diff --git a/surfsense_backend/app/routes/editor_routes.py b/surfsense_backend/app/routes/editor_routes.py
index 829b2cf69..0f986e416 100644
--- a/surfsense_backend/app/routes/editor_routes.py
+++ b/surfsense_backend/app/routes/editor_routes.py
@@ -139,9 +139,19 @@ async def get_editor_content(
                 status_code=409,
                 detail="This document is still being processed. Please wait a moment and try again.",
             )
+        if state == "failed":
+            reason = (
+                doc_status.get("reason", "Unknown error")
+                if isinstance(doc_status, dict)
+                else "Unknown error"
+            )
+            raise HTTPException(
+                status_code=422,
+                detail=f"Processing failed: {reason}. You can delete this document and re-upload it.",
+            )
         raise HTTPException(
             status_code=400,
-            detail="This document has no viewable content yet. It may still be syncing. Try again in a few seconds, or re-upload if the issue persists.",
+            detail="This document has no content. It may not have been processed correctly. Try deleting and re-uploading it.",
         )
 
     markdown_content = "\n\n".join(chunk_contents)
diff --git a/surfsense_web/components/documents/DocumentNode.tsx b/surfsense_web/components/documents/DocumentNode.tsx
index 04cec5f89..478037520 100644
--- a/surfsense_web/components/documents/DocumentNode.tsx
+++ b/surfsense_web/components/documents/DocumentNode.tsx
@@ -82,11 +82,12 @@ export const DocumentNode = React.memo(function DocumentNode({
 	onContextMenuOpenChange,
 }: DocumentNodeProps) {
 	const statusState = doc.status?.state ?? "ready";
-	const isSelectable = statusState !== "pending" && statusState !== "processing";
+	const isFailed = statusState === "failed";
+	const isProcessing = statusState === "pending" || statusState === "processing";
+	const isUnavailable = isProcessing || isFailed;
+	const isSelectable = !isUnavailable;
 	const isEditable =
-		EDITABLE_DOCUMENT_TYPES.has(doc.document_type) &&
-		statusState !== "pending" &&
-		statusState !== "processing";
+		EDITABLE_DOCUMENT_TYPES.has(doc.document_type) && !isUnavailable;
 
 	const handleCheckChange = useCallback(() => {
 		if (isSelectable) {
@@ -103,7 +104,6 @@ export const DocumentNode = React.memo(function DocumentNode({
 		[doc.id]
 	);
 
-	const isProcessing = statusState === "pending" || statusState === "processing";
 	const [dropdownOpen, setDropdownOpen] = useState(false);
 	const [exporting, setExporting] = useState<string | null>(null);
 	const [titleTooltipOpen, setTitleTooltipOpen] = useState(false);
@@ -261,38 +261,38 @@ export const DocumentNode = React.memo(function DocumentNode({
 								className="w-40"
 								onClick={(e) => e.stopPropagation()}
 							>
-								<DropdownMenuItem onClick={() => onPreview(doc)} disabled={isProcessing}>
-									<Eye className="mr-2 h-4 w-4" />
-									Open
+							<DropdownMenuItem onClick={() => onPreview(doc)} disabled={isUnavailable}>
+								<Eye className="mr-2 h-4 w-4" />
+								Open
+							</DropdownMenuItem>
+							{isEditable && (
+								<DropdownMenuItem onClick={() => onEdit(doc)}>
+									<PenLine className="mr-2 h-4 w-4" />
+									Edit
 								</DropdownMenuItem>
-								{isEditable && (
-									<DropdownMenuItem onClick={() => onEdit(doc)}>
-										<PenLine className="mr-2 h-4 w-4" />
-										Edit
-									</DropdownMenuItem>
-								)}
-								<DropdownMenuItem onClick={() => onMove(doc)}>
-									<Move className="mr-2 h-4 w-4" />
-									Move to...
+							)}
+							<DropdownMenuItem onClick={() => onMove(doc)}>
+								<Move className="mr-2 h-4 w-4" />
+								Move to...
+							</DropdownMenuItem>
+							{onExport && (
+								<DropdownMenuSub>
+									<DropdownMenuSubTrigger disabled={isUnavailable}>
+										<Download className="mr-2 h-4 w-4" />
+										Export
+									</DropdownMenuSubTrigger>
+									<DropdownMenuSubContent className="min-w-[180px]">
+										<ExportDropdownItems onExport={handleExport} exporting={exporting} />
+									</DropdownMenuSubContent>
+								</DropdownMenuSub>
+							)}
+							{onVersionHistory && isVersionableType(doc.document_type) && (
+								<DropdownMenuItem disabled={isUnavailable} onClick={() => onVersionHistory(doc)}>
+									<History className="mr-2 h-4 w-4" />
+									Versions
 								</DropdownMenuItem>
-								{onExport && (
-									<DropdownMenuSub>
-										<DropdownMenuSubTrigger disabled={isProcessing}>
-											<Download className="mr-2 h-4 w-4" />
-											Export
-										</DropdownMenuSubTrigger>
-										<DropdownMenuSubContent className="min-w-[180px]">
-											<ExportDropdownItems onExport={handleExport} exporting={exporting} />
-										</DropdownMenuSubContent>
-									</DropdownMenuSub>
-								)}
-								{onVersionHistory && isVersionableType(doc.document_type) && (
-									<DropdownMenuItem disabled={isProcessing} onClick={() => onVersionHistory(doc)}>
-										<History className="mr-2 h-4 w-4" />
-										Versions
-									</DropdownMenuItem>
-								)}
-								<DropdownMenuItem disabled={isProcessing} onClick={() => onDelete(doc)}>
+							)}
+							<DropdownMenuItem disabled={isProcessing} onClick={() => onDelete(doc)}>
 									<Trash2 className="mr-2 h-4 w-4" />
 									Delete
 								</DropdownMenuItem>
@@ -304,38 +304,38 @@ export const DocumentNode = React.memo(function DocumentNode({
 
