diff --git a/apps/emdash-desktop/src/renderer/features/tasks/conversations/sidebar-conversations-list.tsx b/apps/emdash-desktop/src/renderer/features/tasks/conversations/sidebar-conversations-list.tsx
index 63e0e66a58..ff040d3ce0 100644
--- a/apps/emdash-desktop/src/renderer/features/tasks/conversations/sidebar-conversations-list.tsx
+++ b/apps/emdash-desktop/src/renderer/features/tasks/conversations/sidebar-conversations-list.tsx
@@ -1,5 +1,5 @@
 import { useVirtualizer } from '@tanstack/react-virtual';
-import { Pencil, Plus, Trash2 } from 'lucide-react';
+import { Pencil, Plus, Trash2, X } from 'lucide-react';
 import { observer } from 'mobx-react-lite';
 import { useCallback, useRef, useState } from 'react';
 import { formatConversationTitleForDisplay } from '@renderer/features/tasks/conversations/conversation-title-utils';
@@ -9,8 +9,11 @@ import {
   useWorkspaceViewModel,
 } from '@renderer/features/tasks/task-view-context';
 import { AgentIcon } from '@renderer/lib/components/agent-icon';
+import { ListPopoverCard } from '@renderer/lib/components/list-popover-card';
+import { useMultiSelect } from '@renderer/lib/hooks/use-multi-select';
 import { useShowModal } from '@renderer/lib/modal/modal-provider';
 import { Button } from '@renderer/lib/ui/button';
+import { Checkbox } from '@renderer/lib/ui/checkbox';
 import {
   ContextMenu,
   ContextMenuContent,
@@ -25,14 +28,22 @@ import { MAX_CONVERSATION_TITLE_LENGTH } from '@shared/core/conversations/conver
 import { AgentStatusIndicator } from '../components/agent-status-indicator';
 
 const ROW_HEIGHT = 32;
+const getConversationId = (id: string) => id;
 
 const ConversationRow = observer(function ConversationRow({
   conversationId,
+  isSelected,
+  hasSelection,
+  onToggleSelect,
 }: {
   conversationId: string;
+  isSelected: boolean;
+  hasSelection: boolean;
+  onToggleSelect: (shiftKey: boolean) => void;
 }) {
   const [isEditing, setIsEditing] = useState(false);
   const committedRef = useRef(false);
+  const checkboxShiftKeyRef = useRef(false);
   const taskView = useWorkspaceViewModel();
   const conversations = useConversations();
   const { tabManager, tabGroupManager } = taskView;
@@ -74,10 +85,19 @@ const ConversationRow = observer(function ConversationRow({
   };
 
   const handleDoubleClick = () => {
+    if (hasSelection) return;
     tabGroupManager.openConversation(conversationId);
     handleRename();
   };
 
+  const handleRowClick = (shiftKey: boolean) => {
+    if (shiftKey || hasSelection) {
+      onToggleSelect(shiftKey);
+      return;
+    }
+    tabGroupManager.openConversationPreview(conversationId);
+  };
+
   const handleDelete = () => {
     showConfirm({
       title: 'Delete conversation',
@@ -96,17 +116,18 @@ const ConversationRow = observer(function ConversationRow({
         <div
           role="button"
           tabIndex={0}
-          onClick={() => tabGroupManager.openConversationPreview(conversationId)}
+          onClick={(e) => handleRowClick(e.shiftKey)}
           onDoubleClick={handleDoubleClick}
           onKeyDown={(e) => {
             if (e.key === 'Enter' || e.key === ' ') {
               e.preventDefault();
-              tabGroupManager.openConversationPreview(conversationId);
+              handleRowClick(e.shiftKey);
             }
           }}
           className={cn(
-            'flex w-full items-center gap-2 h-8 rounded-md px-2 text-left text-sm text-foreground-muted transition-colors hover:bg-background-1 hover:text-foreground',
-            isActive && 'bg-background-2 text-foreground hover:bg-background-2'
+            'group relative flex w-full items-center gap-2 h-8 rounded-md px-2 text-left text-sm text-foreground-muted transition-colors hover:bg-background-1 hover:text-foreground',
+            isActive && 'bg-background-2 text-foreground hover:bg-background-2',
+            isSelected && 'bg-background-2 text-foreground hover:bg-background-2'
           )}
         >
           <AgentIcon id={conversation.data.providerId} size={16} className="size-4" />
@@ -131,7 +152,12 @@ const ConversationRow = observer(function ConversationRow({
           ) : (
             <span className="min-w-0 flex-1 truncate">{displayTitle}</span>
           )}
-          <span className="shrink-0">
+          <span
+            className={cn(
+              'shrink-0 transition-opacity',
+              isSelected ? 'opacity-0' : 'group-hover:opacity-0'
+            )}
+          >
             {conversation.indicatorStatus ? (
               <AgentStatusIndicator status={conversation.indicatorStatus} disableTooltip />
             ) : (
@@ -142,6 +168,31 @@ const ConversationRow = observer(function ConversationRow({
               />
             )}
           </span>
+          <div
+            onClick={(e) => e.stopPropagation()}
+            className={cn(
+              'absolute top-1/2 right-2 -translate-y-1/2 transition-opacity',
+              isSelected
+                ? 'opacity-100'
+                : 'pointer-events-none opacity-0 group-hover:pointer-events-auto group-hover:opacity-100'
+            )}
+          >
+            <Checkbox
+              checked={isSelected}
+              onMouseDown={(e) => {
+                checkboxShiftKeyRef.current = e.shiftKey;
+              }}
+              onKeyDown={(e) => {
+                e.stopPropagation();
+                checkboxShiftKeyRef.current = e.shiftKey;
+              }}
+              onCheckedChange={() => {
+                onToggleSelect(checkboxShiftKeyRef.current);
+                checkboxShiftKeyRef.current = false;
+              }}
+              aria-label="Select conversation"
+            />
+          </div>
         </div>
       </ContextMenuTrigger>
       <ContextMenuContent finalFocus={false}>
@@ -159,11 +210,39 @@ const ConversationRow = observer(function ConversationRow({
   );
 });
 
