diff --git a/src/main/java/eu/siacs/conversations/crypto/axolotl/AxolotlService.java b/src/main/java/eu/siacs/conversations/crypto/axolotl/AxolotlService.java
index 2c05fbfdc9e278a7d6d1c481179fe4c4930aac4a..1f9903acf6b82b1ac579e1e6aa82ca9cbaed1c42 100644
--- a/src/main/java/eu/siacs/conversations/crypto/axolotl/AxolotlService.java
+++ b/src/main/java/eu/siacs/conversations/crypto/axolotl/AxolotlService.java
@@ -1176,28 +1176,45 @@ public class AxolotlService implements OnAdvancedStreamFeaturesLoaded {
     }
 
     @Nullable
-    public XmppAxolotlMessage encrypt(Message message) {
+    public XmppAxolotlMessage encrypt(final String content, Jid counterpart) {
         final XmppAxolotlMessage axolotlMessage = new XmppAxolotlMessage(account.getJid().asBareJid(), getOwnDeviceId());
-        final String content;
-        if (message.hasFileOnRemoteHost()) {
-            content = message.getFileParams().url;
-        } else {
-            content = message.getRawBody();
+        try {
+            axolotlMessage.encrypt(content);
+        } catch (CryptoFailedException e) {
+            Log.w(Config.LOGTAG, getLogprefix(account) + "Failed to encrypt message: " + e.getMessage());
+            return null;
         }
+        if (!buildHeader(axolotlMessage, counterpart)) return null;
+        return axolotlMessage;
+    }
+
+    @Nullable
+    public XmppAxolotlMessage encrypt(final String content, Conversation conversation) {
+        final XmppAxolotlMessage axolotlMessage = new XmppAxolotlMessage(account.getJid().asBareJid(), getOwnDeviceId());
         try {
             axolotlMessage.encrypt(content);
         } catch (CryptoFailedException e) {
             Log.w(Config.LOGTAG, getLogprefix(account) + "Failed to encrypt message: " + e.getMessage());
             return null;
         }
+        if (!buildHeader(axolotlMessage, conversation)) return null;
+        return axolotlMessage;
+    }
+
+    @Nullable
+    public XmppAxolotlMessage encrypt(Message message) {
+        final String content;
+        if (message.hasFileOnRemoteHost()) {
+            content = message.getFileParams().url;
+        } else {
+            content = message.getRawBody();
+        }
 
-        final boolean success;
         if (message.isPrivateMessage()) {
-            success = buildHeader(axolotlMessage, message.getTrueCounterpart());
+            return encrypt(content, message.getTrueCounterpart());
         } else {
-            success = buildHeader(axolotlMessage, (Conversation) message.getConversation());
+            return encrypt(content, (Conversation) message.getConversation());
         }
-        return success ? axolotlMessage : null;
     }
 
     public void preparePayloadMessage(final Message message, final boolean delay) {
diff --git a/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java b/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
index 2a1b99ec519b749bb0ea4f7a2cd732af14682e74..e591fa4ed23bd7a9bb930d7c0ca32104f9ff9c37 100644
--- a/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
+++ b/src/main/java/eu/siacs/conversations/generator/MessageGenerator.java
@@ -14,8 +14,6 @@ import eu.siacs.conversations.entities.Account;
 import eu.siacs.conversations.entities.Conversation;
 import eu.siacs.conversations.entities.Conversational;
 import eu.siacs.conversations.entities.Message;
-import eu.siacs.conversations.ui.util.QuoteHelper;
-import eu.siacs.conversations.utils.MessageUtils;
 import eu.siacs.conversations.services.XmppConnectionService;
 import eu.siacs.conversations.xml.Element;
 import eu.siacs.conversations.xml.Namespace;
@@ -202,7 +200,7 @@ public class MessageGenerator extends AbstractGenerator {
         return packet;
     }
 
-    public im.conversations.android.xmpp.model.stanza.Message reaction(final Conversational conversation, final Message inReplyTo, final String reactingTo, final Collection<String> ourReactions, final Collection<String> newReactions) {
+    public im.conversations.android.xmpp.model.stanza.Message reaction(final Conversational conversation, final Message inReplyTo, final String reactingTo, final Collection<String> ourReactions) {
         final boolean groupChat = conversation.getMode() == Conversational.MODE_MULTI;
         final Jid to = conversation.getJid().asBareJid();
         final im.conversations.android.xmpp.model.stanza.Message packet = new im.conversations.android.xmpp.model.stanza.Message();
@@ -214,23 +212,6 @@ public class MessageGenerator extends AbstractGenerator {
             reactions.addExtension(new Reaction(ourReaction));
         }
 