 			{contextMenuOpen && (
 				<ContextMenuContent className="w-40" onClick={(e) => e.stopPropagation()}>
-					<ContextMenuItem onClick={() => onPreview(doc)} disabled={isProcessing}>
-						<Eye className="mr-2 h-4 w-4" />
-						Open
+				<ContextMenuItem onClick={() => onPreview(doc)} disabled={isUnavailable}>
+					<Eye className="mr-2 h-4 w-4" />
+					Open
+				</ContextMenuItem>
+				{isEditable && (
+					<ContextMenuItem onClick={() => onEdit(doc)}>
+						<PenLine className="mr-2 h-4 w-4" />
+						Edit
 					</ContextMenuItem>
-					{isEditable && (
-						<ContextMenuItem onClick={() => onEdit(doc)}>
-							<PenLine className="mr-2 h-4 w-4" />
-							Edit
-						</ContextMenuItem>
-					)}
-					<ContextMenuItem onClick={() => onMove(doc)}>
-						<Move className="mr-2 h-4 w-4" />
-						Move to...
+				)}
+				<ContextMenuItem onClick={() => onMove(doc)}>
+					<Move className="mr-2 h-4 w-4" />
+					Move to...
+				</ContextMenuItem>
+				{onExport && (
+					<ContextMenuSub>
+						<ContextMenuSubTrigger disabled={isUnavailable}>
+							<Download className="mr-2 h-4 w-4" />
+							Export
+						</ContextMenuSubTrigger>
+						<ContextMenuSubContent className="min-w-[180px]">
+							<ExportContextItems onExport={handleExport} exporting={exporting} />
+						</ContextMenuSubContent>
+					</ContextMenuSub>
+				)}
+				{onVersionHistory && isVersionableType(doc.document_type) && (
+					<ContextMenuItem disabled={isUnavailable} onClick={() => onVersionHistory(doc)}>
+						<History className="mr-2 h-4 w-4" />
+						Versions
 					</ContextMenuItem>
-					{onExport && (
-						<ContextMenuSub>
-							<ContextMenuSubTrigger disabled={isProcessing}>
-								<Download className="mr-2 h-4 w-4" />
-								Export
-							</ContextMenuSubTrigger>
-							<ContextMenuSubContent className="min-w-[180px]">
-								<ExportContextItems onExport={handleExport} exporting={exporting} />
-							</ContextMenuSubContent>
-						</ContextMenuSub>
-					)}
-					{onVersionHistory && isVersionableType(doc.document_type) && (
-						<ContextMenuItem disabled={isProcessing} onClick={() => onVersionHistory(doc)}>
-							<History className="mr-2 h-4 w-4" />
-							Versions
-						</ContextMenuItem>
-					)}
-					<ContextMenuItem disabled={isProcessing} onClick={() => onDelete(doc)}>
+				)}
+				<ContextMenuItem disabled={isProcessing} onClick={() => onDelete(doc)}>
 						<Trash2 className="mr-2 h-4 w-4" />
 						Delete
 					</ContextMenuItem>
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index 95bd21e3b..d69f48606 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -627,9 +627,10 @@ export function DocumentsSidebar({
 			function collectSubtreeDocs(parentId: number): DocumentNodeDoc[] {
 				const directDocs = (treeDocuments ?? []).filter(
 					(d) =>
-						d.folderId === parentId &&
-						d.status?.state !== "pending" &&
-						d.status?.state !== "processing"
+					d.folderId === parentId &&
+					d.status?.state !== "pending" &&
+					d.status?.state !== "processing" &&
+					d.status?.state !== "failed"
 				);
 				const childFolders = foldersByParent[String(parentId)] ?? [];
 				const descendantDocs = childFolders.flatMap((cf) => collectSubtreeDocs(cf.id));