diff --git a/src/app/api/chat/route.ts b/src/app/api/chat/route.ts
index 607ab2d..68f346b 100644
--- a/src/app/api/chat/route.ts
+++ b/src/app/api/chat/route.ts
@@ -66,11 +66,41 @@ const handleEmitterEvents = async (
   chatId: string,
   startTime: number,
   userMessageId: string,
+  abortController: AbortController,
 ) => {
   let recievedMessage = '';
   let sources: any[] = [];
   let searchQuery: string | undefined;
   let searchUrl: string | undefined;
+  let isStreamActive = true;
+
+  // Keep-alive ping mechanism to prevent reverse proxy timeouts
+  const pingInterval = setInterval(() => {
+    if (isStreamActive) {
+      try {
+        writer.write(
+          encoder.encode(
+            JSON.stringify({
+              type: 'ping',
+              timestamp: Date.now(),
+            }) + '\n',
+          ),
+        );
+      } catch (error) {
+        // If writing fails, the connection is likely closed
+        clearInterval(pingInterval);
+        isStreamActive = false;
+      }
+    } else {
+      clearInterval(pingInterval);
+    }
+  }, 30000); // Send ping every 30 seconds
+
+  // Clean up ping interval if request is cancelled
+  abortController.signal.addEventListener('abort', () => {
+    isStreamActive = false;
+    clearInterval(pingInterval);
+  });
 
   stream.on('data', (data) => {
     const parsedData = JSON.parse(data);
@@ -149,6 +179,9 @@ const handleEmitterEvents = async (
   });
 
   stream.on('end', () => {
+    isStreamActive = false;
+    clearInterval(pingInterval);
+
     const endTime = Date.now();
     const duration = endTime - startTime;
 
@@ -190,6 +223,9 @@ const handleEmitterEvents = async (
       .execute();
   });
   stream.on('error', (data) => {
+    isStreamActive = false;
+    clearInterval(pingInterval);
+
     const parsedData = JSON.parse(data);
     writer.write(
       encoder.encode(
@@ -413,6 +449,7 @@ export const POST = async (req: Request) => {
       message.chatId,
       startTime,
       message.messageId,
+      abortController,
     );
 
     handleHistorySave(message, humanMessageId, body.focusMode, body.files);
diff --git a/src/app/api/search/route.ts b/src/app/api/search/route.ts
index b31babe..c76018f 100644
--- a/src/app/api/search/route.ts
+++ b/src/app/api/search/route.ts
@@ -192,6 +192,7 @@ export const POST = async (req: Request) => {
     const stream = new ReadableStream({
       start(controller) {
         let sources: any[] = [];
+        let isStreamActive = true;
 
         controller.enqueue(
           encoder.encode(
@@ -202,7 +203,31 @@ export const POST = async (req: Request) => {
           ),
         );
 
+        // Keep-alive ping mechanism to prevent reverse proxy timeouts
+        const pingInterval = setInterval(() => {
+          if (isStreamActive && !signal.aborted) {
+            try {
+              controller.enqueue(
+                encoder.encode(
+                  JSON.stringify({
+                    type: 'ping',
+                    timestamp: Date.now(),
+                  }) + '\n',
+                ),
+              );
+            } catch (error) {
+              // If enqueueing fails, the connection is likely closed
+              clearInterval(pingInterval);
+              isStreamActive = false;
+            }
+          } else {
+            clearInterval(pingInterval);
+          }
+        }, 30000); // Send ping every 30 seconds
+
         signal.addEventListener('abort', () => {
+          isStreamActive = false;
+          clearInterval(pingInterval);
           emitter.removeAllListeners();
 
           try {
@@ -244,6 +269,9 @@ export const POST = async (req: Request) => {
         emitter.on('end', () => {
           if (signal.aborted) return;
 
+          isStreamActive = false;
+          clearInterval(pingInterval);
+
           controller.enqueue(
             encoder.encode(
               JSON.stringify({
@@ -257,6 +285,9 @@ export const POST = async (req: Request) => {
         emitter.on('error', (error: any) => {
           if (signal.aborted) return;
 
+          isStreamActive = false;
+          clearInterval(pingInterval);
+
           controller.error(error);
         });
       },
diff --git a/src/components/ChatWindow.tsx b/src/components/ChatWindow.tsx
index f97e827..7581706 100644
--- a/src/components/ChatWindow.tsx
+++ b/src/components/ChatWindow.tsx
@@ -431,6 +431,14 @@ const ChatWindow = ({ id }: { id?: string }) => {
         return;
       }
 
