diff --git a/hermes_cli/prompt_size.py b/hermes_cli/prompt_size.py
index 3b6530bfd68..9ce06ae5a21 100644
--- a/hermes_cli/prompt_size.py
+++ b/hermes_cli/prompt_size.py
@@ -15,16 +15,35 @@ from __future__ import annotations
 
 import json
 import re
-from typing import Any, Dict, List, Tuple
+from pathlib import Path
+from typing import Any, Dict, List, Optional, Tuple
 
 # The skills index is wrapped in this tag pair inside the stable tier.
 _SKILLS_BLOCK_RE = re.compile(r"<available_skills>.*?</available_skills>", re.DOTALL)
 
+# A rendered skill entry inside <available_skills> is ``    - name: desc`` (or
+# ``    - name`` when the skill has no description). Category headers use two
+# leading spaces, so the four-space + ``- `` prefix isolates skill lines.
+_SKILL_LINE_PREFIX = "    - "
+
+# Cap the human-readable "Skills by size" table; ``--json`` always has them all.
+_SKILLS_TABLE_LIMIT = 20
+
 
 def _bytes(s: str) -> int:
     return len(s.encode("utf-8"))
 
 
+def _tool_name(tool: Any) -> str:
+    """Return the callable name of a tool schema (OpenAI ``function`` shape)."""
+    if not isinstance(tool, dict):
+        return ""
+    fn = tool.get("function")
+    if isinstance(fn, dict) and fn.get("name"):
+        return str(fn["name"])
+    return str(tool.get("name", ""))
+
+
 def _build_inspection_agent(platform: str) -> Any:
     """Construct an offline AIAgent for prompt inspection.
 
@@ -57,12 +76,118 @@ def _build_inspection_agent(platform: str) -> Any:
     )
 
 
+def _skill_md_paths_by_name() -> Dict[str, Path]:
+    """Map each installed skill's name to its ``SKILL.md`` path on disk.
+
+    Keyed by both the frontmatter ``name`` (what the index renders) and the
+    skill directory name, so either resolves. Local skills win over external
+    dirs (``get_all_skills_dirs`` yields local first), matching the index's own
+    precedence. Used to attribute the real on-disk read cost per skill.
+    """
+    from agent.skill_utils import (
+        get_all_skills_dirs,
+        iter_skill_index_files,
+        parse_frontmatter,
+    )
+
+    mapping: Dict[str, Path] = {}
+    for skills_dir in get_all_skills_dirs():
+        if not skills_dir.exists():
+            continue
+        for skill_file in iter_skill_index_files(skills_dir, "SKILL.md"):
+            frontmatter_name = skill_file.parent.name
+            try:
+                frontmatter, _ = parse_frontmatter(
+                    skill_file.read_text(encoding="utf-8")
+                )
+                frontmatter_name = str(frontmatter.get("name") or frontmatter_name)
+            except Exception:
+                pass
+            # setdefault keeps the first (local) occurrence on name collisions.
+            mapping.setdefault(frontmatter_name, skill_file)
+            mapping.setdefault(skill_file.parent.name, skill_file)
+    return mapping
+
+
+def _compute_skills_breakdown(skills_block: str) -> List[Dict[str, Any]]:
+    """Per-skill byte breakdown parsed from the rendered ``<available_skills>``.
+
+    Two honest, distinct numbers per skill:
+
+    * ``index_line_bytes`` — the skill's actual rendered line in the always-on
+      index (the fixed per-call cost of *listing* the skill).
+    * ``skill_md_bytes`` — the on-disk size of the skill's ``SKILL.md`` (the
+      real token cost paid only when the model loads it via ``skill_view``).
+      ``None`` when the name can't be mapped to a file (e.g. a plugin skill
+      whose source lives outside the scanned skill dirs).
+
+    Sorted largest-first by ``skill_md_bytes`` (the read cost that dominates
+    pruning decisions), tie-broken by name.
+    """
+    name_to_path = _skill_md_paths_by_name()
+    entries: List[Dict[str, Any]] = []
+    for line in skills_block.splitlines():
+        if not line.startswith(_SKILL_LINE_PREFIX):
+            continue
+        rest = line[len(_SKILL_LINE_PREFIX):]
+        # ``name: desc`` — the first ``": "`` separates name from description.
+        # Namespaced names (``codex:rescue``) have no space after their colon,
+        # so partitioning on ``": "`` keeps the full name intact.
+        name = rest.partition(": ")[0].strip()
+        if not name:
+            continue
+        path = name_to_path.get(name)
+        md_bytes: Optional[int] = None
+        if path is not None:
+            try:
+                md_bytes = path.stat().st_size
+            except OSError:
+                md_bytes = None
+        entries.append({
+            "name": name,
+            "index_line_bytes": _bytes(line),
+            "skill_md_bytes": md_bytes,
+            "path": str(path) if path is not None else "",
+        })
+    entries.sort(key=lambda e: (-(e["skill_md_bytes"] or 0), e["name"]))
+    return entries
+
+
+def _compute_toolsets_breakdown(tools: List[Any]) -> List[Dict[str, Any]]:
+    """Per-toolset schema-byte breakdown of the resolved tool list.
+
+    Each tool is attributed to its single canonical toolset from the registry,
+    so ``json_bytes`` sums are fully attributable: the grand total equals the
+    sum of the individual tool serializations (which is the array total from
+    ``tools['json_bytes']`` minus JSON framing of ``2 * count`` bytes). Sorted
+    largest-first by ``json_bytes``, tie-broken by toolset name.
+    """
+    from tools.registry import registry
+
+    tool_to_toolset = registry.get_tool_to_toolset_map()
+    groups: Dict[str, Dict[str, Any]] = {}
+    for tool in tools:
+        name = _tool_name(tool)
+        toolset = tool_to_toolset.get(name) or "(unknown)"
+        group = groups.setdefault(
+            toolset, {"toolset": toolset, "tool_count": 0, "json_bytes": 0}
+        )
+        group["tool_count"] += 1
+        group["json_bytes"] += _bytes(json.dumps(tool, ensure_ascii=False))
+    out = list(groups.values())
+    out.sort(key=lambda g: (-g["json_bytes"], g["toolset"]))
+    return out
+
+
 def compute_prompt_breakdown(platform: str = "cli") -> Dict[str, Any]:
     """Return a dict of prompt-size measurements for a fresh session.
 