+function SelectionBar({
+  count,
+  onClear,
+  onDelete,
+}: {
+  count: number;
+  onClear: () => void;
+  onDelete: () => void;
+}) {
+  if (count === 0) return null;
+
+  return (
+    <ListPopoverCard className="justify-between">
+      <span className="whitespace-nowrap text-foreground-muted">{count} selected</span>
+      <div className="flex items-center gap-2">
+        <Button variant="destructive" size="sm" onClick={onDelete}>
+          <Trash2 className="size-3.5" />
+          Delete
+        </Button>
+        <Button variant="ghost" size="icon-xs" onClick={onClear} aria-label="Clear selection">
+          <X className="size-3.5" />
+        </Button>
+      </div>
+    </ListPopoverCard>
+  );
+}
+
 export const SidebarConversationsList = observer(function SidebarConversationsList() {
   const { projectId, taskId } = useTaskViewContext();
   const taskView = useWorkspaceViewModel();
   const conversations = useConversations();
   const { tabGroupManager } = taskView;
+  const showConfirm = useShowModal('confirmActionModal');
   const showCreateConversationModal = useShowModal('createConversationModal');
   const conversationIds = Array.from(conversations.conversations.values())
     .sort((a, b) => {
@@ -172,6 +251,13 @@ export const SidebarConversationsList = observer(function SidebarConversationsLi
       return bTime - aTime;
     })
     .map((c) => c.data.id);
+  const {
+    selectedIds,
+    selectedCount,
+    selectedOrderedIds: selectedConversationIds,
+    clear: clearSelection,
+    toggle: toggleSelect,
+  } = useMultiSelect({ items: conversationIds, getId: getConversationId });
 
   const parentRef = useRef<HTMLDivElement>(null);
 
@@ -182,6 +268,25 @@ export const SidebarConversationsList = observer(function SidebarConversationsLi
     overscan: 5,
   });
 
+  const handleBulkDelete = () => {
+    const ids = selectedConversationIds;
+    if (ids.length === 0) return;
+
+    showConfirm({
+      title: ids.length === 1 ? 'Delete conversation' : 'Delete conversations',
+      description:
+        ids.length === 1
+          ? '1 conversation will be permanently deleted. This action cannot be undone.'
+          : `${ids.length} conversations will be permanently deleted. This action cannot be undone.`,
+      confirmLabel: 'Delete',
+      variant: 'destructive',
+      onSuccess: () => {
+        ids.forEach((id) => void conversations.deleteConversation(id));
+        clearSelection();
+      },
+    });
+  };
+
   const handleCreate = () => {
     showCreateConversationModal({
       projectId,
@@ -193,7 +298,7 @@ export const SidebarConversationsList = observer(function SidebarConversationsLi
   };
 
   return (
-    <div className="flex h-full w-full flex-col">
+    <div className="relative flex h-full w-full flex-col">
       <div className="flex shrink-0 items-center justify-between pt-2 pr-2 pb-1 pl-4">
         <MicroLabel>Conversations</MicroLabel>
         <Button size="icon-sm" variant="ghost" onClick={handleCreate}>
@@ -201,8 +306,16 @@ export const SidebarConversationsList = observer(function SidebarConversationsLi
         </Button>
       </div>
 
