diff --git a/src/twc-chat.c b/src/twc-chat.c
index fe124eb..dfaefed 100644
--- a/src/twc-chat.c
+++ b/src/twc-chat.c
@@ -309,6 +309,7 @@ void
 twc_chat_send_message(struct t_twc_chat *chat, const char *message,
                       enum TWC_MESSAGE_TYPE message_type)
 {
+    int64_t rc = 0;
     if (chat->friend_number >= 0)
     {
         twc_message_queue_add_friend_message(chat->profile,
@@ -323,11 +324,30 @@ twc_chat_send_message(struct t_twc_chat *chat, const char *message,
     else if (chat->group_number >= 0)
     {
         if (message_type == TWC_MESSAGE_TYPE_MESSAGE)
-            tox_group_message_send(chat->profile->tox, chat->group_number,
-                                   (uint8_t *)message, strlen(message));
+        {
+            int len = strlen(message);
+            while (len > 0)
+            {
+                int fit_len = twc_fit_utf8(message, TWC_MAX_GROUP_MESSAGE_LENGTH);
+                rc = tox_group_message_send(chat->profile->tox, chat->group_number,
+                                            (uint8_t *)message, fit_len);
+                if (rc < 0)
+                    break;
+                message += fit_len;
+                len -= fit_len;
+            }
+        }
         else if (message_type == TWC_MESSAGE_TYPE_ACTION)
-            tox_group_action_send(chat->profile->tox, chat->group_number,
-                                  (uint8_t *)message, strlen(message));
+            rc = tox_group_action_send(chat->profile->tox, chat->group_number,
+                                      (uint8_t *)message, strlen(message));
+        if (rc < 0)
+        {
+            weechat_printf(chat->buffer,
+                           "%s%sFailed to send message%s",
+                           weechat_prefix("error"),
+                           weechat_color("chat_highlight"),
+                           weechat_color("reset"));
+        }
     }
 }
 
diff --git a/src/twc-message-queue.c b/src/twc-message-queue.c
index 4c28fc2..e16a8ac 100644
--- a/src/twc-message-queue.c
+++ b/src/twc-message-queue.c
@@ -58,21 +58,30 @@ twc_message_queue_add_friend_message(struct t_twc_profile *profile,
                                      const char *message,
                                      enum TWC_MESSAGE_TYPE message_type)
 {
-    struct t_twc_queued_message *queued_message
-        = malloc(sizeof(struct t_twc_queued_message));
+    int len = strlen(message);
+    while (len > 0)
+    {
+        int fit_len = twc_fit_utf8(message, TWC_MAX_FRIEND_MESSAGE_LENGTH);
 
-    time_t rawtime = time(NULL);
-    queued_message->time = malloc(sizeof(struct tm));
-    memcpy(queued_message->time, gmtime(&rawtime), sizeof(struct tm));
+        struct t_twc_queued_message *queued_message
+            = malloc(sizeof(struct t_twc_queued_message));
 
-    queued_message->message = strdup(message);
-    queued_message->message_type = message_type;
+        time_t rawtime = time(NULL);
+        queued_message->time = malloc(sizeof(struct tm));
+        memcpy(queued_message->time, gmtime(&rawtime), sizeof(struct tm));
 
-    // create a queue if needed and add message
-    struct t_twc_list *message_queue
-        = twc_message_queue_get_or_create(profile, friend_number);
-    twc_list_item_new_data_add(message_queue, queued_message);
+        queued_message->message = strndup(message, fit_len);
+        queued_message->message_type = message_type;
 
