diff --git a/frontend/components/confirmation-dialog.tsx b/frontend/components/confirmation-dialog.tsx
new file mode 100644
index 00000000..1ff8a370
--- /dev/null
+++ b/frontend/components/confirmation-dialog.tsx
@@ -0,0 +1,84 @@
+"use client";
+
+import React from "react";
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from "./ui/dialog";
+import { Button } from "./ui/button";
+import { AlertTriangle } from "lucide-react";
+
+interface ConfirmationDialogProps {
+  open: boolean;
+  onOpenChange: (open: boolean) => void;
+  title?: string;
+  description?: string;
+  confirmText?: string;
+  cancelText?: string;
+  onConfirm: () => void | Promise<void>;
+  isLoading?: boolean;
+  variant?: "destructive" | "default";
+}
+
+export const DeleteConfirmationDialog: React.FC<ConfirmationDialogProps> = ({
+  open,
+  onOpenChange,
+  title = "Are you sure?",
+  description = "This action cannot be undone.",
+  confirmText = "Confirm",
+  cancelText = "Cancel",
+  onConfirm,
+  isLoading = false,
+  variant = "destructive",
+}) => {
+  const handleConfirm = async () => {
+    try {
+      await onConfirm();
+    } finally {
+      // Only close if not in loading state (let the parent handle this)
+      if (!isLoading) {
+        onOpenChange(false);
+      }
+    }
+  };
+
+  return (
+    <Dialog open={open} onOpenChange={onOpenChange}>
+      <DialogContent className="sm:max-w-[425px]">
+        <DialogHeader>
+          <div className="flex items-center gap-3">
+            {variant === "destructive" && (
+              <AlertTriangle className="h-6 w-6 text-destructive" />
+            )}
+            <DialogTitle>{title}</DialogTitle>
+          </div>
+          <DialogDescription>{description}</DialogDescription>
+        </DialogHeader>
+
+        <DialogFooter>
+          <Button
+            type="button"
+            variant="outline"
+            onClick={() => onOpenChange(false)}
+            disabled={isLoading}
+          >
+            {cancelText}
+          </Button>
+          <Button
+            type="button"
+            variant={variant}
+            onClick={handleConfirm}
+            loading={isLoading}
+            disabled={isLoading}
+          >
+            {confirmText}
+          </Button>
+        </DialogFooter>
+      </DialogContent>
+    </Dialog>
+  );
+};
diff --git a/frontend/components/knowledge-actions-dropdown.tsx b/frontend/components/knowledge-actions-dropdown.tsx
index 745e66c5..f73ffe25 100644
--- a/frontend/components/knowledge-actions-dropdown.tsx
+++ b/frontend/components/knowledge-actions-dropdown.tsx
@@ -1,5 +1,6 @@
 "use client";
 
+import { useState } from "react";
 import {
   DropdownMenu,
   DropdownMenuContent,
@@ -8,20 +9,72 @@ import {
 } from "@/components/ui/dropdown-menu";
 import { EllipsisVertical } from "lucide-react";
 import { Button } from "./ui/button";
+import { DeleteConfirmationDialog } from "./confirmation-dialog";
+import { useDeleteDocument } from "@/app/api/mutations/useDeleteDocument";
+import { toast } from "sonner";
 
-export function KnowledgeActionsDropdown() {
-  return (
-    <DropdownMenu>
-      <DropdownMenuTrigger>
-        <Button variant="ghost" className="hover:bg-transparent">
-          <EllipsisVertical className="h-4 w-4" />
-        </Button>
-      </DropdownMenuTrigger>
-      <DropdownMenuContent side="right" sideOffset={-10}>
-        <DropdownMenuItem className="text-destructive focus:text-destructive-foreground focus:bg-destructive">
-          Delete
-        </DropdownMenuItem>
-      </DropdownMenuContent>
-    </DropdownMenu>
-  );
+interface KnowledgeActionsDropdownProps {
+  filename: string;
 }
+
+export const KnowledgeActionsDropdown = ({
+  filename,
+}: KnowledgeActionsDropdownProps) => {
+  const [showDeleteDialog, setShowDeleteDialog] = useState(false);
+  const deleteDocumentMutation = useDeleteDocument();
+
+  const handleDelete = async () => {
+    try {
+      await deleteDocumentMutation.mutateAsync({ filename });
+      toast.success(`Successfully deleted "${filename}"`);
+      setShowDeleteDialog(false);
+    } catch (error) {
+      toast.error(
+        error instanceof Error ? error.message : "Failed to delete document"
+      );
+    }
+  };
+
+  return (
+    <>
+      <DropdownMenu>
+        <DropdownMenuTrigger>
+          <Button variant="ghost" className="hover:bg-transparent">
+            <EllipsisVertical className="h-4 w-4" />
+          </Button>
+        </DropdownMenuTrigger>
+        <DropdownMenuContent side="right" sideOffset={-10}>
+          {/* //TODO: Implement rename and sync */}
+          {/* <DropdownMenuItem
+            className="text-primary focus:text-primary"
+            onClick={() => alert("Not implemented")}
+          >
+            Rename
+          </DropdownMenuItem>
+          <DropdownMenuItem
+            className="text-primary focus:text-primary"
+            onClick={() => alert("Not implemented")}
+          >
+            Sync
+          </DropdownMenuItem> */}
+          <DropdownMenuItem
+            className="text-destructive focus:text-destructive"
+            onClick={() => setShowDeleteDialog(true)}
+          >
+            Delete
+          </DropdownMenuItem>
+        </DropdownMenuContent>
+      </DropdownMenu>
+
+      <DeleteConfirmationDialog
+        open={showDeleteDialog}
+        onOpenChange={setShowDeleteDialog}
+        title="Delete Document"
+        description={`Are you sure you want to delete "${filename}"? This will remove all chunks and data associated with this document. This action cannot be undone.`}
+        confirmText="Delete"
+        onConfirm={handleDelete}
+        isLoading={deleteDocumentMutation.isPending}
+      />
+    </>
+  );
+};
diff --git a/frontend/components/knowledge-dropdown.tsx b/frontend/components/knowledge-dropdown.tsx
index 82581de8..f9176311 100644
--- a/frontend/components/knowledge-dropdown.tsx
+++ b/frontend/components/knowledge-dropdown.tsx
@@ -1,10 +1,10 @@
 "use client";
 
-import { useQueryClient } from "@tanstack/react-query";
 import {
   ChevronDown,
   Cloud,
   FolderOpen,
+  Loader2,
   PlugZap,
   Plus,
   Upload,
@@ -44,6 +44,7 @@ export function KnowledgeDropdown({
   const [folderLoading, setFolderLoading] = useState(false);
   const [s3Loading, setS3Loading] = useState(false);
   const [fileUploading, setFileUploading] = useState(false);
+  const [isNavigatingToCloud, setIsNavigatingToCloud] = useState(false);
   const [cloudConnectors, setCloudConnectors] = useState<{
     [key: string]: {
       name: string;
@@ -55,12 +56,6 @@ export function KnowledgeDropdown({
   const fileInputRef = useRef<HTMLInputElement>(null);
   const dropdownRef = useRef<HTMLDivElement>(null);
 