-      <div ref={parentRef} className="min-h-0 flex-1 overflow-y-auto px-2">
-        <div style={{ height: virtualizer.getTotalSize(), position: 'relative' }}>
+      <div
+        ref={parentRef}
+        className={cn('min-h-0 flex-1 overflow-y-auto px-2', selectedCount > 0 && 'pb-20')}
+      >
+        <div
+          style={{
+            height: virtualizer.getTotalSize(),
+            position: 'relative',
+          }}
+        >
           {virtualizer.getVirtualItems().map((virtualItem) => {
             const conversationId = conversationIds[virtualItem.index]!;
             return (
@@ -217,12 +330,19 @@ export const SidebarConversationsList = observer(function SidebarConversationsLi
                   transform: `translateY(${virtualItem.start}px)`,
                 }}
               >
-                <ConversationRow conversationId={conversationId} />
+                <ConversationRow
+                  conversationId={conversationId}
+                  isSelected={selectedIds.has(conversationId)}
+                  hasSelection={selectedCount > 0}
+                  onToggleSelect={(shiftKey) => toggleSelect(conversationId, { range: shiftKey })}
+                />
               </div>
             );
           })}
         </div>
       </div>
+
+      <SelectionBar count={selectedCount} onClear={clearSelection} onDelete={handleBulkDelete} />
     </div>
   );
 });
diff --git a/apps/emdash-desktop/src/renderer/lib/hooks/use-multi-select.ts b/apps/emdash-desktop/src/renderer/lib/hooks/use-multi-select.ts
index 30bfa7c259..c87467a1b1 100644
--- a/apps/emdash-desktop/src/renderer/lib/hooks/use-multi-select.ts
+++ b/apps/emdash-desktop/src/renderer/lib/hooks/use-multi-select.ts
@@ -1,5 +1,10 @@
 import { useCallback, useMemo, useState } from 'react';
 
+interface SelectionAnchor {
+  id: string;
+  orderedIds: string[];
+}
+
 interface UseMultiSelectOptions<T> {
   items: ReadonlyArray<T>;
   getId: (item: T) => string;
@@ -7,7 +12,9 @@ interface UseMultiSelectOptions<T> {
 
 export interface UseMultiSelectResult {
   selectedIds: Set<string>;
-  toggle: (id: string) => void;
+  selectedCount: number;
+  selectedOrderedIds: string[];
+  toggle: (id: string, options?: { range?: boolean }) => void;
   selectAll: () => void;
   clear: () => void;
   isSelected: (id: string) => boolean;
@@ -18,27 +25,61 @@ export function useMultiSelect<T>({
   getId,
 }: UseMultiSelectOptions<T>): UseMultiSelectResult {
   const [selectedIds, setSelectedIds] = useState<Set<string>>(() => new Set());
+  const [selectionAnchor, setSelectionAnchor] = useState<SelectionAnchor | null>(null);
+  const allIds = useMemo(() => items.map(getId), [items, getId]);
+  const selectedOrderedIds = useMemo(
+    () => allIds.filter((id) => selectedIds.has(id)),
+    [allIds, selectedIds]
+  );
 
-  const toggle = useCallback((id: string) => {
-    setSelectedIds((prev) => {
-      const next = new Set(prev);
-      if (next.has(id)) next.delete(id);
-      else next.add(id);
-      return next;
-    });
-  }, []);
+  const toggle = useCallback(
+    (id: string, options?: { range?: boolean }) => {
+      if (options?.range && selectionAnchor && selectionAnchor.id !== id) {
+        const fromIndex = selectionAnchor.orderedIds.indexOf(selectionAnchor.id);
+        const toIndex = selectionAnchor.orderedIds.indexOf(id);
+        if (fromIndex !== -1 && toIndex !== -1) {
+          const [start, end] = fromIndex < toIndex ? [fromIndex, toIndex] : [toIndex, fromIndex];
+          const rangeIds = selectionAnchor.orderedIds.slice(start, end + 1);
+          setSelectedIds((prev) => {
+            const next = new Set(prev);
+            rangeIds.forEach((rangeId) => next.add(rangeId));
+            return next;
+          });
+          setSelectionAnchor({ id, orderedIds: allIds });
+          return;
+        }
+      }
+
+      setSelectedIds((prev) => {
+        const next = new Set(prev);
+        if (next.has(id)) next.delete(id);
+        else next.add(id);
+        return next;
+      });
+      setSelectionAnchor({ id, orderedIds: allIds });
+    },
+    [allIds, selectionAnchor]
+  );
 
   const clear = useCallback(() => {
     setSelectedIds((prev) => (prev.size === 0 ? prev : new Set()));
+    setSelectionAnchor(null);
   }, []);
 
-  const allIds = useMemo(() => items.map(getId), [items, getId]);
-
   const selectAll = useCallback(() => {
     setSelectedIds(new Set(allIds));
+    setSelectionAnchor(null);
   }, [allIds]);
 
   const isSelected = useCallback((id: string) => selectedIds.has(id), [selectedIds]);
 
-  return { selectedIds, toggle, selectAll, clear, isSelected };
+  return {
+    selectedIds,
+    selectedCount: selectedOrderedIds.length,
+    selectedOrderedIds,
+    toggle,
+    selectAll,
+    clear,
+    isSelected,
+  };
 }