diff --git a/src/database.c b/src/database.c
index 6f719aa2..82cd380f 100644
--- a/src/database.c
+++ b/src/database.c
@@ -232,8 +232,9 @@ log_database_get_limits_info(const gchar* const contact_barejid, gboolean is_las
     return msg;
 }
 
+// Query previous chat
 GSList*
-log_database_get_previous_chat(const gchar* const contact_barejid)
+log_database_get_previous_chat(const gchar* const contact_barejid, GDateTime* end_time, gboolean flip)
 {
     sqlite3_stmt* stmt = NULL;
     gchar* query;
@@ -242,12 +243,16 @@ log_database_get_previous_chat(const gchar* const contact_barejid)
     if (!myjid)
         return NULL;
 
-    query = sqlite3_mprintf("SELECT * FROM (SELECT `message`, `timestamp`, `from_jid`, `type` from `ChatLogs` WHERE (`from_jid` = '%q' AND `to_jid` = '%q') OR (`from_jid` = '%q' AND `to_jid` = '%q') ORDER BY `timestamp` DESC LIMIT 10) ORDER BY `timestamp` ASC;", contact_barejid, myjid->barejid, myjid->barejid, contact_barejid);
+    // Flip order when querying older pages
+    char* sort = !flip ? "ASC" : "DESC";
+    gchar* date_fmt = g_date_time_format_iso8601(end_time ? end_time : g_date_time_new_now_local());
+    query = sqlite3_mprintf("SELECT * FROM (SELECT `message`, `timestamp`, `from_jid`, `type` from `ChatLogs` WHERE ((`from_jid` = '%q' AND `to_jid` = '%q') OR (`from_jid` = '%q' AND `to_jid` = '%q')) AND `timestamp` < '%q' ORDER BY `timestamp` DESC LIMIT 10) ORDER BY `timestamp` %s;", contact_barejid, myjid->barejid, myjid->barejid, contact_barejid, date_fmt, sort);
     if (!query) {
         log_error("log_database_get_previous_chat(): SQL query. could not allocate memory");
         return NULL;
     }
 
+    g_free(date_fmt);
     jid_destroy(myjid);
 
     int rc = sqlite3_prepare_v2(g_chatlog_database, query, -1, &stmt, NULL);
diff --git a/src/database.h b/src/database.h
index 21f04595..08a6bab0 100644
--- a/src/database.h
+++ b/src/database.h
@@ -45,7 +45,7 @@ void log_database_add_incoming(ProfMessage* message);
 void log_database_add_outgoing_chat(const char* const id, const char* const barejid, const char* const message, const char* const replace_id, prof_enc_t enc);
 void log_database_add_outgoing_muc(const char* const id, const char* const barejid, const char* const message, const char* const replace_id, prof_enc_t enc);
 void log_database_add_outgoing_muc_pm(const char* const id, const char* const barejid, const char* const message, const char* const replace_id, prof_enc_t enc);
-GSList* log_database_get_previous_chat(const gchar* const contact_barejid);
+GSList* log_database_get_previous_chat(const gchar* const contact_barejid, GDateTime* end_time, gboolean flip);
 ProfMessage* log_database_get_limits_info(const gchar* const contact_barejid, gboolean is_last);
 void log_database_close(void);
 
diff --git a/src/ui/buffer.c b/src/ui/buffer.c
index e38aaaec..0203c35c 100644
--- a/src/ui/buffer.c
+++ b/src/ui/buffer.c
@@ -110,6 +110,34 @@ buffer_append(ProfBuff buffer, const char* show_char, int pad_indent, GDateTime*
     buffer->entries = g_slist_append(buffer->entries, e);
 }
 
