diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index 145074c7717d..bf7c387d3e77 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -1,5 +1,5 @@
 import React, { useRef, useState, useEffect, useMemo } from 'react';
-import { FolderKey } from 'lucide-react';
+import { FolderKey, ScrollText } from 'lucide-react';
 import { Tooltip, TooltipContent, TooltipTrigger } from './ui/Tooltip';
 import { Button } from './ui/button';
 import type { View } from '../App';
@@ -12,7 +12,6 @@ import { Message } from '../types/message';
 import { DirSwitcher } from './bottom_menu/DirSwitcher';
 import ModelsBottomBar from './settings/models/bottom_bar/ModelsBottomBar';
 import { BottomMenuModeSelection } from './bottom_menu/BottomMenuModeSelection';
-import { ManualCompactButton } from './context_management/ManualCompactButton';
 import { AlertType, useAlerts } from './alerts';
 import { useToolCount } from './alerts/useToolCount';
 import { useConfig } from './ConfigContext';
@@ -110,7 +109,7 @@ export default function ChatInput({
   const { alerts, addAlert, clearAlerts } = useAlerts();
   const dropdownRef = useRef<HTMLDivElement>(null);
   const toolCount = useToolCount();
-  const { isLoadingCompaction } = useChatContextManager();
+  const { isLoadingCompaction, handleManualCompaction } = useChatContextManager();
   const { getProviders, read } = useConfig();
   const { getCurrentModelAndProvider, currentModel, currentProvider } = useModelAndProvider();
   const [tokenLimit, setTokenLimit] = useState<number>(TOKEN_LIMIT_DEFAULT);
@@ -420,7 +419,7 @@ export default function ChatInput({
           autoShow: true, // Auto-show token limit warnings
         });
       } else {
-        // Show info alert only when not in warning/error state
+        // Show info alert with summarize button
         addAlert({
           type: AlertType.Info,
           message: 'Context window',
@@ -428,6 +427,11 @@ export default function ChatInput({
             current: numTokens,
             total: tokenLimit,
           },
+          showSummarizeButton: true,
+          onSummarize: () => {
+            handleManualCompaction(messages, setMessages);
+          },
+          summarizeIcon: <ScrollText size={12} />,
         });
       }
     } else if (isTokenLimitLoaded && tokenLimit) {
@@ -439,6 +443,14 @@ export default function ChatInput({
           current: 0,
           total: tokenLimit,
         },
+        showSummarizeButton: messages.length > 0,
+        onSummarize:
+          messages.length > 0
+            ? () => {
+                handleManualCompaction(messages, setMessages);
+              }
+            : undefined,
+        summarizeIcon: messages.length > 0 ? <ScrollText size={12} /> : undefined,
       });
     }
 
@@ -1286,13 +1298,6 @@ export default function ChatInput({
           </Tooltip>
           <div className="w-px h-4 bg-border-default mx-2" />
           <BottomMenuModeSelection />
-          {messages.length > 0 && (
-            <ManualCompactButton
-              messages={messages}
-              isLoading={isLoading}
-              setMessages={setMessages}
-            />
-          )}
           <div className="w-px h-4 bg-border-default mx-2" />
           <div className="flex items-center h-full">
             <Tooltip>
diff --git a/ui/desktop/src/components/alerts/AlertBox.tsx b/ui/desktop/src/components/alerts/AlertBox.tsx
index c93f249f2ff5..0fafdd3bb531 100644
--- a/ui/desktop/src/components/alerts/AlertBox.tsx
+++ b/ui/desktop/src/components/alerts/AlertBox.tsx
@@ -60,6 +60,19 @@ export const AlertBox = ({ alert, className }: AlertBoxProps) => {
                 : alert.progress!.total}
             </span>
           </div>
+          {alert.showSummarizeButton && alert.onSummarize && (
+            <button
+              onClick={(e) => {
+                e.preventDefault();
+                e.stopPropagation();
+                alert.onSummarize!();
+              }}
+              className="flex items-center gap-1.5 text-[11px] hover:opacity-80 cursor-pointer outline-none mt-1"
+            >
+              {alert.summarizeIcon}
+              <span>Summarize now</span>
+            </button>
+          )}
         </div>
       ) : (
         <>
diff --git a/ui/desktop/src/components/alerts/types.ts b/ui/desktop/src/components/alerts/types.ts
index 661191e50b7f..44eeafbd19a0 100644
--- a/ui/desktop/src/components/alerts/types.ts
+++ b/ui/desktop/src/components/alerts/types.ts
@@ -16,4 +16,7 @@ export interface Alert {
     current: number;
     total: number;
   };
+  showSummarizeButton?: boolean;
+  onSummarize?: () => void;
+  summarizeIcon?: React.ReactNode;
 }
diff --git a/ui/desktop/src/components/context_management/ChatContextManager.tsx b/ui/desktop/src/components/context_management/ChatContextManager.tsx
index 2e18e02bf354..4e3493d7d35f 100644
--- a/ui/desktop/src/components/context_management/ChatContextManager.tsx
+++ b/ui/desktop/src/components/context_management/ChatContextManager.tsx
@@ -1,10 +1,20 @@
 import React, { createContext, useContext, useState } from 'react';
+import { ScrollText } from 'lucide-react';
 import { Message } from '../../types/message';
 import {
   manageContextFromBackend,
   convertApiMessageToFrontendMessage,
   createSummarizationRequestMessage,
 } from './index';
+import {
+  Dialog,
+  DialogContent,
+  DialogDescription,
+  DialogFooter,
+  DialogHeader,
+  DialogTitle,
+} from '../ui/dialog';
+import { Button } from '../ui/button';
 