-  const queryClient = useQueryClient();
-
-  const refetchSearch = () => {
-    queryClient.invalidateQueries({ queryKey: ["search"] });
-  };
-
   // Check AWS availability and cloud connectors on mount
   useEffect(() => {
     const checkAvailability = async () => {
@@ -107,7 +102,7 @@ export function KnowledgeDropdown({
                   const connections = statusData.connections || [];
                   const activeConnection = connections.find(
                     (conn: { is_active: boolean; connection_id: string }) =>
-                      conn.is_active,
+                      conn.is_active
                   );
                   const isConnected = activeConnection !== undefined;
 
@@ -117,7 +112,7 @@ export function KnowledgeDropdown({
                     // Check token availability
                     try {
                       const tokenRes = await fetch(
-                        `/api/connectors/${type}/token?connection_id=${activeConnection.connection_id}`,
+                        `/api/connectors/${type}/token?connection_id=${activeConnection.connection_id}`
                       );
                       if (tokenRes.ok) {
                         const tokenData = await tokenRes.json();
@@ -178,7 +173,7 @@ export function KnowledgeDropdown({
       window.dispatchEvent(
         new CustomEvent("fileUploadStart", {
           detail: { filename: files[0].name },
-        }),
+        })
       );
 
       try {
@@ -190,21 +185,38 @@ export function KnowledgeDropdown({
           method: "POST",
           body: formData,
         });
+
         const uploadIngestJson = await uploadIngestRes.json();
+
         if (!uploadIngestRes.ok) {
           throw new Error(
-            uploadIngestJson?.error || "Upload and ingest failed",
+            uploadIngestJson?.error || "Upload and ingest failed"
           );
         }
 
-        // Extract results from the unified response
-        const fileId = uploadIngestJson?.upload?.id;
-        const filePath = uploadIngestJson?.upload?.path;
+        // Extract results from the response - handle both unified and simple formats
+        const fileId = uploadIngestJson?.upload?.id || uploadIngestJson?.id;
+        const filePath =
+          uploadIngestJson?.upload?.path ||
+          uploadIngestJson?.path ||
+          "uploaded";
         const runJson = uploadIngestJson?.ingestion;
         const deleteResult = uploadIngestJson?.deletion;
 
-        if (!fileId || !filePath) {
-          throw new Error("Upload successful but no file id/path returned");
+        if (!fileId) {
+          throw new Error("Upload successful but no file id returned");
+        }
+
+        // Check if ingestion actually succeeded
+        if (
+          runJson &&
+          runJson.status !== "COMPLETED" &&
+          runJson.status !== "SUCCESS"
+        ) {
+          const errorMsg = runJson.error || "Ingestion pipeline failed";
+          throw new Error(
+            `Ingestion failed: ${errorMsg}. Try setting DISABLE_INGEST_WITH_LANGFLOW=true if you're experiencing Langflow component issues.`
+          );
         }
 
         // Log deletion status if provided
@@ -212,12 +224,12 @@ export function KnowledgeDropdown({
           if (deleteResult.status === "deleted") {
             console.log(
               "File successfully cleaned up from Langflow:",
-              deleteResult.file_id,
+              deleteResult.file_id
             );
           } else if (deleteResult.status === "delete_failed") {
             console.warn(
               "Failed to cleanup file from Langflow:",
-              deleteResult.error,
+              deleteResult.error
             );
           }
         }
@@ -235,8 +247,9 @@ export function KnowledgeDropdown({
                 unified: true,
               },
             },
-          }),
+          })
         );
+
         // Trigger search refresh after successful ingestion
         window.dispatchEvent(new CustomEvent("knowledgeUpdated"));
       } catch (error) {
@@ -246,12 +259,12 @@ export function KnowledgeDropdown({
               filename: files[0].name,
               error: error instanceof Error ? error.message : "Upload failed",
             },
-          }),
+          })
         );
       } finally {
         window.dispatchEvent(new CustomEvent("fileUploadComplete"));
         setFileUploading(false);
-        refetchSearch();
+        // Don't call refetchSearch() here - the knowledgeUpdated event will handle it
       }
     }
 
@@ -288,9 +301,15 @@ export function KnowledgeDropdown({
         addTask(taskId);
         setFolderPath("");
         // Trigger search refresh after successful folder processing starts
+        console.log(
+          "Folder upload successful, dispatching knowledgeUpdated event"
+        );
         window.dispatchEvent(new CustomEvent("knowledgeUpdated"));
       } else if (response.ok) {
         setFolderPath("");
+        console.log(
+          "Folder upload successful (direct), dispatching knowledgeUpdated event"
+        );
         window.dispatchEvent(new CustomEvent("knowledgeUpdated"));
       } else {
         console.error("Folder upload failed:", result.error);
@@ -299,7 +318,7 @@ export function KnowledgeDropdown({
       console.error("Folder upload error:", error);
     } finally {
       setFolderLoading(false);
-      refetchSearch();
+      // Don't call refetchSearch() here - the knowledgeUpdated event will handle it
     }
   };
 
@@ -330,6 +349,7 @@ export function KnowledgeDropdown({
         addTask(taskId);
         setBucketUrl("s3://");
         // Trigger search refresh after successful S3 processing starts
+        console.log("S3 upload successful, dispatching knowledgeUpdated event");
         window.dispatchEvent(new CustomEvent("knowledgeUpdated"));
       } else {
         console.error("S3 upload failed:", result.error);
@@ -338,7 +358,7 @@ export function KnowledgeDropdown({
       console.error("S3 upload error:", error);
     } finally {
       setS3Loading(false);
-      refetchSearch();
+      // Don't call refetchSearch() here - the knowledgeUpdated event will handle it
     }
   };
 
@@ -347,10 +367,17 @@ export function KnowledgeDropdown({
     .map(([type, info]) => ({
       label: info.name,
       icon: PlugZap,
-      onClick: () => {
+      onClick: async () => {
         setIsOpen(false);
         if (info.connected && info.hasToken) {
-          router.push(`/upload/${type}`);
+          setIsNavigatingToCloud(true);
+          try {
+            router.push(`/upload/${type}`);
+            // Keep loading state for a short time to show feedback
+            setTimeout(() => setIsNavigatingToCloud(false), 1000);
+          } catch {
+            setIsNavigatingToCloud(false);
+          }
         } else {
           router.push("/settings");
         }
@@ -392,14 +419,16 @@ export function KnowledgeDropdown({
     ...cloudConnectorItems,
   ];
 
