list_files with_metadata mode, deeper JSON outline, MCP connector descriptions in prompt

- list_files: new with_metadata parameter returns {path, line_count?, size}
  per entry (both disk and memory-docs) so the agent can spot large files
  worth outlining before reading
- ast_outline: replaced flat tree-sitter JSON walker with a recursive one
  that shows nested keys at every depth, with inline scalar values and
  container summaries
- message_builder: format active MCP connectors as a table with description
  instead of a bare bullet list
- read_file description now hints to use get_ast_outline first
- tools.md: agent guidance to outline before reading

crates/skald-core/src/db/memory_docs.rs

@@ -34,6 +34,16 @@ pub struct MemoryHit {
     pub snippet: String,
 }
 
+/// A directory listing row carrying cheap size metadata. `line_count` and
+/// `byte_len` are computed in SQL (`LENGTH` / newline count) so the note body
+/// never leaves the database.
+#[derive(Debug, Clone, sqlx::FromRow)]
+pub struct MemoryEntryMeta {
+    pub path:       String,
+    pub line_count: i64,
+    pub byte_len:   i64,
+}
+
 const SELECT: &str = "SELECT id, path, content, created_at, updated_at FROM memory_docs";
 
 /// Fetch one note by its exact path.
@@ -84,6 +94,27 @@ pub async fn list(pool: &SqlitePool, prefix: &str) -> Result<Vec<MemoryEntry>> {
     Ok(rows)
 }
 
+/// Like [`list`], but each row also carries a line count and byte length,
+/// computed in SQL so the body is never transferred. Line count matches the
+/// on-disk convention: an empty note is 0 lines, otherwise newline-count + 1.
+pub async fn list_with_metadata(pool: &SqlitePool, prefix: &str) -> Result<Vec<MemoryEntryMeta>> {
+    let pattern = format!("{}%", escape_like(prefix));
+    let rows = sqlx::query_as::<_, MemoryEntryMeta>(
+        "SELECT path,
+                CASE WHEN content = '' THEN 0
+                     ELSE LENGTH(content) - LENGTH(REPLACE(content, char(10), '')) + 1
+                END AS line_count,
+                LENGTH(CAST(content AS BLOB)) AS byte_len
+         FROM memory_docs
+         WHERE path LIKE ? ESCAPE '\\'
+         ORDER BY updated_at DESC",
+    )
+    .bind(pattern)
+    .fetch_all(pool)
+    .await?;
+    Ok(rows)
+}
+
 /// Full-text search over note bodies and paths, best match first. `query` is
 /// FTS5 MATCH syntax; `snippet` is a short excerpt of the body with the matched
 /// terms wrapped in `[` … `]`.

crates/skald-core/src/session/handler/message_builder.rs

@@ -618,9 +618,13 @@ impl MessageBuilder {
         }
 
         if !active.is_empty() {
-            out.push_str("\n**Active** — tools callable as `mcp__<name>__<tool>`:\n");
+            out.push_str("\n**Active** — tools callable as `mcp__<name>__<tool>`:\n\n");
+            out.push_str("| Server | Description |\n|--------|-------------|\n");
             for name in &active {
-                out.push_str(&format!("- `{name}`\n"));
+                let desc = descriptions.get(*name)
+                    .and_then(|d| d.as_deref())
+                    .unwrap_or("—");
+                out.push_str(&format!("| `{name}` | {desc} |\n"));
             }
         }
 

crates/skald-core/src/tools/ast_outline.rs

@@ -15,12 +15,14 @@ impl Tool for AstOutline {
     fn category(&self) -> crate::tools::ToolCategory { crate::tools::ToolCategory::Filesystem }
 
