diff --git a/src/main/java/eu/siacs/conversations/entities/Conversation.java b/src/main/java/eu/siacs/conversations/entities/Conversation.java
index da60498d3..29f9109b4 100644
--- a/src/main/java/eu/siacs/conversations/entities/Conversation.java
+++ b/src/main/java/eu/siacs/conversations/entities/Conversation.java
@@ -188,6 +188,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
     private int mode;
     private JSONObject attributes;
     private Jid nextCounterpart;
+    private boolean hasPermanentCounterpart;
     private transient SessionImpl otrSession;
     private transient String otrFingerprint = null;
     private Smp mSmp = new Smp();
@@ -229,6 +230,9 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
             this.attributes = new JSONObject();
         }
         this.nextCounterpart = nextCounterpart;
+        if (nextCounterpart != null) {
+            hasPermanentCounterpart = true;
+        }
     }
 
     public String getContactUuid() {
@@ -937,7 +941,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
         values.put(STATUS, status);
         values.put(MODE, mode);
 
-        if (nextCounterpart != null) {
+        if (nextCounterpart != null && hasPermanentCounterpart) {
             values.put(NEXT_COUNTERPART, nextCounterpart.toString());
         }
 
@@ -963,6 +967,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
                     presence,
                     "xmpp");
             this.otrSession = new SessionImpl(sessionId, getAccount().getOtrService());
+            android.util.Log.e("41fd", "new session " + System.identityHashCode(this), new RuntimeException());
             try {
                 if (sendStart) {
                     this.otrSession.startSession();
@@ -981,6 +986,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
     }
 
     public void resetOtrSession() {
+        android.util.Log.e("41fd", "reset " + System.identityHashCode(this), new RuntimeException());
         this.otrFingerprint = null;
         this.otrSession = null;
         this.mSmp.hint = null;
@@ -1109,6 +1115,10 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
         return this.nextCounterpart;
     }
 
+    public boolean hasPermanentCounterpart() {
+        return hasPermanentCounterpart;
+    }
+
     public void setNextCounterpart(Jid jid) {
         this.nextCounterpart = jid;
     }
@@ -1117,6 +1127,11 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
         if (!Config.supportOmemo() && !Config.supportOpenPgp() && !Config.supportOtr()) {
             return Message.ENCRYPTION_NONE;
         }
+
+        if (Config.supportOtr() && nextCounterpart != null && getMode() == MODE_SINGLE && hasPermanentCounterpart) {
+            return Message.ENCRYPTION_OTR;
+        }
+
         if (OmemoSetting.isAlways()) {
             return suitableForOmemoByDefault(this) ? Message.ENCRYPTION_AXOLOTL : Message.ENCRYPTION_NONE;
         }
@@ -1127,7 +1142,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
             defaultEncryption = Message.ENCRYPTION_NONE;
         }
         int encryption = this.getIntAttribute(ATTRIBUTE_NEXT_ENCRYPTION, defaultEncryption);
-        if (encryption == Message.ENCRYPTION_OTR || encryption < 0) {
+        if (encryption < 0) {
             return defaultEncryption;
         } else {
             return encryption;
@@ -1393,14 +1408,14 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
         String res2 = nextCounterpart == null ? null : nextCounterpart.getResource();
 
         if (nextCounterpart == null) {
-            if (!message.isPrivateMessage()) {
+            if (!message.isPrivateMessage() && message.encryption != Message.ENCRYPTION_OTR) {
                 synchronized (this.messages) {
                     this.messages.add(message);
                     actualizeReplyMessages(this.messages, List.of(message));
                 }
             }
         } else {
-            if (message.isPrivateMessage() && Objects.equals(res1, res2)) {
+            if ((message.isPrivateMessage() || message.encryption == Message.ENCRYPTION_OTR) && Objects.equals(res1, res2)) {
                 synchronized (this.messages) {
                     this.messages.add(message);
                     actualizeReplyMessages(this.messages, List.of(message));
@@ -1422,14 +1437,14 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
         }
 
         if (nextCounterpart == null) {
-            if (!message.isPrivateMessage()) {
+            if (!message.isPrivateMessage() && message.encryption != Message.ENCRYPTION_OTR) {
                 synchronized (this.messages) {
                     properListToAdd.add(Math.min(offset, properListToAdd.size()), message);
                     actualizeReplyMessages(properListToAdd, List.of(message));
                 }
             }
         } else {
-            if (message.isPrivateMessage() && Objects.equals(res1, res2)) {
+            if ((message.isPrivateMessage() || message.encryption == Message.ENCRYPTION_OTR) && Objects.equals(res1, res2)) {
                 synchronized (this.messages) {
                     properListToAdd.add(Math.min(offset, properListToAdd.size()), message);
                     actualizeReplyMessages(properListToAdd, List.of(message));
@@ -1453,7 +1468,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
 