+      // Handle ping messages to keep connection alive (no action needed)
+      if (data.type === 'ping') {
+        console.debug('Ping received');
+        // Ping messages are used to keep the connection alive during long requests
+        // No action is required on the frontend
+        return;
+      }
+
       if (data.type === 'agent_action') {
         const agentActionEvent: AgentActionEvent = {
           action: data.data.action,
diff --git a/src/lib/agents/analyzerAgent.ts b/src/lib/agents/analyzerAgent.ts
index 3fad35b..b35ea37 100644
--- a/src/lib/agents/analyzerAgent.ts
+++ b/src/lib/agents/analyzerAgent.ts
@@ -101,10 +101,27 @@ export class AnalyzerAgent {
       );
 
       console.log('Next action response:', nextActionContent);
-      //}
 
-      if (!nextActionContent.startsWith('good_content')) {
-        if (nextActionContent.startsWith('need_user_info')) {
+      if (
+        !nextActionContent.startsWith('good_content') &&
+        !nextActionContent.startsWith('`good_content`')
+      ) {
+        // If we don't have enough information, but we still have available tasks, proceed with the next task
+
+        if (state.tasks && state.tasks.length > 0) {
+          const hasMoreTasks = state.currentTaskIndex < state.tasks.length - 1;
+
+          if (hasMoreTasks) {
+            return new Command({
+              goto: 'task_manager',
+            });
+          }
+        }
+
+        if (
+          nextActionContent.startsWith('need_user_info') ||
+          nextActionContent.startsWith('`need_user_info`')
+        ) {
           const moreUserInfoPrompt = await ChatPromptTemplate.fromTemplate(
             additionalUserInputPrompt,
           ).format({
diff --git a/src/lib/agents/synthesizerAgent.ts b/src/lib/agents/synthesizerAgent.ts
index 431e921..63297f7 100644
--- a/src/lib/agents/synthesizerAgent.ts
+++ b/src/lib/agents/synthesizerAgent.ts
@@ -52,6 +52,8 @@ Your task is to provide answers that are:
 
 ### Citation Requirements
 - Cite every single fact, statement, or sentence using [number] notation corresponding to the source from the provided \`context\`
+- If a statement is based on AI model inference or training data, it must be marked as \`[AI]\` and not cited from the context
+- If a statement is based on previous messages in the conversation history, it must be marked as \`[Hist]\` and not cited from the context
 - Integrate citations naturally at the end of sentences or clauses as appropriate. For example, "The Eiffel Tower is one of the most visited landmarks in the world[1]."
 - Ensure that **every sentence in your response includes at least one citation**, even when information is inferred or connected to general knowledge available in the provided context
 - Use multiple sources for a single detail if applicable, such as, "Paris is a cultural hub, attracting millions of visitors annually[1][2]."
@@ -68,20 +70,29 @@ Your task is to provide answers that are:
 ${this.personaInstructions}
 </personaInstructions>
 
-User Query: ${state.originalQuery || state.query}
+# Conversation History Context:
+${
+  removeThinkingBlocksFromMessages(state.messages)
+    .map((msg) => `<${msg.getType()}>${msg.content}</${msg.getType()}>`)
+    .join('\n') || 'No previous conversation context'
+}
 
-Available Information:
+# Available Information:
 ${state.relevantDocuments
   .map(
     (doc, index) =>
       `<${index + 1}>\n
-<title>${doc.metadata.title}</title>\n
-${doc.metadata?.url.toLowerCase().includes('file') ? '' : '\n<url>' + doc.metadata.url + '</url>\n'}
-<content>\n${doc.pageContent}\n</content>\n
-</${index + 1}>`,
+    <title>${doc.metadata.title}</title>\n
+    ${doc.metadata?.url.toLowerCase().includes('file') ? '' : '\n<url>' + doc.metadata.url + '</url>\n'}
+    <content>\n${doc.pageContent}\n</content>\n
+    </${index + 1}>`,
   )
   .join('\n')}
-`;
+
+# User Query: ${state.originalQuery || state.query}
+
+Answer the user query:
+  `;
 
       // Stream the response in real-time using LLM streaming capabilities
       let fullResponse = '';
@@ -99,7 +110,6 @@ ${doc.metadata?.url.toLowerCase().includes('file') ? '' : '\n<url>' + doc.metada
 
       const stream = await this.llm.stream(
         [
-          ...removeThinkingBlocksFromMessages(state.messages),
           new SystemMessage(synthesisPrompt),
           new HumanMessage(state.originalQuery || state.query),
         ],
diff --git a/src/lib/agents/taskManagerAgent.ts b/src/lib/agents/taskManagerAgent.ts
index 098a104..3d1cb87 100644
--- a/src/lib/agents/taskManagerAgent.ts
+++ b/src/lib/agents/taskManagerAgent.ts
@@ -121,6 +121,8 @@ export class TaskManagerAgent {
 