     fn description(&self) -> &str {
-        "Return the structural outline of a source file: top-level definitions (functions, classes, \
-         structs, methods, traits, interfaces, etc.) without their bodies. \
-         Each entry is formatted as 'START-END | <kind>: <name>' where START and END are 1-based \
-         line numbers of the full definition — same column format as read_file, so you can pass \
-         START/END directly to read_file's start_line/end_line to read just that definition. \
-         Much cheaper than reading the full file when you only need to understand the shape of the code. \
+        "Start here when you need to understand a source file you don't already know — especially a large one. \
+         Returns the file's structural outline: top-level definitions (functions, classes, structs, methods, \
+         traits, interfaces, etc.) without their bodies, so you grasp the whole shape at a fraction of the \
+         tokens of reading it. \
+         Each entry is formatted as 'START-END | <kind>: <name>' where START and END are 1-based line numbers \
+         of the full definition — same column format as read_file, so you pass START/END straight to \
+         read_file's start_line/end_line to read just the definition you care about. \
+         Typical flow: outline first, then read only the ranges you need — far cheaper than reading the whole file. \
          Supported: .rs .py .js .mjs .ts .tsx .go .java .c .h .cpp .cc .hpp .swift .lua .rb .sh .ex .exs \
          .kt .json .toml .yaml .yml .html .css .md .sql"
     }
@@ -67,7 +69,7 @@ impl Tool for AstOutline {
             "rb"                        => outline_ts(path, ts_ruby(), "Ruby"),
             "sh" | "bash"               => outline_ts(path, ts_bash(), "Bash"),
             "ex" | "exs"                => outline_ts(path, ts_elixir(), "Elixir"),
-            "json"                      => outline_ts(path, ts_json(), "JSON"),
+            "json"                      => outline_json(path),
             "yaml" | "yml"              => outline_ts(path, ts_yaml(), "YAML"),
             "html"                      => outline_ts(path, ts_html(), "HTML"),
             "css"                       => outline_ts(path, ts_css(), "CSS"),
@@ -292,15 +294,6 @@ fn ts_elixir() -> LangConfig {
     }
 }
 
-fn ts_json() -> LangConfig {
-    LangConfig {
-        language: tree_sitter_json::LANGUAGE.into(),
-        def_kinds: &["pair"],
-        name_field: "key",
-        container_kinds: &[],
-    }
-}
-
 fn ts_yaml() -> LangConfig {
     LangConfig {
         language: tree_sitter_yaml::LANGUAGE.into(),
@@ -331,6 +324,147 @@ fn ts_css() -> LangConfig {
     }
 }
 