         if (nextCounterpart == null) {
             for(Message m : messages) {
-                if (!m.isPrivateMessage()) {
+                if (!m.isPrivateMessage() && m.encryption != Message.ENCRYPTION_OTR) {
                     newM.add(m);
                 }
             }
@@ -1464,7 +1479,7 @@ public class Conversation extends AbstractEntity implements Blockable, Comparabl
                 String res2 = nextCounterpart == null ? null : nextCounterpart.getResource();
 
 
-                if (m.isPrivateMessage() && Objects.equals(res1, res2)) {
+                if ((m.isPrivateMessage() || m.encryption == Message.ENCRYPTION_OTR) && Objects.equals(res1, res2)) {
                     newM.add(m);
                 }
             }
diff --git a/src/main/java/eu/siacs/conversations/parser/MessageParser.java b/src/main/java/eu/siacs/conversations/parser/MessageParser.java
index 0c9dafcba..76593e291 100644
--- a/src/main/java/eu/siacs/conversations/parser/MessageParser.java
+++ b/src/main/java/eu/siacs/conversations/parser/MessageParser.java
@@ -5,6 +5,8 @@ import android.text.Html;
 import android.util.Log;
 import android.util.Pair;
 
+import com.google.common.base.Strings;
+
 import net.java.otr4j.session.Session;
 import net.java.otr4j.session.SessionStatus;
 
@@ -594,7 +596,9 @@ public class MessageParser extends AbstractParser implements OnMessagePacketRece
 
         final boolean conversationIsProbablyMuc = isTypeGroupChat || mucUserElement != null || account.getXmppConnection().getMucServersWithholdAccount().contains(counterpart.getDomain().toEscapedString());
 
-        if (conversationIsProbablyMuc && !isTypeGroupChat) {
+        final boolean isOTR = body != null && body.content.startsWith("?OTR") && Config.supportOtr();
+
+        if ((conversationIsProbablyMuc && !isTypeGroupChat) || (!Strings.isNullOrEmpty(counterpart.getResource()) && isOTR)) {
             nextCounterpart = counterpart;
         }
 