+  // Comprehensive loading state
+  const isLoading =
+    fileUploading || folderLoading || s3Loading || isNavigatingToCloud;
+
   return (
     <>
       <div ref={dropdownRef} className="relative">
         <button
-          onClick={() =>
-            !(fileUploading || folderLoading || s3Loading) && setIsOpen(!isOpen)
-          }
-          disabled={fileUploading || folderLoading || s3Loading}
+          onClick={() => !isLoading && setIsOpen(!isOpen)}
+          disabled={isLoading}
           className={cn(
             variant === "button"
               ? "rounded-lg h-12 px-4 flex items-center gap-2 bg-primary text-primary-foreground hover:bg-primary/90 transition-colors disabled:opacity-50 disabled:cursor-not-allowed"
@@ -408,44 +437,68 @@ export function KnowledgeDropdown({
               ? "bg-accent text-accent-foreground shadow-sm"
               : variant === "navigation"
               ? "text-foreground hover:text-accent-foreground"
-              : "",
+              : ""
           )}
         >
           {variant === "button" ? (
             <>
-              <Plus className="h-4 w-4" />
-              <span>Add Knowledge</span>
-              <ChevronDown
-                className={cn(
-                  "h-4 w-4 transition-transform",
-                  isOpen && "rotate-180",
-                )}
-              />
+              {isLoading ? (
+                <Loader2 className="h-4 w-4 animate-spin" />
+              ) : (
+                <Plus className="h-4 w-4" />
+              )}
+              <span>
+                {isLoading
+                  ? fileUploading
+                    ? "Uploading..."
+                    : folderLoading
+                    ? "Processing Folder..."
+                    : s3Loading
+                    ? "Processing S3..."
+                    : isNavigatingToCloud
+                    ? "Loading..."
+                    : "Processing..."
+                  : "Add Knowledge"}
+              </span>
+              {!isLoading && (
+                <ChevronDown
+                  className={cn(
+                    "h-4 w-4 transition-transform",
+                    isOpen && "rotate-180"
+                  )}
+                />
+              )}
             </>
           ) : (
             <>
               <div className="flex items-center flex-1">
-                <Upload
-                  className={cn(
-                    "h-4 w-4 mr-3 shrink-0",
-                    active
-                      ? "text-accent-foreground"
-                      : "text-muted-foreground group-hover:text-foreground",
-                  )}
-                />
+                {isLoading ? (
+                  <Loader2 className="h-4 w-4 mr-3 shrink-0 animate-spin" />
+                ) : (
+                  <Upload
+                    className={cn(
+                      "h-4 w-4 mr-3 shrink-0",
+                      active
+                        ? "text-accent-foreground"
+                        : "text-muted-foreground group-hover:text-foreground"
+                    )}
+                  />
+                )}
                 Knowledge
               </div>
-              <ChevronDown
-                className={cn(
-                  "h-4 w-4 transition-transform",
-                  isOpen && "rotate-180",
-                )}
-              />
+              {!isLoading && (
+                <ChevronDown
+                  className={cn(
+                    "h-4 w-4 transition-transform",
+                    isOpen && "rotate-180"
+                  )}
+                />
+              )}
             </>
           )}
         </button>
 
-        {isOpen && (
+        {isOpen && !isLoading && (
           <div className="absolute top-full left-0 right-0 mt-1 bg-popover border border-border rounded-md shadow-md z-50">
             <div className="py-1">
               {menuItems.map((item, index) => (
@@ -458,7 +511,7 @@ export function KnowledgeDropdown({
                     "w-full px-3 py-2 text-left text-sm hover:bg-accent hover:text-accent-foreground",
                     "disabled" in item &&
                       item.disabled &&
-                      "opacity-50 cursor-not-allowed hover:bg-transparent hover:text-current",
+                      "opacity-50 cursor-not-allowed hover:bg-transparent hover:text-current"
                   )}
                 >
                   {item.label}
@@ -497,7 +550,7 @@ export function KnowledgeDropdown({
                 type="text"
                 placeholder="/path/to/documents"
                 value={folderPath}
-                onChange={(e) => setFolderPath(e.target.value)}
+                onChange={e => setFolderPath(e.target.value)}
               />
             </div>
             <div className="flex justify-end gap-2">
@@ -539,7 +592,7 @@ export function KnowledgeDropdown({
                 type="text"
                 placeholder="s3://bucket/path"
                 value={bucketUrl}
-                onChange={(e) => setBucketUrl(e.target.value)}
+                onChange={e => setBucketUrl(e.target.value)}
               />
             </div>
             <div className="flex justify-end gap-2">
diff --git a/frontend/components/ui/input.tsx b/frontend/components/ui/input.tsx
index 3dc0b5f0..1eea9079 100644
--- a/frontend/components/ui/input.tsx
+++ b/frontend/components/ui/input.tsx
@@ -1,7 +1,8 @@
 import * as React from "react";
 import { cn } from "@/lib/utils";
 
-export interface InputProps extends React.InputHTMLAttributes<HTMLInputElement> {
+export interface InputProps
+  extends React.InputHTMLAttributes<HTMLInputElement> {
   icon?: React.ReactNode;
   inputClassName?: string;
 }
@@ -9,7 +10,12 @@ export interface InputProps extends React.InputHTMLAttributes<HTMLInputElement>
 const Input = React.forwardRef<HTMLInputElement, InputProps>(
   ({ className, inputClassName, icon, type, placeholder, ...props }, ref) => {
     return (
-      <label className={cn("relative block h-fit w-full text-sm", icon ? className : "")}>
+      <label
+        className={cn(
+          "relative block h-fit w-full text-sm",
+          icon ? className : ""
+        )}
+      >
         {icon && (
           <div className="pointer-events-none absolute left-3 top-1/2 h-4 w-4 -translate-y-1/2 transform text-muted-foreground">
             {icon}
@@ -22,7 +28,7 @@ const Input = React.forwardRef<HTMLInputElement, InputProps>(
           className={cn(
             "primary-input !placeholder-transparent",
             icon && "pl-9",
-            icon ? inputClassName : className,
+            icon ? inputClassName : className
           )}
           ref={ref}
           {...props}
@@ -31,14 +37,14 @@ const Input = React.forwardRef<HTMLInputElement, InputProps>(
           className={cn(
             "pointer-events-none absolute top-1/2 -translate-y-1/2 pl-px text-placeholder-foreground font-mono",
             icon ? "left-9" : "left-3",
-            props.value && "hidden",
+            props.value && "hidden"
           )}
         >
           {placeholder}
         </span>
       </label>
     );
-  },
+  }
 );
 
