diff --git a/CHANGELOG.md b/CHANGELOG.md
index 66c8989828f..70d21c25422 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -45,6 +45,7 @@ Note that this project **does not** adhere to [Semantic Versioning](http://semve
 - We fixed an issue where a message about changed metadata would occur on saving although nothing changed. [#9159](https://github.com/JabRef/jabref/issues/9159)
 - When adding or editing a subgroup it is placed w.r.t. to alphabetical ordering rather than at the end. [koppor#577](https://github.com/koppor/jabref/issues/577)
 - We modified the Directory of Open Access Books (DOAB) fetcher so that it will now also fetch the ISBN when possible. [#8708](https://github.com/JabRef/jabref/issues/8708)
+- Groups context menu now shows appropriate options depending on number of subgroups. [koppor#579](https://github.com/koppor/jabref/issues/579)
 - We changed the color of found text from red to high-contrast colors (background: yellow; font color: purple). [koppor#552](https://github.com/koppor/jabref/issues/552)
 - We modified the "Delete file" dialog and add the full file path to the dialog text. The file path in the title was changed to file name only. [koppor#534](https://github.com/koppor/jabref/issues/534)
 - Download from URL now automatically fills with URL from clipboard. [koppor#535](https://github.com/koppor/jabref/issues/535)
diff --git a/src/main/java/org/jabref/gui/groups/GroupTreeView.java b/src/main/java/org/jabref/gui/groups/GroupTreeView.java
index 81510b3199c..53495ff6bda 100644
--- a/src/main/java/org/jabref/gui/groups/GroupTreeView.java
+++ b/src/main/java/org/jabref/gui/groups/GroupTreeView.java
@@ -403,7 +403,11 @@ private Optional<TreeItem<GroupNodeViewModel>> getTreeItemByValue(TreeItem<Group
 
     private ContextMenu createContextMenuForGroup(GroupNodeViewModel group) {
         ContextMenu menu = new ContextMenu();
-        Menu removeGroup = new Menu(Localization.lang("Remove group"));
+
+        Menu removeGroupWithSubgroups = new Menu(Localization.lang("Remove group"));
+
+        MenuItem removeGroupNoSubgroups = new MenuItem(Localization.lang("Remove group"));
+        removeGroupNoSubgroups.setOnAction(event -> viewModel.removeGroupNoSubgroups(group));
 
         MenuItem editGroup = new MenuItem(Localization.lang("Edit group"));
         editGroup.setOnAction(event -> {
@@ -425,9 +429,7 @@ private ContextMenu createContextMenuForGroup(GroupNodeViewModel group) {
         });
 
         MenuItem removeSubgroups = new MenuItem(Localization.lang("Remove subgroups"));
-        removeSubgroups.setOnAction(event -> {
-            viewModel.removeSubgroups(group);
-        });
+        removeSubgroups.setOnAction(event -> viewModel.removeSubgroups(group));
 
         MenuItem sortSubgroups = new MenuItem(Localization.lang("Sort subgroups A-Z"));
         sortSubgroups.setOnAction(event -> viewModel.sortAlphabeticallyRecursive(group.getGroupNode()));
@@ -438,17 +440,28 @@ private ContextMenu createContextMenuForGroup(GroupNodeViewModel group) {
         MenuItem removeEntries = new MenuItem(Localization.lang("Remove selected entries from this group"));
         removeEntries.setOnAction(event -> viewModel.removeSelectedEntries(group));
 
