diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4f9cbdc129c..36ef36dedad 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -34,6 +34,7 @@ Note that this project **does not** adhere to [Semantic Versioning](http://semve
 - We improved group expansion arrow that prevent it from activating group when expanding or collapsing. [#7982](https://github.com/JabRef/jabref/issues/7982), [#3176](https://github.com/JabRef/jabref/issues/3176)
 - When configured SSL certificates changed, JabRef warns the user to restart to apply the configuration.
 - We improved the appearances and logic of the "Manage field names & content" dialog, and renamed it to "Automatic field editor". [#6536](https://github.com/JabRef/jabref/issues/6536)
+- We improved the message explaining the options when modifying an automatic keyword group [#8911](https://github.com/JabRef/jabref/issues/8911)
 - We moved the preferences option "Warn about duplicates on import" option from the tab "File" to the tab "Import and Export". [kopper#570](https://github.com/koppor/jabref/issues/570)
 
 ### Fixed
@@ -51,7 +52,7 @@ Note that this project **does not** adhere to [Semantic Versioning](http://semve
 - We fixed an issue where the exception that there are invalid characters in filename. [#8786](https://github.com/JabRef/jabref/issues/8786)
 - When the proxy configuration removed the proxy user/password, this change is applied immediately.
 - We fixed an issue where removing several groups deletes only one of them. [#8390](https://github.com/JabRef/jabref/issues/8390)
-- We fixed an issue where the Sidepane(groups, web search and open office) width is not remembered after restarting JabRef. [#8907](https://github.com/JabRef/jabref/issues/8907)
+- We fixed an issue where the Sidepane (groups, web search and open office) width is not remembered after restarting JabRef. [#8907](https://github.com/JabRef/jabref/issues/8907)
 - We fixed a bug where switching between themes will cause an error/exception. [#8939](https://github.com/JabRef/jabref/pull/8939)
 
 ### Removed
diff --git a/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java b/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
index 6ac27b40419..670130757ad 100644
--- a/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
+++ b/src/main/java/org/jabref/gui/groups/GroupTreeViewModel.java
@@ -17,6 +17,9 @@
 import javafx.beans.property.StringProperty;
 import javafx.collections.FXCollections;
 import javafx.collections.ObservableList;
+import javafx.scene.control.Alert;
+import javafx.scene.control.ButtonBar;
+import javafx.scene.control.ButtonType;
 
 import org.jabref.gui.AbstractViewModel;
 import org.jabref.gui.DialogService;
@@ -29,6 +32,7 @@
 import org.jabref.model.groups.AbstractGroup;
 import org.jabref.model.groups.ExplicitGroup;
 import org.jabref.model.groups.GroupTreeNode;
+import org.jabref.model.groups.WordKeywordGroup;
 import org.jabref.model.metadata.MetaData;
 import org.jabref.preferences.PreferencesService;
 
@@ -192,9 +196,21 @@ public void editGroup(GroupNodeViewModel oldGroup) {
 
             newGroup.ifPresent(group -> {
                 // TODO: Keep assignments
-                boolean keepPreviousAssignments = dialogService.showConfirmationDialogAndWait(
+                String content = Localization.lang("Assign the original group's entries to this group?");
+                ButtonType keepAssignments = new ButtonType(Localization.lang("Assign"), ButtonBar.ButtonData.YES);
+                ButtonType removeAssignments = new ButtonType(Localization.lang("Do not assign"), ButtonBar.ButtonData.NO);
+                ButtonType cancel = new ButtonType(Localization.lang("Cancel"), ButtonBar.ButtonData.CANCEL_CLOSE);
+
+                if (newGroup.get().getClass() == WordKeywordGroup.class) {
+                    content = content + "\n\n" +
+                            Localization.lang("(Note: If original entries lack keywords to qualify for the new group configuration, confirming here will add them)");
+                }
+                Optional<ButtonType> previousAssignments = dialogService.showCustomButtonDialogAndWait(Alert.AlertType.WARNING,
                         Localization.lang("Change of Grouping Method"),
-                        Localization.lang("Assign the original group's entries to this group?"));
+                        content,
+                        keepAssignments,
+                        removeAssignments,
+                        cancel);
                 //        WarnAssignmentSideEffects.warnAssignmentSideEffects(newGroup, panel.frame());
                 boolean removePreviousAssignments = (oldGroup.getGroupNode().getGroup() instanceof ExplicitGroup)
                         && (group instanceof ExplicitGroup);
@@ -209,11 +225,22 @@ public void editGroup(GroupNodeViewModel oldGroup) {
                     removePreviousAssignments = false;
                 }
 
-                oldGroup.getGroupNode().setGroup(
-                        group,
-                        keepPreviousAssignments,
-                        removePreviousAssignments,
-                        database.getEntries());
+                if (previousAssignments.isPresent() && (previousAssignments.get().getButtonData() == ButtonBar.ButtonData.YES)) {
+                    oldGroup.getGroupNode().setGroup(
+                            group,
+                            true,
+                            removePreviousAssignments,
+                            database.getEntries());
+                } else if (previousAssignments.isPresent() && (previousAssignments.get().getButtonData() == ButtonBar.ButtonData.NO)) {
+                    oldGroup.getGroupNode().setGroup(
+                            group,
+                            false,
+                            removePreviousAssignments,
+                            database.getEntries());
+                } else if (previousAssignments.isPresent() && (previousAssignments.get().getButtonData() == ButtonBar.ButtonData.CANCEL_CLOSE)) {
+                    return;
+                }
+
                 // stateManager.getEntriesInCurrentDatabase());
 
                 // TODO: Add undo
diff --git a/src/main/resources/l10n/JabRef_en.properties b/src/main/resources/l10n/JabRef_en.properties
index e66b587e6a1..32c2d62ae61 100644
--- a/src/main/resources/l10n/JabRef_en.properties
+++ b/src/main/resources/l10n/JabRef_en.properties
@@ -2506,3 +2506,7 @@ Move\ value=Move value
 Swap\ values=Swap values
 Copy\ or\ move\ the\ value\ of\ one\ field\ to\ another=Copy or move the value of one field to another
 Automatic\ field\ editor=Automatic field editor
+
+(Note\:\ If\ original\ entries\ lack\ keywords\ to\ qualify\ for\ the\ new\ group\ configuration,\ confirming\ here\ will\ add\ them)=(Note: If original entries lack keywords to qualify for the new group configuration, confirming here will add them)
+Assign=Assign
+Do\ not\ assign=Do not assign