diff --git a/app/src/main/java/eu/faircode/email/AdapterKeyword.java b/app/src/main/java/eu/faircode/email/AdapterKeyword.java
index 31a3e44f9f..9cc45ee9de 100644
--- a/app/src/main/java/eu/faircode/email/AdapterKeyword.java
+++ b/app/src/main/java/eu/faircode/email/AdapterKeyword.java
@@ -23,7 +23,6 @@ import android.content.Context;
 import android.content.DialogInterface;
 import android.content.SharedPreferences;
 import android.os.Bundle;
-import android.text.TextUtils;
 import android.view.LayoutInflater;
 import android.view.View;
 import android.view.ViewGroup;
@@ -42,7 +41,6 @@ import com.flask.colorpicker.builder.ColorPickerClickListener;
 import com.flask.colorpicker.builder.ColorPickerDialogBuilder;
 
 import java.util.ArrayList;
-import java.util.Arrays;
 import java.util.List;
 
 public class AdapterKeyword extends RecyclerView.Adapter<AdapterKeyword.ViewHolder> {
@@ -96,14 +94,14 @@ public class AdapterKeyword extends RecyclerView.Adapter<AdapterKeyword.ViewHold
 
             Bundle args = new Bundle();
             args.putLong("id", id);
-            args.putString("keyword", keyword.name);
+            args.putString("name", keyword.name);
             args.putBoolean("selected", keyword.selected);
 
             new SimpleTask<Void>() {
                 @Override
                 protected Void onExecute(Context context, Bundle args) {
                     long id = args.getLong("id");
-                    String keyword = args.getString("keyword");
+                    String name = args.getString("name");
                     boolean selected = args.getBoolean("selected");
 
                     DB db = DB.getInstance(context);
@@ -112,13 +110,7 @@ public class AdapterKeyword extends RecyclerView.Adapter<AdapterKeyword.ViewHold
                     if (message == null)
                         return null;
 
-                    List<String> keywords = new ArrayList<>(Arrays.asList(message.keywords));
-                    if (selected)
-                        keywords.add(keyword);
-                    else
-                        keywords.remove(keyword);
-
-                    db.message().setMessageKeywords(message.id, TextUtils.join(" ", keywords));
+                    EntityOperation.queue(context, message, EntityOperation.KEYWORD, name, selected);
 
                     return null;
                 }
@@ -192,8 +184,8 @@ public class AdapterKeyword extends RecyclerView.Adapter<AdapterKeyword.ViewHold
                     try {
                         db.beginTransaction();
 
-                        db.message().setMessageKeywords(message.id, "");
-                        db.message().setMessageKeywords(message.id, TextUtils.join(" ", message.keywords));
+                        db.message().setMessageKeywords(message.id, DB.Converters.fromStringArray(null));
+                        db.message().setMessageKeywords(message.id, DB.Converters.fromStringArray(message.keywords));
 
                         db.setTransactionSuccessful();
                     } finally {
diff --git a/app/src/main/java/eu/faircode/email/AdapterMessage.java b/app/src/main/java/eu/faircode/email/AdapterMessage.java
index 0477073bb2..274cc07a93 100644
--- a/app/src/main/java/eu/faircode/email/AdapterMessage.java
+++ b/app/src/main/java/eu/faircode/email/AdapterMessage.java
@@ -886,7 +886,7 @@ public class AdapterMessage extends RecyclerView.Adapter<AdapterMessage.ViewHold
                     String k = message.keywords[i].toLowerCase();
                     if (!IMAP_KEYWORDS_BLACKLIST.contains(k)) {
                         if (keywords.length() > 0)
-                            keywords.append(", ");
+                            keywords.append(" ");
 
                         keywords.append(message.keywords[i]);
 
@@ -4970,7 +4970,7 @@ public class AdapterMessage extends RecyclerView.Adapter<AdapterMessage.ViewHold
             return new AlertDialog.Builder(getContext())
                     .setTitle(R.string.title_manage_keywords)
                     .setView(dview)
-                    .setNegativeButton(android.R.string.cancel, null)
+                    .setPositiveButton(android.R.string.ok, null)
                     .create();
         }
     }
diff --git a/app/src/main/java/eu/faircode/email/Core.java b/app/src/main/java/eu/faircode/email/Core.java
index a6ba54d613..7d5c244c91 100644
--- a/app/src/main/java/eu/faircode/email/Core.java
+++ b/app/src/main/java/eu/faircode/email/Core.java
@@ -665,8 +665,11 @@ class Core {
             if (set) {
                 if (!keywords.contains(keyword))
                     keywords.add(keyword);
-            } else
-                keywords.remove(keyword);
+            } else {
+                while (keywords.remove(keyword))
+                    ;
+            }
+
             db.message().setMessageKeywords(message.id, DB.Converters.fromStringArray(keywords.toArray(new String[0])));
 
             db.setTransactionSuccessful();
diff --git a/app/src/main/java/eu/faircode/email/MessageHelper.java b/app/src/main/java/eu/faircode/email/MessageHelper.java
index db1e0ba8dd..aebc057566 100644
--- a/app/src/main/java/eu/faircode/email/MessageHelper.java
+++ b/app/src/main/java/eu/faircode/email/MessageHelper.java
@@ -48,6 +48,7 @@ import java.nio.charset.Charset;
 import java.nio.charset.StandardCharsets;
 import java.util.ArrayList;
 import java.util.Arrays;
+import java.util.Collections;
 import java.util.Date;
 import java.util.Enumeration;
 import java.util.HashMap;
@@ -629,7 +630,9 @@ public class MessageHelper {
     }
 
     String[] getKeywords() throws MessagingException {
-        return imessage.getFlags().getUserFlags();
+        List<String> keywords = Arrays.asList(imessage.getFlags().getUserFlags());
+        Collections.sort(keywords);
+        return keywords.toArray(new String[0]);
     }
 
     String getMessageID() throws MessagingException {