 Input.displayName = "Input";
diff --git a/frontend/src/app/api/mutations/useDeleteDocument.ts b/frontend/src/app/api/mutations/useDeleteDocument.ts
new file mode 100644
index 00000000..78985498
--- /dev/null
+++ b/frontend/src/app/api/mutations/useDeleteDocument.ts
@@ -0,0 +1,45 @@
+"use client";
+
+import { useMutation, useQueryClient } from "@tanstack/react-query";
+
+interface DeleteDocumentRequest {
+  filename: string;
+}
+
+interface DeleteDocumentResponse {
+  success: boolean;
+  deleted_chunks: number;
+  filename: string;
+  message: string;
+}
+
+const deleteDocument = async (
+  data: DeleteDocumentRequest
+): Promise<DeleteDocumentResponse> => {
+  const response = await fetch("/api/documents/delete-by-filename", {
+    method: "POST",
+    headers: {
+      "Content-Type": "application/json",
+    },
+    body: JSON.stringify(data),
+  });
+
+  if (!response.ok) {
+    const error = await response.json();
+    throw new Error(error.error || "Failed to delete document");
+  }
+
+  return response.json();
+};
+
+export const useDeleteDocument = () => {
+  const queryClient = useQueryClient();
+
+  return useMutation({
+    mutationFn: deleteDocument,
+    onSuccess: () => {
+      // Invalidate and refetch search queries to update the UI
+      queryClient.invalidateQueries({ queryKey: ["search"] });
+    },
+  });
+};
diff --git a/frontend/src/app/api/queries/useGetNudgesQuery.ts b/frontend/src/app/api/queries/useGetNudgesQuery.ts
index 38cc9502..a9fe37a4 100644
--- a/frontend/src/app/api/queries/useGetNudgesQuery.ts
+++ b/frontend/src/app/api/queries/useGetNudgesQuery.ts
@@ -14,7 +14,7 @@ const DEFAULT_NUDGES = [
 
 export const useGetNudgesQuery = (
   chatId?: string | null,
-  options?: Omit<UseQueryOptions, "queryKey" | "queryFn">,
+  options?: Omit<UseQueryOptions, "queryKey" | "queryFn">
 ) => {
   const queryClient = useQueryClient();
 
@@ -26,7 +26,12 @@ export const useGetNudgesQuery = (
     try {
       const response = await fetch(`/api/nudges${chatId ? `/${chatId}` : ""}`);
       const data = await response.json();
-      return data.response.split("\n").filter(Boolean) || DEFAULT_NUDGES;
+
+      if (data.response && typeof data.response === "string") {
+        return data.response.split("\n").filter(Boolean);
+      }
+
+      return DEFAULT_NUDGES;
     } catch (error) {
       console.error("Error getting nudges", error);
       return DEFAULT_NUDGES;
@@ -39,7 +44,7 @@ export const useGetNudgesQuery = (
       queryFn: getNudges,
       ...options,
     },
-    queryClient,
+    queryClient
   );
 
   return { ...queryResult, cancel };
diff --git a/frontend/src/app/api/queries/useGetSearchQuery.ts b/frontend/src/app/api/queries/useGetSearchQuery.ts
index cfe4ed71..de1daeb6 100644
--- a/frontend/src/app/api/queries/useGetSearchQuery.ts
+++ b/frontend/src/app/api/queries/useGetSearchQuery.ts
@@ -48,15 +48,22 @@ export interface File {
 export const useGetSearchQuery = (
   query: string,
   queryData?: ParsedQueryData | null,
-  options?: Omit<UseQueryOptions, "queryKey" | "queryFn">,
+  options?: Omit<UseQueryOptions, "queryKey" | "queryFn">
 ) => {
   const queryClient = useQueryClient();
 
+  // Normalize the query to match what will actually be searched
+  const effectiveQuery = query || queryData?.query || "*";
+
   async function getFiles(): Promise<File[]> {
     try {
       const searchPayload: SearchPayload = {
-        query: query || queryData?.query || "*",
-        limit: queryData?.limit || (query.trim() === "" ? 10000 : 10), // Maximum allowed limit for wildcard searches
+        query: effectiveQuery,
+        limit:
+          queryData?.limit ||
+          (effectiveQuery.trim() === "*" || effectiveQuery.trim() === ""
+            ? 10000
+            : 10), // Maximum allowed limit for wildcard searches
         scoreThreshold: queryData?.scoreThreshold || 0,
       };
       if (queryData?.filters) {
@@ -142,7 +149,7 @@ export const useGetSearchQuery = (
         }
       });
 
-      const files: File[] = Array.from(fileMap.values()).map((file) => ({
+      const files: File[] = Array.from(fileMap.values()).map(file => ({
         filename: file.filename,
         mimetype: file.mimetype,
         chunkCount: file.chunks.length,
@@ -165,12 +172,12 @@ export const useGetSearchQuery = (
 
   const queryResult = useQuery(
     {
-      queryKey: ["search", query],
-      placeholderData: (prev) => prev,
+      queryKey: ["search", effectiveQuery],
+      placeholderData: prev => prev,
       queryFn: getFiles,
       ...options,
     },
-    queryClient,
+    queryClient
   );
 