 // Define the context management interface
 interface ChatContextManagerState {
@@ -14,6 +24,8 @@ interface ChatContextManagerState {
   isLoadingCompaction: boolean;
   errorLoadingSummary: boolean;
   preparingManualSummary: boolean;
+  isConfirmationOpen: boolean;
+  pendingCompactionData: { messages: Message[]; setMessages: (messages: Message[]) => void } | null;
 }
 
 interface ChatContextManagerActions {
@@ -50,6 +62,11 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
   const [isLoadingCompaction, setIsLoadingCompaction] = useState<boolean>(false);
   const [errorLoadingSummary, setErrorLoadingSummary] = useState<boolean>(false);
   const [preparingManualSummary, setPreparingManualSummary] = useState<boolean>(false);
+  const [isConfirmationOpen, setIsConfirmationOpen] = useState<boolean>(false);
+  const [pendingCompactionData, setPendingCompactionData] = useState<{
+    messages: Message[];
+    setMessages: (messages: Message[]) => void;
+  } | null>(null);
 
   const handleContextLengthExceeded = async (messages: Message[]): Promise<void> => {
     setIsLoadingCompaction(true);
@@ -90,6 +107,16 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
     messages: Message[],
     setMessages: (messages: Message[]) => void
   ): void => {
+    // Store the pending compaction data and open confirmation dialog
+    setPendingCompactionData({ messages, setMessages });
+    setIsConfirmationOpen(true);
+  };
+
+  const handleCompactionConfirm = () => {
+    if (!pendingCompactionData) return;
+
+    const { messages, setMessages } = pendingCompactionData;
+
     // add some messages to the message thread
     // these messages will be filtered out in chat view
     // but they will also be what allows us to render some text in the chatview itself, similar to CLE events
@@ -100,6 +127,14 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
 
     // add the message to the message thread
     setMessages([...messages, summarizationRequest]);
+
+    setIsConfirmationOpen(false);
+    setPendingCompactionData(null);
+  };
+
+  const handleCompactionCancel = () => {
+    setIsConfirmationOpen(false);
+    setPendingCompactionData(null);
   };
 
   const updateSummary = (newSummaryContent: string) => {
@@ -242,6 +277,8 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
     isLoadingCompaction,
     errorLoadingSummary,
     preparingManualSummary,
+    isConfirmationOpen,
+    pendingCompactionData,
 
     // Actions
     updateSummary,
@@ -259,6 +296,39 @@ export const ChatContextManagerProvider: React.FC<{ children: React.ReactNode }>
   return (
     <ChatContextManagerContext.Provider value={value}>
       {children}
+
+      {/* Confirmation Modal */}
+      <Dialog open={isConfirmationOpen} onOpenChange={handleCompactionCancel}>
+        <DialogContent className="sm:max-w-[500px]">
+          <DialogHeader>
+            <DialogTitle className="flex items-center gap-2">
+              <ScrollText className="text-iconStandard" size={24} />
+              Compact Conversation
+            </DialogTitle>
+            <DialogDescription>
+              This will compact your conversation by summarizing the context into a single message
+              and will help you save context space for future interactions.
+            </DialogDescription>
+          </DialogHeader>
+
+          <div className="py-4">
+            <p className="text-textStandard">
+              Previous messages will remain visible but only the summary will be included in the
+              active context for Goose. This is useful for long conversations that are approaching
+              the context limit.
+            </p>
+          </div>
+
+          <DialogFooter className="pt-2">
+            <Button type="button" variant="outline" onClick={handleCompactionCancel}>
+              Cancel
+            </Button>
+            <Button type="button" onClick={handleCompactionConfirm}>
+              Compact Conversation
+            </Button>
+          </DialogFooter>
+        </DialogContent>
+      </Dialog>
     </ChatContextManagerContext.Provider>
   );
 };
diff --git a/ui/desktop/src/components/context_management/ManualCompactButton.tsx b/ui/desktop/src/components/context_management/ManualCompactButton.tsx
index daf1b52d3c15..bfc965cb2110 100644
--- a/ui/desktop/src/components/context_management/ManualCompactButton.tsx
+++ b/ui/desktop/src/components/context_management/ManualCompactButton.tsx
@@ -72,7 +72,7 @@ export const ManualCompactButton: React.FC<ManualCompactButtonProps> = ({
         </Tooltip>
       </div>
 
-      {/* Confirmation Modal */}
+      {/* Summarization Confirmation Modal */}
       <Dialog open={isConfirmationOpen} onOpenChange={handleClose}>
         <DialogContent className="sm:max-w-[500px]">
           <DialogHeader>