diff --git a/android/app/src/main/assets/public/main.js b/android/app/src/main/assets/public/main.js
index e9b48c31..27f760e6 100644
--- a/android/app/src/main/assets/public/main.js
+++ b/android/app/src/main/assets/public/main.js
@@ -1838,6 +1838,9 @@ var currentDmId = null;
 var currentDmKey = null; // AES key for encrypting/decrypting messages
 var dmUsernameCache = {};
 var dmPfpCache = {};
+var loadedMessages = {};
+var oldestLoadedMsgId = null;
+var isLoadingOlderMessages = false;
 
 async function openDm(dmId, username, targetId) {
     try {
@@ -1848,6 +1851,9 @@ async function openDm(dmId, username, targetId) {
              throw new Error("Missing DM room key");
         }
         currentDmId = dmId;
+        loadedMessages = {};
+        oldestLoadedMsgId = null;
+        isLoadingOlderMessages = false;
         
         let pfp = await getAvatarUrl(targetId, username);
         let iconHtml = `<img src="${pfp}" style="width: 2.3rem; border-radius: 0.65rem; margin-right: 0.38rem; object-fit: cover; border: var(--border-width) solid rgba(255, 255, 255, 0.2);">`;
@@ -1863,6 +1869,7 @@ async function openDm(dmId, username, targetId) {
         }
         
         await loadDmMessages(dmId);
+        setupChatScrollListener();
         
         if (dmMessagePollInterval) clearInterval(dmMessagePollInterval);
         dmMessagePollInterval = setInterval(() => {
@@ -1886,9 +1893,9 @@ async function openDm(dmId, username, targetId) {
     }
 }
 
-async function loadDmMessages(dmId) {
+async function loadDmMessages(dmId, startOffset = "", isPrepend = false) {
     try {
-        let payload = JSON.stringify({ string1: dmId, string2: "50", string3: "" });
+        let payload = JSON.stringify({ string1: dmId, string2: "50", string3: startOffset });
         let res = await fetchEncrypted("dm/messages/get", payload);
         
         if (res && res.startsWith("error:")) {
@@ -1897,14 +1904,26 @@ async function loadDmMessages(dmId) {
         }
         
         let messages = JSON.parse(res);
-        await renderMessages(messages);
+        let ids = Object.keys(messages).map(id => parseInt(id));
+        if (ids.length > 0) {
+            let minId = Math.min(...ids);
+            if (oldestLoadedMsgId === null || minId < oldestLoadedMsgId) {
+                oldestLoadedMsgId = minId;
+            }
+        }
+        if (ids.length < 50 && startOffset !== "") {
+            oldestLoadedMsgId = 0;
+        }
+
+        Object.assign(loadedMessages, messages);
+        await renderMessages(loadedMessages, isPrepend);
     } catch (e) {
         console.error(e);
         showBlahNotification("error:dm.messages.fetch.failed");
     }
 }
 
-async function renderMessages(messages) {
+async function renderMessages(messages, isPrepend = false) {
     let container = document.getElementById("chat-messages");
     if (!container) return;
     
@@ -1981,16 +2000,37 @@ async function renderMessages(messages) {
         window.forceScrollToBottom = false;
     }
     let oldScrollTop = container.scrollTop;
+    let oldScrollHeight = container.scrollHeight;
     
     container.innerHTML = html;
     
     if (wasAtBottom) {
         container.scrollTop = container.scrollHeight;
+    } else if (isPrepend) {
+        container.scrollTop = oldScrollTop + (container.scrollHeight - oldScrollHeight);
     } else {
         container.scrollTop = oldScrollTop;
     }
 }
 
+function setupChatScrollListener() {
+    let container = document.getElementById("chat-messages");
+    if (!container) return;
+    
+    container.onscroll = async () => {
+        if (container.scrollTop === 0 && !isLoadingOlderMessages && oldestLoadedMsgId !== null && oldestLoadedMsgId > 0) {
+            isLoadingOlderMessages = true;
+            showAction("info.messages.loading.older", "messages.loading.older");
+            try {
+                await loadDmMessages(currentDmId, (oldestLoadedMsgId - 1).toString(), true);
+                isLoadingOlderMessages = false;
+            }
+            catch (e) {}
+            clearAction("messages.loading.older");
+        }
+    };
+}
+
 async function sendMessage() {
     if (!currentDmId || !currentDmKey) return;
     