   return queryResult;
diff --git a/frontend/src/app/knowledge/chunks/page.tsx b/frontend/src/app/knowledge/chunks/page.tsx
new file mode 100644
index 00000000..9385c474
--- /dev/null
+++ b/frontend/src/app/knowledge/chunks/page.tsx
@@ -0,0 +1,212 @@
+"use client";
+
+import {
+  Building2,
+  Cloud,
+  FileText,
+  HardDrive,
+  Loader2,
+  Search,
+} from "lucide-react";
+import { Suspense, useCallback, useEffect, useState } from "react";
+import { useRouter, useSearchParams } from "next/navigation";
+import { SiGoogledrive } from "react-icons/si";
+import { TbBrandOnedrive } from "react-icons/tb";
+import { ProtectedRoute } from "@/components/protected-route";
+import { Button } from "@/components/ui/button";
+import { useKnowledgeFilter } from "@/contexts/knowledge-filter-context";
+import { useTask } from "@/contexts/task-context";
+import {
+  type ChunkResult,
+  type File,
+  useGetSearchQuery,
+} from "../../api/queries/useGetSearchQuery";
+
+// Function to get the appropriate icon for a connector type
+function getSourceIcon(connectorType?: string) {
+  switch (connectorType) {
+    case "google_drive":
+      return <SiGoogledrive className="h-4 w-4 text-foreground" />;
+    case "onedrive":
+      return <TbBrandOnedrive className="h-4 w-4 text-foreground" />;
+    case "sharepoint":
+      return <Building2 className="h-4 w-4 text-foreground" />;
+    case "s3":
+      return <Cloud className="h-4 w-4 text-foreground" />;
+    default:
+      return <HardDrive className="h-4 w-4 text-muted-foreground" />;
+  }
+}
+
+function ChunksPageContent() {
+  const router = useRouter();
+  const searchParams = useSearchParams();
+  const { isMenuOpen } = useTask();
+  const { parsedFilterData, isPanelOpen } = useKnowledgeFilter();
+
+  const filename = searchParams.get("filename");
+  const [chunks, setChunks] = useState<ChunkResult[]>([]);
+
+  // Use the same search query as the knowledge page, but we'll filter for the specific file
+  const { data = [], isFetching } = useGetSearchQuery("*", parsedFilterData);
+
+  // Extract chunks for the specific file
+  useEffect(() => {
+    if (!filename || !(data as File[]).length) {
+      setChunks([]);
+      return;
+    }
+
+    const fileData = (data as File[]).find(
+      (file: File) => file.filename === filename
+    );
+    setChunks(fileData?.chunks || []);
+  }, [data, filename]);
+
+  const handleBack = useCallback(() => {
+    router.back();
+  }, [router]);
+
+  if (!filename) {
+    return (
+      <div className="flex items-center justify-center h-64">
+        <div className="text-center">
+          <Search className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50" />
+          <p className="text-lg text-muted-foreground">No file specified</p>
+          <p className="text-sm text-muted-foreground/70 mt-2">
+            Please select a file from the knowledge page
+          </p>
+        </div>
+      </div>
+    );
+  }
+
+  return (
+    <div
+      className={`fixed inset-0 md:left-72 top-[53px] flex flex-col transition-all duration-300 ${
+        isMenuOpen && isPanelOpen
+          ? "md:right-[704px]"
+          : // Both open: 384px (menu) + 320px (KF panel)
+          isMenuOpen
+          ? "md:right-96"
+          : // Only menu open: 384px
+          isPanelOpen
+          ? "md:right-80"
+          : // Only KF panel open: 320px
+            "md:right-6" // Neither open: 24px
+      }`}
+    >
+      <div className="flex-1 flex flex-col min-h-0 px-6 py-6">
+        {/* Header */}
+        <div className="flex items-center justify-between mb-6">
+          <div className="flex items-center gap-3">
+            <Button
+              variant="ghost"
+              size="sm"
+              onClick={handleBack}
+              className="text-muted-foreground hover:text-foreground px-2"
+            >
+              ← Back
+            </Button>
+            <div className="flex flex-col">
+              <h2 className="text-lg font-semibold">Document Chunks</h2>
+              <p className="text-sm text-muted-foreground truncate max-w-md">
+                {decodeURIComponent(filename)}
+              </p>
+            </div>
+          </div>
+          <div className="text-sm text-muted-foreground">
+            {!isFetching && chunks.length > 0 && (
+              <span>
+                {chunks.length} chunk{chunks.length !== 1 ? "s" : ""} found
+              </span>
+            )}
+          </div>
+        </div>
+
+        {/* Content Area - matches knowledge page structure */}
+        <div className="flex-1 overflow-auto">
+          {isFetching ? (
+            <div className="flex items-center justify-center h-64">
+              <div className="text-center">
+                <Loader2 className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50 animate-spin" />
+                <p className="text-lg text-muted-foreground">
+                  Loading chunks...
+                </p>
+              </div>
+            </div>
+          ) : chunks.length === 0 ? (
+            <div className="flex items-center justify-center h-64">
+              <div className="text-center">
+                <Search className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50" />
+                <p className="text-lg text-muted-foreground">No chunks found</p>
+                <p className="text-sm text-muted-foreground/70 mt-2">
+                  This file may not have been indexed yet
+                </p>
+              </div>
+            </div>
+          ) : (
+            <div className="space-y-4 pb-6">
+              {chunks.map((chunk, index) => (
+                <div
+                  key={chunk.filename + index}
+                  className="bg-muted/20 rounded-lg p-4 border border-border/50"
+                >
+                  <div className="flex items-center justify-between mb-2">
+                    <div className="flex items-center gap-2">
+                      <FileText className="h-4 w-4 text-blue-400" />
+                      <span className="font-medium truncate">
+                        {chunk.filename}
+                      </span>
+                      {chunk.connector_type && (
+                        <div className="ml-2">
+                          {getSourceIcon(chunk.connector_type)}
+                        </div>
+                      )}
+                    </div>
+                    <span className="text-xs text-green-400 bg-green-400/20 px-2 py-1 rounded">
+                      {chunk.score.toFixed(2)}
+                    </span>
+                  </div>
+                  <div className="flex items-center gap-4 text-sm text-muted-foreground mb-3">
+                    <span>{chunk.mimetype}</span>
+                    <span>Page {chunk.page}</span>
+                    {chunk.owner_name && <span>Owner: {chunk.owner_name}</span>}
+                  </div>
+                  <p className="text-sm text-foreground/90 leading-relaxed">
+                    {chunk.text}
+                  </p>
+                </div>
+              ))}
+            </div>
+          )}
+        </div>
+      </div>
+    </div>
+  );
+}
+
+function ChunksPage() {
+  return (
+    <Suspense
+      fallback={
+        <div className="flex items-center justify-center h-64">
+          <div className="text-center">
+            <Loader2 className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50 animate-spin" />
+            <p className="text-lg text-muted-foreground">Loading...</p>
+          </div>
+        </div>
+      }
+    >
+      <ChunksPageContent />
+    </Suspense>
+  );
+}
+
+export default function ProtectedChunksPage() {
+  return (
+    <ProtectedRoute>
+      <ChunksPage />
+    </ProtectedRoute>
+  );
+}
diff --git a/frontend/src/app/knowledge/page.tsx b/frontend/src/app/knowledge/page.tsx
index 8b85313e..b23acf84 100644
--- a/frontend/src/app/knowledge/page.tsx
+++ b/frontend/src/app/knowledge/page.tsx
@@ -3,10 +3,10 @@
 import {
   Building2,
   Cloud,
-  FileText,
   HardDrive,
   Loader2,
   Search,
+  Trash2,
 } from "lucide-react";
 import { AgGridReact, CustomCellRendererProps } from "ag-grid-react";
 import {
@@ -16,6 +16,7 @@ import {
   useState,
   useRef,
 } from "react";
+import { useRouter } from "next/navigation";
 import { SiGoogledrive } from "react-icons/si";
 import { TbBrandOnedrive } from "react-icons/tb";
 import { KnowledgeDropdown } from "@/components/knowledge-dropdown";
@@ -25,33 +26,46 @@ import { Input } from "@/components/ui/input";
 import { useKnowledgeFilter } from "@/contexts/knowledge-filter-context";
 import { useTask } from "@/contexts/task-context";
 import { type File, useGetSearchQuery } from "../api/queries/useGetSearchQuery";
-import { ColDef, RowClickedEvent } from "ag-grid-community";
+import { ColDef } from "ag-grid-community";
 import "@/components/AgGrid/registerAgGridModules";
 import "@/components/AgGrid/agGridStyles.css";
 import { KnowledgeActionsDropdown } from "@/components/knowledge-actions-dropdown";
+import { DeleteConfirmationDialog } from "../../../components/confirmation-dialog";
+import { useDeleteDocument } from "../api/mutations/useDeleteDocument";
+import { toast } from "sonner";
 