@@ -658,7 +662,7 @@ public class MessageParser extends AbstractParser implements OnMessagePacketRece
                 }
             }
             final Message message;
-            if (body != null && body.content.startsWith("?OTR") && Config.supportOtr()) {
+            if (isOTR) {
                 if (!isForwarded && !isTypeGroupChat && isProperlyAddressed && !conversationMultiMode) {
                     message = parseOtrChat(body.content, from, remoteMsgId, conversation);
                     if (message == null) {
diff --git a/src/main/java/eu/siacs/conversations/persistance/DatabaseBackend.java b/src/main/java/eu/siacs/conversations/persistance/DatabaseBackend.java
index 41ab36dff..3c06561e9 100644
--- a/src/main/java/eu/siacs/conversations/persistance/DatabaseBackend.java
+++ b/src/main/java/eu/siacs/conversations/persistance/DatabaseBackend.java
@@ -50,6 +50,7 @@ import eu.siacs.conversations.crypto.axolotl.SQLiteAxolotlStore;
 import eu.siacs.conversations.entities.Account;
 import eu.siacs.conversations.entities.Contact;
 import eu.siacs.conversations.entities.Conversation;
+import eu.siacs.conversations.entities.Conversational;
 import eu.siacs.conversations.entities.Message;
 import eu.siacs.conversations.entities.PresenceTemplate;
 import eu.siacs.conversations.entities.Roster;
@@ -887,30 +888,40 @@ public class DatabaseBackend extends SQLiteOpenHelper {
         String comparsionOperation = isForward ? ">?" : "<?";
         String sorting = isForward ? " ASC" : " DESC";
         if (timestamp == -1) {
-            if (conversation.getNextCounterpart() == null) {
-                String[] selectionArgs = {conversation.getUuid()};
-                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
-                        + "=?", selectionArgs, null, null, Message.TIME_SENT
-                        + sorting, String.valueOf(limit));
-            } else {
+            if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart() && conversation.getMode() == Conversational.MODE_MULTI) {
                 String[] selectionArgs = {conversation.getUuid(), String.valueOf(Message.TYPE_PRIVATE), String.valueOf(Message.TYPE_PRIVATE_FILE), conversation.getNextCounterpart().toString()};
                 cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
                     + "=? and (" + Message.TYPE + "=? or " + Message.TYPE + "=?) and " + Message.COUNTERPART + "=?" , selectionArgs, null, null, Message.TIME_SENT
                     + sorting, String.valueOf(limit));
+            } else if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart()) {
+                String[] selectionArgs = {conversation.getUuid(), String.valueOf(Message.ENCRYPTION_OTR), conversation.getNextCounterpart().toString()};
+                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
+                        + "=? and " + Message.ENCRYPTION + "=? and " + Message.COUNTERPART + "=?" , selectionArgs, null, null, Message.TIME_SENT
+                        + sorting, String.valueOf(limit));
+            } else {
+                String[] selectionArgs = {conversation.getUuid()};
+                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
+                        + "=?", selectionArgs, null, null, Message.TIME_SENT
+                        + sorting, String.valueOf(limit));
             }
         } else {
-            if (conversation.getNextCounterpart() == null) {
+            if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart() && conversation.getMode() == Conversational.MODE_MULTI) {
+                String[] selectionArgs = {conversation.getUuid(), String.valueOf(Message.TYPE_PRIVATE), String.valueOf(Message.TYPE_PRIVATE_FILE), conversation.getNextCounterpart().toString(), Long.toString(timestamp)};
+                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
+                        + "=? and (" + Message.TYPE + "=? or " + Message.TYPE + "=?) and " + Message.COUNTERPART + "=? and " + Message.TIME_SENT + comparsionOperation, selectionArgs, null, null, Message.TIME_SENT
+                        + sorting, String.valueOf(limit));
+            } else if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart()) {
+                String[] selectionArgs = {conversation.getUuid(), String.valueOf(Message.ENCRYPTION_OTR), conversation.getNextCounterpart().toString(), Long.toString(timestamp)};
+                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
+                        + "=? and " + Message.ENCRYPTION + "=? and " + Message.COUNTERPART + "=? and " + Message.TIME_SENT + comparsionOperation, selectionArgs, null, null, Message.TIME_SENT
+                        + sorting, String.valueOf(limit));
+            } else {
                 String[] selectionArgs = {conversation.getUuid(),
                         Long.toString(timestamp)};
                 cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
                                 + "=? and " + Message.TIME_SENT + comparsionOperation, selectionArgs,
                         null, null, Message.TIME_SENT + sorting,
                         String.valueOf(limit));
-            } else {
-                String[] selectionArgs = {conversation.getUuid(), String.valueOf(Message.TYPE_PRIVATE), String.valueOf(Message.TYPE_PRIVATE_FILE), conversation.getNextCounterpart().toString(), Long.toString(timestamp)};
-                cursor = db.query(Message.TABLENAME, null, Message.CONVERSATION
-                        + "=? and (" + Message.TYPE + "=? or " + Message.TYPE + "=?) and " + Message.COUNTERPART + "=? and " + Message.TIME_SENT + comparsionOperation, selectionArgs, null, null, Message.TIME_SENT
-                        + sorting, String.valueOf(limit));
             }
         }
         CursorUtils.upgradeCursorWindowSize(cursor);
diff --git a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
index bf3f07a35..575e8c8e7 100644
--- a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
+++ b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
@@ -2550,6 +2550,7 @@ public class XmppConnectionService extends Service {
                 if ((account == null || conversation.getAccount() == account)
                         && (conversation.getJid().asBareJid().equals(jid.asBareJid()))
                         && Objects.equal(conversation.getNextCounterpart(), counterpart)
+                        && conversation.hasPermanentCounterpart()
                 ) {
                     return conversation;
                 }
@@ -2558,7 +2559,7 @@ public class XmppConnectionService extends Service {
             for (final Conversation conversation : haystack) {
                 if ((account == null || conversation.getAccount() == account)
                         && (conversation.getJid().asBareJid().equals(jid.asBareJid()))
-                        && conversation.getNextCounterpart() == null
+                        && (conversation.getNextCounterpart() == null || !conversation.hasPermanentCounterpart())
                 ) {
                     return conversation;
                 }
@@ -2616,10 +2617,15 @@ public class XmppConnectionService extends Service {
 