diff --git a/webroot/main.js b/webroot/main.js
index e9b48c31..27f760e6 100644
--- a/webroot/main.js
+++ b/webroot/main.js
@@ -1838,6 +1838,9 @@ var currentDmId = null;
 var currentDmKey = null; // AES key for encrypting/decrypting messages
 var dmUsernameCache = {};
 var dmPfpCache = {};
+var loadedMessages = {};
+var oldestLoadedMsgId = null;
+var isLoadingOlderMessages = false;
 
 async function openDm(dmId, username, targetId) {
     try {
@@ -1848,6 +1851,9 @@ async function openDm(dmId, username, targetId) {
              throw new Error("Missing DM room key");
         }
         currentDmId = dmId;
+        loadedMessages = {};
+        oldestLoadedMsgId = null;
+        isLoadingOlderMessages = false;
         
         let pfp = await getAvatarUrl(targetId, username);
         let iconHtml = `<img src="${pfp}" style="width: 2.3rem; border-radius: 0.65rem; margin-right: 0.38rem; object-fit: cover; border: var(--border-width) solid rgba(255, 255, 255, 0.2);">`;
@@ -1863,6 +1869,7 @@ async function openDm(dmId, username, targetId) {
         }
         
         await loadDmMessages(dmId);
+        setupChatScrollListener();
         
         if (dmMessagePollInterval) clearInterval(dmMessagePollInterval);
         dmMessagePollInterval = setInterval(() => {
@@ -1886,9 +1893,9 @@ async function openDm(dmId, username, targetId) {
     }
 }
 
-async function loadDmMessages(dmId) {
+async function loadDmMessages(dmId, startOffset = "", isPrepend = false) {
     try {
-        let payload = JSON.stringify({ string1: dmId, string2: "50", string3: "" });
+        let payload = JSON.stringify({ string1: dmId, string2: "50", string3: startOffset });
         let res = await fetchEncrypted("dm/messages/get", payload);
         
         if (res && res.startsWith("error:")) {
@@ -1897,14 +1904,26 @@ async function loadDmMessages(dmId) {
         }
         
         let messages = JSON.parse(res);
-        await renderMessages(messages);
+        let ids = Object.keys(messages).map(id => parseInt(id));
+        if (ids.length > 0) {
+            let minId = Math.min(...ids);
+            if (oldestLoadedMsgId === null || minId < oldestLoadedMsgId) {
+                oldestLoadedMsgId = minId;
+            }
+        }
+        if (ids.length < 50 && startOffset !== "") {
+            oldestLoadedMsgId = 0;
+        }
+
+        Object.assign(loadedMessages, messages);
+        await renderMessages(loadedMessages, isPrepend);
     } catch (e) {
         console.error(e);
         showBlahNotification("error:dm.messages.fetch.failed");
     }
 }
 
-async function renderMessages(messages) {
+async function renderMessages(messages, isPrepend = false) {
     let container = document.getElementById("chat-messages");
     if (!container) return;
     
@@ -1981,16 +2000,37 @@ async function renderMessages(messages) {
         window.forceScrollToBottom = false;
     }
     let oldScrollTop = container.scrollTop;
+    let oldScrollHeight = container.scrollHeight;
     
     container.innerHTML = html;
     
     if (wasAtBottom) {
         container.scrollTop = container.scrollHeight;
+    } else if (isPrepend) {
+        container.scrollTop = oldScrollTop + (container.scrollHeight - oldScrollHeight);
     } else {
         container.scrollTop = oldScrollTop;
     }
 }
 
+function setupChatScrollListener() {
+    let container = document.getElementById("chat-messages");
+    if (!container) return;
+    
+    container.onscroll = async () => {
+        if (container.scrollTop === 0 && !isLoadingOlderMessages && oldestLoadedMsgId !== null && oldestLoadedMsgId > 0) {
+            isLoadingOlderMessages = true;
+            showAction("info.messages.loading.older", "messages.loading.older");
+            try {
+                await loadDmMessages(currentDmId, (oldestLoadedMsgId - 1).toString(), true);
+                isLoadingOlderMessages = false;
+            }
+            catch (e) {}
+            clearAction("messages.loading.older");
+        }
+    };
+}
+
 async function sendMessage() {
     if (!currentDmId || !currentDmKey) return;