diff --git a/public/index.html b/public/index.html
index 9cc57bbc7..2656a6b96 100644
--- a/public/index.html
+++ b/public/index.html
@@ -550,6 +550,18 @@
                                 </div>
                             </div>
                             <div id="range_block_poe">
+                                <div>
+                                    Use "Unlocked Context" to enable chunked generation.
+                                    It extends the context window in exchange for reply generation speed.
+                                </div>
+                                <div class="flex-container spaceEvenly">
+                                    <div id="poe_send_jailbreak" class="menu_button widthFitContent" title="Attempts to automatically jailbreak the bot">
+                                        Send Jailbreak
+                                    </div>
+                                    <div id="poe_purge_chat" class="menu_button widthFitContent" title="Purges the chat history on Poe site">
+                                        Purge Poe Chat
+                                    </div>
+                                </div>
                                 <div class="range-block">
                                     <label for="poe_streaming" class="checkbox_label widthFreeExpand">
                                         <input id="poe_streaming" type="checkbox" />
diff --git a/public/scripts/poe.js b/public/scripts/poe.js
index a69a66b71..a9e5bc19d 100644
--- a/public/scripts/poe.js
+++ b/public/scripts/poe.js
@@ -57,7 +57,7 @@ const poe_settings = {
 };
 
 let auto_jailbroken = false;
-let got_reply = false;
+let messages_to_purge = 0;
 let is_get_status_poe = false;
 let is_poe_button_press = false;
 
@@ -105,40 +105,82 @@ export function appendPoeAnchors(type, prompt) {
     return prompt;
 }
 
+async function onPurgeChatClick() {
+    toastr.info('Purging the conversation. Please wait...');
+    await purgeConversation();
+    toastr.success('Conversation purged! Jailbreak the bot to continue.');
+    auto_jailbroken = false;
+    messages_to_purge = 0;
+}
+
+async function onSendJailbreakClick() {
+    auto_jailbroken = false;
+    toastr.info('Sending jailbreak message. Please wait...');
+    await autoJailbreak();
+
+    if (auto_jailbroken) {
+        toastr.success('Jailbreak successful!');
+    } else {
+        toastr.error('Jailbreak unsuccessful!');
+    }
+}
+
+async function autoJailbreak() {
+    for (let retryNumber = 0; retryNumber < MAX_RETRIES_FOR_ACTIVATION; retryNumber++) {
+        const reply = await sendMessage(substituteParams(poe_settings.jailbreak_message), false);
+
+        if (reply.toLowerCase().includes(poe_settings.jailbreak_response.toLowerCase())) {
+            auto_jailbroken = true;
+            break;
+        }
+    }
+}
+
 async function generatePoe(type, finalPrompt, signal) {
     if (poe_settings.auto_purge) {
-        let count_to_delete = -1;
+        console.debug('Auto purge is enabled');
+        let count_to_delete = 0;
 
-        if (auto_jailbroken && got_reply) {
-            count_to_delete = 2;
+        if (auto_jailbroken) {
+            console.debug(`Purging ${messages_to_purge} messages`);
+            count_to_delete = messages_to_purge;
+        }
+        else {
+            console.debug('Purging all messages');
+            count_to_delete = -1;
         }
 
         await purgeConversation(count_to_delete);
     }
 
-    if (poe_settings.auto_jailbreak && !auto_jailbroken) {
-        for (let retryNumber = 0; retryNumber < MAX_RETRIES_FOR_ACTIVATION; retryNumber++) {
-            const reply = await sendMessage(substituteParams(poe_settings.jailbreak_message), false);
-
-            if (reply.toLowerCase().includes(poe_settings.jailbreak_response.toLowerCase())) {
-                auto_jailbroken = true;
-                break;
-            }
+    if (!auto_jailbroken) {
+        if (poe_settings.auto_jailbreak) {
+            console.debug('Attempting auto-jailbreak');
+            await autoJailbreak();
+        } else {
+            console.debug('Auto jailbreak is disabled');
         }
     }
-    else {
-        auto_jailbroken = false;
-    }
 
     if (poe_settings.auto_jailbreak && !auto_jailbroken) {
         console.log('Could not jailbreak the bot');
     }
 
     const isQuiet = type === 'quiet';
-    const reply = max_context > POE_TOKEN_LENGTH
-        ? await sendChunkedMessage(finalPrompt, !isQuiet, signal)
-        : await sendMessage(finalPrompt, !isQuiet, signal);
-    got_reply = true;
+    let reply = '';
+
+    if (max_context > POE_TOKEN_LENGTH) {
+        console.debug('Prompt is too long, sending in chunks');
+        const result = await sendChunkedMessage(finalPrompt, !isQuiet, signal)
+        reply = result.reply;
+        messages_to_purge = result.chunks + 1; // +1 for the reply
+    }
+    else {
+        console.debug('Sending prompt in one message');
+        reply = await sendMessage(finalPrompt, !isQuiet, signal);
+        messages_to_purge = 2; // prompt and the reply
+    }
+
     return reply;
 }
 
@@ -165,10 +207,17 @@ async function sendChunkedMessage(finalPrompt, withStreaming, signal) {
         }
     }
 
-    return reply;
+    return { reply: reply, chunks: promptChunks.length };
 }
 
+// If count is -1, purge all messages
+// If count is 0, do nothing
+// If count is > 0, purge that many messages
 async function purgeConversation(count = -1) {
+    if (count == 0) {
+        return true;
+    }
+
     const body = JSON.stringify({
         bot: poe_settings.bot,
         count,
@@ -302,7 +351,7 @@ async function checkStatusPoe() {
 function setPoeOnlineStatus(value) {
     is_get_status_poe = value;
     auto_jailbroken = false;
-    got_reply = false;
+    messages_to_purge = 0;
 }
 
 function onResponseInput() {
@@ -384,4 +433,6 @@ $('document').ready(function () {
     $('#poe_nudge_text_restore').on('click', onCharacterNudgeMessageRestoreClick);
     $('#poe_activation_response_restore').on('click', onResponseRestoreClick);
     $('#poe_activation_message_restore').on('click', onMessageRestoreClick);
+    $('#poe_send_jailbreak').on('click', onSendJailbreakClick);
+    $('#poe_purge_chat').on('click', onPurgeChatClick);
 });
diff --git a/public/style.css b/public/style.css
index 0160a1784..b648c8a4f 100644
--- a/public/style.css
+++ b/public/style.css
@@ -4150,6 +4150,10 @@ body.waifuMode #avatar_zoom_popup {
     height: fit-content;
 }
 
+.widthFitContent {
+    width: fit-content;
+}
+
 .flexGap5 {
     gap: 5px;
 }
diff --git a/server.js b/server.js
index c716579f1..f3502cd7b 100644
--- a/server.js
+++ b/server.js
@@ -2193,7 +2193,12 @@ app.post('/purge_poe', jsonParser, async (request, response) => {
 
     try {
         const client = await getPoeClient(token, true);
-        await client.purge_conversation(bot, count);
+        if (count > 0) {
+            await client.purge_conversation(bot, count);
+        }
+        else {
+            await client.send_chat_break(bot);
+        }
         client.disconnect_ws();
 
         return response.send({ "ok": true });