diff --git a/backend/alembic/versions/35e518e0ddf4_properly_cascade.py b/backend/alembic/versions/35e518e0ddf4_properly_cascade.py
new file mode 100644
index 00000000000..c18c988fddd
--- /dev/null
+++ b/backend/alembic/versions/35e518e0ddf4_properly_cascade.py
@@ -0,0 +1,121 @@
+"""properly_cascade
+
+Revision ID: 35e518e0ddf4
+Revises: 91a0a4d62b14
+Create Date: 2024-09-20 21:24:04.891018
+
+"""
+from alembic import op
+
+
+# revision identifiers, used by Alembic.
+revision = "35e518e0ddf4"
+down_revision = "91a0a4d62b14"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    # Update chat_message foreign key constraint
+    op.drop_constraint(
+        "chat_message_chat_session_id_fkey", "chat_message", type_="foreignkey"
+    )
+    op.create_foreign_key(
+        "chat_message_chat_session_id_fkey",
+        "chat_message",
+        "chat_session",
+        ["chat_session_id"],
+        ["id"],
+        ondelete="CASCADE",
+    )
+
+    # Update chat_message__search_doc foreign key constraints
+    op.drop_constraint(
+        "chat_message__search_doc_chat_message_id_fkey",
+        "chat_message__search_doc",
+        type_="foreignkey",
+    )
+    op.drop_constraint(
+        "chat_message__search_doc_search_doc_id_fkey",
+        "chat_message__search_doc",
+        type_="foreignkey",
+    )
+
+    op.create_foreign_key(
+        "chat_message__search_doc_chat_message_id_fkey",
+        "chat_message__search_doc",
+        "chat_message",
+        ["chat_message_id"],
+        ["id"],
+        ondelete="CASCADE",
+    )
+    op.create_foreign_key(
+        "chat_message__search_doc_search_doc_id_fkey",
+        "chat_message__search_doc",
+        "search_doc",
+        ["search_doc_id"],
+        ["id"],
+        ondelete="CASCADE",
+    )
+
+    # Add CASCADE delete for tool_call foreign key
+    op.drop_constraint("tool_call_message_id_fkey", "tool_call", type_="foreignkey")
+    op.create_foreign_key(
+        "tool_call_message_id_fkey",
+        "tool_call",
+        "chat_message",
+        ["message_id"],
+        ["id"],
+        ondelete="CASCADE",
+    )
+
+
+def downgrade() -> None:
+    # Revert chat_message foreign key constraint
+    op.drop_constraint(
+        "chat_message_chat_session_id_fkey", "chat_message", type_="foreignkey"
+    )
+    op.create_foreign_key(
+        "chat_message_chat_session_id_fkey",
+        "chat_message",
+        "chat_session",
+        ["chat_session_id"],
+        ["id"],
+    )
+
+    # Revert chat_message__search_doc foreign key constraints
+    op.drop_constraint(
+        "chat_message__search_doc_chat_message_id_fkey",
+        "chat_message__search_doc",
+        type_="foreignkey",
+    )
+    op.drop_constraint(
+        "chat_message__search_doc_search_doc_id_fkey",
+        "chat_message__search_doc",
+        type_="foreignkey",
+    )
+
+    op.create_foreign_key(
+        "chat_message__search_doc_chat_message_id_fkey",
+        "chat_message__search_doc",
+        "chat_message",
+        ["chat_message_id"],
+        ["id"],
+    )
+    op.create_foreign_key(
+        "chat_message__search_doc_search_doc_id_fkey",
+        "chat_message__search_doc",
+        "search_doc",
+        ["search_doc_id"],
+        ["id"],
+    )
+
+    # Revert tool_call foreign key constraint
+    op.drop_constraint("tool_call_message_id_fkey", "tool_call", type_="foreignkey")
+    op.create_foreign_key(
+        "tool_call_message_id_fkey",
+        "tool_call",
+        "chat_message",
+        ["message_id"],
+        ["id"],
+    )
diff --git a/backend/onyx/db/chat.py b/backend/onyx/db/chat.py
index a2cda0a30c7..3601fdc67cf 100644
--- a/backend/onyx/db/chat.py
+++ b/backend/onyx/db/chat.py
@@ -316,6 +316,23 @@ def update_chat_session(
     return chat_session
 