+// ── JSON outline (dedicated tree-sitter walker: nested keys) ────────────────
+//
+// The generic `collect_nodes` only descends through `container_kinds`, which for
+// JSON tops out at the first level of the root object (and never enters arrays
+// of objects). This walker recurses through the parse tree instead: it lists
+// every key at every depth, shows scalar values inline, and expands nested
+// objects/arrays. Line ranges keep the read_file contract (`START-END | …`).
+
+const JSON_VALUE_KINDS: &[&str] =
+    &["object", "array", "string", "number", "true", "false", "null"];
+
+fn outline_json(path: &str) -> Result<String> {
+    let source = read_to_string(path)?;
+    let mut parser = tree_sitter::Parser::new();
+    let language: tree_sitter::Language = tree_sitter_json::LANGUAGE.into();
+    parser.set_language(&language)
+        .map_err(|e| anyhow::anyhow!("tree-sitter language load error: {e}"))?;
+    let tree = parser.parse(source.as_bytes(), None)
+        .ok_or_else(|| anyhow::anyhow!("tree-sitter parse returned None for {path}"))?;
+
+    let mut out = format!("--- JSON outline: {path} ---\n\n");
+    // document → single top-level value (object or array).
+    if let Some(top) = json_first_value(tree.root_node()) {
+        json_walk(top, &source, 0, &mut out);
+    }
+    Ok(out)
+}
+
+/// First JSON value child of `document` (skips comments/whitespace nodes).
+fn json_first_value(document: tree_sitter::Node) -> Option<tree_sitter::Node> {
+    for i in 0..document.child_count() {
+        let c = document.child(i as u32).unwrap();
+        if JSON_VALUE_KINDS.contains(&c.kind()) {
+            return Some(c);
+        }
+    }
+    None
+}
+
+/// Emit one line per entry of an object/array, recursing into nested containers.
+/// Scalars are shown inline; scalar array elements are summarised by the array's
+/// header only (not listed) to stay readable on large value arrays.
+fn json_walk(node: tree_sitter::Node, source: &str, depth: usize, out: &mut String) {
+    const MAX_JSON_DEPTH: usize = 16;
+    if depth > MAX_JSON_DEPTH {
+        return;
+    }
+    match node.kind() {
+        "object" => {
+            for i in 0..node.child_count() {
+                let pair = node.child(i as u32).unwrap();
+                if pair.kind() != "pair" {
+                    continue;
+                }
+                let (Some(key), Some(val)) = (
+                    pair.child_by_field_name("key"),
+                    pair.child_by_field_name("value"),
+                ) else {
+                    continue;
+                };
+                json_emit(&json_key_text(key, source), val, pair, source, depth, out);
+            }
+        }
+        "array" => {
+            let mut idx = 0usize;
+            for i in 0..node.child_count() {
+                let el = node.child(i as u32).unwrap();
+                if !JSON_VALUE_KINDS.contains(&el.kind()) {
+                    continue;
+                }
+                let this = idx;
+                idx += 1;
+                // Only expand container elements; scalars are covered by the count.
+                if el.kind() == "object" || el.kind() == "array" {
+                    json_emit(&format!("[{this}]"), el, el, source, depth, out);
+                }
+            }
+        }
+        _ => {}
+    }
+}
+
+/// Emit one entry line (`name: <value-descriptor>`) spanning `span`'s rows,
+/// then recurse when the value is itself a container.
+fn json_emit(
+    name: &str,
+    val: tree_sitter::Node,
+    span: tree_sitter::Node,
+    source: &str,
+    depth: usize,
+    out: &mut String,
+) {
+    let start = span.start_position().row + 1;
+    let end   = span.end_position().row + 1;
+    let indent = "  ".repeat(depth);
+    let desc = json_value_desc(val, source);
+    out.push_str(&format!("{start:>4}-{end:>4} | {indent}{name}: {desc}\n"));
+    if val.kind() == "object" || val.kind() == "array" {
+        json_walk(val, source, depth + 1, out);
+    }
+}
+
+/// Short descriptor of a value: `{N keys}`, `[N items]`, or the scalar literal.
+fn json_value_desc(node: tree_sitter::Node, source: &str) -> String {
+    match node.kind() {
+        "object" => {
+            let n = json_count(node, &["pair"]);
+            format!("{{{n} {}}}", if n == 1 { "key" } else { "keys" })
+        }
+        "array" => {
+            let n = json_count(node, JSON_VALUE_KINDS);
+            format!("[{n} {}]", if n == 1 { "item" } else { "items" })
+        }
+        _ => {
+            let raw = source.get(node.byte_range()).unwrap_or("");
+            let one = raw.split_whitespace().collect::<Vec<_>>().join(" ");
+            truncate_label(&one, MAX_LABEL_SHORT)
+        }
+    }
+}
+
+/// Number of direct children whose kind is in `kinds`.
+fn json_count(node: tree_sitter::Node, kinds: &[&str]) -> usize {
+    let mut n = 0;
+    for i in 0..node.child_count() {
+        if kinds.contains(&node.child(i as u32).unwrap().kind()) {
+            n += 1;
+        }
+    }
+    n
+}
+
+/// Object key text with the surrounding double-quotes stripped.
+fn json_key_text(key: tree_sitter::Node, source: &str) -> String {
+    let raw = source.get(key.byte_range()).unwrap_or("");
+    raw.strip_prefix('"')
+        .and_then(|s| s.strip_suffix('"'))
+        .unwrap_or(raw)
+        .to_string()
+}
+
 // ── text-based fallbacks (crates incompatible with tree-sitter 0.26) ───────
 
 fn outline_kotlin(path: &str) -> Result<String> {

crates/skald-core/src/tools/fs/list_files.rs

@@ -36,6 +36,8 @@ impl Tool for ListFiles {
          Skips .git, target, node_modules, .cache. \
          Returns a JSON array of paths relative to the requested directory. \
          Use depth=1 for immediate contents only, depth=2-3 for moderate exploration. \
+         Set with_metadata=true to instead return objects {path, line_count?, size} — handy for spotting a \
+         large file worth outlining with get_ast_outline before you read it. \
          Listing under user-memory/ (private) or shared-memory/ (shared) lists your memory notes instead of disk."
     }
 
