diff --git a/app/src/main/java/awais/instagrabber/adapters/DirectItemsAdapter.java b/app/src/main/java/awais/instagrabber/adapters/DirectItemsAdapter.java
index 5b7fc442..785aad31 100644
--- a/app/src/main/java/awais/instagrabber/adapters/DirectItemsAdapter.java
+++ b/app/src/main/java/awais/instagrabber/adapters/DirectItemsAdapter.java
@@ -4,6 +4,7 @@ import android.text.format.DateFormat;
 import android.view.LayoutInflater;
 import android.view.ViewGroup;
 
+import androidx.annotation.IdRes;
 import androidx.annotation.NonNull;
 import androidx.annotation.Nullable;
 import androidx.recyclerview.widget.AdapterListUpdateCallback;
@@ -392,6 +393,8 @@ public final class DirectItemsAdapter extends RecyclerView.Adapter<RecyclerView.
         void onReaction(DirectItem item, Emoji emoji);
 
         void onReactionClick(DirectItem item, int position);
+
+        void onOptionSelect(DirectItem item, @IdRes int itemId);
     }
 
     public interface DirectItemInternalLongClickListener {
diff --git a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemActionLogViewHolder.java b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemActionLogViewHolder.java
index 8d9ed41f..7acb4dae 100644
--- a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemActionLogViewHolder.java
+++ b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemActionLogViewHolder.java
@@ -81,4 +81,9 @@ public class DirectItemActionLogViewHolder extends DirectItemViewHolder {
     protected boolean showMessageInfo() {
         return false;
     }
+
+    @Override
+    protected boolean allowLongClick() {
+        return false;
+    }
 }
diff --git a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemDefaultViewHolder.java b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemDefaultViewHolder.java
index b0c31a1b..0a395d5b 100644
--- a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemDefaultViewHolder.java
+++ b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemDefaultViewHolder.java
@@ -30,4 +30,9 @@ public class DirectItemDefaultViewHolder extends DirectItemViewHolder {
         final Context context = itemView.getContext();
         binding.tvMessage.setText(context.getText(R.string.dms_inbox_raven_message_unknown));
     }
+
+    @Override
+    protected boolean allowLongClick() {
+        return false;
+    }
 }
diff --git a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemPlaceholderViewHolder.java b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemPlaceholderViewHolder.java
index d4bf903b..46f53a69 100644
--- a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemPlaceholderViewHolder.java
+++ b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemPlaceholderViewHolder.java
@@ -33,4 +33,9 @@ public class DirectItemPlaceholderViewHolder extends DirectItemViewHolder {
     protected boolean showBackground() {
         return true;
     }
+
+    @Override
+    protected boolean allowLongClick() {
+        return false;
+    }
 }
diff --git a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemVideoCallEventViewHolder.java b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemVideoCallEventViewHolder.java
index 1c316d1a..39c52b81 100644
--- a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemVideoCallEventViewHolder.java
+++ b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemVideoCallEventViewHolder.java
@@ -71,4 +71,9 @@ public class DirectItemVideoCallEventViewHolder extends DirectItemViewHolder {
     protected boolean showMessageInfo() {
         return false;
     }
+
+    @Override
+    protected boolean allowLongClick() {
+        return false;
+    }
 }
diff --git a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemViewHolder.java b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemViewHolder.java
index 2503bcbd..6402a429 100644
--- a/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemViewHolder.java
+++ b/app/src/main/java/awais/instagrabber/adapters/viewholder/directmessages/DirectItemViewHolder.java
@@ -22,6 +22,7 @@ import androidx.recyclerview.widget.RecyclerView;
 import androidx.transition.TransitionManager;
 
 import com.google.android.material.transition.MaterialFade;
+import com.google.common.collect.ImmutableList;
 
 import java.util.List;
 import java.util.stream.Collectors;
@@ -110,7 +111,7 @@ public abstract class DirectItemViewHolder extends RecyclerView.ViewHolder {
         final MessageDirection messageDirection = isSelf(item) ? MessageDirection.OUTGOING : MessageDirection.INCOMING;
         itemView.post(() -> bindBase(item, messageDirection, position));
         itemView.post(() -> bindItem(item, messageDirection));
-        itemView.post(() -> setupLongClickListener(position));
+        itemView.post(() -> setupLongClickListener(position, messageDirection));
         // bindBase(item, messageDirection);
         // bindItem(item, messageDirection);
         // setupLongClickListener(position);
@@ -479,7 +480,7 @@ public abstract class DirectItemViewHolder extends RecyclerView.ViewHolder {
     }
 