 
+def delete_all_chat_sessions_for_user(
+    user: User | None, db_session: Session, hard_delete: bool = HARD_DELETE_CHATS
+) -> None:
+    user_id = user.id if user is not None else None
+
+    query = db_session.query(ChatSession).filter(
+        ChatSession.user_id == user_id, ChatSession.onyxbot_flow.is_(False)
+    )
+
+    if hard_delete:
+        query.delete(synchronize_session=False)
+    else:
+        query.update({ChatSession.deleted: True}, synchronize_session=False)
+
+    db_session.commit()
+
+
 def delete_chat_session(
     user_id: UUID | None,
     chat_session_id: UUID,
diff --git a/backend/onyx/db/models.py b/backend/onyx/db/models.py
index e5644c98320..a356e397a94 100644
--- a/backend/onyx/db/models.py
+++ b/backend/onyx/db/models.py
@@ -1010,7 +1010,7 @@ class ChatSession(Base):
         "ChatFolder", back_populates="chat_sessions"
     )
     messages: Mapped[list["ChatMessage"]] = relationship(
-        "ChatMessage", back_populates="chat_session"
+        "ChatMessage", back_populates="chat_session", cascade="all, delete-orphan"
     )
     persona: Mapped["Persona"] = relationship("Persona")
 
@@ -1078,6 +1078,8 @@ class ChatMessage(Base):
         "SearchDoc",
         secondary=ChatMessage__SearchDoc.__table__,
         back_populates="chat_messages",
+        cascade="all, delete-orphan",
+        single_parent=True,
     )
 
     tool_call: Mapped["ToolCall"] = relationship(
diff --git a/backend/onyx/server/query_and_chat/chat_backend.py b/backend/onyx/server/query_and_chat/chat_backend.py
index 21499032980..b9e3dc06686 100644
--- a/backend/onyx/server/query_and_chat/chat_backend.py
+++ b/backend/onyx/server/query_and_chat/chat_backend.py
@@ -35,6 +35,7 @@
 from onyx.db.chat import add_chats_to_session_from_slack_thread
 from onyx.db.chat import create_chat_session
 from onyx.db.chat import create_new_chat_message
+from onyx.db.chat import delete_all_chat_sessions_for_user
 from onyx.db.chat import delete_chat_session
 from onyx.db.chat import duplicate_chat_session_for_user_from_slack
 from onyx.db.chat import get_chat_message
@@ -280,6 +281,17 @@ def patch_chat_session(
     return None
 
 
+@router.delete("/delete-all-chat-sessions")
+def delete_all_chat_sessions(
+    user: User | None = Depends(current_user),
+    db_session: Session = Depends(get_session),
+) -> None:
+    try:
+        delete_all_chat_sessions_for_user(user=user, db_session=db_session)
+    except ValueError as e:
+        raise HTTPException(status_code=400, detail=str(e))
+
+
 @router.delete("/delete-chat-session/{session_id}")
 def delete_chat_session_by_id(
     session_id: UUID,
diff --git a/backend/onyx/server/query_and_chat/models.py b/backend/onyx/server/query_and_chat/models.py
index 16b7d1b061f..068591c0a52 100644
--- a/backend/onyx/server/query_and_chat/models.py
+++ b/backend/onyx/server/query_and_chat/models.py
@@ -11,6 +11,7 @@
 from onyx.configs.constants import DocumentSource
 from onyx.configs.constants import MessageType
 from onyx.configs.constants import SearchFeedbackType
+from onyx.configs.constants import SessionType
 from onyx.context.search.models import BaseFilters
 from onyx.context.search.models import ChunkContext
 from onyx.context.search.models import RerankingDetails
@@ -151,6 +152,10 @@ class ChatSessionUpdateRequest(BaseModel):
     sharing_status: ChatSessionSharedStatus
 
