diff --git a/CHANGELOG.md b/CHANGELOG.md
index b97d56b6608..0d068702b0e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,7 +24,8 @@ We refer to [GitHub issues](https://github.com/JabRef/jabref/issues) by using `#
 - The [ACM fetcher](https://help.jabref.org/en/ACMPortal) does no longer add HTML code to the bib-file. Fixes [#2472](https://github.com/JabRef/jabref/issues/2472).
 - When [finding unlinked files](https://help.jabref.org/en/FindUnlinkedFiles), JabRef does not freeze any more. Fixes [#2309]()https://github.com/JabRef/jabref/issues/2309).
 - Collapse and expand all buttons in the group assignment dialog no longer lead to a crash of JabRef.
-- The aux export command line function does no longer add duplicates of references that were resolved via `crossref`. Fixes [#2475](https://github.com/JabRef/jabref/issues/2475). 
+- The aux export command line function does no longer add duplicates of references that were resolved via `crossref`. Fixes [#2475](https://github.com/JabRef/jabref/issues/2475).
+- When the database is changed external, JabRef is no longer prevented from an orderly shutdown. Fixes [#2486](https://github.com/JabRef/jabref/issues/2486).
 - Parsing of damaged metadata is now more robust and reports a more detailed error message. Fixes [#2477](https://github.com/JabRef/jabref/issues/2477).
 - Dynamic groups with regular expression can be edited again. Fixes [#2481](https://github.com/JabRef/jabref/issues/2481).
 
diff --git a/src/main/java/net/sf/jabref/logic/autosaveandbackup/AutosaveManager.java b/src/main/java/net/sf/jabref/logic/autosaveandbackup/AutosaveManager.java
index 65908e2c971..323358afa9b 100644
--- a/src/main/java/net/sf/jabref/logic/autosaveandbackup/AutosaveManager.java
+++ b/src/main/java/net/sf/jabref/logic/autosaveandbackup/AutosaveManager.java
@@ -89,6 +89,11 @@ public void registerListener(Object listener) {
     }
 
     public void unregisterListener(Object listener) {
-        eventBus.unregister(listener);
+        try {
+            eventBus.unregister(listener);
+        } catch (IllegalArgumentException e) {
+            // occurs if the event source has not been registered, should not prevent shutdown
+            LOGGER.debug(e);
+        }
     }
 }
diff --git a/src/main/java/net/sf/jabref/logic/search/SearchQueryHighlightObservable.java b/src/main/java/net/sf/jabref/logic/search/SearchQueryHighlightObservable.java
index d7e4144e84a..2902fa749d5 100644
--- a/src/main/java/net/sf/jabref/logic/search/SearchQueryHighlightObservable.java
+++ b/src/main/java/net/sf/jabref/logic/search/SearchQueryHighlightObservable.java
@@ -31,7 +31,11 @@ public void addSearchListener(SearchQueryHighlightListener newListener) {
     public void removeSearchListener(SearchQueryHighlightListener listener) {
         Objects.requireNonNull(listener);
 
-        eventBus.unregister(listener);
+        try {
+            eventBus.unregister(listener);
+        } catch (IllegalArgumentException e) {
+            // occurs if the event source has not been registered, should not prevent shutdown
+        }
     }
     /**
      * Fires an event if a search was started (or cleared)
diff --git a/src/main/java/net/sf/jabref/model/database/BibDatabase.java b/src/main/java/net/sf/jabref/model/database/BibDatabase.java
index b19e3a66523..fdd4e1e3cda 100644
--- a/src/main/java/net/sf/jabref/model/database/BibDatabase.java
+++ b/src/main/java/net/sf/jabref/model/database/BibDatabase.java
@@ -530,7 +530,12 @@ public void registerListener(Object listener) {
      * @param listener listener (subscriber) to remove
      */
     public void unregisterListener(Object listener) {
-        this.eventBus.unregister(listener);
+        try {
+            this.eventBus.unregister(listener);
+        } catch (IllegalArgumentException e) {
+            // occurs if the event source has not been registered, should not prevent shutdown
+            LOGGER.debug(e);
+        }
     }
 
     @Subscribe
diff --git a/src/main/java/net/sf/jabref/model/entry/BibEntry.java b/src/main/java/net/sf/jabref/model/entry/BibEntry.java
index f1e55b73751..7656456ff28 100644
--- a/src/main/java/net/sf/jabref/model/entry/BibEntry.java
+++ b/src/main/java/net/sf/jabref/model/entry/BibEntry.java
@@ -764,7 +764,12 @@ public void registerListener(Object object) {
     }
 
     public void unregisterListener(Object object) {
-        this.eventBus.unregister(object);
+        try {
+            this.eventBus.unregister(object);
+        } catch (IllegalArgumentException e) {
+            // occurs if the event source has not been registered, should not prevent shutdown
+            LOGGER.debug(e);
+        }
     }
 
     public BibEntry withField(String field, String value) {
diff --git a/src/main/java/net/sf/jabref/model/metadata/MetaData.java b/src/main/java/net/sf/jabref/model/metadata/MetaData.java
index c55e3d52718..c9be65a839f 100644
--- a/src/main/java/net/sf/jabref/model/metadata/MetaData.java
+++ b/src/main/java/net/sf/jabref/model/metadata/MetaData.java
@@ -254,7 +254,11 @@ public void registerListener(Object listener) {
     }
 
     public void unregisterListener(Object listener) {
-        this.eventBus.unregister(listener);
+        try {
+            this.eventBus.unregister(listener);
+        } catch (IllegalArgumentException e) {
+            // occurs if the event source has not been registered, should not prevent shutdown
+        }
     }
 
     private Optional<String> getDefaultCiteKeyPattern() {