@@ -54,6 +56,10 @@ impl Tool for ListFiles {
                 "dirs_only": {
                     "type":        "boolean",
                     "description": "If true, return only directories and omit files (default false)."
+                },
+                "with_metadata": {
+                    "type":        "boolean",
+                    "description": "If true, return objects {path, line_count?, size} instead of bare path strings. size is human-readable; line_count is included only for text files (omitted for binaries and very large files). Use it to decide whether to get_ast_outline a large file before reading it."
                 }
             }
         })
@@ -71,6 +77,7 @@ impl Tool for ListFiles {
     /// under the prefix is returned, keyed relative to the requested directory.
     fn run_with<'a>(&'a self, ctx: &ToolContext, args: Value) -> Box<dyn ToolExecution + 'a> {
         let path = args["path"].as_str().unwrap_or("").to_string();
+        let with_metadata = args["with_metadata"].as_bool().unwrap_or(false);
         let Some(m) = classify_memory(&path) else {
             return match super::rewrite_to_host(&ctx.fs, &path, args) {
                 Ok(args) => self.run(args),
@@ -87,6 +94,21 @@ impl Tool for ListFiles {
             // Treat `rel` as a directory prefix: match `rel/…` (or everything at
             // the root), then strip it so results are relative to what was asked.
             let prefix = if rel.is_empty() || rel.ends_with('/') { rel } else { format!("{rel}/") };
+
+            if with_metadata {
+                let mut entries: Vec<FileEntry> = crate::db::memory_docs::list_with_metadata(&pool, &prefix)
+                    .await?
+                    .into_iter()
+                    .map(|e| FileEntry {
+                        path:       e.path.strip_prefix(&prefix).unwrap_or(&e.path).to_string(),
+                        line_count: Some(e.line_count.max(0) as usize),
+                        size:       Some(human_size(e.byte_len.max(0) as u64)),
+                    })
+                    .collect();
+                entries.sort_by(|a, b| a.path.cmp(&b.path));
+                return Ok(ToolResult::Text(serde_json::to_string(&entries)?));
+            }
+
             let entries = crate::db::memory_docs::list(&pool, &prefix).await?;
             let mut paths: Vec<String> = entries.into_iter()
                 .map(|e| e.path.strip_prefix(&prefix).unwrap_or(&e.path).to_string())
@@ -100,12 +122,81 @@ impl Tool for ListFiles {
         let user_path = args["path"].as_str().unwrap_or(".");
         let max_depth = args["depth"].as_u64().unwrap_or(3) as usize;
         let dirs_only = args["dirs_only"].as_bool().unwrap_or(false);
+        let with_metadata = args["with_metadata"].as_bool().unwrap_or(false);
         let dir = resolve(user_path)?;
 