 
+class DeleteAllSessionsRequest(BaseModel):
+    session_type: SessionType
+
+
 class RenameChatSessionResponse(BaseModel):
     new_name: str  # This is only really useful if the name is generated
 
diff --git a/web/src/app/chat/ChatPage.tsx b/web/src/app/chat/ChatPage.tsx
index bcc790e56fe..89ba2960f0d 100644
--- a/web/src/app/chat/ChatPage.tsx
+++ b/web/src/app/chat/ChatPage.tsx
@@ -27,6 +27,7 @@ import {
   buildLatestMessageChain,
   checkAnyAssistantHasSearch,
   createChatSession,
+  deleteAllChatSessions,
   deleteChatSession,
   getCitedDocumentsFromMessage,
   getHumanAndAIMessageFromMessageNumber,
@@ -1837,6 +1838,7 @@ export function ChatPage({
 
   const innerSidebarElementRef = useRef<HTMLDivElement>(null);
   const [settingsToggled, setSettingsToggled] = useState(false);
+  const [showDeleteAllModal, setShowDeleteAllModal] = useState(false);
 
   const currentPersona = alternativeAssistant || liveAssistant;
   useEffect(() => {
@@ -1903,11 +1905,6 @@ export function ChatPage({
   const showShareModal = (chatSession: ChatSession) => {
     setSharedChatSession(chatSession);
   };
-  const [documentSelection, setDocumentSelection] = useState(false);
-  // const toggleDocumentSelectionAspects = () => {
-  //   setDocumentSelection((documentSelection) => !documentSelection);
-  //   setShowDocSidebar(false);
-  // };
 
   const toggleDocumentSidebar = () => {
     if (!documentSidebarToggled) {
@@ -1972,6 +1969,32 @@ export function ChatPage({
 
       <ChatPopup />
 
+      {showDeleteAllModal && (
+        <DeleteEntityModal
+          entityType="All Chats"
+          entityName="all your chat sessions"
+          onClose={() => setShowDeleteAllModal(false)}
+          additionalDetails="This action cannot be undone. All your chat sessions will be deleted."
+          onSubmit={async () => {
+            const response = await deleteAllChatSessions("Chat");
+            if (response.ok) {
+              setShowDeleteAllModal(false);
+              setPopup({
+                message: "All your chat sessions have been deleted.",
+                type: "success",
+              });
+              refreshChatSessions();
+              router.push("/chat");
+            } else {
+              setPopup({
+                message: "Failed to delete all chat sessions.",
+                type: "error",
+              });
+            }
+          }}
+        />
+      )}
+
       {currentFeedback && (
         <FeedbackModal
           feedbackType={currentFeedback[0]}
@@ -2132,6 +2155,7 @@ export function ChatPage({
                   removeToggle={removeToggle}
                   showShareModal={showShareModal}
                   showDeleteModal={showDeleteModal}
+                  showDeleteAllModal={() => setShowDeleteAllModal(true)}
                 />
               </div>
             </div>
@@ -2739,6 +2763,10 @@ export function ChatPage({
                               removeDocs={() => {
                                 clearSelectedDocuments();
                               }}
+                              showDocs={() => {
+                                setFiltersToggled(false);
+                                setDocumentSidebarToggled(true);
+                              }}
                               removeFilters={() => {
                                 filterManager.setSelectedSources([]);
                                 filterManager.setSelectedTags([]);
@@ -2751,7 +2779,6 @@ export function ChatPage({
                               chatState={currentSessionChatState}
                               stopGenerating={stopGenerating}
                               openModelSettings={() => setSettingsToggled(true)}
-                              showDocs={() => setDocumentSelection(true)}
                               selectedDocuments={selectedDocuments}
                               // assistant stuff
                               selectedAssistant={liveAssistant}
diff --git a/web/src/app/chat/input/ChatInputBar.tsx b/web/src/app/chat/input/ChatInputBar.tsx
index ed828ad9a5f..e7517f25e40 100644
--- a/web/src/app/chat/input/ChatInputBar.tsx
+++ b/web/src/app/chat/input/ChatInputBar.tsx
@@ -31,14 +31,7 @@ import { SettingsContext } from "@/components/settings/SettingsProvider";
 import { ChatState } from "../types";
 import UnconfiguredProviderText from "@/components/chat_search/UnconfiguredProviderText";
 import { useAssistants } from "@/components/context/AssistantsContext";
-import AnimatedToggle from "@/components/search/SearchBar";
-import { Popup } from "@/components/admin/connectors/Popup";
-import { AssistantsTab } from "../modal/configuration/AssistantsTab";
-import { IconType } from "react-icons";
-import { LlmTab } from "../modal/configuration/LlmTab";
 import { XIcon } from "lucide-react";
-import { FilterPills } from "./FilterPills";
-import { Tag } from "@/lib/types";
 import FiltersDisplay from "./FilterDisplay";
 