       // Parse the response to extract tasks
       const responseContent = taskBreakdownResult.content as string;
+
+      console.log('Task breakdown response:', responseContent);
       const taskLines = responseContent
         .split('\n')
         .filter((line) => line.trim().startsWith('TASK:'))
diff --git a/src/lib/agents/webSearchAgent.ts b/src/lib/agents/webSearchAgent.ts
index f562da5..a2c2e41 100644
--- a/src/lib/agents/webSearchAgent.ts
+++ b/src/lib/agents/webSearchAgent.ts
@@ -17,23 +17,27 @@ import { AgentState } from './agentState';
 import { setTemperature } from '../utils/modelUtils';
 import { Embeddings } from '@langchain/core/embeddings';
 import { removeThinkingBlocksFromMessages } from '../utils/contentUtils';
+import computeSimilarity from '../utils/computeSimilarity';
 
 export class WebSearchAgent {
   private llm: BaseChatModel;
   private emitter: EventEmitter;
   private systemInstructions: string;
   private signal: AbortSignal;
+  private embeddings: Embeddings;
 
   constructor(
     llm: BaseChatModel,
     emitter: EventEmitter,
     systemInstructions: string,
     signal: AbortSignal,
+    embeddings: Embeddings,
   ) {
     this.llm = llm;
     this.emitter = emitter;
     this.systemInstructions = systemInstructions;
     this.signal = signal;
+    this.embeddings = embeddings;
   }
 
   /**
@@ -138,16 +142,33 @@ export class WebSearchAgent {
 
       let bannedSummaryUrls = state.bannedSummaryUrls || [];
       let bannedPreviewUrls = state.bannedPreviewUrls || [];
+      const queryVector = await this.embeddings.embedQuery(
+        state.originalQuery + ' ' + currentTask,
+      );
 
-      // Extract preview content from top 8 search results for analysis
-      const previewContents: PreviewContent[] = searchResults.results
-        .filter(
-          (result) =>
-            !bannedSummaryUrls.includes(result.url) &&
-            !bannedPreviewUrls.includes(result.url),
-        ) // Filter out banned URLs first
-        .slice(0, 8) // Then take top 8 results
-        .map((result) => ({
+      // Filter out banned URLs first
+      const filteredResults = searchResults.results.filter(
+        (result) =>
+          !bannedSummaryUrls.includes(result.url) &&
+          !bannedPreviewUrls.includes(result.url),
+      );
+
+      // Calculate similarities for all filtered results
+      const resultsWithSimilarity = await Promise.all(
+        filteredResults.map(async (result) => {
+          const vector = await this.embeddings.embedQuery(
+            result.title + ' ' + result.content || '',
+          );
+          const similarity = computeSimilarity(vector, queryVector);
+          return { result, similarity };
+        }),
+      );
+
+      // Sort by relevance score and take top 8 results
+      const previewContents: PreviewContent[] = resultsWithSimilarity
+        .sort((a, b) => b.similarity - a.similarity)
+        .slice(0, 8)
+        .map(({ result }) => ({
           title: result.title || 'Untitled',
           snippet: result.content || '',
           url: result.url,
@@ -181,6 +202,7 @@ export class WebSearchAgent {
 
         previewAnalysisResult = await analyzePreviewContent(
           previewContents,
+          state.query,
           currentTask,
           removeThinkingBlocksFromMessages(state.messages),
           this.llm,
@@ -267,7 +289,9 @@ export class WebSearchAgent {
         });
 
         // Summarize the top 2 search results
-        for (const result of searchResults.results.slice(0, 8)) {
+        for (const result of resultsWithSimilarity
+          .slice(0, 8)
+          .map((r) => r.result)) {
           if (this.signal.aborted) {
             console.warn('Search operation aborted by signal');
             break; // Exit if the operation is aborted
@@ -381,7 +405,7 @@ export class WebSearchAgent {
       console.log(responseMessage);
 
       return new Command({
-        goto: 'task_manager', // Route back to task manager to check if more tasks remain
+        goto: 'analyzer', // Route back to analyzer to process the results
         update: {
           messages: [new AIMessage(responseMessage)],
           relevantDocuments: documents,
diff --git a/src/lib/prompts/analyzer.ts b/src/lib/prompts/analyzer.ts
index f6c2fce..aec9fc0 100644
--- a/src/lib/prompts/analyzer.ts
+++ b/src/lib/prompts/analyzer.ts
@@ -9,6 +9,7 @@ Your task is to analyze the provided context and determine if we have enough inf
 # Response Options Decision Tree
 
