diff --git a/apps/server/src/services/llm/constants/llm_prompt_constants.ts b/apps/server/src/services/llm/constants/llm_prompt_constants.ts
index 63dc72987..6a061aea9 100644
--- a/apps/server/src/services/llm/constants/llm_prompt_constants.ts
+++ b/apps/server/src/services/llm/constants/llm_prompt_constants.ts
@@ -184,6 +184,22 @@ When responding:
 
         INSTRUCTIONS_WRAPPER: (instructions: string) =>
             `<instructions>\n${instructions}\n</instructions>`,
+            
+        // Tool instructions for Anthropic Claude
+        TOOL_INSTRUCTIONS: `<instructions>
+When using tools to search for information, follow these requirements:
+
+1. ALWAYS TRY MULTIPLE SEARCH APPROACHES before concluding information isn't available
+2. YOU MUST PERFORM AT LEAST 3 DIFFERENT SEARCHES with varied parameters before giving up
+3. If a search returns no results:
+   - Try broader terms (e.g., "Kubernetes" instead of "Kubernetes deployment")
+   - Use synonyms (e.g., "meeting" instead of "conference")
+   - Remove specific qualifiers (e.g., "report" instead of "Q3 financial report")
+   - Try different search tools (vector_search for conceptual matches, keyword_search for exact matches)
+4. NEVER tell the user "there are no notes about X" until you've tried multiple search variations
+5. EXPLAIN your search strategy when adjusting parameters (e.g., "I'll try a broader search for...")
+6. When searches fail, AUTOMATICALLY try different approaches rather than asking the user what to do
+</instructions>`,
 
         ACKNOWLEDGMENT: "I understand. I'll follow those instructions.",
         CONTEXT_ACKNOWLEDGMENT: "I'll help you with your notes based on the context provided.",
@@ -203,7 +219,21 @@ ${context}
 
 Focus on relevant information from these notes when answering.
 Be concise and informative in your responses.
-</system_prompt>`
+</system_prompt>`,
+        
+        // Tool instructions for OpenAI models
+        TOOL_INSTRUCTIONS: `When using tools to search for information, you must follow these requirements:
+
+1. ALWAYS TRY MULTIPLE SEARCH APPROACHES before concluding information isn't available
+2. YOU MUST PERFORM AT LEAST 3 DIFFERENT SEARCHES with varied parameters before giving up
+3. If a search returns no results:
+   - Try broader terms (e.g., "Kubernetes" instead of "Kubernetes deployment")
+   - Use synonyms (e.g., "meeting" instead of "conference")
+   - Remove specific qualifiers (e.g., "report" instead of "Q3 financial report")
+   - Try different search tools (vector_search for conceptual matches, keyword_search for exact matches)
+4. NEVER tell the user "there are no notes about X" until you've tried multiple search variations
+5. EXPLAIN your search strategy when adjusting parameters (e.g., "I'll try a broader search for...")
+6. When searches fail, AUTOMATICALLY try different approaches rather than asking the user what to do`
     },
 
     OLLAMA: {
diff --git a/apps/server/src/services/llm/formatters/openai_formatter.ts b/apps/server/src/services/llm/formatters/openai_formatter.ts
index 301edd3a7..d09a3675a 100644
--- a/apps/server/src/services/llm/formatters/openai_formatter.ts
+++ b/apps/server/src/services/llm/formatters/openai_formatter.ts
@@ -1,7 +1,7 @@
 import sanitizeHtml from 'sanitize-html';
 import type { Message } from '../ai_interface.js';
 import { BaseMessageFormatter } from './base_formatter.js';
-import { PROVIDER_PROMPTS, FORMATTING_PROMPTS } from '../constants/llm_prompt_constants.js';
+import { PROVIDER_PROMPTS } from '../constants/llm_prompt_constants.js';
 import { LLM_CONSTANTS } from '../constants/provider_constants.js';
 import {
     HTML_ALLOWED_TAGS,
@@ -10,6 +10,7 @@ import {
     HTML_ENTITY_REPLACEMENTS,
     FORMATTER_LOGS
 } from '../constants/formatter_constants.js';
+import log from '../../log.js';
 
 /**
  * OpenAI-specific message formatter
@@ -24,8 +25,13 @@ export class OpenAIMessageFormatter extends BaseMessageFormatter {
 
     /**
      * Format messages for the OpenAI API
+     * @param messages The messages to format
+     * @param systemPrompt Optional system prompt to use
+     * @param context Optional context to include
+     * @param preserveSystemPrompt When true, preserves existing system messages
+     * @param useTools Flag indicating if tools will be used in this request
      */
-    formatMessages(messages: Message[], systemPrompt?: string, context?: string): Message[] {
+    formatMessages(messages: Message[], systemPrompt?: string, context?: string, preserveSystemPrompt?: boolean, useTools?: boolean): Message[] {
         const formattedMessages: Message[] = [];
 
