diff --git a/crates/goose-server/src/routes/session.rs b/crates/goose-server/src/routes/session.rs
index 95f4ee1dbf32..432bbc398104 100644
--- a/crates/goose-server/src/routes/session.rs
+++ b/crates/goose-server/src/routes/session.rs
@@ -7,7 +7,7 @@ use crate::state::AppState;
 use axum::{
     extract::{Path, State},
     http::{HeaderMap, StatusCode},
-    routing::{get, put},
+    routing::{delete, get, put},
     Json, Router,
 };
 use goose::conversation::message::Message;
@@ -310,11 +310,54 @@ async fn update_session_metadata(
     Ok(StatusCode::OK)
 }
 
+#[utoipa::path(
+    delete,
+    path = "/sessions/{session_id}/delete",
+    params(
+        ("session_id" = String, Path, description = "Unique identifier for the session")
+    ),
+    responses(
+        (status = 200, description = "Session deleted successfully"),
+        (status = 401, description = "Unauthorized - Invalid or missing API key"),
+        (status = 404, description = "Session not found"),
+        (status = 500, description = "Internal server error")
+    ),
+    security(
+        ("api_key" = [])
+    ),
+    tag = "Session Management"
+)]
+// Delete a session
+async fn delete_session(
+    State(state): State<Arc<AppState>>,
+    headers: HeaderMap,
+    Path(session_id): Path<String>,
+) -> Result<StatusCode, StatusCode> {
+    verify_secret_key(&headers, &state)?;
+
+    // Get the session path
+    let session_path = match session::get_path(session::Identifier::Name(session_id.clone())) {
+        Ok(path) => path,
+        Err(_) => return Err(StatusCode::BAD_REQUEST),
+    };
+
+    // Check if session file exists
+    if !session_path.exists() {
+        return Err(StatusCode::NOT_FOUND);
+    }
+
+    // Delete the session file
+    std::fs::remove_file(&session_path).map_err(|_| StatusCode::INTERNAL_SERVER_ERROR)?;
+
+    Ok(StatusCode::OK)
+}
+
 // Configure routes for this module
 pub fn routes(state: Arc<AppState>) -> Router {
     Router::new()
         .route("/sessions", get(list_sessions))
         .route("/sessions/{session_id}", get(get_session_history))
+        .route("/sessions/{session_id}/delete", delete(delete_session))
         .route("/sessions/insights", get(get_session_insights))
         .route(
             "/sessions/{session_id}/metadata",
diff --git a/ui/desktop/src/components/sessions/SessionListView.tsx b/ui/desktop/src/components/sessions/SessionListView.tsx
index a108903d9549..935a47e5757d 100644
--- a/ui/desktop/src/components/sessions/SessionListView.tsx
+++ b/ui/desktop/src/components/sessions/SessionListView.tsx
@@ -1,6 +1,14 @@
 import React, { useEffect, useState, useRef, useCallback, useMemo, startTransition } from 'react';
-import { MessageSquareText, Target, AlertCircle, Calendar, Folder, Edit2 } from 'lucide-react';
-import { fetchSessions, updateSessionMetadata, type Session } from '../../sessions';
+import {
+  MessageSquareText,
+  Target,
+  AlertCircle,
+  Calendar,
+  Folder,
+  Edit2,
+  Trash2,
+} from 'lucide-react';
+import { fetchSessions, updateSessionMetadata, deleteSession, type Session } from '../../sessions';
 import { Card } from '../ui/card';
 import { Button } from '../ui/button';
 import { ScrollArea } from '../ui/scroll-area';
@@ -12,6 +20,7 @@ import { MainPanelLayout } from '../Layout/MainPanelLayout';
 import { groupSessionsByDate, type DateGroup } from '../../utils/dateUtils';
 import { Skeleton } from '../ui/skeleton';
 import { toast } from 'react-toastify';
+import { ConfirmationModal } from '../ui/ConfirmationModal';
 
 interface EditSessionModalProps {
   session: Session | null;
@@ -177,6 +186,10 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
     const [showEditModal, setShowEditModal] = useState(false);
     const [editingSession, setEditingSession] = useState<Session | null>(null);
 