 const MAX_INPUT_HEIGHT = 200;
@@ -47,7 +40,6 @@ interface ChatInputBarProps {
   removeFilters: () => void;
   removeDocs: () => void;
   openModelSettings: () => void;
-  showDocs: () => void;
   showConfigureAPIKey: () => void;
   selectedDocuments: OnyxDocument[];
   message: string;
@@ -57,6 +49,7 @@ interface ChatInputBarProps {
   filterManager: FilterManager;
   llmOverrideManager: LlmOverrideManager;
   chatState: ChatState;
+  showDocs: () => void;
   alternativeAssistant: Persona | null;
   // assistants
   selectedAssistant: Persona;
@@ -75,8 +68,8 @@ export function ChatInputBar({
   removeFilters,
   removeDocs,
   openModelSettings,
-  showDocs,
   showConfigureAPIKey,
+  showDocs,
   selectedDocuments,
   message,
   setMessage,
@@ -284,10 +277,6 @@ export function ChatInputBar({
             </div>
           )}
 
-          {/* <div>
-            <SelectedFilterDisplay filterManager={filterManager} />
-          </div> */}
-
           <UnconfiguredProviderText showConfigureAPIKey={showConfigureAPIKey} />
 
           <div
diff --git a/web/src/app/chat/lib.tsx b/web/src/app/chat/lib.tsx
index 2b44da8ce0d..123805410c2 100644
--- a/web/src/app/chat/lib.tsx
+++ b/web/src/app/chat/lib.tsx
@@ -278,6 +278,16 @@ export async function deleteChatSession(chatSessionId: string) {
   return response;
 }
 
+export async function deleteAllChatSessions(sessionType: "Chat" | "Search") {
+  const response = await fetch(`/api/chat/delete-all-chat-sessions`, {
+    method: "DELETE",
+    headers: {
+      "Content-Type": "application/json",
+    },
+  });
+  return response;
+}
+
 export async function* simulateLLMResponse(input: string, delay: number = 30) {
   // Split the input string into tokens. This is a simple example, and in real use case, tokenization can be more complex.
   // Iterate over tokens and yield them one by one
diff --git a/web/src/app/chat/sessionSidebar/HistorySidebar.tsx b/web/src/app/chat/sessionSidebar/HistorySidebar.tsx
index c3c4a098fe0..5561d60850b 100644
--- a/web/src/app/chat/sessionSidebar/HistorySidebar.tsx
+++ b/web/src/app/chat/sessionSidebar/HistorySidebar.tsx
@@ -30,6 +30,7 @@ interface HistorySidebarProps {
   showDeleteModal?: (chatSession: ChatSession) => void;
   stopGenerating?: () => void;
   explicitlyUntoggle: () => void;
+  showDeleteAllModal?: () => void;
   backgroundToggled?: boolean;
 }
 
@@ -49,6 +50,7 @@ export const HistorySidebar = forwardRef<HTMLDivElement, HistorySidebarProps>(
       stopGenerating = () => null,
       showShareModal,
       showDeleteModal,
+      showDeleteAllModal,
       backgroundToggled,
     },
     ref: ForwardedRef<HTMLDivElement>
@@ -176,6 +178,7 @@ export const HistorySidebar = forwardRef<HTMLDivElement, HistorySidebarProps>(
             currentChatId={currentChatId}
             folders={folders}
             openedFolders={openedFolders}
+            showDeleteAllModal={showDeleteAllModal}
           />
         </div>
       </>
diff --git a/web/src/app/chat/sessionSidebar/PagesTab.tsx b/web/src/app/chat/sessionSidebar/PagesTab.tsx
index 8879506cb60..7bab1a18961 100644
--- a/web/src/app/chat/sessionSidebar/PagesTab.tsx
+++ b/web/src/app/chat/sessionSidebar/PagesTab.tsx
@@ -9,6 +9,8 @@ import { usePopup } from "@/components/admin/connectors/Popup";
 import { useRouter } from "next/navigation";
 import { useState } from "react";
 import { pageType } from "./types";
+import { FiTrash2 } from "react-icons/fi";
+import { NEXT_PUBLIC_DELETE_ALL_CHATS_ENABLED } from "@/lib/constants";
 