     @SuppressLint("ClickableViewAccessibility")
-    private void setupLongClickListener(final int position) {
+    private void setupLongClickListener(final int position, final MessageDirection messageDirection) {
         if (!allowLongClick()) return;
         binding.getRoot().setOnItemLongClickListener(new DirectItemFrameLayout.OnItemLongClickListener() {
             @Override
@@ -498,17 +499,24 @@ public abstract class DirectItemViewHolder extends RecyclerView.ViewHolder {
                 // longClickListener.onLongClick(position, this);
                 itemView.post(() -> grow());
                 setSelected(true);
-                showLongClickOptions(new Point((int) x, (int) y));
+                showLongClickOptions(new Point((int) x, (int) y), messageDirection);
             }
         });
     }
 
-    private void showLongClickOptions(final Point location) {
-        final DirectItemContextMenu menu = new DirectItemContextMenu(itemView.getContext(), allowReaction(), getLongClickOptions());
+    private void showLongClickOptions(final Point location, final MessageDirection messageDirection) {
+        final List<DirectItemContextMenu.MenuItem> longClickOptions = getLongClickOptions();
+        final ImmutableList.Builder<DirectItemContextMenu.MenuItem> builder = ImmutableList.builder();
+        if (longClickOptions != null) {
+            builder.addAll(longClickOptions);
+        }
+        if (messageDirection == MessageDirection.OUTGOING) {
+            builder.add(new DirectItemContextMenu.MenuItem(R.id.unsend, R.string.dms_inbox_unsend));
+        }
+        final DirectItemContextMenu menu = new DirectItemContextMenu(itemView.getContext(), allowReaction(), builder.build());
         menu.setOnDismissListener(() -> setSelected(false));
-        menu.setOnReactionClickListener(emoji -> {
-            callback.onReaction(item, emoji);
-        });
+        menu.setOnReactionClickListener(emoji -> callback.onReaction(item, emoji));
+        menu.setOnOptionSelectListener(itemId -> callback.onOptionSelect(item, itemId));
         menu.show(itemView, location);
     }
 
diff --git a/app/src/main/java/awais/instagrabber/fragments/directmessages/DirectMessageThreadFragment.java b/app/src/main/java/awais/instagrabber/fragments/directmessages/DirectMessageThreadFragment.java
index 3d64f18c..11708e0c 100644
--- a/app/src/main/java/awais/instagrabber/fragments/directmessages/DirectMessageThreadFragment.java
+++ b/app/src/main/java/awais/instagrabber/fragments/directmessages/DirectMessageThreadFragment.java
@@ -222,6 +222,14 @@ public class DirectMessageThreadFragment extends Fragment implements DirectReact
         public void onReactionClick(final DirectItem item, final int position) {
             showReactionsDialog(item);
         }
+
+        @Override
+        public void onOptionSelect(final DirectItem item, final int itemId) {
+            if (itemId == R.id.unsend) {
+                handleSentMessage(viewModel.unsend(item));
+                return;
+            }
+        }
     };
 
     private final DirectItemLongClickListener directItemLongClickListener = position -> {
diff --git a/app/src/main/java/awais/instagrabber/repositories/DirectMessagesRepository.java b/app/src/main/java/awais/instagrabber/repositories/DirectMessagesRepository.java
index 37b0df1e..ff52bf27 100644
--- a/app/src/main/java/awais/instagrabber/repositories/DirectMessagesRepository.java
+++ b/app/src/main/java/awais/instagrabber/repositories/DirectMessagesRepository.java
@@ -56,4 +56,10 @@ public interface DirectMessagesRepository {
     @POST("/api/v1/direct_v2/threads/{threadId}/remove_admins/")
     Call<String> removeAdmins(@Path("threadId") String threadId,
                               @FieldMap final Map<String, String> form);
+
+    @FormUrlEncoded
+    @POST("/api/v1/direct_v2/threads/{threadId}/items/{itemId}/delete/")
+    Call<String> deleteItem(@Path("threadId") String threadId,
+                            @Path("itemId") String itemId,
+                            @FieldMap final Map<String, String> form);
 }
diff --git a/app/src/main/java/awais/instagrabber/viewmodels/DirectThreadViewModel.java b/app/src/main/java/awais/instagrabber/viewmodels/DirectThreadViewModel.java
index 3e8ba883..5f0d93f0 100644
--- a/app/src/main/java/awais/instagrabber/viewmodels/DirectThreadViewModel.java
+++ b/app/src/main/java/awais/instagrabber/viewmodels/DirectThreadViewModel.java
@@ -186,14 +186,7 @@ public class DirectThreadViewModel extends AndroidViewModel {
         reactions.setEmojis(emojis);
         List<DirectItem> list = this.items.getValue();
         list = list == null ? new LinkedList<>() : new LinkedList<>(list);
-        int index = -1;
-        for (int i = 0; i < list.size(); i++) {
-            final DirectItem directItem = list.get(i);
-            if (directItem.getItemId().equals(item.getItemId())) {
-                index = i;
-                break;
-            }
-        }
+        int index = getItemIndex(item, list);
         if (index >= 0) {
             try {
                 final DirectItem clone = (DirectItem) list.get(index).clone();
@@ -255,14 +248,7 @@ public class DirectThreadViewModel extends AndroidViewModel {
             itemClone.setReactions(reactionsClone);
             List<DirectItem> list = this.items.getValue();
             list = list == null ? new LinkedList<>() : new LinkedList<>(list);
-            int index = -1;
-            for (int i = 0; i < list.size(); i++) {
-                final DirectItem directItem = list.get(i);
-                if (directItem.getItemId().equals(item.getItemId())) {
-                    index = i;
-                    break;
-                }
-            }
+            int index = getItemIndex(item, list);
             if (index >= 0) {
                 list.set(index, itemClone);
             }
@@ -272,6 +258,30 @@ public class DirectThreadViewModel extends AndroidViewModel {
         }
     }
 