 // Function to get the appropriate icon for a connector type
 function getSourceIcon(connectorType?: string) {
   switch (connectorType) {
     case "google_drive":
-      return <SiGoogledrive className="h-4 w-4 text-foreground" />;
+      return (
+        <SiGoogledrive className="h-4 w-4 text-foreground flex-shrink-0" />
+      );
     case "onedrive":
-      return <TbBrandOnedrive className="h-4 w-4 text-foreground" />;
+      return (
+        <TbBrandOnedrive className="h-4 w-4 text-foreground flex-shrink-0" />
+      );
     case "sharepoint":
-      return <Building2 className="h-4 w-4 text-foreground" />;
+      return <Building2 className="h-4 w-4 text-foreground flex-shrink-0" />;
     case "s3":
-      return <Cloud className="h-4 w-4 text-foreground" />;
+      return <Cloud className="h-4 w-4 text-foreground flex-shrink-0" />;
     default:
-      return <HardDrive className="h-4 w-4 text-muted-foreground" />;
+      return (
+        <HardDrive className="h-4 w-4 text-muted-foreground flex-shrink-0" />
+      );
   }
 }
 
 function SearchPage() {
+  const router = useRouter();
   const { isMenuOpen } = useTask();
   const { parsedFilterData, isPanelOpen } = useKnowledgeFilter();
   const [query, setQuery] = useState("");
   const [queryInputText, setQueryInputText] = useState("");
-  const [selectedFile, setSelectedFile] = useState<string | null>(null);
+  const [selectedRows, setSelectedRows] = useState<File[]>([]);
+  const [showBulkDeleteDialog, setShowBulkDeleteDialog] = useState(false);
+
+  const deleteDocumentMutation = useDeleteDocument();
 
   const {
     data = [],
@@ -86,9 +100,22 @@ function SearchPage() {
     {
       field: "filename",
       headerName: "Source",
+      checkboxSelection: true,
+      headerCheckboxSelection: true,
+      initialFlex: 2,
+      minWidth: 220,
       cellRenderer: ({ data, value }: CustomCellRendererProps<File>) => {
         return (
-          <div className="flex items-center gap-2">
+          <div
+            className="flex items-center gap-2 cursor-pointer hover:text-blue-600 transition-colors"
+            onClick={() => {
+              router.push(
+                `/knowledge/chunks?filename=${encodeURIComponent(
+                  data?.filename ?? ""
+                )}`
+              );
+            }}
+          >
             {getSourceIcon(data?.connector_type)}
             <span className="font-medium text-foreground truncate">
               {value}
@@ -111,12 +138,8 @@ function SearchPage() {
       field: "owner",
       headerName: "Owner",
       valueFormatter: (params) =>
-        params.value ||
-        params.data?.owner_name ||
-        params.data?.owner_email ||
-        "—",
+        params.data?.owner_name || params.data?.owner_email || "—",
     },
-
     {
       field: "chunkCount",
       headerName: "Chunks",
@@ -133,19 +156,20 @@ function SearchPage() {
       },
     },
     {
-      cellRenderer: () => {
-        return <KnowledgeActionsDropdown />;
+      cellRenderer: ({ data }: CustomCellRendererProps<File>) => {
+        return <KnowledgeActionsDropdown filename={data?.filename || ""} />;
       },
       cellStyle: {
-        alignItems: 'center',
-        display: 'flex',
-        justifyContent: 'center',
+        alignItems: "center",
+        display: "flex",
+        justifyContent: "center",
         padding: 0,
       },
-      colId: 'actions',
+      colId: "actions",
       filter: false,
-      maxWidth: 60,
+      width: 60,
       minWidth: 60,
+      maxWidth: 60,
       resizable: false,
       sortable: false,
       initialFlex: 0,
@@ -153,14 +177,49 @@ function SearchPage() {
   ]);
 
   const defaultColDef: ColDef<File> = {
-    cellStyle: () => ({
-      display: "flex",
-      alignItems: "center",
-    }),
-    initialFlex: 1,
-    minWidth: 100,
     resizable: false,
     suppressMovable: true,
+    initialFlex: 1,
+    minWidth: 100,
+  };
+
+  const onSelectionChanged = useCallback(() => {
+    if (gridRef.current) {
+      const selectedNodes = gridRef.current.api.getSelectedRows();
+      setSelectedRows(selectedNodes);
+    }
+  }, []);
+
+  const handleBulkDelete = async () => {
+    if (selectedRows.length === 0) return;
+
+    try {
+      // Delete each file individually since the API expects one filename at a time
+      const deletePromises = selectedRows.map((row) =>
+        deleteDocumentMutation.mutateAsync({ filename: row.filename })
+      );
+
+      await Promise.all(deletePromises);
+
+      toast.success(
+        `Successfully deleted ${selectedRows.length} document${
+          selectedRows.length > 1 ? "s" : ""
+        }`
+      );
+      setSelectedRows([]);
+      setShowBulkDeleteDialog(false);
+
+      // Clear selection in the grid
+      if (gridRef.current) {
+        gridRef.current.api.deselectAll();
+      }
+    } catch (error) {
+      toast.error(
+        error instanceof Error
+          ? error.message
+          : "Failed to delete some documents"
+      );
+    }
   };
 
