diff --git a/rust/crates/runtime/src/compact.rs b/rust/crates/runtime/src/compact.rs
index 42e63ed..e227019 100644
--- a/rust/crates/runtime/src/compact.rs
+++ b/rust/crates/runtime/src/compact.rs
@@ -152,6 +152,31 @@ fn summarize_messages(messages: &[ConversationMessage]) -> String {
         lines.push(format!("- Tools mentioned: {}.", tool_names.join(", ")));
     }
 
+    let recent_user_requests = collect_recent_role_summaries(messages, MessageRole::User, 3);
+    if !recent_user_requests.is_empty() {
+        lines.push("- Recent user requests:".to_string());
+        lines.extend(
+            recent_user_requests
+                .into_iter()
+                .map(|request| format!("  - {request}")),
+        );
+    }
+
+    let pending_work = infer_pending_work(messages);
+    if !pending_work.is_empty() {
+        lines.push("- Pending work:".to_string());
+        lines.extend(pending_work.into_iter().map(|item| format!("  - {item}")));
+    }
+
+    let key_files = collect_key_files(messages);
+    if !key_files.is_empty() {
+        lines.push(format!("- Key files referenced: {}.", key_files.join(", ")));
+    }
+
+    if let Some(current_work) = infer_current_work(messages) {
+        lines.push(format!("- Current work: {current_work}"));
+    }
+
     lines.push("- Key timeline:".to_string());
     for message in messages {
         let role = match message.role {
@@ -189,6 +214,106 @@ fn summarize_block(block: &ContentBlock) -> String {
     truncate_summary(&raw, 160)
 }
 
+fn collect_recent_role_summaries(
+    messages: &[ConversationMessage],
+    role: MessageRole,
+    limit: usize,
+) -> Vec<String> {
+    messages
+        .iter()
+        .filter(|message| message.role == role)
+        .rev()
+        .filter_map(|message| first_text_block(message))
+        .take(limit)
+        .map(|text| truncate_summary(text, 160))
+        .collect::<Vec<_>>()
+        .into_iter()
+        .rev()
+        .collect()
+}
+
+fn infer_pending_work(messages: &[ConversationMessage]) -> Vec<String> {
+    messages
+        .iter()
+        .rev()
+        .filter_map(first_text_block)
+        .filter(|text| {
+            let lowered = text.to_ascii_lowercase();
+            lowered.contains("todo")
+                || lowered.contains("next")
+                || lowered.contains("pending")
+                || lowered.contains("follow up")
+                || lowered.contains("remaining")
+        })
+        .take(3)
+        .map(|text| truncate_summary(text, 160))
+        .collect::<Vec<_>>()
+        .into_iter()
+        .rev()
+        .collect()
+}
+
+fn collect_key_files(messages: &[ConversationMessage]) -> Vec<String> {
+    let mut files = messages
+        .iter()
+        .flat_map(|message| message.blocks.iter())
+        .map(|block| match block {
+            ContentBlock::Text { text } => text.as_str(),
+            ContentBlock::ToolUse { input, .. } => input.as_str(),
+            ContentBlock::ToolResult { output, .. } => output.as_str(),
+        })
+        .flat_map(extract_file_candidates)
+        .collect::<Vec<_>>();
+    files.sort();
+    files.dedup();
+    files.into_iter().take(8).collect()
+}
+
+fn infer_current_work(messages: &[ConversationMessage]) -> Option<String> {
+    messages
+        .iter()
+        .rev()
+        .filter_map(first_text_block)
+        .find(|text| !text.trim().is_empty())
+        .map(|text| truncate_summary(text, 200))
+}
+
+fn first_text_block(message: &ConversationMessage) -> Option<&str> {
+    message.blocks.iter().find_map(|block| match block {
+        ContentBlock::Text { text } if !text.trim().is_empty() => Some(text.as_str()),
+        ContentBlock::ToolUse { .. }
+        | ContentBlock::ToolResult { .. }
+        | ContentBlock::Text { .. } => None,
+    })
+}
+
+fn has_interesting_extension(candidate: &str) -> bool {
+    std::path::Path::new(candidate)
+        .extension()
+        .and_then(|extension| extension.to_str())
+        .is_some_and(|extension| {
+            ["rs", "ts", "tsx", "js", "json", "md"]
+                .iter()
+                .any(|expected| extension.eq_ignore_ascii_case(expected))
+        })
+}
+
+fn extract_file_candidates(content: &str) -> Vec<String> {
+    content
+        .split_whitespace()
+        .filter_map(|token| {
+            let candidate = token.trim_matches(|char: char| {
+                matches!(char, ',' | '.' | ':' | ';' | ')' | '(' | '"' | '\'' | '`')
+            });
+            if candidate.contains('/') && has_interesting_extension(candidate) {
+                Some(candidate.to_string())
+            } else {
+                None
+            }
+        })
+        .collect()
+}
+
 fn truncate_summary(content: &str, max_chars: usize) -> String {
     if content.chars().count() <= max_chars {
         return content.to_string();
@@ -252,8 +377,8 @@ fn collapse_blank_lines(content: &str) -> String {
 #[cfg(test)]
 mod tests {
     use super::{
-        compact_session, estimate_session_tokens, format_compact_summary, should_compact,
-        CompactionConfig,
+        collect_key_files, compact_session, estimate_session_tokens, format_compact_summary,
+        infer_pending_work, should_compact, CompactionConfig,
     };
     use crate::session::{ContentBlock, ConversationMessage, MessageRole, Session};
 
@@ -336,4 +461,25 @@ mod tests {
         assert!(summary.ends_with('…'));
         assert!(summary.chars().count() <= 161);
     }
+
+    #[test]
+    fn extracts_key_files_from_message_content() {
+        let files = collect_key_files(&[ConversationMessage::user_text(
+            "Update rust/crates/runtime/src/compact.rs and rust/crates/rusty-claude-cli/src/main.rs next.",
+        )]);
+        assert!(files.contains(&"rust/crates/runtime/src/compact.rs".to_string()));
+        assert!(files.contains(&"rust/crates/rusty-claude-cli/src/main.rs".to_string()));
+    }
+
+    #[test]
+    fn infers_pending_work_from_recent_messages() {
+        let pending = infer_pending_work(&[
+            ConversationMessage::user_text("done"),
+            ConversationMessage::assistant(vec![ContentBlock::Text {
+                text: "Next: update tests and follow up on remaining CLI polish.".to_string(),
+            }]),
+        ]);
+        assert_eq!(pending.len(), 1);
+        assert!(pending[0].contains("Next: update tests"));
+    }
 }