diff --git a/libs/agent/chat/message_builder.rs b/libs/agent/chat/message_builder.rs
index 7ffe2f9..d93e278 100644
--- a/libs/agent/chat/message_builder.rs
+++ b/libs/agent/chat/message_builder.rs
@@ -7,7 +7,7 @@ use crate::client::types::ChatRequestMessage;
 use crate::compact::CompactService;
 use crate::embed::EmbedService;
 use crate::error::Result;
-use crate::perception::{PerceptionService, SkillEntry};
+use crate::perception::{PerceptionService, SkillContext, SkillEntry};
 
 #[derive(Clone)]
 pub struct MessageBuilder {
@@ -393,21 +393,25 @@ impl MessageBuilder {
                     .await;
             }
         }
-        let mut seen = std::collections::HashSet::new();
         let mut result = Vec::new();
-        for ctx in vector_skills {
-            if seen.insert(ctx.label.clone()) {
-                result.push(ctx);
-            }
-        }
         for ctx in keyword_skills {
-            if seen.insert(ctx.label.clone()) {
-                result.push(ctx);
-            }
+            Self::push_unique_skill_context(&mut result, ctx);
+        }
+        for ctx in vector_skills {
+            Self::push_unique_skill_context(&mut result, ctx);
         }
         result
     }
 
+    pub fn push_unique_skill_context(result: &mut Vec<SkillContext>, ctx: SkillContext) {
+        let key = ctx.dedupe_key();
+        if result.iter().any(|existing| existing.dedupe_key() == key) {
+            return;
+        }
+        result.push(ctx);
+        result.sort_by_key(|ctx| ctx.activation.rank());
+    }
+
     async fn build_memory_context(
         &self,
         request: &AiRequest,
diff --git a/libs/agent/chat/nonstreaming_execution.rs b/libs/agent/chat/nonstreaming_execution.rs
index 8756bdc..1537a7b 100644
--- a/libs/agent/chat/nonstreaming_execution.rs
+++ b/libs/agent/chat/nonstreaming_execution.rs
@@ -94,22 +94,10 @@ pub async fn execute_process(
                 .collect();
             let tool_names: Vec<String> = calls.iter().map(|call| call.name.clone()).collect();
 
-            let tool_messages = execute_tools(
-                &request,
-                &calls,
-                session_id,
-                tool_registry,
-                message_builder,
-            )
-            .await;
+            let tool_messages =
+                execute_tools(&request, &calls, session_id, tool_registry, message_builder).await;
             messages.extend(tool_messages);
-            inject_passive_skills(
-                &request,
-                message_builder,
-                &tool_names,
-                &mut messages,
-            )
-            .await;
+            inject_passive_skills(&request, message_builder, &tool_names, &mut messages).await;
 
             tool_depth += 1;
             if tool_depth >= max_tool_depth {
@@ -261,7 +249,7 @@ async fn inject_passive_skills(
         .all(&request.db)
         .await
     {
-        let skill_entries: Vec<SkillEntry> = skills
+        let mut skill_entries: Vec<SkillEntry> = skills
             .into_iter()
             .map(|s| SkillEntry {
                 slug: s.slug,
@@ -270,6 +258,16 @@ async fn inject_passive_skills(
                 content: s.content,
             })
             .collect();
+        for built_in in crate::skills::all_skills() {
+            if !skill_entries.iter().any(|s| s.slug == built_in.slug) {
+                skill_entries.push(SkillEntry {
+                    slug: built_in.slug.to_string(),
+                    name: built_in.name.to_string(),
+                    description: Some(built_in.description.to_string()),
+                    content: built_in.content.clone(),
+                });
+            }
+        }
         let tool_events: Vec<ToolCallEvent> = tool_names
             .iter()
             .map(|name| ToolCallEvent {
@@ -277,14 +275,18 @@ async fn inject_passive_skills(
                 arguments: String::new(),
             })
             .collect();
+        let mut contexts = Vec::new();
         for event in &tool_events {
             if let Some(ctx) = message_builder
                 .perception_service
                 .passive
                 .detect(event, &skill_entries)
             {
-                messages.push(ctx.to_system_message());
+                MessageBuilder::push_unique_skill_context(&mut contexts, ctx);
             }
         }
+        for ctx in contexts {
+            messages.push(ctx.to_system_message());
+        }
     }
 }
diff --git a/libs/agent/chat/streaming_execution.rs b/libs/agent/chat/streaming_execution.rs
index dfc9954..b051697 100644
--- a/libs/agent/chat/streaming_execution.rs
+++ b/libs/agent/chat/streaming_execution.rs
@@ -9,9 +9,9 @@ use super::message_builder::MessageBuilder;
 use super::service::StreamResult;
 use super::session_recording::record_ai_session;
 use super::{AiChunkType, AiRequest, AiStreamChunk, StreamCallback};
-use crate::client::types::{ChatRequestMessage, ToolCall};
 use crate::client::AiClientConfig;
-use crate::client::{call_stream, StreamChunk, StreamChunkType, StreamedToolCall};
+use crate::client::types::{ChatRequestMessage, ToolCall};
+use crate::client::{StreamChunk, StreamChunkType, StreamedToolCall, call_stream};
 use crate::error::Result;
 use crate::perception::{SkillEntry, ToolCallEvent};
 use crate::tool::{ToolCall as AgentToolCall, ToolContext, ToolExecutor};
@@ -266,7 +266,8 @@ async fn drain_tool_call_notifications(
                     chunk_type: AiChunkType::ToolCall,
                     metadata: Some(metadata),
                     children_id: None,
-                }).await;
+                })
+                .await;
                 all_chunks.push(StreamChunk {
                     chunk_type: StreamChunkType::ToolCall,
                     content: tool_display,
@@ -467,7 +468,7 @@ async fn inject_passive_skills_stream(
         .all(&request.db)
         .await
     {
-        let skill_entries: Vec<SkillEntry> = skills
+        let mut skill_entries: Vec<SkillEntry> = skills
             .into_iter()
             .map(|s| SkillEntry {
                 slug: s.slug,
@@ -476,6 +477,16 @@ async fn inject_passive_skills_stream(
                 content: s.content,
             })
             .collect();
+        for built_in in crate::skills::all_skills() {
+            if !skill_entries.iter().any(|s| s.slug == built_in.slug) {
+                skill_entries.push(SkillEntry {
+                    slug: built_in.slug.to_string(),
+                    name: built_in.name.to_string(),
+                    description: Some(built_in.description.to_string()),
+                    content: built_in.content.clone(),
+                });
+            }
+        }
         let tool_events: Vec<ToolCallEvent> = tool_calls
             .iter()
             .map(|tc| ToolCallEvent {
@@ -483,14 +494,18 @@ async fn inject_passive_skills_stream(
                 arguments: tc.arguments.clone(),
             })
             .collect();
+        let mut contexts = Vec::new();
         for event in &tool_events {
             if let Some(ctx) = message_builder
                 .perception_service
                 .passive
                 .detect(event, &skill_entries)
             {
-                messages.push(ctx.to_system_message());
+                MessageBuilder::push_unique_skill_context(&mut contexts, ctx);
             }
         }
+        for ctx in contexts {
+            messages.push(ctx.to_system_message());
+        }
     }
 }