+    // Delete confirmation modal state
+    const [showDeleteConfirmation, setShowDeleteConfirmation] = useState(false);
+    const [sessionToDelete, setSessionToDelete] = useState<Session | null>(null);
+
     // Search state for debouncing
     const [searchTerm, setSearchTerm] = useState('');
     const [caseSensitive, setCaseSensitive] = useState(false);
@@ -355,12 +368,43 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
       setShowEditModal(true);
     }, []);
 
+    const handleDeleteSession = useCallback((session: Session) => {
+      setSessionToDelete(session);
+      setShowDeleteConfirmation(true);
+    }, []);
+
+    const handleConfirmDelete = useCallback(async () => {
+      if (!sessionToDelete) return;
+
+      setShowDeleteConfirmation(false);
+      const sessionToDeleteId = sessionToDelete.id;
+      const sessionName = sessionToDelete.metadata.description || sessionToDelete.id;
+      setSessionToDelete(null);
+
+      try {
+        await deleteSession(sessionToDeleteId);
+        toast.success('Session deleted successfully');
+        loadSessions();
+      } catch (error) {
+        console.error('Error deleting session:', error);
+        const errorMessage = error instanceof Error ? error.message : 'Unknown error';
+        toast.error(`Failed to delete session "${sessionName}": ${errorMessage}`);
+      }
+    }, [sessionToDelete, loadSessions]);
+
+    const handleCancelDelete = useCallback(() => {
+      setShowDeleteConfirmation(false);
+      setSessionToDelete(null);
+    }, []);
+
     const SessionItem = React.memo(function SessionItem({
       session,
       onEditClick,
+      onDeleteClick,
     }: {
       session: Session;
       onEditClick: (session: Session) => void;
+      onDeleteClick: (session: Session) => void;
     }) {
       const handleEditClick = useCallback(
         (e: React.MouseEvent) => {
@@ -370,6 +414,14 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
         [onEditClick, session]
       );
 
+      const handleDeleteClick = useCallback(
+        (e: React.MouseEvent) => {
+          e.stopPropagation(); // Prevent card click
+          onDeleteClick(session);
+        },
+        [onDeleteClick, session]
+      );
+
       const handleCardClick = useCallback(() => {
         onSelectSession(session.id);
       }, [session.id]);
@@ -380,16 +432,25 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
           className="session-item h-full py-3 px-4 hover:shadow-default cursor-pointer transition-all duration-150 flex flex-col justify-between relative group"
           ref={(el) => setSessionRefs(session.id, el)}
         >
-          <button
-            onClick={handleEditClick}
-            className="absolute top-3 right-4 p-2 rounded opacity-0 group-hover:opacity-100 transition-opacity hover:bg-gray-100 dark:hover:bg-gray-700 cursor-pointer"
-            title="Edit session name"
-          >
-            <Edit2 className="w-3 h-3 text-textSubtle hover:text-textStandard" />
-          </button>
+          <div className="absolute top-3 right-4 flex gap-1 opacity-0 group-hover:opacity-100 transition-opacity">
+            <button
+              onClick={handleEditClick}
+              className="p-2 rounded hover:bg-gray-100 dark:hover:bg-gray-700 cursor-pointer"
+              title="Edit session name"
+            >
+              <Edit2 className="w-3 h-3 text-textSubtle hover:text-textStandard" />
+            </button>
+            <button
+              onClick={handleDeleteClick}
+              className="p-2 rounded hover:bg-red-50 dark:hover:bg-red-900/20 cursor-pointer transition-colors"
+              title="Delete session"
+            >
+              <Trash2 className="w-3 h-3 text-red-500 hover:text-red-600" />
+            </button>
+          </div>
 
           <div className="flex-1">
-            <h3 className="text-base mb-1 pr-6 break-words">
+            <h3 className="text-base mb-1 pr-16 break-words">
               {session.metadata.description || session.id}
             </h3>
 