-        menu.getItems().add(editGroup);
-        removeGroup.getItems().add(removeGroupKeepSubgroups);
-        removeGroup.getItems().add(removeGroupAndSubgroups);
-        menu.getItems().add(removeGroup);
-        menu.getItems().add(new SeparatorMenuItem());
-        menu.getItems().add(addSubgroup);
-        menu.getItems().add(removeSubgroups);
-        menu.getItems().add(sortSubgroups);
-        menu.getItems().add(new SeparatorMenuItem());
-        menu.getItems().add(addEntries);
-        menu.getItems().add(removeEntries);
+        menu.setOnShown(event -> {
+            menu.getItems().clear();
+            menu.getItems().add(editGroup);
+            if (group.getChildren().size() > 0) {
+                menu.getItems().add(removeGroupWithSubgroups);
+                menu.getItems().add(new SeparatorMenuItem());
+                menu.getItems().add(addSubgroup);
+                menu.getItems().add(removeSubgroups);
+                menu.getItems().add(sortSubgroups);
+            } else {
+                menu.getItems().add(removeGroupNoSubgroups);
+                menu.getItems().add(new SeparatorMenuItem());
+                menu.getItems().add(addSubgroup);
+            }
+            menu.getItems().add(new SeparatorMenuItem());
+            menu.getItems().add(addEntries);
+            menu.getItems().add(removeEntries);
+        });
+
+        menu.getItems().add(new Menu());
+        removeGroupWithSubgroups.getItems().add(removeGroupKeepSubgroups);
+        removeGroupWithSubgroups.getItems().add(removeGroupAndSubgroups);
 
         // TODO: Disable some actions under certain conditions
         // if (group.canBeEdited()) {
diff --git a/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java b/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
index 8cf74178629..08a9465b2cf 100644
--- a/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
+++ b/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
@@ -471,6 +471,43 @@ public void removeGroupAndSubgroups(GroupNodeViewModel group) {
         }
     }
 
+    /**
+     * Removes the specified group (after asking for confirmation).
+     */
+    public void removeGroupNoSubgroups(GroupNodeViewModel group) {
+        boolean confirmed;
+        if (selectedGroups.size() <= 1) {
+            confirmed = dialogService.showConfirmationDialogAndWait(
+                    Localization.lang("Remove group"),
+                    Localization.lang("Remove group \"%0\"?", group.getDisplayName()),
+                    Localization.lang("Remove"));
+        } else {
+            confirmed = dialogService.showConfirmationDialogAndWait(
+                    Localization.lang("Remove groups and subgroups"),
+                    Localization.lang("Remove all selected groups and their subgroups?"),
+                    Localization.lang("Remove all"));
+        }
+
+        if (confirmed) {
+            // TODO: Add undo
+            // final UndoableAddOrRemoveGroup undo = new UndoableAddOrRemoveGroup(groupsRoot, node, UndoableAddOrRemoveGroup.REMOVE_NODE_WITHOUT_CHILDREN);
+            // panel.getUndoManager().addEdit(undo);
+
+            ArrayList<GroupNodeViewModel> selectedGroupNodes = new ArrayList<>(selectedGroups);
+            selectedGroupNodes.forEach(eachNode -> {
+                removeGroupsAndSubGroupsFromEntries(eachNode);
+                eachNode.getGroupNode().removeFromParent();
+            });
+
+            if (selectedGroupNodes.size() > 1) {
+                dialogService.notify(Localization.lang("Removed all selected groups."));
+            } else {
+                dialogService.notify(Localization.lang("Removed group \"%0\".", group.getDisplayName()));
+            }
+            writeGroupChangesToMetaData();
+        }
+    }
+
     void removeGroupsAndSubGroupsFromEntries(GroupNodeViewModel group) {
         for (GroupNodeViewModel child : group.getChildren()) {
             removeGroupsAndSubGroupsFromEntries(child);
diff --git a/src/main/resources/l10n/JabRef_en.properties b/src/main/resources/l10n/JabRef_en.properties
index bd40ee3d0f1..c355aecce47 100644
--- a/src/main/resources/l10n/JabRef_en.properties
+++ b/src/main/resources/l10n/JabRef_en.properties
@@ -707,6 +707,8 @@ Remove\ all\ selected\ groups\ and\ their\ subgroups?=Remove all selected groups
 
 Removed\ all\ selected\ groups\ and\ their\ subgroups.=Removed all selected groups and their subgroups.
 
+Remove\ group\ "%0"?=Remove group "%0"?
+
 Remove\ link=Remove link
 
 Remove\ string\ %0=Remove string %0