   return (
@@ -183,6 +242,7 @@ function SearchPage() {
           <h2 className="text-lg font-semibold">Project Knowledge</h2>
           <KnowledgeDropdown variant="button" />
         </div>
+
         {/* Search Input Area */}
         <div className="flex-shrink-0 mb-6 lg:max-w-[75%] xl:max-w-[50%]">
           <form onSubmit={handleSearch} className="flex gap-3">
@@ -194,12 +254,12 @@ function SearchPage() {
               value={queryInputText}
               onChange={(e) => setQueryInputText(e.target.value)}
               placeholder="Search your documents..."
-              className="flex-1 bg-muted/20 rounded-lg border border-border/50 px-4 py-3 h-12 focus-visible:ring-1 focus-visible:ring-ring"
+              className="flex-1 bg-muted/20 rounded-lg border border-border/50 px-4 py-3 focus-visible:ring-1 focus-visible:ring-ring"
             />
             <Button
               type="submit"
               variant="outline"
-              className="rounded-lg h-12 w-12 p-0 flex-shrink-0"
+              className="rounded-lg p-0 flex-shrink-0"
             >
               {isFetching ? (
                 <Loader2 className="h-4 w-4 animate-spin" />
@@ -207,75 +267,70 @@ function SearchPage() {
                 <Search className="h-4 w-4" />
               )}
             </Button>
+            {/* //TODO: Implement sync button */}
+            {/* <Button
+              type="button"
+              variant="outline"
+              className="rounded-lg flex-shrink-0"
+              onClick={() => alert("Not implemented")}
+            >
+              Sync
+            </Button> */}
+            <Button
+              type="button"
+              variant="destructive"
+              className="rounded-lg flex-shrink-0"
+              onClick={() => setShowBulkDeleteDialog(true)}
+              disabled={selectedRows.length === 0}
+            >
+              <Trash2 className="h-4 w-4" /> Delete
+            </Button>
           </form>
         </div>
-        {selectedFile ? (
-          // Show chunks for selected file
-          <>
-            <div className="flex items-center gap-2 mb-4">
-              <Button
-                variant="ghost"
-                size="sm"
-                onClick={() => setSelectedFile(null)}
-              >
-                ← Back to files
-              </Button>
-              <span className="text-sm text-muted-foreground">
-                Chunks from {selectedFile}
-              </span>
+        <AgGridReact
+          className="w-full overflow-auto"
+          columnDefs={columnDefs}
+          defaultColDef={defaultColDef}
+          loading={isFetching}
+          ref={gridRef}
+          rowData={fileResults}
+          rowSelection="multiple"
+          rowMultiSelectWithClick={false}
+          suppressRowClickSelection={true}
+          getRowId={(params) => params.data.filename}
+          onSelectionChanged={onSelectionChanged}
+          suppressHorizontalScroll={false}
+          noRowsOverlayComponent={() => (
+            <div className="text-center">
+              <Search className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50" />
+              <p className="text-lg text-muted-foreground">
+                No documents found
+              </p>
+              <p className="text-sm text-muted-foreground/70 mt-2">
+                Try adjusting your search terms
+              </p>
             </div>
-            {fileResults
-              .filter((file) => file.filename === selectedFile)
-              .flatMap((file) => file.chunks)
-              .map((chunk, index) => (
-                <div
-                  key={chunk.filename + index}
-                  className="bg-muted/20 rounded-lg p-4 border border-border/50"
-                >
-                  <div className="flex items-center justify-between mb-2">
-                    <div className="flex items-center gap-2">
-                      <FileText className="h-4 w-4 text-blue-400" />
-                      <span className="font-medium truncate">
-                        {chunk.filename}
-                      </span>
-                    </div>
-                    <span className="text-xs text-green-400 bg-green-400/20 px-2 py-1 rounded">
-                      {chunk.score.toFixed(2)}
-                    </span>
-                  </div>
-                  <div className="text-sm text-muted-foreground mb-2">
-                    {chunk.mimetype} • Page {chunk.page}
-                  </div>
-                  <p className="text-sm text-foreground/90 leading-relaxed">
-                    {chunk.text}
-                  </p>
-                </div>
-              ))}
-          </>
-        ) : (
-          <AgGridReact
-            columnDefs={columnDefs}
-            defaultColDef={defaultColDef}
-            loading={isFetching}
-            ref={gridRef}
-            rowData={fileResults}
-            onRowClicked={(params: RowClickedEvent<File>) => {
-              setSelectedFile(params.data?.filename ?? "");
-            }}
-            noRowsOverlayComponent={() => (
-              <div className="text-center">
-                <Search className="h-12 w-12 mx-auto mb-4 text-muted-foreground/50" />
-                <p className="text-lg text-muted-foreground">
-                  No documents found
-                </p>
-                <p className="text-sm text-muted-foreground/70 mt-2">
-                  Try adjusting your search terms
-                </p>
-              </div>
-            )}
-          />
-        )}
+          )}
+        />
       </div>
+
+      {/* Bulk Delete Confirmation Dialog */}
+      <DeleteConfirmationDialog
+        open={showBulkDeleteDialog}
+        onOpenChange={setShowBulkDeleteDialog}
+        title="Delete Documents"
+        description={`Are you sure you want to delete ${
+          selectedRows.length
+        } document${
+          selectedRows.length > 1 ? "s" : ""
+        }? This will remove all chunks and data associated with these documents. This action cannot be undone.
+
+Documents to be deleted:
+${selectedRows.map((row) => `• ${row.filename}`).join("\n")}`}
+        confirmText="Delete All"
+        onConfirm={handleBulkDelete}
+        isLoading={deleteDocumentMutation.isPending}
+      />
     </div>
   );
 }
diff --git a/frontend/src/components/AgGrid/agGridStyles.css b/frontend/src/components/AgGrid/agGridStyles.css
index b595e18c..590046c2 100644
--- a/frontend/src/components/AgGrid/agGridStyles.css
+++ b/frontend/src/components/AgGrid/agGridStyles.css
@@ -11,11 +11,30 @@ body {
   --ag-wrapper-border: none;
   --ag-font-family: var(--font-sans);
 
+  /* Checkbox styling */
+  --ag-checkbox-background-color: hsl(var(--background));
+  --ag-checkbox-border-color: hsl(var(--border));
+  --ag-checkbox-checked-color: hsl(var(--primary));
+  --ag-checkbox-unchecked-color: transparent;
+
   .ag-header {
     border-bottom: 1px solid hsl(var(--border));
     margin-bottom: 0.5rem;
   }
-  .ag-row {
-    cursor: pointer;
+
+  /* Make sure checkboxes are visible */
+  .ag-selection-checkbox,
+  .ag-header-select-all {
+    opacity: 1 !important;
+  }
+
+  .ag-checkbox-input-wrapper {
+    border: 1px solid hsl(var(--border));
+    background-color: hsl(var(--background));
+  }
+
+  .ag-checkbox-input-wrapper.ag-checked {
+    background-color: hsl(var(--primary));
+    border-color: hsl(var(--primary));
   }
 }
diff --git a/frontend/src/components/AgGrid/registerAgGridModules.ts b/frontend/src/components/AgGrid/registerAgGridModules.ts
index da2c5280..6f3f7bc2 100644
--- a/frontend/src/components/AgGrid/registerAgGridModules.ts
+++ b/frontend/src/components/AgGrid/registerAgGridModules.ts
@@ -11,6 +11,7 @@ import {
     DateFilterModule,
     EventApiModule,
     GridStateModule,
+    RowSelectionModule,
   } from 'ag-grid-community';
   
   // Importing necessary modules from ag-grid-community
@@ -27,6 +28,7 @@ import {
     DateFilterModule,
     EventApiModule,
     GridStateModule,
+    RowSelectionModule,
     // The ValidationModule adds helpful console warnings/errors that can help identify bad configuration during development.
     ...(process.env.NODE_ENV !== 'production' ? [ValidationModule] : []),
   ]);
diff --git a/frontend/src/contexts/task-context.tsx b/frontend/src/contexts/task-context.tsx
index f84b0f95..c58e1d19 100644
--- a/frontend/src/contexts/task-context.tsx
+++ b/frontend/src/contexts/task-context.tsx
@@ -57,7 +57,10 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
   const queryClient = useQueryClient();
 
   const refetchSearch = () => {
-    queryClient.invalidateQueries({ queryKey: ["search"] });
+    queryClient.invalidateQueries({
+      queryKey: ["search"],
+      exact: false,
+    });
   };
 
   const fetchTasks = useCallback(async () => {
@@ -71,12 +74,12 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
         const newTasks = data.tasks || [];
 