 export function PagesTab({
   page,
@@ -20,6 +22,7 @@ export function PagesTab({
   newFolderId,
   showShareModal,
   showDeleteModal,
+  showDeleteAllModal,
 }: {
   page: pageType;
   existingChats?: ChatSession[];
@@ -30,6 +33,7 @@ export function PagesTab({
   newFolderId: number | null;
   showShareModal?: (chatSession: ChatSession) => void;
   showDeleteModal?: (chatSession: ChatSession) => void;
+  showDeleteAllModal?: () => void;
 }) {
   const groupedChatSessions = existingChats
     ? groupSessionsByDateRange(existingChats)
@@ -63,82 +67,98 @@ export function PagesTab({
   const isHistoryEmpty = !existingChats || existingChats.length === 0;
 
   return (
-    <div className="mb-1 text-text-sidebar ml-3 relative miniscroll mobile:pb-40 overflow-y-auto h-full">
-      {folders && folders.length > 0 && (
-        <div className="py-2 border-b border-border">
-          <div className="text-xs text-subtle flex pb-0.5 mb-1.5 mt-2 font-bold">
-            Chat Folders
-          </div>
-          <FolderList
-            newFolderId={newFolderId}
-            folders={folders}
-            currentChatId={currentChatId}
-            openedFolders={openedFolders}
-            showShareModal={showShareModal}
-            showDeleteModal={showDeleteModal}
-          />
-        </div>
-      )}
+    <div className="flex flex-col relative h-full overflow-y-auto mb-1 ml-3 miniscroll mobile:pb-40">
       <div
-        onDragOver={(event) => {
-          event.preventDefault();
-          setIsDragOver(true);
-        }}
-        onDragLeave={() => setIsDragOver(false)}
-        onDrop={handleDropToRemoveFromFolder}
-        className={`pt-1 transition duration-300 ease-in-out mr-3 ${
-          isDragOver ? "bg-hover" : ""
-        } rounded-md`}
+        className={` flex-grow overflow-y-auto ${
+          NEXT_PUBLIC_DELETE_ALL_CHATS_ENABLED && "pb-20  "
+        }`}
       >
-        {(page == "chat" || page == "search") && (
-          <p className="my-2 text-xs text-sidebar-subtle flex font-bold">
-            {page == "chat" && "Chat "}
-            {page == "search" && "Search "}
-            History
-          </p>
+        {folders && folders.length > 0 && (
+          <div className="py-2 border-b border-border">
+            <div className="text-xs text-subtle flex pb-0.5 mb-1.5 mt-2 font-bold">
+              Chat Folders
+            </div>
+            <FolderList
+              newFolderId={newFolderId}
+              folders={folders}
+              currentChatId={currentChatId}
+              openedFolders={openedFolders}
+              showShareModal={showShareModal}
+              showDeleteModal={showDeleteModal}
+            />
+          </div>
         )}
-        {isHistoryEmpty ? (
-          <p className="text-sm mt-2 w-[250px]">
-            {page === "search"
-              ? "Try running a search! Your search history will appear here."
-              : "Try sending a message! Your chat history will appear here."}
-          </p>
-        ) : (
-          Object.entries(groupedChatSessions).map(
-            ([dateRange, chatSessions], ind) => {
-              if (chatSessions.length > 0) {
-                return (
-                  <div key={dateRange}>
-                    <div
-                      className={`text-xs text-text-sidebar-subtle ${
-                        ind != 0 && "mt-5"
-                      } flex pb-0.5 mb-1.5 font-medium`}
-                    >
-                      {dateRange}
+
+        <div
+          onDragOver={(event) => {
+            event.preventDefault();
+            setIsDragOver(true);
+          }}
+          onDragLeave={() => setIsDragOver(false)}
+          onDrop={handleDropToRemoveFromFolder}
+          className={`pt-1 transition duration-300 ease-in-out mr-3 ${
+            isDragOver ? "bg-hover" : ""
+          } rounded-md`}
+        >
+          {(page == "chat" || page == "search") && (
+            <p className="my-2 text-xs text-sidebar-subtle flex font-bold">
+              {page == "chat" && "Chat "}
+              {page == "search" && "Search "}
+              History
+            </p>
+          )}
+          {isHistoryEmpty ? (
+            <p className="text-sm mt-2 w-[250px]">
+              Try sending a message! Your chat history will appear here.
+            </p>
+          ) : (
