diff --git a/src/apps/chat/components/ChatDrawer.tsx b/src/apps/chat/components/ChatDrawer.tsx
index 4d86aac6b..8f5ba93d4 100644
--- a/src/apps/chat/components/ChatDrawer.tsx
+++ b/src/apps/chat/components/ChatDrawer.tsx
@@ -78,7 +78,7 @@ function ChatDrawer(props: {
   // external state
   const { closeDrawer, closeDrawerOnMobile } = useOptimaDrawers();
   const { activeFolder, allFolders, enableFolders, toggleEnableFolders } = useFolders(props.activeFolderId);
-  const { filteredChatsCount, filteredChatIDs, filteredChatsAreEmpty, filterefChatsBarBasis, renderNavItems } = useChatNavRenderItems(
+  const { filteredChatsCount, filteredChatIDs, filteredChatsAreEmpty, filteredChatsBarBasis, filteredChatsIncludeActive, renderNavItems } = useChatNavRenderItems(
     props.activeConversationId, props.chatPanesConversationIds, debouncedSearchQuery, activeFolder, allFolders, navGrouping,
   );
   const { contentScaling, showSymbols } = useUIPreferencesStore(state => ({
@@ -90,11 +90,13 @@ function ChatDrawer(props: {
   // New/Activate/Delete Conversation
 
   const isMultiPane = props.chatPanesConversationIds.length >= 2;
+  const disableNewButton = props.disableNewButton && filteredChatsIncludeActive;
+  const newButtonDontRecycle = isMultiPane || !filteredChatsIncludeActive;
 
   const handleButtonNew = React.useCallback(() => {
-    onConversationNew(isMultiPane);
+    onConversationNew(newButtonDontRecycle);
     closeDrawerOnMobile();
-  }, [closeDrawerOnMobile, isMultiPane, onConversationNew]);
+  }, [closeDrawerOnMobile, newButtonDontRecycle, onConversationNew]);
 
   const handleConversationActivate = React.useCallback((conversationId: DConversationId, closeMenu: boolean) => {
     onConversationActivate(conversationId);
@@ -208,8 +210,8 @@ function ChatDrawer(props: {
       <ListItem sx={{ mx: '0.25rem', mb: 0.5 }}>
         <ListItemButton
           // variant='outlined'
-          variant={props.disableNewButton ? undefined : 'outlined'}
-          disabled={props.disableNewButton}
+          variant={disableNewButton ? undefined : 'outlined'}
+          disabled={disableNewButton}
           onClick={handleButtonNew}
           sx={{
             // ...PageDrawerTallItemSx,
@@ -221,7 +223,7 @@ function ChatDrawer(props: {
 
             // style
             borderRadius: 'md',
-            boxShadow: (props.disableNewButton || props.isMobile) ? 'none' : 'sm',
+            boxShadow: (disableNewButton || props.isMobile) ? 'none' : 'sm',
             backgroundColor: 'background.popup',
             transition: 'box-shadow 0.2s',
           }}
@@ -254,7 +256,7 @@ function ChatDrawer(props: {
               key={'nav-chat-' + item.conversationId}
               item={item}
               showSymbols={showSymbols}
-              bottomBarBasis={showSymbols ? filterefChatsBarBasis : 0}
+              bottomBarBasis={showSymbols ? filteredChatsBarBasis : 0}
               onConversationActivate={handleConversationActivate}
               onConversationBranch={onConversationBranch}
               onConversationDelete={handleConversationDeleteNoConfirmation}
@@ -265,6 +267,10 @@ function ChatDrawer(props: {
             <Typography key={'nav-divider-' + idx} level='body-xs' sx={{ textAlign: 'center', my: 'calc(var(--ListItem-minHeight) / 4)' }}>
               {item.title}
             </Typography>
+          ) : item.type === 'nav-item-info-message' ? (
+            <Typography key={'nav-info-' + idx} level='body-xs' sx={{ textAlign: 'center', my: 'calc(var(--ListItem-minHeight) / 2)' }}>
+              {item.message}
+            </Typography>
           ) : null,
         )}
       </Box>
diff --git a/src/apps/chat/components/useChatNavRenderItems.tsx b/src/apps/chat/components/useChatNavRenderItems.tsx
index fd060d643..85d203bd7 100644
--- a/src/apps/chat/components/useChatNavRenderItems.tsx
+++ b/src/apps/chat/components/useChatNavRenderItems.tsx
@@ -13,12 +13,17 @@ const SEARCH_MIN_CHARS = 3;
 
 export type ChatNavGrouping = false | 'date' | 'persona';
 
-export interface ChatNavigationGroupData {
+interface ChatNavigationGroupData {
   type: 'nav-item-group',
   title: string,
 }
 
-type ChatRenderItemData = ChatNavigationItemData | ChatNavigationGroupData;
+interface ChatNavigationInfoMessage {
+  type: 'nav-item-info-message',
+  message: string,
+}
+
+type ChatRenderItemData = ChatNavigationItemData | ChatNavigationGroupData | ChatNavigationInfoMessage;
 
 
 // Returns a string with the pane indices where the conversation is also open, or false if it's not
@@ -79,7 +84,8 @@ export function useChatNavRenderItems(
   filteredChatIDs: DConversationId[],
   filteredChatsCount: number,
   filteredChatsAreEmpty: boolean,
-  filterefChatsBarBasis: number,
+  filteredChatsBarBasis: number,
+  filteredChatsIncludeActive: boolean,
 } {
   return useChatStore(({ conversations }) => {
 
@@ -125,6 +131,9 @@ export function useChatNavRenderItems(
         };
       }).filter(item => !isSearching || item.searchFrequency > 0);
 
+      // check if the active conversation has an item in the list
+      const filteredChatsIncludeActive = chatNavItems.some(_c => _c.conversationId === activeConversationId);
+
 
       // [sort by frequency, don't group] if there's a search query
       chatNavItems.sort((a, b) => b.searchFrequency - a.searchFrequency);
@@ -160,11 +169,15 @@ export function useChatNavRenderItems(
         ]);
       }
 
+      // [empty message] if there are no items
+      if (!renderNavItems.length)
+        renderNavItems.push({ type: 'nav-item-info-message', message: isSearching ? 'No results found' : 'No conversations in folder' });
+
       // other derived state
       const filteredChatIDs = chatNavItems.map(_c => _c.conversationId);
       const filteredChatsCount = chatNavItems.length;
       const filteredChatsAreEmpty = !filteredChatsCount || (filteredChatsCount === 1 && chatNavItems[0].isEmpty);
-      const filterefChatsBarBasis = (filteredChatsCount >= AUTO_UNDERLINE_COUNT || isSearching)
+      const filteredChatsBarBasis = (filteredChatsCount >= AUTO_UNDERLINE_COUNT || isSearching)
         ? chatNavItems.reduce((longest, _c) => Math.max(longest, isSearching ? _c.searchFrequency : _c.messageCount), 1)
         : 0;
 
@@ -173,7 +186,8 @@ export function useChatNavRenderItems(
         filteredChatIDs,
         filteredChatsCount,
         filteredChatsAreEmpty,
-        filterefChatsBarBasis,
+        filteredChatsBarBasis,
+        filteredChatsIncludeActive,
       };
     },
     (a, b) => {