-        if (newReactions.size() > 0) {
-            final var quote = QuoteHelper.quote(MessageUtils.prepareQuote(inReplyTo)) + "\n";
-            packet.setBody(quote + String.join(" ", newReactions));
-
-            packet.addChild("reply", "urn:xmpp:reply:0")
-                .setAttribute("to", inReplyTo.getCounterpart())
-                .setAttribute("id", reactingTo);
-            final var replyFallback = packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", "urn:xmpp:reply:0");
-            replyFallback.addChild("body", "urn:xmpp:fallback:0")
-                .setAttribute("start", "0")
-                .setAttribute("end", "" + quote.codePointCount(0, quote.length()));
-
-
-            final var fallback = packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", "urn:xmpp:reactions:0");
-            fallback.addChild("body", "urn:xmpp:fallback:0");
-        }
-
         final var thread = inReplyTo.getThread();
         if (thread != null) packet.addChild(thread);
 
diff --git a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
index 5aafa03e5269b7d005ea5308ec0e3b6c1adbe85d..ba8b4baf34c801418f8e439c3fa74a214578415a 100644
--- a/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
+++ b/src/main/java/eu/siacs/conversations/services/XmppConnectionService.java
@@ -158,6 +158,7 @@ import eu.siacs.conversations.ui.UiCallback;
 import eu.siacs.conversations.ui.interfaces.OnAvatarPublication;
 import eu.siacs.conversations.ui.interfaces.OnMediaLoaded;
 import eu.siacs.conversations.ui.interfaces.OnSearchResultsAvailable;
+import eu.siacs.conversations.ui.util.QuoteHelper;
 import eu.siacs.conversations.utils.AccountUtils;
 import eu.siacs.conversations.utils.Compatibility;
 import eu.siacs.conversations.utils.ConversationsFileObserver;
@@ -166,6 +167,7 @@ import eu.siacs.conversations.utils.Emoticons;
 import eu.siacs.conversations.utils.EasyOnboardingInvite;
 import eu.siacs.conversations.utils.ExceptionHelper;
 import eu.siacs.conversations.utils.FileUtils;
+import eu.siacs.conversations.utils.MessageUtils;
 import eu.siacs.conversations.utils.MimeUtils;
 import eu.siacs.conversations.utils.PhoneHelper;
 import eu.siacs.conversations.utils.QuickLoader;
@@ -5307,11 +5309,43 @@ public class XmppConnectionService extends Service {
             if (Strings.isNullOrEmpty(reactToId)) {
                 return false;
             }
-            final var reactionMessage =
-                    mMessageGenerator.reaction(conversation, message, reactToId, reactions, newReactions);
-            sendMessagePacket(conversation.getAccount(), reactionMessage);
-            message.setReactions(combinedReactions);
-            updateMessage(message, false);
+            final var packet =
+                    mMessageGenerator.reaction(conversation, message, reactToId, reactions);
+
+            final var quote = QuoteHelper.quote(MessageUtils.prepareQuote(message)) + "\n";
+            final var body  = quote + String.join(" ", newReactions);
+            if (conversation.getNextEncryption() == Message.ENCRYPTION_AXOLOTL && newReactions.size() > 0) {
+                FILE_ATTACHMENT_EXECUTOR.execute(() -> {
+                    XmppAxolotlMessage axolotlMessage = conversation.getAccount().getAxolotlService().encrypt(body, conversation);
+                    packet.setAxolotlMessage(axolotlMessage.toElement());
+                    packet.addChild("encryption", "urn:xmpp:eme:0")
+                        .setAttribute("name", "OMEMO")
+                        .setAttribute("namespace", AxolotlService.PEP_PREFIX);
+                    sendMessagePacket(conversation.getAccount(), packet);
+                    message.setReactions(combinedReactions);
+                    updateMessage(message, false);
+                });
+            } else if (conversation.getNextEncryption() == Message.ENCRYPTION_NONE || newReactions.size() < 1) {
+                if (newReactions.size() > 0) {
+                    packet.setBody(body);
+
+                    packet.addChild("reply", "urn:xmpp:reply:0")
+                        .setAttribute("to", message.getCounterpart())
+                        .setAttribute("id", reactToId);
+                    final var replyFallback = packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", "urn:xmpp:reply:0");
+                    replyFallback.addChild("body", "urn:xmpp:fallback:0")
+                        .setAttribute("start", "0")
+                        .setAttribute("end", "" + quote.codePointCount(0, quote.length()));
+
+                    final var fallback = packet.addChild("fallback", "urn:xmpp:fallback:0").setAttribute("for", "urn:xmpp:reactions:0");
+                    fallback.addChild("body", "urn:xmpp:fallback:0");
+                }
+
+                sendMessagePacket(conversation.getAccount(), packet);
+                message.setReactions(combinedReactions);
+                updateMessage(message, false);
+            }
+
             return true;
         } else {
             return false;