     public Conversation findOrCreateConversation(final Account account, final Jid jid, final MessageArchiveService.Query query, final boolean muc, final boolean joinAfterCreate, final boolean async, Jid counterpart) {
         synchronized (this.conversations) {
+            android.util.Log.e("41fd", jid.toString() + " "  + counterpart);
+
             Conversation conversation = find(account, jid, counterpart);
             if (conversation != null) {
                 return conversation;
             }
+
+            android.util.Log.e("41fd 1 not find", jid.toString() + " "  + counterpart);
+
             conversation = databaseBackend.findConversation(account, jid, counterpart);
             final boolean loadMessagesFromDb;
             if (conversation != null) {
@@ -2651,6 +2657,8 @@ public class XmppConnectionService extends Service {
                             Conversation.MODE_SINGLE, counterpart);
                 }
                 this.databaseBackend.createConversation(conversation);
+                android.util.Log.e("41fd 2 not find", jid.toString() + " "  + counterpart);
+
                 loadMessagesFromDb = false;
             }
             final Conversation c = conversation;
diff --git a/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java b/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
index 50c870489..7f56cc57a 100644
--- a/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
+++ b/src/main/java/eu/siacs/conversations/ui/ConversationFragment.java
@@ -1090,6 +1090,7 @@ public class ConversationFragment extends XmppFragment
         switch (conversation.getNextEncryption()) {
             case Message.ENCRYPTION_OTR:
                 sendOtrMessage(message);
+                break;
             case Message.ENCRYPTION_PGP:
                 sendPgpMessage(message);
                 break;
@@ -1406,6 +1407,11 @@ public class ConversationFragment extends XmppFragment
         final MenuItem menuVideoCall = menu.findItem(R.id.action_video_call);
         final MenuItem menuTogglePinned = menu.findItem(R.id.action_toggle_pinned);
         final MenuItem deleteCustomBg = menu.findItem(R.id.action_delete_custom_bg);
+        final MenuItem startSecretChat = menu.findItem(R.id.action_start_secret_chat);
+        final MenuItem encryption = menu.findItem(R.id.action_security);
+
+        boolean considerAsSecretChat = conversation.getMode() == Conversational.MODE_SINGLE &&
+                conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart();
 
         if (conversation != null) {
             if (conversation.getMode() == Conversation.MODE_MULTI) {
@@ -1417,6 +1423,7 @@ public class ConversationFragment extends XmppFragment
                                 : R.string.channel_details);
                 menuCall.setVisible(false);
                 menuOngoingCall.setVisible(false);
+                startSecretChat.setVisible(false);
             } else {
                 menuMucParticipants.setVisible(false);
                 final XmppConnectionService service =
@@ -1458,6 +1465,10 @@ public class ConversationFragment extends XmppFragment
                 menuTogglePinned.setTitle(R.string.add_to_favorites);
             }
 
+            if (considerAsSecretChat) {
+                encryption.setVisible(false);
+            }
+
             deleteCustomBg.setVisible(ChatBackgroundHelper.getBgFile(activity, conversation.getUuid()).exists());
         }
 
@@ -2048,6 +2059,9 @@ public class ConversationFragment extends XmppFragment
             case R.id.action_archive:
                 activity.xmppConnectionService.archiveConversation(conversation);
                 break;
+            case R.id.action_start_secret_chat:
+                startOtrChat();
+                break;
             case R.id.action_contact_details:
                 activity.switchToContactDetails(conversation.getContact());
                 break;
@@ -3979,11 +3993,20 @@ public class ConversationFragment extends XmppFragment
     protected void sendOtrMessage(final Message message) {
         final ConversationsActivity activity = (ConversationsActivity) getActivity();
         final XmppConnectionService xmppService = activity.xmppConnectionService;
+        message.setCounterpart(conversation.getNextCounterpart());
+        xmppService.sendMessage(message);
+        messageSent();
+    }
+
+    protected void startOtrChat() {
+        final ConversationsActivity activity = (ConversationsActivity) getActivity();
         activity.selectPresence(conversation,
                 () -> {
-                    message.setCounterpart(conversation.getNextCounterpart());
-                    xmppService.sendMessage(message);
-                    messageSent();
+                    Conversation c = activity.xmppConnectionService.findOrCreateConversation(conversation.getAccount(), conversation.getJid(), null, false, false, false, conversation.getNextCounterpart());
+                    conversation.setNextCounterpart(null);
+                    if (c != conversation) {
+                        activity.switchToConversation(c);
+                    }
                 });
     }
 
