diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index 7467dfe3c176..3b4e2fe24370 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -1179,7 +1179,7 @@ export default function ChatInput({
         )}
 
         {/* Secondary actions and controls row below input */}
-        <div className="flex flex-row items-center gap-1 p-2 relative">
+        <div className="flex flex-wrap flex-row items-center gap-x-1 gap-y-2 p-2 relative">
           {/* Directory path */}
           <DirSwitcher hasMessages={messages.length > 0} className="mr-0" />
           <div className="w-px h-4 bg-border-default mx-2" />
diff --git a/ui/desktop/src/components/CheckpointActions.tsx b/ui/desktop/src/components/CheckpointActions.tsx
index 90b401513ca7..36a62274fc8d 100644
--- a/ui/desktop/src/components/CheckpointActions.tsx
+++ b/ui/desktop/src/components/CheckpointActions.tsx
@@ -1,5 +1,6 @@
 import { useState } from 'react';
 import { ResourceContent } from '../types/message';
+import { useSidecar } from './SidecarLayout';
 
 interface CheckpointActionsProps {
   checkpointContent: ResourceContent;
@@ -7,6 +8,7 @@ interface CheckpointActionsProps {
 
 export default function CheckpointActions({ checkpointContent }: CheckpointActionsProps) {
   const [showDiff, setShowDiff] = useState(false);
+  const sidecar = useSidecar();
 
   // Parse the checkpoint payload
   let checkpointData: {
@@ -23,7 +25,21 @@ export default function CheckpointActions({ checkpointContent }: CheckpointActio
   }
 
   const handleViewDiff = () => {
-    setShowDiff(!showDiff);
+    if (sidecar && checkpointData.diff) {
+      // Check if diff viewer is already active
+      if (sidecar.activeView === 'diff') {
+        // If diff viewer is open, close it
+        sidecar.hideDiffViewer();
+        setShowDiff(false);
+      } else {
+        // Show diff in sidecar
+        sidecar.showDiffViewer(checkpointData.diff, checkpointData.file || 'File');
+        setShowDiff(true);
+      }
+    } else {
+      // Fallback to inline diff display
+      setShowDiff(!showDiff);
+    }
   };
 
   const handleRestore = async () => {
@@ -62,7 +78,7 @@ export default function CheckpointActions({ checkpointContent }: CheckpointActio
           onClick={handleViewDiff}
           className="text-xs px-2 py-1 bg-bgStandard hover:bg-bgSubtle border border-borderSubtle rounded transition-colors"
         >
-          {showDiff ? 'Hide Diff' : 'View Diff'}
+          {sidecar && sidecar.activeView === 'diff' ? 'Hide Diff' : 'View Diff'}
         </button>
         {checkpointData.checkpoint && (
           <button
diff --git a/ui/desktop/src/components/GooseMessage.tsx b/ui/desktop/src/components/GooseMessage.tsx
index 5c0ed1a21cd6..8d51719b71cb 100644
--- a/ui/desktop/src/components/GooseMessage.tsx
+++ b/ui/desktop/src/components/GooseMessage.tsx
@@ -252,24 +252,30 @@ export default function GooseMessage({
             <TooltipTrigger asChild>
               <button
                 onClick={() => {
-                  // Find the first tool request with diff content and show its diff
-                  const toolRequestWithDiff = toolRequests.find((toolRequest) =>
-                    hasDiffContent(toolResponsesMap.get(toolRequest.id))
-                  );
-                  if (toolRequestWithDiff) {
-                    const diffContent = extractDiffContent(
-                      toolResponsesMap.get(toolRequestWithDiff.id)
+                  // Check if diff viewer is already active
+                  if (sidecar.activeView === 'diff') {
+                    // If diff viewer is open, close it
+                    sidecar.hideDiffViewer();
+                  } else {
+                    // Find the first tool request with diff content and show its diff
+                    const toolRequestWithDiff = toolRequests.find((toolRequest) =>
+                      hasDiffContent(toolResponsesMap.get(toolRequest.id))
                     );
-                    if (diffContent) {
-                      // Extract filename from tool arguments if available
-                      const toolCall =
-                        toolRequestWithDiff.toolCall.status === 'success'
-                          ? toolRequestWithDiff.toolCall.value
-                          : null;
-                      const args = toolCall?.arguments as Record<string, never>;
-                      const fileName = args?.path ? String(args.path) : 'File';
-
-                      sidecar.showDiffViewer(diffContent, fileName);
+                    if (toolRequestWithDiff) {
+                      const diffContent = extractDiffContent(
+                        toolResponsesMap.get(toolRequestWithDiff.id)
+                      );
+                      if (diffContent) {
+                        // Extract filename from tool arguments if available
+                        const toolCall =
+                          toolRequestWithDiff.toolCall.status === 'success'
+                            ? toolRequestWithDiff.toolCall.value
+                            : null;
+                        const args = toolCall?.arguments as Record<string, never>;
+                        const fileName = args?.path ? String(args.path) : 'File';
+
+                        sidecar.showDiffViewer(diffContent, fileName);
+                      }
                     }
                   }
                 }}
@@ -278,7 +284,9 @@ export default function GooseMessage({
                 <FileDiff size={16} />
               </button>
             </TooltipTrigger>
-            <TooltipContent side="top">View diff</TooltipContent>
+            <TooltipContent side="top">
+              {sidecar.activeView === 'diff' ? 'Hide diff' : 'View diff'}
+            </TooltipContent>
           </Tooltip>
         </div>
       )}
diff --git a/ui/desktop/src/components/SidecarLayout.tsx b/ui/desktop/src/components/SidecarLayout.tsx
index ee874ad64c23..01a94f33f43e 100644
--- a/ui/desktop/src/components/SidecarLayout.tsx
+++ b/ui/desktop/src/components/SidecarLayout.tsx
@@ -304,8 +304,8 @@ export function SidecarProvider({ children, showSidecar = true }: SidecarProvide
 
