diff --git a/src/main/java/org/jabref/gui/StateManager.java b/src/main/java/org/jabref/gui/StateManager.java
index 7b2d27d1292..017c5d8b320 100644
--- a/src/main/java/org/jabref/gui/StateManager.java
+++ b/src/main/java/org/jabref/gui/StateManager.java
@@ -71,7 +71,7 @@ public class StateManager {
     private final ObservableList<SidePaneType> visibleSidePanes = FXCollections.observableArrayList();
     private final ObjectProperty<LastAutomaticFieldEditorEdit> lastAutomaticFieldEditorEdit = new SimpleObjectProperty<>();
     private final ObservableList<String> searchHistory = FXCollections.observableArrayList();
-    private final OptionalObjectProperty<AiChatWindow> aiChatWindow = OptionalObjectProperty.empty();
+    private final List<AiChatWindow> aiChatWindows = new ArrayList<>();
 
     public ObservableList<SidePaneType> getVisibleSidePaneComponents() {
         return visibleSidePanes;
@@ -211,7 +211,7 @@ public void clearSearchHistory() {
         searchHistory.clear();
     }
 
-    public OptionalObjectProperty<AiChatWindow> getAiChatWindow() {
-        return aiChatWindow;
+    public List<AiChatWindow> getAiChatWindows() {
+        return aiChatWindows;
     }
 }
diff --git a/src/main/java/org/jabref/gui/ai/components/aichat/AiChatWindow.java b/src/main/java/org/jabref/gui/ai/components/aichat/AiChatWindow.java
index 2ae892021ea..8359eec5f05 100644
--- a/src/main/java/org/jabref/gui/ai/components/aichat/AiChatWindow.java
+++ b/src/main/java/org/jabref/gui/ai/components/aichat/AiChatWindow.java
@@ -23,6 +23,9 @@ public class AiChatWindow extends BaseWindow {
     private final FilePreferences filePreferences;
     private final TaskExecutor taskExecutor;
 
+    // This field is used for finding an existing AI chat window when user wants to chat with the same group again.
+    private String chatName;
+
     public AiChatWindow(AiService aiService,
                         DialogService dialogService,
                         AiPreferences aiPreferences,
@@ -38,6 +41,7 @@ public AiChatWindow(AiService aiService,
 
     public void setChat(StringProperty name, ObservableList<ChatMessage> chatHistory, BibDatabaseContext bibDatabaseContext, ObservableList<BibEntry> entries) {
         setTitle(Localization.lang("AI chat with %0", name.getValue()));
+        chatName = name.getValue();
         setScene(
                 new Scene(
                         new AiChatGuardedComponent(
@@ -56,4 +60,8 @@ public void setChat(StringProperty name, ObservableList<ChatMessage> chatHistory
                 )
         );
     }
+
+    public String getChatName() {
+        return chatName;
+    }
 }
diff --git a/src/main/java/org/jabref/logic/ai/AiService.java b/src/main/java/org/jabref/logic/ai/AiService.java
index 1d10663389c..0503307df27 100644
--- a/src/main/java/org/jabref/logic/ai/AiService.java
+++ b/src/main/java/org/jabref/logic/ai/AiService.java
@@ -135,7 +135,11 @@ public SummariesService getSummariesService() {
     }
 
     public void openAiChat(StringProperty name, ObservableList<ChatMessage> chatHistory, BibDatabaseContext bibDatabaseContext, ObservableList<BibEntry> entries) {
-        if (stateManager.getAiChatWindow().get().isEmpty()) {
+        Optional<AiChatWindow> existingWindow = stateManager.getAiChatWindows().stream().filter(window -> window.getChatName().equals(name.get())).findFirst();
+
+        if (existingWindow.isPresent()) {
+            existingWindow.get().requestFocus();
+        } else {
             AiChatWindow aiChatWindow = new AiChatWindow(
                     this,
                     dialogService,
@@ -144,16 +148,15 @@ public void openAiChat(StringProperty name, ObservableList<ChatMessage> chatHist
                     taskExecutor
             );
 
-            aiChatWindow.setOnCloseRequest(event -> {
-                stateManager.getAiChatWindow().set(Optional.empty());
-            });
+            aiChatWindow.setOnCloseRequest(event ->
+                stateManager.getAiChatWindows().remove(aiChatWindow)
+            );
 
-            stateManager.getAiChatWindow().set(Optional.of(aiChatWindow));
+            stateManager.getAiChatWindows().add(aiChatWindow);
             dialogService.showCustomWindow(aiChatWindow);
+            aiChatWindow.setChat(name, chatHistory, bibDatabaseContext, entries);
+            aiChatWindow.requestFocus();
         }
-
-        stateManager.getAiChatWindow().get().get().setChat(name, chatHistory, bibDatabaseContext, entries);
-        stateManager.getAiChatWindow().get().get().requestFocus();
     }
 
     @Override
diff --git a/src/main/resources/l10n/JabRef_en.properties b/src/main/resources/l10n/JabRef_en.properties
index 2b066a08184..42b3d3999df 100644
--- a/src/main/resources/l10n/JabRef_en.properties
+++ b/src/main/resources/l10n/JabRef_en.properties
@@ -2646,9 +2646,7 @@ An\ error\ occurred\ while\ opening\ the\ embeddings\ cache\ file.\ Embeddings\
 An\ error\ occurred\ while\ opening\ the\ fully\ ingested\ documents\ cache\ file.\ Fully\ ingested\ documents\ will\ not\ be\ stored\ in\ the\ next\ session.=An error occurred while opening the fully ingested documents cache file. Fully ingested documents will not be stored in the next session.
 Invalid\ citation\ key\ for\ %0\ (%1)=Invalid citation key for %0 (%1)
 No\ citation\ key\ for\ %0=No citation key for %0
-No\ files\ attached\ to\ %0=No files attached to %0
 Please\ attach\ at\ least\ one\ PDF\ file\ to\ enable\ summarization\ of\ PDF\ file(s).=Please attach at least one PDF file to enable summarization of PDF file(s).
-The\ AI\ will\ not\ be\ able\ to\ find\ information\ in\ this\ entry=The AI will not be able to find information in this entry
 Unable\ to\ generate\ summary=Unable to generate summary
 Group\ %0=Group %0
 AI\ chat\ with\ %0=AI chat with %0