diff --git a/src/main/java/eu/siacs/conversations/ui/ConversationsActivity.java b/src/main/java/eu/siacs/conversations/ui/ConversationsActivity.java
index e98fb8f4e..a999c3bf6 100644
--- a/src/main/java/eu/siacs/conversations/ui/ConversationsActivity.java
+++ b/src/main/java/eu/siacs/conversations/ui/ConversationsActivity.java
@@ -757,8 +757,12 @@ public class ConversationsActivity extends XmppActivity implements OnConversatio
         if (mainFragment instanceof ConversationFragment) {
             final Conversation conversation = ((ConversationFragment) mainFragment).getConversation();
             if (conversation != null) {
-                if (conversation.getNextCounterpart() != null) {
-                    actionBar.setTitle(getString(R.string.muc_private_conversation_title, conversation.getNextCounterpart().getResource(), conversation.getName()));
+                if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart()) {
+                    if (conversation.getMode() == Conversational.MODE_MULTI) {
+                        actionBar.setTitle(getString(R.string.muc_private_conversation_title, conversation.getNextCounterpart().getResource(), conversation.getName()));
+                    } else {
+                        actionBar.setTitle(getString(R.string.secret_chat_title, conversation.getName(), ""));
+                    }
                 } else {
                     actionBar.setTitle(conversation.getName());
                 }
@@ -780,7 +784,9 @@ public class ConversationsActivity extends XmppActivity implements OnConversatio
                 } else if (conversation.getMode() == Conversation.MODE_SINGLE) {
                     Contact contact = conversation.getContact();
                     List<String> statuses = contact.getPresences().getStatusMessages();
-                    if (!statuses.isEmpty() && !statuses.get(0).isBlank()) {
+                    if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart()) {
+                        actionBar.setSubtitle(conversation.getNextCounterpart().getResource());
+                    } else if (!statuses.isEmpty() && !statuses.get(0).isBlank()) {
                         actionBar.setSubtitle(statuses.get(0));
                         handler.postDelayed(refreshTitleRunnable, 5000L);
                     } else {
diff --git a/src/main/java/eu/siacs/conversations/ui/adapter/ConversationAdapter.java b/src/main/java/eu/siacs/conversations/ui/adapter/ConversationAdapter.java
index bac12514b..d1a9a3f1f 100644
--- a/src/main/java/eu/siacs/conversations/ui/adapter/ConversationAdapter.java
+++ b/src/main/java/eu/siacs/conversations/ui/adapter/ConversationAdapter.java
@@ -338,8 +338,12 @@ public class ConversationAdapter
         }
 
         CharSequence name = conversation.getName();
-        if (conversation.getNextCounterpart() != null) {
-            name = viewHolder.binding.getRoot().getResources().getString(R.string.muc_private_conversation_title, conversation.getNextCounterpart().getResource(), conversation.getName());
+        if (conversation.getNextCounterpart() != null && conversation.hasPermanentCounterpart()) {
+            if (conversation.getMode() == Conversational.MODE_MULTI) {
+                name = viewHolder.binding.getRoot().getResources().getString(R.string.muc_private_conversation_title, conversation.getNextCounterpart().getResource(), conversation.getName());
+            } else {
+                name = viewHolder.binding.getRoot().getResources().getString(R.string.secret_chat_title, conversation.getName(), conversation.getNextCounterpart().getResource());
+            }
         }
 
         if  (conversation.withSelf()) {
diff --git a/src/main/res/menu/fragment_conversation.xml b/src/main/res/menu/fragment_conversation.xml
index 86ea78d67..ef3f8e792 100644
--- a/src/main/res/menu/fragment_conversation.xml
+++ b/src/main/res/menu/fragment_conversation.xml
@@ -121,6 +121,11 @@
         android:orderInCategory="60"
         android:title="@string/action_end_conversation"
         app:showAsAction="never" />
+    <item
+        android:id="@+id/action_start_secret_chat"
+        android:orderInCategory="65"
+        android:title="@string/action_start_secret_chat"
+        app:showAsAction="never" />
     <item
         android:orderInCategory="70"
         android:title="@string/more_options">
diff --git a/src/main/res/values/strings.xml b/src/main/res/values/strings.xml
index 8cd41d4bc..dd56a19d9 100644
--- a/src/main/res/values/strings.xml
+++ b/src/main/res/values/strings.xml
@@ -6,6 +6,7 @@
     <string name="action_accounts">Manage accounts</string>
     <string name="action_account">Manage account</string>
     <string name="action_end_conversation">Close conversation</string>
+    <string name="action_start_secret_chat">Start secret chat</string>
     <string name="action_contact_details">Contact details</string>
     <string name="action_muc_details">Group chat details</string>
     <string name="channel_details">Channel details</string>
@@ -1089,6 +1090,7 @@
     <string name="resize">resize</string>
     <string name="filter">filter</string>
     <string name="could_not_create_file">could_not_create_file</string>
+    <string name="secret_chat_title">%1$s (Secret Chat / %2$s)</string>
     <string name="muc_private_conversation_title">%1$s (%2$s)</string>
     <string name="note_to_self_conversation_title">Note to self (%1$s)</string>
     <string name="muc_private_conversation_info_title">Private conversation with:</string>