         // Update tasks and check for status changes in the same state update
-        setTasks((prevTasks) => {
+        setTasks(prevTasks => {
           // Check for newly completed tasks to show toasts
           if (prevTasks.length > 0) {
             newTasks.forEach((newTask: Task) => {
               const oldTask = prevTasks.find(
-                (t) => t.task_id === newTask.task_id,
+                t => t.task_id === newTask.task_id
               );
               if (
                 oldTask &&
@@ -92,6 +95,11 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
                   },
                 });
                 refetchSearch();
+                // Dispatch knowledge updated event for all knowledge-related pages
+                console.log(
+                  "Task completed successfully, dispatching knowledgeUpdated event"
+                );
+                window.dispatchEvent(new CustomEvent("knowledgeUpdated"));
               } else if (
                 oldTask &&
                 oldTask.status !== "failed" &&
@@ -130,21 +138,19 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
           const data = await response.json();
           const newTasks = data.tasks || [];
           const foundTask = newTasks.find(
-            (task: Task) => task.task_id === taskId,
+            (task: Task) => task.task_id === taskId
           );
 
           if (foundTask) {
             // Task found! Update the tasks state
-            setTasks((prevTasks) => {
+            setTasks(prevTasks => {
               // Check if task is already in the list
-              const exists = prevTasks.some((t) => t.task_id === taskId);
+              const exists = prevTasks.some(t => t.task_id === taskId);
               if (!exists) {
                 return [...prevTasks, foundTask];
               }
               // Update existing task
-              return prevTasks.map((t) =>
-                t.task_id === taskId ? foundTask : t,
-              );
+              return prevTasks.map(t => (t.task_id === taskId ? foundTask : t));
             });
             return; // Stop polling, we found it
           }
@@ -169,7 +175,7 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
   }, [fetchTasks]);
 
   const removeTask = useCallback((taskId: string) => {
-    setTasks((prev) => prev.filter((task) => task.task_id !== taskId));
+    setTasks(prev => prev.filter(task => task.task_id !== taskId));
   }, []);
 
   const cancelTask = useCallback(
@@ -196,11 +202,11 @@ export function TaskProvider({ children }: { children: React.ReactNode }) {
         });
       }
     },
-    [fetchTasks],
+    [fetchTasks]
   );
 
   const toggleMenu = useCallback(() => {
-    setIsMenuOpen((prev) => !prev);
+    setIsMenuOpen(prev => !prev);
   }, []);
 
   // Periodic polling for task updates
diff --git a/src/api/connectors.py b/src/api/connectors.py
index 2b08d1cb..c8bd6636 100644
--- a/src/api/connectors.py
+++ b/src/api/connectors.py
@@ -388,3 +388,5 @@ async def connector_token(request: Request, connector_service, session_manager):
     except Exception as e:
         logger.error("Error getting connector token", error=str(e))
         return JSONResponse({"error": str(e)}, status_code=500)
+
+
diff --git a/src/api/documents.py b/src/api/documents.py
new file mode 100644
index 00000000..57a4abb3
--- /dev/null
+++ b/src/api/documents.py
@@ -0,0 +1,59 @@
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+from utils.logging_config import get_logger
+from config.settings import INDEX_NAME
+
+logger = get_logger(__name__)
+
+
+async def delete_documents_by_filename(request: Request, document_service, session_manager):
+    """Delete all documents with a specific filename"""
+    data = await request.json()
+    filename = data.get("filename")
+    
+    if not filename:
+        return JSONResponse({"error": "filename is required"}, status_code=400)
+    
+    user = request.state.user
+    jwt_token = request.state.jwt_token
+    
+    try:
+        # Get user's OpenSearch client
+        opensearch_client = session_manager.get_user_opensearch_client(
+            user.user_id, jwt_token
+        )
+        
+        # Delete by query to remove all chunks of this document
+        delete_query = {
+            "query": {
+                "bool": {
+                    "must": [
+                        {"term": {"filename": filename}}
+                    ]
+                }
+            }
+        }
+        
+        result = await opensearch_client.delete_by_query(
+            index=INDEX_NAME,
+            body=delete_query,
+            conflicts="proceed"
+        )
+        
+        deleted_count = result.get("deleted", 0)
+        logger.info(f"Deleted {deleted_count} chunks for filename {filename}", user_id=user.user_id)
+        
+        return JSONResponse({
+            "success": True,
+            "deleted_chunks": deleted_count,
+            "filename": filename,
+            "message": f"All documents with filename '{filename}' deleted successfully"
+        }, status_code=200)
+        
+    except Exception as e:
+        logger.error("Error deleting documents by filename", filename=filename, error=str(e))
+        error_str = str(e)
+        if "AuthenticationException" in error_str:
+            return JSONResponse({"error": "Access denied: insufficient permissions"}, status_code=403)
+        else:
+            return JSONResponse({"error": str(e)}, status_code=500)
diff --git a/src/config/settings.py b/src/config/settings.py
index 715146fb..c4e36b51 100644
--- a/src/config/settings.py
+++ b/src/config/settings.py
@@ -397,4 +397,4 @@ class AppClients:
 
 
 # Global clients instance
-clients = AppClients()
+clients = AppClients()
\ No newline at end of file
diff --git a/src/main.py b/src/main.py
index 1b50dfce..c97bb22a 100644
--- a/src/main.py
+++ b/src/main.py
@@ -30,6 +30,7 @@ from api import (
     auth,
     chat,
     connectors,
+    documents,
     flows,
     knowledge_filter,
     langflow_files,
@@ -877,6 +878,18 @@ async def create_app():
             ),
             methods=["POST", "GET"],
         ),
+        # Document endpoints
+        Route(
+            "/documents/delete-by-filename",
+            require_auth(services["session_manager"])(
+                partial(
+                    documents.delete_documents_by_filename,
+                    document_service=services["document_service"],
+                    session_manager=services["session_manager"],
+                )
+            ),
+            methods=["POST"],
+        ),
         # OIDC endpoints
         Route(
             "/.well-known/openid-configuration",
diff --git a/src/services/document_service.py b/src/services/document_service.py
index 70a70942..949515e3 100644
--- a/src/services/document_service.py
+++ b/src/services/document_service.py
@@ -435,3 +435,4 @@ class DocumentService:
 
             if upload_task.processed_files >= upload_task.total_files:
                 upload_task.status = TaskStatus.COMPLETED
+
diff --git a/src/session_manager.py b/src/session_manager.py
index 6eef5c70..6b2023d5 100644
--- a/src/session_manager.py
+++ b/src/session_manager.py
@@ -232,4 +232,4 @@ class SessionManager:
     def _create_anonymous_jwt(self) -> str:
         """Create JWT token for anonymous user in no-auth mode"""
         anonymous_user = AnonymousUser()
-        return self.create_jwt_token(anonymous_user)
+        return self.create_jwt_token(anonymous_user)
\ No newline at end of file