diff --git a/src/main/java/net/rptools/maptool/client/ui/players/PlayerDatabaseDialogController.java b/src/main/java/net/rptools/maptool/client/ui/players/PlayerDatabaseDialogController.java
index a43d99b7eb..7c53942358 100644
--- a/src/main/java/net/rptools/maptool/client/ui/players/PlayerDatabaseDialogController.java
+++ b/src/main/java/net/rptools/maptool/client/ui/players/PlayerDatabaseDialogController.java
@@ -212,7 +212,7 @@ public void close() {
         | InvalidKeySpecException
         | PasswordDatabaseException
         | InvalidKeyException e) {
-      MapTool.showError("playerDB.dialog.error.undoingChanges", e);
+      MapTool.showError("playerDB.dialog.error.savingChanges", e);
     }
     ;
     Players.removePropertyChangeListener(changeListener);
diff --git a/src/main/java/net/rptools/maptool/model/player/PasswordFilePlayerDatabase.java b/src/main/java/net/rptools/maptool/model/player/PasswordFilePlayerDatabase.java
index fe781ba15e..db50a23f3e 100644
--- a/src/main/java/net/rptools/maptool/model/player/PasswordFilePlayerDatabase.java
+++ b/src/main/java/net/rptools/maptool/model/player/PasswordFilePlayerDatabase.java
@@ -218,7 +218,7 @@ private Map<String, PlayerDetails> readPasswordFile(File file)
         }
         return players;
       } catch (IOException ioe) {
-        throw new PasswordDatabaseException("msg.err.passFile.errorReadingFile", ioe);
+        throw new PasswordDatabaseException("msg.error.passFile.errorReadingFile", ioe);
       }
     } finally {
       passwordFileLock.unlock();
@@ -233,7 +233,9 @@ private void writePasswordFile() throws PasswordDatabaseException {
       if (dirty.compareAndSet(true, false)) {
 
         try {
-          Files.copy(passwordFile.toPath(), backupPasswordFile.toPath(), REPLACE_EXISTING);
+          if (passwordFile.exists()) {
+            Files.copy(passwordFile.toPath(), backupPasswordFile.toPath(), REPLACE_EXISTING);
+          }
         } catch (IOException ioe) {
           String msg = I18N.getText("msg.err.passFile.errorCopyingBackup");
           log.error(msg, ioe);
@@ -293,6 +295,16 @@ private void writePasswordFile() throws PasswordDatabaseException {
   private void writePublicKeys(PlayerDetails playerDetails) throws IOException {
     try {
       passwordFileLock.lock();
+      File keyDir = passwordFile.getParentFile().toPath().resolve(PUBLIC_KEY_DIR).toFile();
+      if (!keyDir.exists()) {
+        keyDir.mkdirs();
+      }
+      File keyBackupDir =
+          passwordFile.getParentFile().toPath().resolve(PUBLIC_KEY_DIR).resolve("backup").toFile();
+      if (!keyBackupDir.exists()) {
+        keyBackupDir.mkdirs();
+      }
+
       Set<PublicKeyDetails> publicKeyDetails = playerDetails.publicKeyDetails();
 
       // First get all the public keys files with a public key marked dirty
@@ -550,8 +562,8 @@ public void commitChanges()
       removeOldPublicKeys();
       savedDetails.clear();
       savedDetails.putAll(playerDetails);
-      dirty.set(true);
     }
+    dirty.set(true);
     writePasswordFile();
   }
 
diff --git a/src/main/resources/net/rptools/maptool/language/i18n.properties b/src/main/resources/net/rptools/maptool/language/i18n.properties
index 4898580741..f9d206644f 100644
--- a/src/main/resources/net/rptools/maptool/language/i18n.properties
+++ b/src/main/resources/net/rptools/maptool/language/i18n.properties
@@ -2546,8 +2546,7 @@ playerDB.dialog.error.passwordTooShort = Password is too short
 playerDB.dialog.error.invalidPublicKey = Invalid Public Key
 playerDB.dialog.error.emptyBlockReason = Blocked reason can not be empty
 playerDB.dialog.error.playerExists = Player already exists
-playerDB.dialog.error.undoingChanges = Error Unding database changes
-
+playerDB.dialog.error.savingChanges = Error saving database changes
 # Text to display instead of the password
 playerDB.dialog.encodedPassword = -- Encoded Password --