diff --git a/rklipd/src/database.rs b/rklipd/src/database.rs
index 3b79d75..421bab5 100644
--- a/rklipd/src/database.rs
+++ b/rklipd/src/database.rs
@@ -112,4 +112,10 @@ impl Database {
 
         Ok(entries)
     }
+
+    pub fn delete_entry_by_content(&self, content: &str) -> Result<(), Box<dyn Error>> {
+        self.conn
+            .execute("DELETE FROM history WHERE content = ?1", [content])?;
+        Ok(())
+    }
 }
diff --git a/rklipd/src/ipc.rs b/rklipd/src/ipc.rs
index d0dc095..5a3c9e9 100644
--- a/rklipd/src/ipc.rs
+++ b/rklipd/src/ipc.rs
@@ -11,6 +11,7 @@ use std::sync::{Arc, Mutex};
 pub enum IpcRequest {
     GetHistory { limit: usize },
     SetClipboard { content: String },
+    DeleteEntry { content: String },
 }
 
 #[derive(Serialize, Deserialize, Debug)]
@@ -90,6 +91,29 @@ pub fn start_server(db: Arc<Mutex<Database>>, socket_path: &Path) {
                                         }
                                     }
                                 }
+
+                                IpcRequest::DeleteEntry { content } => {
+                                    {
+                                        let db_lock = db_clone.lock().unwrap();
+                                        let _ = db_lock.delete_entry_by_content(&content);
+                                    }
+
+                                    if content.ends_with(".jpg") || content.ends_with(".png") {
+                                        if let Some(proj_dirs) =
+                                            directories::ProjectDirs::from("com", "zefad", "rklipd")
+                                        {
+                                            let img_path =
+                                                proj_dirs.data_dir().join("images").join(&content);
+                                            if img_path.exists() {
+                                                if let Err(e) = std::fs::remove_file(&img_path) {
+                                                    eprintln!("Error while deleting image: {}", e);
+                                                } else {
+                                                    println!("Image deleted : {}", content);
+                                                }
+                                            }
+                                        }
+                                    }
+                                }
                             }
                         }
                     }
diff --git a/src/app.rs b/src/app.rs
index 274b13a..33385e7 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -8,6 +8,7 @@ pub enum Mode {
     Normal,
     Command,
     Search,
+    ConfirmDelete,
 }
 
 pub struct App {
diff --git a/src/ipc.rs b/src/ipc.rs
index be0d8f5..2372f56 100644
--- a/src/ipc.rs
+++ b/src/ipc.rs
@@ -6,6 +6,7 @@ use std::os::unix::net::UnixStream;
 pub enum IpcRequest {
     GetHistory { limit: usize },
     SetClipboard { content: String },
+    DeleteEntry { content: String },
 }
 
 #[derive(Serialize, Deserialize, Debug)]
@@ -49,3 +50,16 @@ pub fn set_clipboard(content: String) {
         }
     }
 }
+
+pub fn delete_entry(content: String) {
+    if let Some(base_dir) = directories::ProjectDirs::from("com", "zefad", "rklipd") {
+        let socket_path = base_dir.data_dir().join("rklip.sock");
+        if let Ok(mut stream) = UnixStream::connect(&socket_path) {
+            let req = IpcRequest::DeleteEntry { content };
+            if let Ok(req_json) = serde_json::to_string(&req) {
+                let _ = stream.write_all(req_json.as_bytes());
+                let _ = stream.shutdown(std::net::Shutdown::Write);
+            }
+        }
+    }
+}
diff --git a/src/main.rs b/src/main.rs
index 0f3e517..5641af7 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -60,7 +60,7 @@ fn run_app(terminal: &mut Terminal<CrosstermBackend<io::Stdout>>, app: &mut App)
                         }
                         KeyCode::Char('d') => {
                             if last_key_was_d {
-                                app.delete_selected();
+                                app.mode = Mode::ConfirmDelete;
                                 last_key_was_d = false;
                             } else {
                                 last_key_was_d = true;
@@ -150,6 +150,19 @@ fn run_app(terminal: &mut Terminal<CrosstermBackend<io::Stdout>>, app: &mut App)
                         }
                         _ => {}
                     },
+                    Mode::ConfirmDelete => match key.code {
+                        KeyCode::Char('y') | KeyCode::Char('Y') | KeyCode::Enter => {
+                            if let Some(selected) = app.get_selected_item() {
+                                crate::ipc::delete_entry(selected.clone());
+                                app.delete_selected();
+                            }
+                            app.mode = Mode::Normal;
+                        }
+                        KeyCode::Char('n') | KeyCode::Char('N') | KeyCode::Esc => {
+                            app.mode = Mode::Normal;
+                        }
+                        _ => {}
+                    },
                 }
             }
         } else {
diff --git a/src/ui.rs b/src/ui.rs
index ece3a40..d2c7c97 100644
--- a/src/ui.rs
+++ b/src/ui.rs
@@ -21,7 +21,7 @@ pub fn render(f: &mut Frame, app: &mut App) {
 
     let content_chunks = Layout::default()
         .direction(Direction::Horizontal)
-        .constraints([Constraint::Percentage(50), Constraint::Percentage(50)])
+        .constraints([Constraint::Length(50), Constraint::Min(0)])
         .split(main_chunks[0]);
 
     let items: Vec<ListItem> = app
@@ -72,6 +72,10 @@ pub fn render(f: &mut Frame, app: &mut App) {
             Span::styled("/", Style::default().fg(Color::Cyan)),
             Span::raw(&app.input_buffer),
         ]),
+        Mode::ConfirmDelete => Line::from(vec![Span::styled(
+            "Delete ? (y/n)",
+            Style::default().fg(Color::Red).add_modifier(Modifier::BOLD),
+        )]),
     };
 
     let bottom_bar = Paragraph::new(bottom_text).block(Block::default().borders(Borders::ALL));