudIsAuthenticated, sharingEnabled])
 
+	// Cleanup effect to reset flag on unmount
+	useEffect(() => {
+		return () => {
+			initiatedAuthFromThisButtonRef.current = false
+		}
+	}, [])
+
 	// Listen for share success messages from the extension
 	useEffect(() => {
 		const handleMessage = (event: MessageEvent) => {
@@ -92,6 +104,8 @@ export const ShareButton = ({ item, disabled = false }: ShareButtonProps) => {
 		// 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" })
 		setShareDropdownOpen(false)
 		setConnectModalOpen(false)
diff --git a/webview-ui/src/components/chat/__tests__/TaskActions.spec.tsx b/webview-ui/src/components/chat/__tests__/TaskActions.spec.tsx
index 2d9ea0cac1..5db6287747 100644
--- a/webview-ui/src/components/chat/__tests__/TaskActions.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/TaskActions.spec.tsx
@@ -265,7 +265,7 @@ describe("TaskActions", () => {
 			expect(screen.queryByText("Connect to Cloud")).not.toBeInTheDocument()
 		})
 
-		it("automatically opens popover when user becomes authenticated", () => {
+		it("does not automatically open popover when user becomes authenticated from elsewhere", () => {
 			// Start with unauthenticated state
 			mockUseExtensionState.mockReturnValue({
 				sharingEnabled: false,
@@ -277,7 +277,7 @@ describe("TaskActions", () => {
 			// Verify popover is not open initially
 			expect(screen.queryByText("Share with Organization")).not.toBeInTheDocument()
 
-			// Simulate user becoming authenticated
+			// Simulate user becoming authenticated (e.g., from AccountView)
 			mockUseExtensionState.mockReturnValue({
 				sharingEnabled: true,
 				cloudIsAuthenticated: true,
@@ -288,7 +288,47 @@ describe("TaskActions", () => {
 
 			rerender(<TaskActions item={mockItem} buttonsDisabled={false} />)
 
-			// Verify popover automatically opens and shows sharing options
+			// Verify popover does NOT automatically open when auth happens from elsewhere
+			expect(screen.queryByText("Share with Organization")).not.toBeInTheDocument()
+			expect(screen.queryByText("Share Publicly")).not.toBeInTheDocument()
+		})
+
+		it("automatically opens popover when user authenticates from share button", () => {
+			// Start with unauthenticated state
+			mockUseExtensionState.mockReturnValue({
+				sharingEnabled: false,
+				cloudIsAuthenticated: false,
+			} as any)
+
+			const { rerender } = render(<TaskActions item={mockItem} buttonsDisabled={false} />)
+
+			// Click share button to open connect modal
+			const buttons = screen.getAllByRole("button")
+			const shareButton = buttons.find((btn) => btn.querySelector(".codicon-link"))
+			expect(shareButton).toBeDefined()
+			fireEvent.click(shareButton!)
+
+			// Click connect button to initiate authentication
+			const connectButton = screen.getByText("Connect")
+			fireEvent.click(connectButton)
+
+			// Verify rooCloudSignIn message was sent
+			expect(mockPostMessage).toHaveBeenCalledWith({
+				type: "rooCloudSignIn",
+			})
+
+			// Simulate user becoming authenticated after clicking connect from share button
+			mockUseExtensionState.mockReturnValue({
+				sharingEnabled: true,
+				cloudIsAuthenticated: true,
+				cloudUserInfo: {
+					organizationName: "Test Organization",
+				},
+			} as any)
+
+			rerender(<TaskActions item={mockItem} buttonsDisabled={false} />)
+
+			// Verify popover automatically opens when auth was initiated from share button
 			expect(screen.getByText("Share with Organization")).toBeInTheDocument()
 			expect(screen.getByText("Share Publicly")).toBeInTheDocument()
 		})