+void
+buffer_prepend(ProfBuff buffer, const char* show_char, int pad_indent, GDateTime* time, int flags, theme_item_t theme_item, const char* const display_from, const char* const from_jid, const char* const message, DeliveryReceipt* receipt, const char* const id)
+{
+    ProfBuffEntry* e = malloc(sizeof(struct prof_buff_entry_t));
+    e->show_char = strdup(show_char);
+    e->pad_indent = pad_indent;
+    e->flags = flags;
+    e->theme_item = theme_item;
+    e->time = g_date_time_ref(time);
+    e->display_from = display_from ? strdup(display_from) : NULL;
+    e->from_jid = from_jid ? strdup(from_jid) : NULL;
+    e->message = strdup(message);
+    e->receipt = receipt;
+    if (id) {
+        e->id = strdup(id);
+    } else {
+        e->id = NULL;
+    }
+
+    if (g_slist_length(buffer->entries) == BUFF_SIZE) {
+        GSList* last = g_slist_last(buffer->entries);
+        _free_entry(last->data);
+        buffer->entries = g_slist_delete_link(buffer->entries, last);
+    }
+
+    buffer->entries = g_slist_prepend(buffer->entries, e);
+}
+
 void
 buffer_remove_entry_by_id(ProfBuff buffer, const char* const id)
 {
diff --git a/src/ui/buffer.h b/src/ui/buffer.h
index 5d363902..e3e79655 100644
--- a/src/ui/buffer.h
+++ b/src/ui/buffer.h
@@ -70,6 +70,7 @@ typedef struct prof_buff_t* ProfBuff;
 ProfBuff buffer_create();
 void buffer_free(ProfBuff buffer);
 void buffer_append(ProfBuff buffer, const char* show_char, int pad_indent, GDateTime* time, int flags, theme_item_t theme_item, const char* const display_from, const char* const barejid, const char* const message, DeliveryReceipt* receipt, const char* const id);
+void buffer_prepend(ProfBuff buffer, const char* show_char, int pad_indent, GDateTime* time, int flags, theme_item_t theme_item, const char* const display_from, const char* const barejid, const char* const message, DeliveryReceipt* receipt, const char* const id);
 void buffer_remove_entry_by_id(ProfBuff buffer, const char* const id);
 int buffer_size(ProfBuff buffer);
 ProfBuffEntry* buffer_get_entry(ProfBuff buffer, int entry);
diff --git a/src/ui/chatwin.c b/src/ui/chatwin.c
index b9fae2af..02068837 100644
--- a/src/ui/chatwin.c
+++ b/src/ui/chatwin.c
@@ -66,7 +66,7 @@ chatwin_new(const char* const barejid)
     ProfWin* window = wins_new_chat(barejid);
     ProfChatWin* chatwin = (ProfChatWin*)window;
 
-    if (!prefs_get_boolean(PREF_MAM) && prefs_get_boolean(PREF_CHLOG) && prefs_get_boolean(PREF_HISTORY)) {
+    if (prefs_get_boolean(PREF_MAM) || (prefs_get_boolean(PREF_CHLOG) && prefs_get_boolean(PREF_HISTORY))) {
         _chatwin_history(chatwin, barejid);
     }
 
@@ -518,7 +518,7 @@ static void
 _chatwin_history(ProfChatWin* chatwin, const char* const contact_barejid)
 {
     if (!chatwin->history_shown) {
-        GSList* history = log_database_get_previous_chat(contact_barejid);
+        GSList* history = log_database_get_previous_chat(contact_barejid, NULL, FALSE);
         GSList* curr = history;
 
         while (curr) {
@@ -537,6 +537,32 @@ _chatwin_history(ProfChatWin* chatwin, const char* const contact_barejid)
     }
 }
 
+gboolean
+chatwin_old_history(ProfChatWin* chatwin)
+{
+    // TODO: not correct location but check whether notifications get screwed
+    GDateTime* time = buffer_size(((ProfWin*)chatwin)->layout->buffer) == 0 ? NULL : buffer_get_entry(((ProfWin*)chatwin)->layout->buffer, 0)->time;
+    GSList* history = log_database_get_previous_chat(chatwin->barejid, time, TRUE);
+    gboolean has_items = g_slist_length(history) != 0;
+    GSList* curr = history;
+
+    while (curr) {
+        ProfMessage* msg = curr->data;
+        char* msg_plain = msg->plain;
+        msg->plain = plugins_pre_chat_message_display(msg->from_jid->barejid, msg->from_jid->resourcepart, msg->plain);
+        // This is dirty workaround for memory leak. We reassign msg->plain above so have to free previous object
+        // TODO: Make a better solution, for example, pass msg object to the function and it will replace msg->plain properly if needed.
+        free(msg_plain);
+        win_print_old_history((ProfWin*)chatwin, msg);
+        curr = g_slist_next(curr);
+    }
+
+    g_slist_free_full(history, (GDestroyNotify)message_free);
+    win_redraw((ProfWin*)chatwin);
+
+    return has_items;
+}
+
 static void
 _chatwin_set_last_message(ProfChatWin* chatwin, const char* const id, const char* const message)
 {
diff --git a/src/ui/ui.h b/src/ui/ui.h
index a7886ab3..264ce38b 100644
--- a/src/ui/ui.h
+++ b/src/ui/ui.h
@@ -145,6 +145,7 @@ void chatwin_set_incoming_char(ProfChatWin* chatwin, const char* const ch);
 void chatwin_unset_incoming_char(ProfChatWin* chatwin);
 void chatwin_set_outgoing_char(ProfChatWin* chatwin, const char* const ch);
 void chatwin_unset_outgoing_char(ProfChatWin* chatwin);
+gboolean chatwin_old_history(ProfChatWin* chatwin);
 
