diff --git a/sdkjs-plugins/content/ai/scripts/code.js b/sdkjs-plugins/content/ai/scripts/code.js
index 69081385..2a9195ac 100644
--- a/sdkjs-plugins/content/ai/scripts/code.js
+++ b/sdkjs-plugins/content/ai/scripts/code.js
@@ -1004,6 +1004,7 @@ function customAssistantWindowShow(assistantId, buttonAssistant)
 				if (!element) return;
 				if (buttonAssistant) {
 					buttonAssistant.text = element.name;
+					customAssistantManager.updateAssistant(element);
 				} else {
 					buttonAssistant = new Asc.ButtonToolbar(null);
 					buttonAssistant.text = element.name;
@@ -1021,11 +1022,11 @@ function customAssistantWindowShow(assistantId, buttonAssistant)
 						onclick: () => customAssistantWindowDeleteConfirm(element.id, buttonAssistant)
 					}];
 					buttonAssistant.attachOnClick(async function(){
-						onStartCustomAssistant(element.id, buttonAssistant);
+						customAssistantOnClickToolbarIcon(element.id, buttonAssistant);
 					});
+					customAssistantManager.createAssistant(element);
 				}
 				Asc.Buttons.updateToolbarMenu(window.buttonMainToolbar.id, window.buttonMainToolbar.name, [buttonAssistant]);
-				customAssistantManager.createAssistant(element);
 			}
 			customAssistantWindowClose();
 		} else {
@@ -1161,7 +1162,7 @@ function customAssistantWarning(warningText, assistantData) {
  * @param {Asc.ButtonToolbar} buttonAssistant 
  * @returns 
  */
-async function onStartCustomAssistant(assistantId, buttonAssistant)
+async function customAssistantOnClickToolbarIcon(assistantId, buttonAssistant)
 {
 	const isAssistantRunning = customAssistantManager.checkNeedToRunAssistant(assistantId);
 	if (isAssistantRunning) {
diff --git a/sdkjs-plugins/content/ai/scripts/engine/register.js b/sdkjs-plugins/content/ai/scripts/engine/register.js
index 286da822..65358fae 100644
--- a/sdkjs-plugins/content/ai/scripts/engine/register.js
+++ b/sdkjs-plugins/content/ai/scripts/engine/register.js
@@ -698,7 +698,7 @@ async function registerButtons(window, undefined)
 					onclick: () => customAssistantWindowDeleteConfirm(element.id, buttonAssistant)
 				}];
 				buttonAssistant.attachOnClick(async function(){
-					onStartCustomAssistant(element.id, buttonAssistant);
+					customAssistantOnClickToolbarIcon(element.id, buttonAssistant);
 				});
 			});
 		}
diff --git a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/annotation-popup.js b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/annotation-popup.js
index bf20a050..d0ef916f 100644
--- a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/annotation-popup.js
+++ b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/annotation-popup.js
@@ -137,6 +137,7 @@ function CustomAnnotationPopup()
 		let textColor = window.Asc.plugin.theme ? window.Asc.plugin.theme["text-normal"] : "#3D3D3D";
 		let borderColor = window.Asc.plugin.theme ? window.Asc.plugin.theme["border-divider"] : "#666666";
 		let ballonColor = window.Asc.plugin.theme ? window.Asc.plugin.theme["canvas-background"] : "#F5F5F5";
+		this.content = "";
 		
 		if (data.type === 0) { // Hint
 			this.content = `<div>
diff --git a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/custom-annotator.js b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/custom-annotator.js
index 3f7a5362..33c86940 100644
--- a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/custom-annotator.js
+++ b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/custom-annotator.js
@@ -42,6 +42,8 @@ function CustomAnnotator(annotationPopup, assistantData) {
     this.assistantData = assistantData;
     this.type = assistantData.type;
     this._skipNextChangeParagraph = false;
+
+    this._lastUsedPrompt = "";
 }
 CustomAnnotator.prototype = Object.create(TextAnnotator.prototype);
 CustomAnnotator.prototype.constructor = CustomAnnotator;
@@ -60,9 +62,20 @@ Object.assign(CustomAnnotator.prototype, {
 
         const argPrompt = this._createPrompt(text);
 