     Keys: ``system_prompt`` (chars/bytes), ``skills_index``, ``memory``,
-    ``user_profile``, ``tools`` (count + json bytes), and ``sections`` (a list
-    of (label, chars, bytes) for the three prompt tiers).
+    ``user_profile``, ``tools`` (count + json bytes), ``sections`` (a list of
+    (label, chars, bytes) for the three prompt tiers), ``skills_breakdown``
+    (per-skill index-line + on-disk SKILL.md bytes, largest-first), and
+    ``toolsets_breakdown`` (per-toolset tool count + schema json bytes,
+    largest-first). The last two answer "what should I disable to cut tokens?".
     """
     from agent.system_prompt import build_system_prompt, build_system_prompt_parts
 
@@ -114,6 +239,8 @@ def compute_prompt_breakdown(platform: str = "cli") -> Dict[str, Any]:
         "user_profile": {"chars": len(user_block), "bytes": _bytes(user_block)},
         "tools": {"count": len(tools), "json_bytes": _bytes(tools_json)},
         "sections": sections,
+        "skills_breakdown": _compute_skills_breakdown(skills_index),
+        "toolsets_breakdown": _compute_toolsets_breakdown(tools),
     }
 
 
@@ -143,6 +270,41 @@ def render_breakdown(data: Dict[str, Any]) -> str:
     lines.append("")
     tools = data["tools"]
     lines.append(f"  Tool schemas         : {tools['json_bytes']:>8,} B  ({_fmt_kb(tools['json_bytes'])}, {tools['count']} tools)")
+
+    # Per-toolset schema cost — which toolset's tools cost the most to ship.
+    toolsets = data.get("toolsets_breakdown") or []
+    if toolsets:
+        lines.append("")
+        lines.append("  Toolsets by size (tool-schema JSON, largest first):")
+        lines.append(f"    {'toolset':<22} {'tools':>5}  {'schema':>10}")
+        for ts in toolsets:
+            lines.append(
+                f"    {ts['toolset']:<22} {ts['tool_count']:>5}  "
+                f"{ts['json_bytes']:>8,} B  ({_fmt_kb(ts['json_bytes'])})"
+            )
+
+    # Per-skill cost — index line (always shipped) vs SKILL.md (read on load).
+    skills = data.get("skills_breakdown") or []
+    if skills:
+        lines.append("")
+        lines.append(
+            "  Skills by size (SKILL.md on-disk = read cost; index line = "
+            "always-on cost, largest first):"
+        )
+        lines.append(f"    {'skill':<28} {'SKILL.md':>10}  {'index line':>10}")
+        shown = skills[:_SKILLS_TABLE_LIMIT]
+        for sk in shown:
+            md = sk["skill_md_bytes"]
+            md_str = f"{md:>8,} B" if md is not None else f"{'n/a':>10}"
+            name = sk["name"]
+            if len(name) > 28:
+                name = name[:27] + "…"
+            lines.append(
+                f"    {name:<28} {md_str}  {sk['index_line_bytes']:>8,} B"
+            )
+        remaining = len(skills) - len(shown)
+        if remaining > 0:
+            lines.append(f"    … and {remaining} more (use --json for the full list)")
     return "\n".join(lines)
 
 
diff --git a/tests/hermes_cli/test_prompt_size.py b/tests/hermes_cli/test_prompt_size.py
index e536c971300..c6fb8ed1934 100644
--- a/tests/hermes_cli/test_prompt_size.py
+++ b/tests/hermes_cli/test_prompt_size.py
@@ -2,6 +2,7 @@
 
 import json
 import sys
+from pathlib import Path
 from types import SimpleNamespace
 
 import pytest
@@ -9,6 +10,7 @@ import pytest
 from hermes_cli.prompt_size import (
     _SKILLS_BLOCK_RE,
     _build_inspection_agent,
+    _compute_skills_breakdown,
     compute_prompt_breakdown,
     render_breakdown,
 )
@@ -155,6 +157,94 @@ def test_skills_block_regex_matches_tagged_block():
     assert m.group(0).endswith("</available_skills>")
 
