diff --git a/surfsense_web/components/free-chat/free-composer.tsx b/surfsense_web/components/free-chat/free-composer.tsx
index 57a3e8dd9..a22d2b205 100644
--- a/surfsense_web/components/free-chat/free-composer.tsx
+++ b/surfsense_web/components/free-chat/free-composer.tsx
@@ -9,7 +9,7 @@ import { Switch } from "@/components/ui/switch";
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
 import { useAnonymousMode } from "@/contexts/anonymous-mode";
 import { useLoginGate } from "@/contexts/login-gate";
-import { BACKEND_URL } from "@/lib/env-config";
+import { anonymousChatApiService } from "@/lib/apis/anonymous-chat-api.service";
 import { cn } from "@/lib/utils";
 
 const ANON_ALLOWED_EXTENSIONS = new Set([
@@ -128,24 +128,12 @@ export const FreeComposer: FC = () => {
 			}
 
 			try {
-				const formData = new FormData();
-				formData.append("file", file);
-				const res = await fetch(`${BACKEND_URL}/api/v1/public/anon-chat/upload`, {
-					method: "POST",
-					credentials: "include",
-					body: formData,
-				});
-
-				if (res.status === 409) {
-					gate("upload more documents");
+				const result = await anonymousChatApiService.uploadDocument(file);
+				if (!result.ok) {
+					if (result.reason === "quota_exceeded") gate("upload more documents");
 					return;
 				}
-				if (!res.ok) {
-					const body = await res.json().catch(() => ({}));
-					throw new Error(body.detail || `Upload failed: ${res.status}`);
-				}
-
-				const data = await res.json();
+				const data = result.data;
 				if (anonMode.isAnonymous) {
 					anonMode.setUploadedDoc({
 						filename: data.filename,
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index daed8747d..b7f4cff07 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -68,11 +68,11 @@ import type { DocumentTypeEnum } from "@/contracts/types/document.types";
 import { useDebouncedValue } from "@/hooks/use-debounced-value";
 import { useMediaQuery } from "@/hooks/use-media-query";
 import { useElectronAPI } from "@/hooks/use-platform";
+import { anonymousChatApiService } from "@/lib/apis/anonymous-chat-api.service";
 import { documentsApiService } from "@/lib/apis/documents-api.service";
 import { foldersApiService } from "@/lib/apis/folders-api.service";
 import { searchSpacesApiService } from "@/lib/apis/search-spaces-api.service";
 import { authenticatedFetch } from "@/lib/auth-utils";
-import { BACKEND_URL } from "@/lib/env-config";
 import { uploadFolderScan } from "@/lib/folder-sync-upload";
 import { getSupportedExtensionsSet } from "@/lib/supported-extensions";
 import { queries } from "@/zero/queries/index";
@@ -1312,24 +1312,12 @@ function AnonymousDocumentsSidebar({
 
 			setIsUploading(true);
 			try {
-				const formData = new FormData();
-				formData.append("file", file);
-				const res = await fetch(`${BACKEND_URL}/api/v1/public/anon-chat/upload`, {
-					method: "POST",
-					credentials: "include",
-					body: formData,
-				});
-
-				if (res.status === 409) {
-					gate("upload more documents");
+				const result = await anonymousChatApiService.uploadDocument(file);
+				if (!result.ok) {
+					if (result.reason === "quota_exceeded") gate("upload more documents");
 					return;
 				}
-				if (!res.ok) {
-					const body = await res.json().catch(() => ({}));
-					throw new Error(body.detail || `Upload failed: ${res.status}`);
-				}
-
-				const data = await res.json();
+				const data = result.data;
 				if (anonMode.isAnonymous) {
 					anonMode.setUploadedDoc({
 						filename: data.filename,
diff --git a/surfsense_web/lib/apis/anonymous-chat-api.service.ts b/surfsense_web/lib/apis/anonymous-chat-api.service.ts
index 968f58be2..843576a50 100644
--- a/surfsense_web/lib/apis/anonymous-chat-api.service.ts
+++ b/surfsense_web/lib/apis/anonymous-chat-api.service.ts
@@ -12,6 +12,10 @@ import { ValidationError } from "../error";
 
 const BASE = "/api/v1/public/anon-chat";
 
+export type AnonUploadResult =
+	| { ok: true; data: { filename: string; size_bytes: number } }
+	| { ok: false; reason: "quota_exceeded" };
+
 class AnonymousChatApiService {
 	private baseUrl: string;
 
@@ -71,7 +75,7 @@ class AnonymousChatApiService {
 		});
 	};
 
-	uploadDocument = async (file: File): Promise<{ filename: string; size_bytes: number }> => {
+	uploadDocument = async (file: File): Promise<AnonUploadResult> => {
 		const formData = new FormData();
 		formData.append("file", file);
 		const res = await fetch(this.fullUrl("/upload"), {
@@ -79,11 +83,15 @@ class AnonymousChatApiService {
 			credentials: "include",
 			body: formData,
 		});
+		if (res.status === 409) {
+			return { ok: false, reason: "quota_exceeded" };
+		}
 		if (!res.ok) {
 			const body = await res.json().catch(() => ({}));
 			throw new Error(body.detail || `Upload failed: ${res.status}`);
 		}
-		return res.json();
+		const data = await res.json();
+		return { ok: true, data };
 	};
 
 	getDocument = async (): Promise<{ filename: string; size_bytes: number } | null> => {