 ## Step 1: Check if content is sufficient
+- If your training data and the provided context contain enough information to answer the user's query → respond with \`good_content\`
 - If the context fully answers the user's query with complete information → respond with \`good_content\`
 - If the user is requesting to use the existing context to answer their query → respond with \`good_content\`
 - If the user is requesting to avoid web searches → respond with \`good_content\`
diff --git a/src/lib/prompts/taskBreakdown.ts b/src/lib/prompts/taskBreakdown.ts
index 045821c..2d811b4 100644
--- a/src/lib/prompts/taskBreakdown.ts
+++ b/src/lib/prompts/taskBreakdown.ts
@@ -22,6 +22,8 @@ export const taskBreakdownPrompt = `You are a task breakdown specialist. Your jo
 3. Maintain **specific details** like quantities, measurements, and qualifiers
 4. Use **clear, unambiguous language** in each sub-question
 5. Keep the **same question type** (factual, analytical, etc.)
+6. Avoid introducing **new concepts** or information not present in the original question
+7. **Do not** repeat the same question multiple times; each sub-question should be unique and focused on a specific aspect of the original query
 
 ## Examples:
 
@@ -58,6 +60,11 @@ TASK: What are the side effects of aspirin?
 TASK: What are the side effects of ibuprofen?
 TASK: What are the side effects of acetaminophen?
 
+**Input**: "What day is New Year's Day this year?"
+**Analysis**: Single focused question, no breakdown needed
+**Output**:
+TASK: What day is New Year's Day this year?
+
 ## Your Task:
 
 Analyze this user question: "{query}"
diff --git a/src/lib/search/agentSearch.ts b/src/lib/search/agentSearch.ts
index 829cdc1..41729c2 100644
--- a/src/lib/search/agentSearch.ts
+++ b/src/lib/search/agentSearch.ts
@@ -61,6 +61,7 @@ export class AgentSearch {
       emitter,
       systemInstructions,
       signal,
+      embeddings,
     );
     this.analyzerAgent = new AnalyzerAgent(
       llm,
diff --git a/src/lib/utils/analyzePreviewContent.ts b/src/lib/utils/analyzePreviewContent.ts
index 4325276..f8638bf 100644
--- a/src/lib/utils/analyzePreviewContent.ts
+++ b/src/lib/utils/analyzePreviewContent.ts
@@ -19,6 +19,7 @@ export type PreviewContent = {
 export const analyzePreviewContent = async (
   previewContents: PreviewContent[],
   query: string,
+  taskQuery: string,
   chatHistory: BaseMessage[],
   llm: BaseChatModel,
   systemInstructions: string,
@@ -60,14 +61,15 @@ Snippet: ${content.snippet}
     console.log(`Invoking LLM for preview content analysis`);
 
     const analysisResponse = await llm.invoke(
-      `${systemPrompt}You are a preview content analyzer, tasked with determining if search result snippets contain sufficient information to answer a user's query.
+      `${systemPrompt}You are a preview content analyzer, tasked with determining if search result snippets contain sufficient information to answer the Task Query.
 
 # Instructions
-- Analyze the provided search result previews (titles + snippets), and chat history context to determine if they collectively contain enough information to provide a complete and accurate answer to the user's query
+- Analyze the provided search result previews (titles + snippets), and chat history context to determine if they collectively contain enough information to provide a complete and accurate answer to the Task Query
 - You must make a binary decision: either the preview content is sufficient OR it is not sufficient
-- If the preview content can provide a complete answer to the query, respond with "sufficient"
-- If the preview content lacks important details, requires deeper analysis, or cannot fully answer the query, respond with "not_needed: [specific reason why full content analysis is required]"
+- If the preview content can provide a complete answer to the Task Query, respond with "sufficient"
+- If the preview content lacks important details, requires deeper analysis, or cannot fully answer the Task Query, respond with "not_needed: [specific reason why full content analysis is required]"
 - Be specific in your reasoning when the content is not sufficient
+- The original query is provided for additional context, only use it for clarification of overall expectations and intent. You do **not** need to answer the original query directly or completely
 - Output your decision inside a \`decision\` XML tag
 
 # Information Context:
@@ -79,6 +81,9 @@ ${formattedChatHistory ? formattedChatHistory : 'No previous conversation contex
 # User Query:
 ${query}
 
+# Task Query (what to answer):
+${taskQuery}
+
 # Search Result Previews to Analyze:
 ${formattedPreviewContent}
 `,