+        message += fit_len;
+        len -= fit_len;
+
+        // create a queue if needed and add message
+        struct t_twc_list *message_queue
+            = twc_message_queue_get_or_create(profile, friend_number);
+        twc_list_item_new_data_add(message_queue, queued_message);
+    }
+    
     // flush if friend is online
     if (profile->tox
         && (tox_friend_get_connection_status(profile->tox, friend_number, NULL) != TOX_CONNECTION_NONE))
@@ -88,6 +97,8 @@ twc_message_queue_flush_friend(struct t_twc_profile *profile,
 {
     struct t_twc_list *message_queue
         = twc_message_queue_get_or_create(profile, friend_number);
+    struct t_twc_chat *friend_chat
+        = twc_chat_search_friend(profile, friend_number, true);
 
     size_t index;
     struct t_twc_list_item *item;
@@ -106,14 +117,47 @@ twc_message_queue_flush_friend(struct t_twc_profile *profile,
                                       strlen(queued_message->message),
                                       &err);
 
-        if (err != TOX_ERR_FRIEND_SEND_MESSAGE_OK)
+        if (err == TOX_ERR_FRIEND_SEND_MESSAGE_FRIEND_NOT_CONNECTED)
         {
             // break if message send failed
             break;
         }
         else
         {
-            // message was sent, free it
+            char *err_str;
+            // check if error occured
+            switch (err)
+            {
+                case TOX_ERR_FRIEND_SEND_MESSAGE_TOO_LONG:
+                    err_str = "message too long";
+                    break;
+                case TOX_ERR_FRIEND_SEND_MESSAGE_NULL:
+                    err_str = "NULL fields for tox_friend_send_message";
+                    break;
+                case TOX_ERR_FRIEND_SEND_MESSAGE_FRIEND_NOT_FOUND:
+                    err_str = "friend not found";
+                    break;
+                case TOX_ERR_FRIEND_SEND_MESSAGE_SENDQ:
+                    err_str = "queue allocation error";
+                    break;
+                case TOX_ERR_FRIEND_SEND_MESSAGE_EMPTY:
+                    err_str = "tried to send empty message";
+                    break;
+                case TOX_ERR_FRIEND_SEND_MESSAGE_OK:
+                    err_str = "no error";
+                    break;
+                default:
+                    err_str = "unknown error";
+            }
+            if (err != TOX_ERR_FRIEND_SEND_MESSAGE_OK)
+            {
+                weechat_printf(friend_chat->buffer,
+                               "%s%sFailed to send message: %s%s",
+                               weechat_prefix("error"),
+                               weechat_color("highlight"),
+                               err_str,
+                               weechat_color("reset"));
+            }
             twc_message_queue_free_message(queued_message);
             item->queued_message = NULL;
         }
diff --git a/src/twc-utils.c b/src/twc-utils.c
index c397f3d..f6f3cc9 100644
--- a/src/twc-utils.c
+++ b/src/twc-utils.c
@@ -198,3 +198,12 @@ twc_hash_tox_id(const uint8_t *tox_id)
 
     return hash;
 }
+
+/**
+ * Fit correct unicode string into max chars. Return number of bytes
+ */
+int
+twc_fit_utf8(const char *str, int max)
+{
+    return weechat_utf8_real_pos(str, weechat_utf8_strnlen(str, max));
+}
diff --git a/src/twc-utils.h b/src/twc-utils.h
index 8687dab..78dee94 100644
--- a/src/twc-utils.h
+++ b/src/twc-utils.h
@@ -54,5 +54,8 @@ twc_uint32_reverse_bytes(uint32_t num);
 unsigned long long
 twc_hash_tox_id(const uint8_t *tox_id);
 
+int
+twc_fit_utf8(const char *str, int max);
+
 #endif // TOX_WEECHAT_UTILS_H
 
diff --git a/src/twc.h b/src/twc.h
index aea6638..ab4a1cd 100644
--- a/src/twc.h
+++ b/src/twc.h
@@ -32,5 +32,8 @@ enum t_twc_rc
     TWC_RC_ERROR_MALLOC = -2,
 };
 
+#define TWC_MAX_FRIEND_MESSAGE_LENGTH (TOX_MAX_MESSAGE_LENGTH-1)
+#define TWC_MAX_GROUP_MESSAGE_LENGTH  (TOX_MAX_MESSAGE_LENGTH-9)
+
 #endif // TOX_WEECHAT_H