 // MUC window
 ProfMucWin* mucwin_new(const char* const barejid);
diff --git a/src/ui/window.c b/src/ui/window.c
index 7bd403da..b6130348 100644
--- a/src/ui/window.c
+++ b/src/ui/window.c
@@ -600,6 +600,10 @@ win_page_up(ProfWin* window)
 
     *page_start -= page_space;
 
+    if (*page_start == -page_space && prefs_get_boolean(PREF_MAM) && window->type == WIN_CHAT) {
+        ProfChatWin* chatwin = (ProfChatWin*) window;
+        chatwin_old_history(chatwin);
+    }
     // went past beginning, show first page
     if (*page_start < 0)
         *page_start = 0;
@@ -1289,6 +1293,34 @@ win_print_history(ProfWin* window, const ProfMessage* const message)
     g_date_time_unref(message->timestamp);
 }
 
+void
+win_print_old_history(ProfWin* window, const ProfMessage* const message)
+{
+    g_date_time_ref(message->timestamp);
+
+    char* display_name;
+    int flags = 0;
+    const char* jid = connection_get_fulljid();
+    Jid* jidp = jid_create(jid);
+
+    if (g_strcmp0(jidp->barejid, message->from_jid->barejid) == 0) {
+        display_name = strdup("me");
+    } else {
+        display_name = roster_get_msg_display_name(message->from_jid->barejid, message->from_jid->resourcepart);
+        flags = NO_ME;
+    }
+
+    jid_destroy(jidp);
+
+    buffer_prepend(window->layout->buffer, "-", 0, message->timestamp, flags, THEME_TEXT_HISTORY, display_name, NULL, message->plain, NULL, NULL);
+    _win_print_internal(window, "-", 0, message->timestamp, flags, THEME_TEXT_HISTORY, display_name, message->plain, NULL);
+
+    free(display_name);
+
+    inp_nonblocking(TRUE);
+    g_date_time_unref(message->timestamp);
+}
+
 void
 win_print(ProfWin* window, theme_item_t theme_item, const char* show_char, const char* const message, ...)
 {
@@ -1504,9 +1536,10 @@ _win_printf(ProfWin* window, const char* show_char, int pad_indent, GDateTime* t
     GString* fmt_msg = g_string_new(NULL);
     g_string_vprintf(fmt_msg, message, arg);
 
-    buffer_append(window->layout->buffer, show_char, pad_indent, timestamp, flags, theme_item, display_from, from_jid, fmt_msg->str, NULL, message_id);
-
-    _win_print_internal(window, show_char, pad_indent, timestamp, flags, theme_item, display_from, fmt_msg->str, NULL);
+    if (buffer_size(window->layout->buffer) == 0 || g_date_time_compare(buffer_get_entry(window->layout->buffer, 0)->time, timestamp) != 1) {
+        buffer_append(window->layout->buffer, show_char, pad_indent, timestamp, flags, theme_item, display_from, from_jid, fmt_msg->str, NULL, message_id);
+        _win_print_internal(window, show_char, pad_indent, timestamp, flags, theme_item, display_from, fmt_msg->str, NULL);
+    }
 
     inp_nonblocking(TRUE);
     g_date_time_unref(timestamp);
diff --git a/src/ui/window.h b/src/ui/window.h
index 669734ff..174785b1 100644
--- a/src/ui/window.h
+++ b/src/ui/window.h
@@ -71,6 +71,7 @@ void win_print_outgoing_with_receipt(ProfWin* window, const char* show_char, con
 void win_println_incoming_muc_msg(ProfWin* window, char* show_char, int flags, const ProfMessage* const message);
 void win_print_outgoing_muc_msg(ProfWin* window, char* show_char, const char* const me, const char* const id, const char* const replace_id, const char* const message);
 void win_print_history(ProfWin* window, const ProfMessage* const message);
+void win_print_old_history(ProfWin* window, const ProfMessage* const message);
 
 void win_print_http_transfer(ProfWin* window, const char* const message, char* url);
 
diff --git a/src/xmpp/iq.c b/src/xmpp/iq.c
index 9918354e..dd28b358 100644
--- a/src/xmpp/iq.c
+++ b/src/xmpp/iq.c
@@ -66,6 +66,7 @@
 #include "xmpp/roster_list.h"
 #include "xmpp/roster.h"
 #include "xmpp/muc.h"
+#include "src/database.h"
 
 #ifdef HAVE_OMEMO
 #include "omemo/omemo.h"
@@ -105,7 +106,8 @@ typedef struct command_config_data_t
 typedef struct mam_rsm_userdata
 {
     char* barejid;
-    char* datestr;
+    char* start_datestr;
+    char* end_datestr;
 } MamRsmUserdata;
 
 static int _iq_handler(xmpp_conn_t* const conn, xmpp_stanza_t* const stanza, void* const userdata);