         let mut paths: Vec<String> = Vec::new();
         walk(&dir, &dir, 0, max_depth, dirs_only, &mut paths)?;
         paths.sort();
-        Ok(serde_json::to_string(&paths)?)
+
+        if !with_metadata {
+            return Ok(serde_json::to_string(&paths)?);
+        }
+        let entries: Vec<FileEntry> = paths.into_iter()
+            .map(|rel| file_entry(&dir.join(&rel), rel))
+            .collect();
+        Ok(serde_json::to_string(&entries)?)
+    }
+}
+
+/// A `with_metadata` listing row. Field order (declaration order) is the wire
+/// order; `line_count` and `size` are omitted when unavailable.
+#[derive(serde::Serialize)]
+struct FileEntry {
+    path: String,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    line_count: Option<usize>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    size: Option<String>,
+}
+
+/// Largest file we'll read to count lines; bigger files report `size` only, so
+/// a metadata listing never turns into a full read of the tree.
+const LINE_COUNT_SIZE_CAP: u64 = 2 * 1024 * 1024;
+
+/// Build a metadata row for one on-disk path. `size` comes free from a stat;
+/// `line_count` is read only for text files within the size cap.
+fn file_entry(abs: &Path, rel: String) -> FileEntry {
+    let meta = std::fs::metadata(abs).ok();
+    let len = meta.as_ref().map(|m| m.len());
+    let is_file = meta.as_ref().map(|m| m.is_file()).unwrap_or(false);
+    let line_count = match len {
+        Some(l) if is_file && l <= LINE_COUNT_SIZE_CAP => count_lines_if_text(abs),
+        _ => None,
+    };
+    FileEntry { path: rel, line_count, size: len.map(human_size) }
+}
+
+/// Line count of a text file, or `None` if it reads as binary (contains a NUL).
+fn count_lines_if_text(abs: &Path) -> Option<usize> {
+    let bytes = std::fs::read(abs).ok()?;
+    if bytes.contains(&0) { return None; }
+    Some(count_lines(&bytes))
+}
+
+/// Number of lines an editor would show: 0 for empty, else newline-count plus
+/// one when the file does not end in a newline.
+fn count_lines(bytes: &[u8]) -> usize {
+    if bytes.is_empty() { return 0; }
+    let nl = bytes.iter().filter(|&&b| b == b'\n').count();
+    if bytes.last() == Some(&b'\n') { nl } else { nl + 1 }
+}
+
+/// Human-readable byte size, `ls -h` style (base 1024): "512 B", "18 KB", "1.4 MB".
+fn human_size(bytes: u64) -> String {
+    const UNITS: &[&str] = &["B", "KB", "MB", "GB", "TB"];
+    let mut size = bytes as f64;
+    let mut unit = 0;
+    while size >= 1024.0 && unit < UNITS.len() - 1 {
+        size /= 1024.0;
+        unit += 1;
+    }
+    if unit == 0 {
+        format!("{bytes} B")
+    } else {
+        let s = format!("{size:.1}");
+        let s = s.strip_suffix(".0").unwrap_or(&s);
+        format!("{s} {}", UNITS[unit])
     }
 }
 
@@ -138,3 +229,43 @@ fn walk(root: &Path, dir: &Path, depth: usize, max_depth: usize, dirs_only: bool
     }
     Ok(())
 }
+
+#[cfg(test)]
+mod meta_smoke {
+    use super::*;
+    const SP: &str = "/private/tmp/claude-501/-Users-dguiducci-projects-skald-circle/1cb4c456-6a62-4c67-abf8-bb93ef73e30c/scratchpad/lf";
+
+    #[test]
+    fn human_size_fmt() {
+        assert_eq!(human_size(0), "0 B");
+        assert_eq!(human_size(512), "512 B");
+        assert_eq!(human_size(18 * 1024), "18 KB");
+        assert_eq!(human_size(1024 * 1024 + 400 * 1024), "1.4 MB");
+    }
+
+    #[test]
+    fn line_counts() {
+        assert_eq!(count_lines(b""), 0);
+        assert_eq!(count_lines(b"a\nb\nc\n"), 3);
+        assert_eq!(count_lines(b"no newline"), 1);
+    }
+
+    #[test]
+    fn entries() {
+        let t = std::path::Path::new(SP).join("three.txt");
+        let e = file_entry(&t, "three.txt".into());
+        println!("three.txt -> {}", serde_json::to_string(&e).unwrap());
+        assert_eq!(e.line_count, Some(3));
+
+        let o = std::path::Path::new(SP).join("one.txt");
+        let e = file_entry(&o, "one.txt".into());
+        println!("one.txt   -> {}", serde_json::to_string(&e).unwrap());
+        assert_eq!(e.line_count, Some(1));
+
+        let b = std::path::Path::new(SP).join("blob.bin");
+        let e = file_entry(&b, "blob.bin".into());
+        println!("blob.bin  -> {}", serde_json::to_string(&e).unwrap());
+        assert_eq!(e.line_count, None); // binary: size only
+        assert!(e.size.is_some());
+    }
+}

crates/skald-core/src/tools/fs/read_file.rs

@@ -78,6 +78,8 @@ impl Tool for ReadFile {
          Use instead of cat/head/tail in the terminal. \
          Returns text prefixed as '  N | line'. When calling edit_file, copy the text after '| ' exactly. \
          For large files use start_line/end_line to read in chunks — files over ~2000 lines should never be read whole. \
+         For an unfamiliar source file, call get_ast_outline first to get each definition's line range, then read \
+         just the range you need instead of the whole file. \
          Use limit to cap output when end_line is unknown. \
          Paths under user-memory/ (private) or shared-memory/ (shared) read a note from your memory instead of disk."
     }