diff --git a/src/ai/handlers.rs b/src/ai/handlers.rs
index 210aece..2d4f905 100644
--- a/src/ai/handlers.rs
+++ b/src/ai/handlers.rs
@@ -249,7 +249,7 @@ pub async fn generate_agentic_insight_handler(
     let max_iterations: usize = std::env::var("AGENTIC_MAX_ITERATIONS")
         .ok()
         .and_then(|v| v.parse().ok())
-        .unwrap_or(10);
+        .unwrap_or(12);
 
     span.set_attribute(KeyValue::new("max_iterations", max_iterations as i64));
 
diff --git a/src/ai/insight_generator.rs b/src/ai/insight_generator.rs
index e7af5ca..4c0f266 100644
--- a/src/ai/insight_generator.rs
+++ b/src/ai/insight_generator.rs
@@ -2482,17 +2482,16 @@ Return ONLY the summary, nothing else."#,
             None => String::new(),
         };
         let base_system = format!(
-            "You are a personal photo memory assistant helping to reconstruct a memory from a photo. \
-            You are writing from the perspective of Cameron, the owner of this photo collection.{cameron_id_note}\n\n\
+            "You are a personal photo memory assistant helping to reconstruct a memory from a photo.{cameron_id_note}\n\n\
             IMPORTANT INSTRUCTIONS:\n\
             1. You MUST call multiple tools to gather context BEFORE writing any final insight. Do not produce a final answer after only one or two tool calls.\n\
             2. Always call ALL of the following tools that are relevant: search_rag (search conversation summaries), get_sms_messages (fetch nearby messages), get_calendar_events (check what was happening that day), get_location_history (find where this was taken), get_file_tags (retrieve tags).\n\
-            3. Use recall_facts_for_photo to load any previously stored knowledge about subjects in this photo.\n\
-            4. Use recall_entities to look up known people, places, or things that appear in this photo.\n\
-            5. When you identify people, places, events, or notable things in this photo: use store_entity to record them and store_fact to record key facts (relationships, roles, attributes). This builds a persistent memory for future insights.\n\
-            6. Only produce your final insight AFTER you have gathered context from at least 3-4 tools.\n\
-            7. If a tool returns no results, that is useful information — continue calling the remaining tools anyway.\n\
-            8. Your final insight must be written in first person as Cameron, in a journal/memoir style.",
+            3. When calling get_sms_messages and search_rag, always make at least one call WITHOUT a contact filter to capture what else was happening in Cameron's life around this date — other conversations, events, and activities provide important wider context even when a specific contact is known.\n\
+            4. Use recall_facts_for_photo to load any previously stored knowledge about subjects in this photo.\n\
+            5. Use recall_entities to look up known people, places, or things that appear in this photo.\n\
+            6. When you identify people, places, events, or notable things in this photo: use store_entity to record them and store_fact to record key facts (relationships, roles, attributes). This builds a persistent memory for future insights.\n\
+            7. Only produce your final insight AFTER you have gathered context from at least 3-4 tools.\n\
+            8. If a tool returns no results, that is useful information — continue calling the remaining tools anyway.",
             cameron_id_note = cameron_id_note
         );
         let system_content = if let Some(ref custom) = custom_system_prompt {
@@ -2525,14 +2524,14 @@ Return ONLY the summary, nothing else."#,
             .unwrap_or_else(|| "Contact/Person: unknown".to_string());
 
         let user_content = format!(
-            "Please analyze this photo and gather context to write a personal journal-style insight.\n\n\
+            "Please analyze this photo and gather context to write an insight.\n\n\
              Photo file path: {}\n\
              Date taken: {}\n\
              {}\n\
              {}\n\
              {}\n\n\
              Use the available tools to gather more context about this moment (messages, calendar events, location history, etc.), \
-             then write a detailed personal insight with a title and summary. Write in first person as Cameron.",
+             then write a detailed insight with a title and summary.",
             file_path,
             date_taken.format("%B %d, %Y"),
             contact_info,