diff --git a/MacPass/MPAppDelegate.h b/MacPass/MPAppDelegate.h
index 6c159652..caf9f770 100644
--- a/MacPass/MPAppDelegate.h
+++ b/MacPass/MPAppDelegate.h
@@ -36,8 +36,9 @@ APPKIT_EXTERN NSString *const MPDidChangeStoredKeyFilesSettings;
 @property (strong) IBOutlet NSMenu *exportMenu;
 
 @property (strong, readonly) MPEntryContextMenuDelegate *itemActionMenuDelegate;
+@property (readonly) BOOL isTerminating;
 
-@property (nonatomic, assign) BOOL isAllowedToStoreKeyFile;
+@property (nonatomic) BOOL isAllowedToStoreKeyFile;
 
 - (IBAction)checkForUpdates:(id)sender;
 - (IBAction)showPreferences:(id)sender;
diff --git a/MacPass/MPAppDelegate.m b/MacPass/MPAppDelegate.m
index cfb655e0..84d1e5a4 100644
--- a/MacPass/MPAppDelegate.m
+++ b/MacPass/MPAppDelegate.m
@@ -92,6 +92,7 @@ typedef NS_OPTIONS(NSInteger, MPAppStartupState) {
     _userNotificationCenterDelegate = [[MPUserNotificationCenterDelegate alloc] init];
     self.itemActionMenuDelegate = [[MPEntryContextMenuDelegate alloc] init];
     _shouldOpenFile = NO;
+    _isTerminating = NO;
     self.startupState = MPAppStartupStateNone;
     
     [NSNotificationCenter.defaultCenter addObserver:self
@@ -185,6 +186,7 @@ typedef NS_OPTIONS(NSInteger, MPAppStartupState) {
 }
 
 - (NSApplicationTerminateReply)applicationShouldTerminate:(NSApplication *)sender {
+  _isTerminating = YES;
   [self hideWelcomeWindow];
   if(MPTemporaryFileStorageCenter.defaultCenter.hasPendingStorages) {
     dispatch_async(dispatch_get_main_queue(), ^{
diff --git a/MacPass/MPDocument.m b/MacPass/MPDocument.m
index f6d4b08b..68cb8060 100644
--- a/MacPass/MPDocument.m
+++ b/MacPass/MPDocument.m
@@ -240,13 +240,6 @@ NSString *const MPDocumentGroupKey                            = @"MPDocumentGrou
 
 - (void)close {
   [self _cleanupLock];
-  /*
-   We store the last url. Restored windows are automatically handled.
-   If closeAllDocuments is set, all docs get this message
-   */
-  if(self.fileURL.isFileURL) {
-    [[NSUserDefaults standardUserDefaults] setObject:self.fileURL.absoluteString forKey:kMPSettingsKeyLastDatabasePath];
-  }
   self.tree = nil;
   [super close];
 }
diff --git a/MacPass/MPDocumentController.m b/MacPass/MPDocumentController.m
index bccf5692..77754dd2 100644
--- a/MacPass/MPDocumentController.m
+++ b/MacPass/MPDocumentController.m
@@ -83,6 +83,16 @@
   [super addDocument:document];
 }
 
+- (void)removeDocument:(NSDocument *)document {
+  MPAppDelegate *appDelegate = (MPAppDelegate *)NSApp.delegate;
+  if(appDelegate.isTerminating) {
+    if(document.fileURL.isFileURL) {
+      [[NSUserDefaults standardUserDefaults] setObject:document.fileURL.absoluteString forKey:kMPSettingsKeyLastDatabasePath];
+    }
+  }
+  [super removeDocument:document];
+}
+
 - (BOOL)reopenLastDocument {
   if(self.documents.count > 0) {
     return YES; // The document is already open
@@ -93,7 +103,12 @@
   }
   else {
     NSString *lastPath = [NSUserDefaults.standardUserDefaults stringForKey:kMPSettingsKeyLastDatabasePath];
-    documentUrl =[NSURL URLWithString:lastPath];
+    documentUrl = [NSURL URLWithString:lastPath];
+    NSError *error;
+    if(![documentUrl checkResourceIsReachableAndReturnError:&error]) {
+      [NSUserDefaults.standardUserDefaults removeObjectForKey:kMPSettingsKeyLastDatabasePath];
+      documentUrl = nil;
+    }
   }
   BOOL isFileURL = documentUrl.fileURL;
   if(isFileURL) {