diff --git a/public/scripts/PromptManager.js b/public/scripts/PromptManager.js
index e3d5cf8f1..c6b8aecd9 100644
--- a/public/scripts/PromptManager.js
+++ b/public/scripts/PromptManager.js
@@ -1,5 +1,5 @@
 import {DraggablePromptListModule as DraggableList} from "./DraggableList.js";
-import {eventSource, substituteParams} from "../script.js";
+import {event_types, eventSource, substituteParams} from "../script.js";
 import {IdentifierNotFoundError, TokenHandler} from "./openai.js";
 
 class Prompt {
@@ -35,6 +35,14 @@ class PromptCollection {
         this.collection.push(...prompts);
     }
 
+    set(prompt, position) {
+        if(!(prompt instanceof Prompt)) {
+            throw new Error('Only Prompt instances can be added to PromptCollection');
+        }
+
+        this.collection[position] = prompt;
+    }
+
     get(identifier) {
         const index = this.index(identifier);
         if (0 > index) return null;
@@ -66,6 +74,9 @@ function PromptManagerModule() {
     this.tokenHandler = null;
     this.error = null;
 
+    this.tryGenerate = () => { };
+    this.saveServiceSettings = () => { };
+
     this.handleToggle = () => { };
     this.handleEdit = () => { };
     this.handleDetach = () => { };
@@ -73,8 +84,6 @@ function PromptManagerModule() {
     this.handleNewPrompt = () => { };
     this.handleDeletePrompt = () => { };
     this.handleAppendPrompt = () => { };
-    this.saveServiceSettings = () => { };
-    this.tryGenerate = () => { };
     this.handleAdvancedSettingsToggle = () => { };
 }
 
@@ -193,6 +202,24 @@ PromptManagerModule.prototype.init = function (moduleConfiguration, serviceSetti
         this.saveServiceSettings().then(() => this.render());
     });
 
+    // Apply character specific overrides for prompts
+    eventSource.on(event_types.OAI_BEFORE_CHATCOMPLETION, (prompts) => {
+        const systemPromptOverride = this.activeCharacter.data.system_prompt ?? null;
+        if (systemPromptOverride) {
+            const override = prompts.get('main');
+            override.content = systemPromptOverride;
+            prompts.set(override, prompts.index('main'));
+        }
+
+        const jailbreakPromptOverride = this.activeCharacter.data.system_prompt ?? null;
+        if (jailbreakPromptOverride) {
+            const override = prompts.get('jailbreak');
+            override.content = jailbreakPromptOverride;
+            prompts.set(override, prompts.index('jailbreak'));
+        }
+    });
+
+    // Trigger re-render when token settings are changed
     document.getElementById('openai_max_context').addEventListener('change', (event) => {
         if (this.activeCharacter) this.render();
     });
diff --git a/public/scripts/openai.js b/public/scripts/openai.js
index 2bdbf14ae..b8b0c507f 100644
--- a/public/scripts/openai.js
+++ b/public/scripts/openai.js
@@ -575,6 +575,7 @@ async function prepareOpenAIMessages({
     try {
         populateChatCompletion(prompts, chatCompletion, {bias, quietPrompt, type});
     } catch (error) {
+        toastr.error('An error occurred while counting tokens.')
         if (error instanceof TokenBudgetExceededError) {
             chatCompletion.log('Token budget exceeded.');
             promptManager.error = 'Not enough free tokens for mandatory prompts. Raise your token Limit or disable custom prompts.';
diff --git a/public/style.css b/public/style.css
index e1f211f27..e7b74384f 100644
--- a/public/style.css
+++ b/public/style.css
@@ -208,6 +208,18 @@ table.responsiveTable {
     padding: 0.25em;
 }
 
+.text_warning {
+    color: var(--orangered);
+}
+
+.text_danger {
+    color: var(--fullred);
+}
+
+.tooltip {
+    cursor: help;
+}
+
 .mes_text p {
     margin-top: 0;
     margin-bottom: 10px;
@@ -5491,3 +5503,4 @@ body.waifuMode .zoomed_avatar {
     line-height: 14px;
 }
 
+