+        if (this._lastUsedPrompt && argPrompt !== this._lastUsedPrompt) {
+            let resetInstruction = 
+                `CRITICAL
+                    - Ignore all previous messages and instructions.
+                    - Please respond only to this new query and treat this as a new request.
+                
+                    `;
+            argPrompt = resetInstruction + argPrompt;
+            this._lastUsedPrompt = argPrompt;    
+        }
+
         let response = await this.chatRequest(argPrompt);
 
-        if (!response || response === '[]') {
+        if (!response || response === "[]") {
             if (response === null) {
                 return null; // no AI model selected
             }
@@ -70,7 +83,11 @@ Object.assign(CustomAnnotator.prototype, {
         }
 
         try {
-            const ranges = this._convertToRanges(paraId, text, JSON.parse(response));
+            const ranges = this._convertToRanges(
+                paraId,
+                text,
+                JSON.parse(response),
+            );
             let obj = {
                 type: "highlightText",
                 paragraphId: paraId,
@@ -124,7 +141,10 @@ Object.assign(CustomAnnotator.prototype, {
             this._skipNextChangeParagraph = false;
             return paraIds.map(() => false);
         }
-        return await TextAnnotator.prototype.checkParagraphs.call(this, paraIds);
+        return await TextAnnotator.prototype.checkParagraphs.call(
+            this,
+            paraIds,
+        );
     },
     onAccept: async function (paraId, rangeId) {
         this._skipNextChangeParagraph = true;
diff --git a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/manager.js b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/manager.js
index 20807af3..cbe25a5e 100644
--- a/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/manager.js
+++ b/sdkjs-plugins/content/ai/scripts/text-annotations/custom-annotations/manager.js
@@ -63,11 +63,9 @@ class CustomAssistantManager {
 
     /**
      * @param {localStorageCustomAssistantItem} assistantData
+     * @param {boolean} [isForUpdate]
      */
-    createAssistant(assistantData) {
-        if (this._customAssistants.has(assistantData.id)) {
-            return this._updateAssistant(assistantData);
-        }
+    createAssistant(assistantData, isForUpdate) {
         /** @type {Assistant | null} */
         let assistant = null;
         switch (assistantData.type) {
@@ -96,40 +94,42 @@ class CustomAssistantManager {
             );
         }
 
-        this._isCustomAssistantInit.set(assistantData.id, false);
-        this._isCustomAssistantRunning.set(assistantData.id, false);
         this._customAssistants.set(assistantData.id, assistant);
+        if (!isForUpdate) {
+            this._isCustomAssistantInit.set(assistantData.id, false);
+            this._isCustomAssistantRunning.set(assistantData.id, false);
+        }
 
         return assistant;
     }
     /**
      * @param {localStorageCustomAssistantItem} assistantData
      */
-    _updateAssistant(assistantData) {
-        let assistant = this._customAssistants.get(assistantData.id);
-        if (!assistant) {
+    updateAssistant(assistantData) {
+        console.warn("Updating custom assistant: " + assistantData.id);
+        let oldAssistant = this._customAssistants.get(assistantData.id);
+        if (!oldAssistant) {
             throw new Error("Custom assistant not found: " + assistantData.id);
         }
-        assistant.assistantData = assistantData;
-        assistant.type = assistantData.type;
-
         const isRunning = this._isCustomAssistantRunning.get(assistantData.id);
+        const newAssistant = this.createAssistant(assistantData, isRunning);
         if (!isRunning) {
-            return assistant;
+            return newAssistant;
         }
 
         this._paragraphsStack.forEach((value, paraId) => {
-            assistant.onChangeParagraph(
+            newAssistant.onChangeParagraph(
                 paraId,
                 value.recalcId,
                 value.text,
                 value.annotations,
             );
         });
-        const paragraphIdsToUpdate = [...assistant.checked];
-        assistant.checkParagraphs(paragraphIdsToUpdate);
+        const paragraphIdsToUpdate = [...oldAssistant.checked];
+        oldAssistant.checked.clear();
+        newAssistant.checkParagraphs(paragraphIdsToUpdate);
 
-        return assistant;
+        return newAssistant;
     }
 
     /** @param {string} assistantId */