diff --git a/src/harness/message/mod.rs b/src/harness/message/mod.rs
index 679aabc..67ffe03 100644
--- a/src/harness/message/mod.rs
+++ b/src/harness/message/mod.rs
@@ -14,6 +14,16 @@ mod types;
 
 pub use types::*;
 
+/// Approximate token-estimation weight of a single image content block, in
+/// "characters" (the token estimator divides char weight by 4, so this is
+/// ~1024 tokens per image).
+///
+/// Vision models tokenize an image into a roughly fixed count that is
+/// independent of the encoded byte length, so this is a flat conservative
+/// estimate rather than the (potentially huge, e.g. a base64 `data:` URI)
+/// [`ImageRef::url`] length, which would wildly over-count.
+const IMAGE_CHAR_WEIGHT: usize = 4 * 1024;
+
 impl ContentBlock {
     /// Returns the text of this block if it is a [`ContentBlock::Text`].
     ///
@@ -55,6 +65,29 @@ impl ContentBlock {
             ContentBlock::Thinking { .. } | ContentBlock::RedactedThinking { .. }
         )
     }
+
+    /// Approximate character weight of this block for token estimation.
+    ///
+    /// Unlike [`as_text`](Self::as_text) — which returns only visible
+    /// [`Text`](Self::Text) so reasoning never leaks into assistant output —
+    /// this accounts for *every* block that occupies model context: text,
+    /// structured JSON, reasoning ([`Thinking`](Self::Thinking) /
+    /// [`RedactedThinking`](Self::RedactedThinking)), provider extensions, and
+    /// a flat [`IMAGE_CHAR_WEIGHT`] per image. It is used only by token
+    /// budgeting / compaction gating, never by the visible-text accessors, so a
+    /// transcript dominated by images, large tool-result JSON, or model
+    /// reasoning no longer under-counts to near-zero and silently defeats
+    /// summarization.
+    pub fn estimated_char_weight(&self) -> usize {
+        match self {
+            ContentBlock::Text(text) => text.chars().count(),
+            ContentBlock::Json(value) => value.to_string().chars().count(),
+            ContentBlock::Image(_) => IMAGE_CHAR_WEIGHT,
+            ContentBlock::Thinking { text, .. } => text.chars().count(),
+            ContentBlock::RedactedThinking { data } => data.chars().count(),
+            ContentBlock::ProviderExtension(value) => value.to_string().chars().count(),
+        }
+    }
 }
 
 /// Concatenates the text of all [`ContentBlock::Text`] blocks in `content`.
@@ -128,6 +161,28 @@ impl Message {
             .map(|t| t.chars().count())
             .sum()
     }
+
+    /// Approximate character weight of the message across *all* content blocks
+    /// (text, JSON, images, reasoning, provider extensions), for token
+    /// estimation and context-window gating.
+    ///
+    /// Distinct from [`char_len`](Self::char_len), which counts only visible
+    /// text: a transcript dominated by images, large tool-result JSON, or model
+    /// reasoning under-counts badly under `char_len`, so compaction/trim would
+    /// silently never trigger even as the real context window overflows. See
+    /// [`ContentBlock::estimated_char_weight`].
+    pub fn estimated_char_weight(&self) -> usize {
+        let content = match self {
+            Message::System(m) => &m.content,
+            Message::User(m) => &m.content,
+            Message::Assistant(m) => &m.content,
+            Message::Tool(m) => &m.content,
+        };
+        content
+            .iter()
+            .map(ContentBlock::estimated_char_weight)
+            .sum()
+    }
 }
 
 #[cfg(test)]
diff --git a/src/harness/message/test.rs b/src/harness/message/test.rs
index bf5d6dc..5db7b96 100644
--- a/src/harness/message/test.rs
+++ b/src/harness/message/test.rs
@@ -49,6 +49,46 @@ fn char_len_matches_text_char_count_including_multibyte() {
     );
 }
 