   // Import and use the window manager hook
   const { toggleWindow } = useWindowManager({
-    expandPercentage: 100,
-    maxWidthForExpansion: 2200,
+    expandPercentage: 60,
+    maxWidthForExpansion: 1200,
     transitionDuration: 300,
   });
 
@@ -323,8 +323,10 @@ export function SidecarProvider({ children, showSidecar = true }: SidecarProvide
     setActiveView(view.id);
   };
 
-  const hideView = () => {
+  const hideView = async () => {
     setActiveView(null);
+    // Collapse window when hiding sidecar
+    await toggleWindow();
   };
 
   const showDiffViewer = (content: string, fileName = 'File') => {
@@ -338,10 +340,12 @@ export function SidecarProvider({ children, showSidecar = true }: SidecarProvide
     showView(diffView);
   };
 
-  const hideDiffViewer = () => {
+  const hideDiffViewer = async () => {
     setViews((prev) => prev.filter((v) => v.id !== 'diff'));
     if (activeView === 'diff') {
       setActiveView(null);
+      // Collapse window when hiding diff viewer
+      await toggleWindow();
     }
   };
 
diff --git a/ui/desktop/src/hooks/useWindowManager.ts b/ui/desktop/src/hooks/useWindowManager.ts
index c08a2335071f..4dfe7806cc38 100644
--- a/ui/desktop/src/hooks/useWindowManager.ts
+++ b/ui/desktop/src/hooks/useWindowManager.ts
@@ -177,12 +177,6 @@ export function useWindowManager(options: WindowManagerOptions = {}): WindowMana
       return;
     }
 
-    // Don't resize if window is already expanded
-    if (windowState.isExpanded) {
-      console.log('Window is already expanded, skipping resize operation');
-      return;
-    }
-
     try {
       resizeInProgressRef.current = true;
 
@@ -191,33 +185,52 @@ export function useWindowManager(options: WindowManagerOptions = {}): WindowMana
         isTransitioning: true,
       }));
 
-      // Only expanding logic remains since we skip when already expanded
-      if (!canExpand) {
-        console.log('Window too wide for expansion, skipping resize');
-        setWindowState((prev) => ({
-          ...prev,
-          isTransitioning: false,
-        }));
-        // Still mount the component even if we don't resize
-        setIsComponentMounted(true);
-        return;
-      }
+      if (windowState.isExpanded) {
+        // Collapse the window back to original size
+        console.log('Window is expanded, collapsing back to original size');
+
+        const success = await window.electron.resizeWindow(0); // 0 means reset to original size
+
+        if (success) {
+          setWindowState((prev) => ({
+            ...prev,
+            isExpanded: false,
+            currentWidth: prev.originalWidth,
+            isTransitioning: false,
+          }));
+        } else {
+          throw new Error('Failed to resize window for collapse');
+        }
+      } else {
+        // Expand the window
+        if (!canExpand) {
+          console.log('Window too wide for expansion, skipping resize but showing sidecar');
+          setWindowState((prev) => ({
+            ...prev,
+            isExpanded: true, // Mark as expanded even though we didn't resize
+            isTransitioning: false,
+          }));
+          // Still mount the component even if we don't resize
+          setIsComponentMounted(true);
+          return;
+        }
 
-      const success = await window.electron.resizeWindow(opts.expandPercentage);
+        const success = await window.electron.resizeWindow(opts.expandPercentage);
 
-      if (success) {
-        const newWidth = Math.floor(windowState.currentWidth * (1 + opts.expandPercentage / 100));
+        if (success) {
+          const newWidth = Math.floor(windowState.currentWidth * (1 + opts.expandPercentage / 100));
 
-        setWindowState((prev) => ({
-          ...prev,
-          isExpanded: true,
-          currentWidth: newWidth,
-          isTransitioning: false,
-        }));
+          setWindowState((prev) => ({
+            ...prev,
+            isExpanded: true,
+            currentWidth: newWidth,
+            isTransitioning: false,
+          }));
 
-        // Component will be mounted by the useEffect above
-      } else {
-        throw new Error('Failed to resize window for expansion');
+          // Component will be mounted by the useEffect above
+        } else {
+          throw new Error('Failed to resize window for expansion');
+        }
       }
     } catch (error) {
       console.error('Error during window toggle:', error);