diff --git a/espanso-engine/src/event/internal.rs b/espanso-engine/src/event/internal.rs
index 872a7ce..0ffb83d 100644
--- a/espanso-engine/src/event/internal.rs
+++ b/espanso-engine/src/event/internal.rs
@@ -89,3 +89,10 @@ pub struct SecureInputEnabledEvent {
   pub app_name: String,
   pub app_path: String,
 }
+
+#[derive(Debug, Clone, PartialEq)]
+pub struct UndoEvent {
+  pub match_id: i32,
+  pub trigger: String,
+  pub replace: String,
+}
\ No newline at end of file
diff --git a/espanso-engine/src/event/mod.rs b/espanso-engine/src/event/mod.rs
index 5d9c53f..f43eb96 100644
--- a/espanso-engine/src/event/mod.rs
+++ b/espanso-engine/src/event/mod.rs
@@ -71,6 +71,7 @@ pub enum EventType {
   ImageResolved(internal::ImageResolvedEvent),
   MatchInjected,
   DiscardPrevious(internal::DiscardPreviousEvent),
+  Undo(internal::UndoEvent),
 
   Disabled,
   Enabled,
diff --git a/espanso-engine/src/process/default.rs b/espanso-engine/src/process/default.rs
index 95e42f5..36670b8 100644
--- a/espanso-engine/src/process/default.rs
+++ b/espanso-engine/src/process/default.rs
@@ -19,8 +19,7 @@
 
 use log::trace;
 
-use super::{
-  middleware::{
+use super::{DisableOptions, MatchFilter, MatchInfoProvider, MatchProvider, MatchSelector, Matcher, MatcherMiddlewareConfigProvider, Middleware, Multiplexer, PathProvider, Processor, Renderer, UndoEnabledProvider, middleware::{
     action::{ActionMiddleware, EventSequenceProvider},
     cause::CauseCompensateMiddleware,
     cursor_hint::CursorHintMiddleware,
@@ -31,18 +30,8 @@ use super::{
     multiplex::MultiplexMiddleware,
     past_discard::PastEventsDiscardMiddleware,
     render::RenderMiddleware,
-  },
-  DisableOptions, MatchFilter, MatchInfoProvider, MatchProvider, MatchSelector, Matcher,
-  MatcherMiddlewareConfigProvider, Middleware, Multiplexer, PathProvider, Processor, Renderer,
-};
-use crate::{
-  event::{Event, EventType},
-  process::middleware::{
-    context_menu::ContextMenuMiddleware, disable::DisableMiddleware, exit::ExitMiddleware,
-    hotkey::HotKeyMiddleware, icon_status::IconStatusMiddleware,
-    image_resolve::ImageResolverMiddleware, search::SearchMiddleware,
-  },
-};
+  }};
+use crate::{event::{Event, EventType}, process::middleware::{context_menu::ContextMenuMiddleware, disable::DisableMiddleware, exit::ExitMiddleware, hotkey::HotKeyMiddleware, icon_status::IconStatusMiddleware, image_resolve::ImageResolverMiddleware, search::SearchMiddleware, undo::UndoMiddleware}};
 use std::collections::VecDeque;
 
 pub struct DefaultProcessor<'a> {
@@ -65,6 +54,7 @@ impl<'a> DefaultProcessor<'a> {
     disable_options: DisableOptions,
     matcher_options_provider: &'a dyn MatcherMiddlewareConfigProvider,
     match_provider: &'a dyn MatchProvider,
+    undo_enabled_provider: &'a dyn UndoEnabledProvider,
   ) -> DefaultProcessor<'a> {
     Self {
       event_queue: VecDeque::new(),
@@ -82,6 +72,7 @@ impl<'a> DefaultProcessor<'a> {
         Box::new(ImageResolverMiddleware::new(path_provider)),
         Box::new(CursorHintMiddleware::new()),
         Box::new(ExitMiddleware::new()),
+        Box::new(UndoMiddleware::new(undo_enabled_provider)),
         Box::new(ActionMiddleware::new(
           match_info_provider,
           event_sequence_provider,
diff --git a/espanso-engine/src/process/middleware/action.rs b/espanso-engine/src/process/middleware/action.rs
index 5d65651..41d97ed 100644
--- a/espanso-engine/src/process/middleware/action.rs
+++ b/espanso-engine/src/process/middleware/action.rs
@@ -126,10 +126,28 @@ impl<'a> Middleware for ActionMiddleware<'a> {
           }),
         )
       }
+      EventType::Undo(m_event) => {
+        // We subtract one, because the backspace that triggered the undo feature
+        // already removed the last char
+        let backspace_count = m_event.replace.chars().count() - 1;
+
+        dispatch(Event::caused_by(
+          event.source_id,
+          EventType::TextInject(TextInjectRequest {
+            text: m_event.trigger.clone(),
+            force_mode: self.match_info_provider.get_force_mode(m_event.match_id),
+          }),
+        ));
+
+        Event::caused_by(
+          event.source_id,
+          EventType::KeySequenceInject(KeySequenceInjectRequest {
+            keys: (0..backspace_count).map(|_| Key::Backspace).collect(),
+          }),
+        )
+      }
       _ => event,
     }
-
-    // TODO: handle images
   }
 }
 