@@ -505,7 +566,12 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
               </div>
               <div className="grid grid-cols-1 sm:grid-cols-2 lg:grid-cols-3 xl:grid-cols-4 2xl:grid-cols-5 gap-4">
                 {group.sessions.map((session) => (
-                  <SessionItem key={session.id} session={session} onEditClick={handleEditSession} />
+                  <SessionItem
+                    key={session.id}
+                    session={session}
+                    onEditClick={handleEditSession}
+                    onDeleteClick={handleDeleteSession}
+                  />
                 ))}
               </div>
             </div>
@@ -605,6 +671,17 @@ const SessionListView: React.FC<SessionListViewProps> = React.memo(
           onClose={handleModalClose}
           onSave={handleModalSave}
         />
+
+        <ConfirmationModal
+          isOpen={showDeleteConfirmation}
+          title="Delete Session"
+          message={`Are you sure you want to delete the session "${sessionToDelete?.metadata.description || sessionToDelete?.id}"? This action cannot be undone.`}
+          confirmLabel="Delete Session"
+          cancelLabel="Cancel"
+          confirmVariant="destructive"
+          onConfirm={handleConfirmDelete}
+          onCancel={handleCancelDelete}
+        />
       </>
     );
   }
diff --git a/ui/desktop/src/components/ui/ConfirmationModal.tsx b/ui/desktop/src/components/ui/ConfirmationModal.tsx
index 3a07337156f6..e3add6562106 100644
--- a/ui/desktop/src/components/ui/ConfirmationModal.tsx
+++ b/ui/desktop/src/components/ui/ConfirmationModal.tsx
@@ -17,6 +17,7 @@ export function ConfirmationModal({
   confirmLabel = 'Yes',
   cancelLabel = 'No',
   isSubmitting = false,
+  confirmVariant = 'default',
 }: {
   isOpen: boolean;
   title: string;
@@ -26,20 +27,21 @@ export function ConfirmationModal({
   confirmLabel?: string;
   cancelLabel?: string;
   isSubmitting?: boolean; // To handle debounce state
+  confirmVariant?: 'default' | 'destructive' | 'outline' | 'secondary' | 'ghost' | 'link';
 }) {
   return (
     <Dialog open={isOpen} onOpenChange={(open) => !open && onCancel()}>
       <DialogContent className="sm:max-w-[425px]">
         <DialogHeader>
           <DialogTitle>{title}</DialogTitle>
-          <DialogDescription className="whitespace-pre-wrap">{message}</DialogDescription>
+          <DialogDescription>{message}</DialogDescription>
         </DialogHeader>
 
         <DialogFooter className="pt-2">
           <Button variant="outline" onClick={onCancel} disabled={isSubmitting}>
             {cancelLabel}
           </Button>
-          <Button onClick={onConfirm} disabled={isSubmitting}>
+          <Button variant={confirmVariant} onClick={onConfirm} disabled={isSubmitting}>
             {isSubmitting ? 'Processing...' : confirmLabel}
           </Button>
         </DialogFooter>
diff --git a/ui/desktop/src/sessions.ts b/ui/desktop/src/sessions.ts
index a19220945931..bb488b4ee8ab 100644
--- a/ui/desktop/src/sessions.ts
+++ b/ui/desktop/src/sessions.ts
@@ -151,3 +151,30 @@ export function resumeSession(session: SessionDetails | Session) {
     resumedSessionId
   );
 }
+
+/**
+ * Deletes a specific session
+ * @param sessionId The ID of the session to delete
+ * @returns Promise that resolves when the deletion is complete
+ */
+export async function deleteSession(sessionId: string): Promise<void> {
+  try {
+    const url = getApiUrl(`/sessions/${sessionId}/delete`);
+    const secretKey = await window.electron.getSecretKey();
+
+    const response = await fetch(url, {
+      method: 'DELETE',
+      headers: {
+        'X-Secret-Key': secretKey,
+      },
+    });
+
+    if (!response.ok) {
+      const errorText = await response.text();
+      throw new Error(`Failed to delete session: ${response.statusText} - ${errorText}`);
+    }
+  } catch (error) {
+    console.error(`Error deleting session ${sessionId}:`, error);
+    throw error;
+  }
+}