 
+def test_toolsets_breakdown_reconciles_and_sorted(isolated_home):
+    """Per-toolset schema bytes attribute every tool exactly once.
+
+    Each resolved tool belongs to one registry toolset, so the grand total of
+    per-toolset json bytes equals the whole-array total minus JSON framing
+    (``2 * count`` bytes: brackets + ``", "`` separators between items).
+    """
+    data = compute_prompt_breakdown("cli")
+    toolsets = data["toolsets_breakdown"]
+    assert toolsets  # CLI always resolves at least terminal + file
+    for ts in toolsets:
+        assert set(ts) >= {"toolset", "tool_count", "json_bytes"}
+        assert ts["tool_count"] >= 1
+        assert ts["json_bytes"] > 0
+    # Sorted largest-first.
+    byte_sizes = [ts["json_bytes"] for ts in toolsets]
+    assert byte_sizes == sorted(byte_sizes, reverse=True)
+    # Every tool attributed to exactly one toolset.
+    assert sum(ts["tool_count"] for ts in toolsets) == data["tools"]["count"]
+    # Bytes reconcile to the existing whole-array total.
+    grand = sum(ts["json_bytes"] for ts in toolsets)
+    assert grand == data["tools"]["json_bytes"] - 2 * data["tools"]["count"]
+
+
+def test_skills_breakdown_shape_sorted_and_attributed(isolated_home):
+    """Per-skill breakdown reports index-line + on-disk SKILL.md bytes.
+
+    Seeded before the first build (skills prompt is cached per-process).
+    """
+    _seed_skill(isolated_home, "small-skill", "short desc")
+    _seed_skill(isolated_home, "big-skill", "a much longer description " * 20)
+    data = compute_prompt_breakdown("cli")
+    skills = data["skills_breakdown"]
+    names = {s["name"] for s in skills}
+    assert {"small-skill", "big-skill"} <= names
+    for s in skills:
+        assert set(s) >= {"name", "index_line_bytes", "skill_md_bytes", "path"}
+        assert s["index_line_bytes"] > 0
+    # Sorted largest-first by on-disk SKILL.md size.
+    md_sizes = [s["skill_md_bytes"] or 0 for s in skills]
+    assert md_sizes == sorted(md_sizes, reverse=True)
+    # On-disk bytes match the real file; big-skill's SKILL.md is the larger.
+    by_name = {s["name"]: s for s in skills}
+    big = by_name["big-skill"]
+    assert big["path"] and Path(big["path"]).stat().st_size == big["skill_md_bytes"]
+    assert big["skill_md_bytes"] > by_name["small-skill"]["skill_md_bytes"]
+    # Per-skill index lines are a subset of the whole <available_skills> block,
+    # so they never exceed it (on-disk SKILL.md bytes are separate and don't).
+    assert sum(s["index_line_bytes"] for s in skills) <= data["skills_index"]["bytes"]
+
+
+def test_skills_breakdown_unmapped_name_is_none():
+    """A skill line with no matching SKILL.md on disk reports None, not a crash."""
+    block = (
+        "<available_skills>\n"
+        "  demo:\n"
+        "    - phantom-skill: not on disk\n"
+        "</available_skills>\n"
+    )
+    entries = _compute_skills_breakdown(block)
+    assert len(entries) == 1
+    assert entries[0]["name"] == "phantom-skill"
+    assert entries[0]["skill_md_bytes"] is None
+    assert entries[0]["path"] == ""
+    assert entries[0]["index_line_bytes"] > 0
+
+
+def test_skills_breakdown_parses_namespaced_names():
+    """Namespaced names (``ns:skill``) survive the ``name: desc`` split."""
+    block = (
+        "<available_skills>\n"
+        "  plugins:\n"
+        "    - codex:rescue: rescue helper\n"
+        "</available_skills>\n"
+    )
+    entries = _compute_skills_breakdown(block)
+    assert [e["name"] for e in entries] == ["codex:rescue"]
+
+
+def test_render_includes_per_component_tables(isolated_home):
+    """The rendered report gains the two new sorted tables (additive)."""
+    _seed_skill(isolated_home, "demo-skill", "a demo skill")
+    data = compute_prompt_breakdown("cli")
+    out = render_breakdown(data)
+    assert "Toolsets by size" in out
+    assert "Skills by size" in out
+
+
 def test_render_breakdown_is_plain_text(isolated_home):
     data = compute_prompt_breakdown("cli")
     out = render_breakdown(data)