diff --git a/FEATURE_PARITY.md b/FEATURE_PARITY.md
index d6952cbd..61e32b0c 100644
--- a/FEATURE_PARITY.md
+++ b/FEATURE_PARITY.md
@@ -53,7 +53,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Trusted-proxy auth mode | ✅ | ❌ | Header-based auth for reverse proxies |
 | APNs push pipeline | ✅ | ❌ | Wake disconnected iOS nodes via push |
 | Oversized payload guard | ✅ | 🚧 | HTTP webhook has 64KB body limit + Content-Length check; no chat.history cap |
-| Pre-prompt context diagnostics | ✅ | ❌ | Context size logging before prompt |
+| Pre-prompt context diagnostics | ✅ | 🚧 | Token breakdown logged before LLM call (conversational dispatcher path); other LLM entry points not yet covered |
 
 ### Owner: _Unassigned_
 
diff --git a/src/agent/dispatcher.rs b/src/agent/dispatcher.rs
index 99feed9d..b1678d89 100644
--- a/src/agent/dispatcher.rs
+++ b/src/agent/dispatcher.rs
@@ -10,6 +10,7 @@ use tokio::task::JoinSet;
 use uuid::Uuid;
 
 use crate::agent::Agent;
+use crate::agent::context_monitor::{ContextBreakdown, estimate_text_tokens};
 use crate::agent::session::{PendingApproval, Session, ThreadState};
 use crate::channels::{IncomingMessage, StatusUpdate};
 use crate::context::JobContext;
@@ -254,6 +255,27 @@ impl Agent {
                 );
             }
 
+            // Pre-prompt context diagnostics: log token breakdown before LLM call
+            {
+                let breakdown = ContextBreakdown::analyze(&context_messages);
+                let system_prompt_tokens =
+                    estimate_text_tokens(context.system_prompt.as_deref().unwrap_or(""));
+                let total_tokens = breakdown.total_tokens + system_prompt_tokens;
+                tracing::debug!(
+                    iteration,
+                    messages = breakdown.message_count,
+                    total_tokens,
+                    system_prompt_tokens,
+                    system_msg_tokens = breakdown.system_tokens,
+                    user_tokens = breakdown.user_tokens,
+                    assistant_tokens = breakdown.assistant_tokens,
+                    tool_tokens = breakdown.tool_tokens,
+                    tools_available = context.available_tools.len(),
+                    force_text,
+                    "Pre-prompt context diagnostics"
+                );
+            }
+
             let _ = self
                 .channels
                 .send_status(