diff --git a/surfsense_web/atoms/folder-sync/folder-sync.atoms.ts b/surfsense_web/atoms/folder-sync/folder-sync.atoms.ts
new file mode 100644
index 000000000..a9ae2bfcc
--- /dev/null
+++ b/surfsense_web/atoms/folder-sync/folder-sync.atoms.ts
@@ -0,0 +1,12 @@
+import { atom } from "jotai";
+
+export interface SelectedFolder {
+	path: string;
+	name: string;
+}
+
+// Atom to control the folder watch dialog open state
+export const folderWatchDialogOpenAtom = atom(false);
+
+// Atom to store initial folder selection for the dialog
+export const folderWatchInitialFolderAtom = atom<SelectedFolder | null>(null);
diff --git a/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts b/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts
index 2e92f637b..da6885ffe 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts
+++ b/surfsense_web/components/assistant-ui/connector-popup/constants/connector-constants.ts
@@ -180,9 +180,8 @@ export const OTHER_CONNECTORS = [
 	{
 		id: "obsidian-connector",
 		title: "Obsidian",
-		description: "Index your Obsidian vault (self-hosted only)",
+		description: "Index your Obsidian vault (Local folder scan on Desktop)",
 		connectorType: EnumConnectorName.OBSIDIAN_CONNECTOR,
-		selfHostedOnly: true,
 	},
 ] as const;
 
diff --git a/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts b/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts
index 7331549b5..03922c997 100644
--- a/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts
+++ b/surfsense_web/components/assistant-ui/connector-popup/hooks/use-connector-dialog.ts
@@ -1,5 +1,5 @@
 import { format } from "date-fns";
-import { useAtom, useAtomValue } from "jotai";
+import { useAtom, useAtomValue, useSetAtom } from "jotai";
 import { useCallback, useEffect, useRef, useState } from "react";
 import { toast } from "sonner";
 import { connectorDialogOpenAtom } from "@/atoms/connector-dialog/connector-dialog.atoms";
@@ -33,6 +33,13 @@ import {
 	OAUTH_CONNECTORS,
 	OTHER_CONNECTORS,
 } from "../constants/connector-constants";
+import { usePlatform } from "@/hooks/use-platform";
+import { isSelfHosted } from "@/lib/env-config";
+import {
+	folderWatchDialogOpenAtom,
+	folderWatchInitialFolderAtom,
+} from "@/atoms/folder-sync/folder-sync.atoms";
+
 import {
 	dateRangeSchema,
 	frequencyMinutesSchema,
@@ -61,6 +68,11 @@ export const useConnectorDialog = () => {
 	const { mutateAsync: updateConnector } = useAtomValue(updateConnectorMutationAtom);
 	const { mutateAsync: deleteConnector } = useAtomValue(deleteConnectorMutationAtom);
 	const { mutateAsync: createConnector } = useAtomValue(createConnectorMutationAtom);
+	const setFolderWatchOpen = useSetAtom(folderWatchDialogOpenAtom);
+	const setFolderWatchInitialFolder = useSetAtom(folderWatchInitialFolderAtom);
+	const { isDesktop } = usePlatform();
+	const selfHosted = isSelfHosted();
+
 
 	// Use global atom for dialog open state so it can be controlled from anywhere
 	const [isOpen, setIsOpen] = useAtom(connectorDialogOpenAtom);
@@ -440,11 +452,21 @@ export const useConnectorDialog = () => {
 	const handleConnectNonOAuth = useCallback(
 		(connectorType: string) => {
 			if (!searchSpaceId) return;
+
+			// Handle Obsidian specifically on Desktop & Cloud
+			if (connectorType === EnumConnectorName.OBSIDIAN_CONNECTOR && !selfHosted && isDesktop) {
+				setIsOpen(false);
+				setFolderWatchInitialFolder(null);
+				setFolderWatchOpen(true);
+				return;
+			}
+
 			setConnectingConnectorType(connectorType);
 		},
-		[searchSpaceId]
+		[searchSpaceId, selfHosted, isDesktop, setIsOpen, setFolderWatchOpen, setFolderWatchInitialFolder]
 	);
 
+
 	// Handle submitting connect form
 	const handleSubmitConnectForm = useCallback(
 		async (
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index ee0826595..71f2c5f68 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -14,6 +14,10 @@ import { deleteDocumentMutationAtom } from "@/atoms/documents/document-mutation.
 import { expandedFolderIdsAtom } from "@/atoms/documents/folder.atoms";
 import { agentCreatedDocumentsAtom } from "@/atoms/documents/ui.atoms";
 import { openEditorPanelAtom } from "@/atoms/editor/editor-panel.atom";
+import {
+	folderWatchDialogOpenAtom,
+	folderWatchInitialFolderAtom,
+} from "@/atoms/folder-sync/folder-sync.atoms";
 import { rightPanelCollapsedAtom } from "@/atoms/layout/right-panel.atom";
 import { searchSpacesAtom } from "@/atoms/search-spaces/search-space-query.atoms";
 import { CreateFolderDialog } from "@/components/documents/CreateFolderDialog";
@@ -106,8 +110,8 @@ export function DocumentsSidebar({
 	const debouncedSearch = useDebouncedValue(search, 250);
 	const [activeTypes, setActiveTypes] = useState<DocumentTypeEnum[]>([]);
 	const [watchedFolderIds, setWatchedFolderIds] = useState<Set<number>>(new Set());
-	const [folderWatchOpen, setFolderWatchOpen] = useState(false);
-	const [watchInitialFolder, setWatchInitialFolder] = useState<SelectedFolder | null>(null);
+	const [folderWatchOpen, setFolderWatchOpen] = useAtom(folderWatchDialogOpenAtom);
+	const [watchInitialFolder, setWatchInitialFolder] = useAtom(folderWatchInitialFolderAtom);
 	const isElectron = typeof window !== "undefined" && !!window.electronAPI;
 
 	// AI File Sort state
@@ -161,7 +165,8 @@ export function DocumentsSidebar({
 		const folderName = folderPath.split("/").pop() || folderPath.split("\\").pop() || folderPath;
 		setWatchInitialFolder({ path: folderPath, name: folderName });
 		setFolderWatchOpen(true);
-	}, []);
+	}, [setWatchInitialFolder, setFolderWatchOpen]);
+
 
 	const refreshWatchedIds = useCallback(async () => {
 		if (!electronAPI?.getWatchedFolders) return;