+#[test]
+fn estimated_char_weight_counts_non_text_blocks() {
+    let text = "hello";
+    let reasoning = "some private reasoning";
+    let json_block = json!({"key": "value", "n": 42});
+    let msg = Message::User(UserMessage {
+        content: vec![
+            ContentBlock::Text(text.into()),
+            ContentBlock::Json(json_block.clone()),
+            ContentBlock::thinking(reasoning),
+        ],
+    });
+
+    // Visible-text accounting still ignores JSON and reasoning.
+    assert_eq!(msg.char_len(), text.chars().count());
+
+    // Token-estimation weight additionally counts JSON and reasoning, which
+    // occupy real context, so it is strictly larger than the visible-text len.
+    let expected =
+        text.chars().count() + json_block.to_string().chars().count() + reasoning.chars().count();
+    assert_eq!(msg.estimated_char_weight(), expected);
+    assert!(msg.estimated_char_weight() > msg.char_len());
+}
+
+#[test]
+fn estimated_char_weight_costs_images_that_carry_no_visible_text() {
+    let msg = Message::User(UserMessage {
+        content: vec![ContentBlock::Image(ImageRef {
+            url: "data:image/png;base64,AAAA".into(),
+            mime_type: Some("image/png".into()),
+        })],
+    });
+
+    // An image contributes no visible text but a flat, non-trivial weight, so a
+    // vision-heavy transcript can no longer under-count to zero and defeat
+    // compaction gating.
+    assert_eq!(msg.char_len(), 0);
+    assert_eq!(msg.estimated_char_weight(), super::IMAGE_CHAR_WEIGHT);
+}
+
 #[test]
 fn assistant_holds_tool_calls_and_usage() {
     let msg = Message::Assistant(AssistantMessage {
diff --git a/src/harness/model/mod.rs b/src/harness/model/mod.rs
index aa24cb1..ea3e6b8 100644
--- a/src/harness/model/mod.rs
+++ b/src/harness/model/mod.rs
@@ -753,10 +753,10 @@ impl StreamAccumulator {
     fn push_tool_chunk(&mut self, call_id: &str, content: &str, tool_name: Option<&str>) {
         if let Some(entry) = self.tool_chunks.iter_mut().find(|(id, ..)| id == call_id) {
             entry.1.push_str(content);
-            if entry.2.is_none() {
-                if let Some(name) = tool_name.filter(|n| !n.is_empty()) {
-                    entry.2 = Some(name.to_string());
-                }
+            if entry.2.is_none()
+                && let Some(name) = tool_name.filter(|n| !n.is_empty())
+            {
+                entry.2 = Some(name.to_string());
             }
         } else {
             self.tool_chunks.push((
diff --git a/src/harness/stream/mod.rs b/src/harness/stream/mod.rs
index 14411f0..1712142 100644
--- a/src/harness/stream/mod.rs
+++ b/src/harness/stream/mod.rs
@@ -143,6 +143,5 @@ pub fn stream(chunks: &[StreamChunk], modes: &[StreamMode]) -> Vec<StreamChunk>
         .collect()
 }
 
-#[cfg(test)]
 #[cfg(test)]
 mod test;
diff --git a/src/harness/summarization/mod.rs b/src/harness/summarization/mod.rs
index 3938d8e..74b0c6d 100644
--- a/src/harness/summarization/mod.rs
+++ b/src/harness/summarization/mod.rs
@@ -48,10 +48,16 @@ pub fn estimate_tokens(text: &str) -> u64 {
 }
 
 /// Estimate the total tokens for a [`Message`] using the same `chars / 4`
-/// heuristic as [`estimate_tokens`], but counting characters directly over the
-/// message's text blocks rather than allocating the concatenated string first.
+/// heuristic as [`estimate_tokens`], counting weight directly over the message
+/// content rather than allocating the concatenated string first.
+///
+/// Uses [`Message::estimated_char_weight`] (all content blocks) rather than
+/// `char_len` (visible text only): images, structured JSON, and model reasoning
+/// occupy real context, so counting only text would under-estimate a
+/// multimodal or tool-heavy transcript to near-zero and silently prevent
+/// [`SummarizationPolicy::should_summarize`] from ever triggering.
 fn message_token_estimate(msg: &Message) -> u64 {
-    let chars = msg.char_len() as u64;
+    let chars = msg.estimated_char_weight() as u64;
     if chars == 0 { 0 } else { (chars / 4).max(1) }
 }