diff --git a/espanso-engine/src/process/middleware/mod.rs b/espanso-engine/src/process/middleware/mod.rs
index 40c72b6..3a7e3eb 100644
--- a/espanso-engine/src/process/middleware/mod.rs
+++ b/espanso-engine/src/process/middleware/mod.rs
@@ -34,3 +34,4 @@ pub mod multiplex;
 pub mod past_discard;
 pub mod render;
 pub mod search;
+pub mod undo;
diff --git a/espanso-engine/src/process/middleware/undo.rs b/espanso-engine/src/process/middleware/undo.rs
new file mode 100644
index 0000000..29421e2
--- /dev/null
+++ b/espanso-engine/src/process/middleware/undo.rs
@@ -0,0 +1,115 @@
+/*
+ * This file is part of espanso.
+ *
+ * Copyright (C) 2019-2021 Federico Terzi
+ *
+ * espanso is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * espanso is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ *
+ * You should have received a copy of the GNU General Public License
+ * along with espanso.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+use std::cell::RefCell;
+
+use super::super::Middleware;
+use crate::event::{
+  input::{Key, Status},
+  internal::{TextFormat, UndoEvent},
+  Event, EventType,
+};
+
+pub trait UndoEnabledProvider {
+  fn is_undo_enabled(&self) -> bool;
+}
+
+pub struct UndoMiddleware<'a> {
+  undo_enabled_provider: &'a dyn UndoEnabledProvider,
+  record: RefCell<Option<InjectionRecord>>,
+}
+
+impl<'a> UndoMiddleware<'a> {
+  pub fn new(undo_enabled_provider: &'a dyn UndoEnabledProvider) -> Self {
+    Self {
+      undo_enabled_provider,
+      record: RefCell::new(None),
+    }
+  }
+}
+
+impl<'a> Middleware for UndoMiddleware<'a> {
+  fn name(&self) -> &'static str {
+    "undo"
+  }
+
+  fn next(&self, event: Event, _: &mut dyn FnMut(Event)) -> Event {
+    let mut record = self.record.borrow_mut();
+
+    if let EventType::TriggerCompensation(m_event) = &event.etype {
+      *record = Some(InjectionRecord {
+        id: Some(event.source_id),
+        trigger: Some(m_event.trigger.clone()),
+        ..Default::default()
+      });
+    } else if let EventType::Rendered(m_event) = &event.etype {
+      if let TextFormat::Plain = m_event.format {
+        if let Some(record) = &mut *record {
+          if record.id == Some(event.source_id) {
+            record.injected_text = Some(m_event.body.clone());
+            record.match_id = Some(m_event.match_id);
+          }
+        }
+      }
+    } else if let EventType::Keyboard(m_event) = &event.etype {
+      if m_event.status == Status::Pressed {
+        if m_event.key == Key::Backspace {
+          if let Some(record) = (*record).take() {
+            if let (Some(trigger), Some(injected_text), Some(match_id)) =
+              (record.trigger, record.injected_text, record.match_id)
+            {
+              if self.undo_enabled_provider.is_undo_enabled() {
+                return Event::caused_by(
+                  event.source_id,
+                  EventType::Undo(UndoEvent {
+                    match_id,
+                    trigger,
+                    replace: injected_text,
+                  }),
+                );
+              }
+            }
+          }
+        }
+        *record = None;
+      }
+    } else if let EventType::Mouse(_) = &event.etype {
+      // Any mouse event invalidates the undo feature, as it could
+      // represent a change in application
+      *record = None;
+    } else if let EventType::CursorHintCompensation(_) = &event.etype {
+      // Cursor hints invalidate the undo feature, as it would be pretty
+      // complex to determine which delete operations should be performed.
+      // This might change in the future.
+      *record = None;
+    }
+
+    event
+  }
+}
+
+#[derive(Default)]
+struct InjectionRecord {
+  id: Option<u32>,
+  match_id: Option<i32>,
+  trigger: Option<String>,
+  injected_text: Option<String>,
+}
+
+// TODO: test
diff --git a/espanso-engine/src/process/mod.rs b/espanso-engine/src/process/mod.rs
index 8102ad0..2d30cc7 100644
--- a/espanso-engine/src/process/mod.rs
+++ b/espanso-engine/src/process/mod.rs
@@ -44,6 +44,7 @@ pub use middleware::matcher::{
 pub use middleware::multiplex::Multiplexer;
 pub use middleware::render::{Renderer, RendererError};
 pub use middleware::search::MatchProvider;
+pub use middleware::undo::UndoEnabledProvider;
 
 #[allow(clippy::too_many_arguments)]
 pub fn default<'a, MatcherState>(
@@ -59,6 +60,7 @@ pub fn default<'a, MatcherState>(
   disable_options: DisableOptions,
   matcher_options_provider: &'a dyn MatcherMiddlewareConfigProvider,
   match_provider: &'a dyn MatchProvider,
+  undo_enabled_provider: &'a dyn UndoEnabledProvider,
 ) -> impl Processor + 'a {
   default::DefaultProcessor::new(
     matchers,
@@ -73,5 +75,6 @@ pub fn default<'a, MatcherState>(
     disable_options,
     matcher_options_provider,
     match_provider,
+    undo_enabled_provider,
   )
 }