+    private int removeItem(final DirectItem item) {
+        if (item == null) return 0;
+        List<DirectItem> list = this.items.getValue();
+        list = list == null ? new LinkedList<>() : new LinkedList<>(list);
+        int index = getItemIndex(item, list);
+        if (index >= 0) {
+            list.remove(index);
+            this.items.postValue(list);
+        }
+        return index;
+    }
+
+    private int getItemIndex(final DirectItem item, final List<DirectItem> list) {
+        int index = -1;
+        for (int i = 0; i < list.size(); i++) {
+            final DirectItem directItem = list.get(i);
+            if (directItem.getItemId().equals(item.getItemId())) {
+                index = i;
+                break;
+            }
+        }
+        return index;
+    }
+
     private void updateItemSent(final String clientContext, final long timestamp) {
         if (clientContext == null) return;
         List<DirectItem> list = this.items.getValue();
@@ -675,7 +685,10 @@ public class DirectThreadViewModel extends AndroidViewModel {
     public LiveData<Resource<DirectItem>> sendReaction(final DirectItem item, final Emoji emoji) {
         final MutableLiveData<Resource<DirectItem>> data = new MutableLiveData<>();
         final Long userId = handleCurrentUser(data);
-        if (userId == null) return data;
+        if (userId == null) {
+            data.postValue(Resource.error("userId is null", null));
+            return data;
+        }
         final String clientContext = UUID.randomUUID().toString();
         // Log.d(TAG, "sendText: sending: itemId: " + directItem.getItemId());
         data.postValue(Resource.loading(item));
@@ -710,6 +723,39 @@ public class DirectThreadViewModel extends AndroidViewModel {
         return data;
     }
 
+    public LiveData<Resource<DirectItem>> unsend(final DirectItem item) {
+        final MutableLiveData<Resource<DirectItem>> data = new MutableLiveData<>();
+        if (item == null) {
+            data.postValue(Resource.error("item is null", null));
+            return data;
+        }
+        final int index = removeItem(item);
+        final Call<String> request = service.deleteItem(threadId, item.getItemId());
+        request.enqueue(new Callback<String>() {
+            @Override
+            public void onResponse(@NonNull final Call<String> call, @NonNull final Response<String> response) {
+                if (response.isSuccessful()) {
+                    // Log.d(TAG, "onResponse: " + response.body());
+                    return;
+                }
+                // add the item back if unsuccessful
+                addItems(index, Collections.singletonList(item));
+                if (response.errorBody() != null) {
+                    handleErrorBody(call, response, data, item);
+                    return;
+                }
+                data.postValue(Resource.error("request was not successful and response error body was null", item));
+            }
+
+            @Override
+            public void onFailure(@NonNull final Call<String> call, @NonNull final Throwable t) {
+                data.postValue(Resource.error(t.getMessage(), item));
+                Log.e(TAG, "enqueueRequest: onFailure: ", t);
+            }
+        });
+        return data;
+    }
+
     private void handleBroadcastReactionRequest(final MutableLiveData<Resource<DirectItem>> data,
                                                 final DirectItem item,
                                                 @NonNull final Call<DirectThreadBroadcastResponse> request) {
diff --git a/app/src/main/java/awais/instagrabber/webservices/DirectMessagesService.java b/app/src/main/java/awais/instagrabber/webservices/DirectMessagesService.java
index 89f74aa3..48dd5863 100644
--- a/app/src/main/java/awais/instagrabber/webservices/DirectMessagesService.java
+++ b/app/src/main/java/awais/instagrabber/webservices/DirectMessagesService.java
@@ -238,4 +238,13 @@ public class DirectMessagesService extends BaseService {
         );
         return repository.removeAdmins(threadId, form);
     }
+
+    public Call<String> deleteItem(final String threadId,
+                                   final String itemId) {
+        final ImmutableMap<String, String> form = ImmutableMap.of(
+                "_csrftoken", csrfToken,
+                "_uuid", deviceUuid
+        );
+        return repository.deleteItem(threadId, itemId, form);
+    }
 }