+            Object.entries(groupedChatSessions).map(
+              ([dateRange, chatSessions], ind) => {
+                if (chatSessions.length > 0) {
+                  return (
+                    <div key={dateRange}>
+                      <div
+                        className={`text-xs text-text-sidebar-subtle ${
+                          ind != 0 && "mt-5"
+                        } flex pb-0.5 mb-1.5 font-medium`}
+                      >
+                        {dateRange}
+                      </div>
+                      {chatSessions
+                        .filter((chat) => chat.folder_id === null)
+                        .map((chat) => {
+                          const isSelected = currentChatId === chat.id;
+                          return (
+                            <div key={`${chat.id}-${chat.name}`}>
+                              <ChatSessionDisplay
+                                showDeleteModal={showDeleteModal}
+                                showShareModal={showShareModal}
+                                closeSidebar={closeSidebar}
+                                search={page == "search"}
+                                chatSession={chat}
+                                isSelected={isSelected}
+                                skipGradient={isDragOver}
+                              />
+                            </div>
+                          );
+                        })}
                     </div>
-                    {chatSessions
-                      .filter((chat) => chat.folder_id === null)
-                      .map((chat) => {
-                        const isSelected = currentChatId === chat.id;
-                        return (
-                          <div key={`${chat.id}-${chat.name}`}>
-                            <ChatSessionDisplay
-                              showDeleteModal={showDeleteModal}
-                              showShareModal={showShareModal}
-                              closeSidebar={closeSidebar}
-                              search={page == "search"}
-                              chatSession={chat}
-                              isSelected={isSelected}
-                              skipGradient={isDragOver}
-                            />
-                          </div>
-                        );
-                      })}
-                  </div>
-                );
+                  );
+                }
               }
-            }
-          )
+            )
+          )}
+        </div>
+        {showDeleteAllModal && NEXT_PUBLIC_DELETE_ALL_CHATS_ENABLED && (
+          <div className="absolute w-full border-t border-t-border bg-background-100 bottom-0 left-0 p-4">
+            <button
+              className="w-full py-2 px-4 text-text-600 hover:text-text-800 bg-background-125 border border-border-strong/50 shadow-sm rounded-md transition-colors duration-200 flex items-center justify-center text-sm"
+              onClick={showDeleteAllModal}
+            >
+              <FiTrash2 className="mr-2" size={14} />
+              Clear All History
+            </button>
+          </div>
         )}
       </div>
     </div>
diff --git a/web/src/components/modals/DeleteEntityModal.tsx b/web/src/components/modals/DeleteEntityModal.tsx
index 85cda2fd4d5..0670416f4b9 100644
--- a/web/src/components/modals/DeleteEntityModal.tsx
+++ b/web/src/components/modals/DeleteEntityModal.tsx
@@ -22,8 +22,7 @@ export const DeleteEntityModal = ({
           <h2 className="my-auto text-2xl font-bold">Delete {entityType}?</h2>
         </div>
         <p className="mb-4">
-          Click below to confirm that you want to delete{" "}
-          <b>&quot;{entityName}&quot;</b>
+          Click below to confirm that you want to delete <b>{entityName}</b>
         </p>
         {additionalDetails && <p className="mb-4">{additionalDetails}</p>}
         <div className="flex">
diff --git a/web/src/lib/constants.ts b/web/src/lib/constants.ts
index c84bc2eeeff..83fbb1174c7 100644
--- a/web/src/lib/constants.ts
+++ b/web/src/lib/constants.ts
@@ -75,3 +75,6 @@ export const REGISTRATION_URL =
   process.env.INTERNAL_URL || "http://127.0.0.1:3001";
 
 export const TEST_ENV = process.env.TEST_ENV?.toLowerCase() === "true";
+
+export const NEXT_PUBLIC_DELETE_ALL_CHATS_ENABLED =
+  process.env.NEXT_PUBLIC_DELETE_ALL_CHATS_ENABLED?.toLowerCase() === "true";