         // Check if we already have a system message
@@ -47,9 +53,22 @@ export class OpenAIMessageFormatter extends BaseMessageFormatter {
         }
         // If we don't have explicit context but have a system prompt
         else if (!hasSystemMessage && systemPrompt) {
+            let baseSystemPrompt = systemPrompt || PROVIDER_PROMPTS.COMMON.DEFAULT_ASSISTANT_INTRO;
+            
+            // Check if this is a tool-using conversation
+            const hasPreviousToolCalls = messages.some(msg => msg.tool_calls && msg.tool_calls.length > 0);
+            const hasToolResults = messages.some(msg => msg.role === 'tool');
+            const isToolUsingConversation = useTools || hasPreviousToolCalls || hasToolResults;
+            
+            // Add tool instructions for OpenAI when tools are being used
+            if (isToolUsingConversation && PROVIDER_PROMPTS.OPENAI.TOOL_INSTRUCTIONS) {
+                log.info('Adding tool instructions to system prompt for OpenAI');
+                baseSystemPrompt = `${baseSystemPrompt}\n\n${PROVIDER_PROMPTS.OPENAI.TOOL_INSTRUCTIONS}`;
+            }
+            
             formattedMessages.push({
                 role: 'system',
-                content: systemPrompt
+                content: baseSystemPrompt
             });
         }
         // If neither context nor system prompt is provided, use default system prompt
diff --git a/apps/server/src/services/llm/providers/openai_service.ts b/apps/server/src/services/llm/providers/openai_service.ts
index a9a833163..e0633ca1f 100644
--- a/apps/server/src/services/llm/providers/openai_service.ts
+++ b/apps/server/src/services/llm/providers/openai_service.ts
@@ -3,6 +3,8 @@ import { BaseAIService } from '../base_ai_service.js';
 import type { ChatCompletionOptions, ChatResponse, Message, StreamChunk } from '../ai_interface.js';
 import { getOpenAIOptions } from './providers.js';
 import OpenAI from 'openai';
+import { PROVIDER_PROMPTS } from '../constants/llm_prompt_constants.js';
+import log from '../../log.js';
 
 export class OpenAIService extends BaseAIService {
     private openai: OpenAI | null = null;
@@ -36,7 +38,17 @@ export class OpenAIService extends BaseAIService {
         // Initialize the OpenAI client
         const client = this.getClient(providerOptions.apiKey, providerOptions.baseUrl);
 
-        const systemPrompt = this.getSystemPrompt(providerOptions.systemPrompt || options.getOption('aiSystemPrompt'));
+        // Get base system prompt
+        let systemPrompt = this.getSystemPrompt(providerOptions.systemPrompt || options.getOption('aiSystemPrompt'));
+        
+        // Check if tools are enabled for this request
+        const willUseTools = providerOptions.enableTools && providerOptions.tools && providerOptions.tools.length > 0;
+        
+        // Add tool instructions to system prompt if tools are enabled
+        if (willUseTools && PROVIDER_PROMPTS.OPENAI.TOOL_INSTRUCTIONS) {
+            log.info('Adding tool instructions to system prompt for OpenAI');
+            systemPrompt = `${systemPrompt}\n\n${PROVIDER_PROMPTS.OPENAI.TOOL_INSTRUCTIONS}`;
+        }
 
         // Ensure we have a system message
         const systemMessageExists = messages.some(m => m.role === 'system');
@@ -67,7 +79,7 @@ export class OpenAIService extends BaseAIService {
             }
 
             // Log the request parameters
-            console.log('OpenAI API Request:', JSON.stringify({
+            log.info(`OpenAI API Request: ${JSON.stringify({
                 endpoint: 'chat.completions.create',
                 model: params.model,
                 messages: params.messages,
@@ -76,7 +88,7 @@ export class OpenAIService extends BaseAIService {
                 stream: params.stream,
                 tools: params.tools,
                 tool_choice: params.tool_choice
-            }, null, 2));
+            }, null, 2)}`);
 
             // If streaming is requested
             if (providerOptions.stream) {
@@ -84,10 +96,10 @@ export class OpenAIService extends BaseAIService {
 
                 // Get stream from OpenAI SDK
                 const stream = await client.chat.completions.create(params);
-                console.log('OpenAI API Stream Started');
+                log.info('OpenAI API Stream Started');
 
                 // Create a closure to hold accumulated tool calls
-                let accumulatedToolCalls: any[] = [];
+                const accumulatedToolCalls: OpenAI.Chat.ChatCompletionMessageToolCall[] = [];
 
                 // Return a response with the stream handler
                 const response: ChatResponse = {
@@ -104,7 +116,8 @@ export class OpenAIService extends BaseAIService {
                             if (Symbol.asyncIterator in stream) {
                                 for await (const chunk of stream as AsyncIterable<OpenAI.Chat.ChatCompletionChunk>) {
                                     // Log each chunk received from OpenAI
-                                    console.log('OpenAI API Stream Chunk:', JSON.stringify(chunk, null, 2));
+                                    // Use info level as debug is not available
+                                    log.info(`OpenAI API Stream Chunk: ${JSON.stringify(chunk, null, 2)}`);
 
                                     const content = chunk.choices[0]?.delta?.content || '';
                                     const isDone = !!chunk.choices[0]?.finish_reason;