diff --git a/tests/test_cli.py b/tests/test_cli.py
index 8045e2b..9ee3f29 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -81,7 +81,7 @@ def test_init_honors_docs_dir_flag(tmp_path: Path, monkeypatch) -> None:
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["init", "--docs-dir", str(override)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(override), "init"])
 
     assert result.exit_code == 0
     assert (override / "schema.md").is_file()
@@ -147,7 +147,7 @@ def test_doctor_docs_dir_flag_is_reported_as_source(tmp_path: Path, monkeypatch,
     docs_dir = make_docs_tree()
     monkeypatch.chdir(tmp_path)
 
-    result = CliRunner().invoke(cli, ["doctor", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "doctor"])
 
     assert f"Config: docs_dir={docs_dir} (source: flag)" in result.output
     assert result.exit_code == 0
@@ -181,7 +181,7 @@ def test_config_show_honors_docs_dir_flag(tmp_path: Path, monkeypatch) -> None:
     monkeypatch.chdir(tmp_path)
     override = tmp_path / "other-docs"
 
-    result = CliRunner().invoke(cli, ["config", "show", "--docs-dir", str(override)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(override), "config", "show"])
 
     assert result.exit_code == 0
     assert f"docs_dir={override} (source: flag)" in result.output
@@ -241,7 +241,7 @@ def test_build_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_docs_tree,
     _init_git(tmp_path)
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["build", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "build"])
 
     assert result.exit_code == 0
     assert (docs_dir / "catalog.jsonl").exists()
@@ -283,7 +283,7 @@ def test_source_scan_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_docs
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["source-scan", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "source-scan"])
 
     assert result.exit_code == 0
     assert "jira:ABC-1" in result.output
@@ -378,7 +378,7 @@ def test_lint_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_docs_tree,
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["lint", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "lint"])
 
     assert result.exit_code == 0
 
@@ -433,7 +433,7 @@ def test_source_dedupe_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_do
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["source-dedupe", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "source-dedupe"])
 
     assert result.exit_code == 1
     assert "[GROUP] jira:ABC-1" in result.output
@@ -503,7 +503,7 @@ def test_source_lint_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_docs
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["source-lint", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "source-lint"])
 
     assert result.exit_code == 1
 
@@ -558,7 +558,7 @@ def test_source_coverage_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["source-coverage", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "source-coverage"])
 
     assert result.exit_code == 0
     assert "[COVERED]" in result.output
@@ -593,7 +593,7 @@ def test_search_catalog_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_d
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["search-catalog", "--query", "auth", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "search-catalog", "--query", "auth"])
 
     assert result.exit_code == 0
     assert "Auth Middleware" in result.output
@@ -678,7 +678,7 @@ def test_log_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_docs_tree) -
     monkeypatch.chdir(elsewhere)
 
     result = CliRunner().invoke(
-        cli, ["log", "--title", "x", "--details", "y", "--action", "create", "--docs-dir", str(docs_dir)]
+        cli, ["--docs-dir", str(docs_dir), "log", "--title", "x", "--details", "y", "--action", "create"]
     )
 
     assert result.exit_code == 0
@@ -771,7 +771,7 @@ def test_source_delta_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_doc
     elsewhere.mkdir()
     monkeypatch.chdir(elsewhere)
 
-    result = CliRunner().invoke(cli, ["source-delta", "jira:ABC-1", "--docs-dir", str(docs_dir)])
+    result = CliRunner().invoke(cli, ["--docs-dir", str(docs_dir), "source-delta", "jira:ABC-1"])
 
     assert result.exit_code == 0
     assert "[NEW] status" in result.output
@@ -838,7 +838,7 @@ def test_source_snapshot_honors_docs_dir_flag(tmp_path: Path, monkeypatch, make_
     monkeypatch.chdir(elsewhere)
 
     result = CliRunner().invoke(
-        cli, ["source-snapshot", "jira:ABC-1", "--units", "fields", "--docs-dir", str(docs_dir)]
+        cli, ["--docs-dir", str(docs_dir), "source-snapshot", "jira:ABC-1", "--units", "fields"]
     )
 
     assert result.exit_code == 0
diff --git a/wiki_toolkit/cli.py b/wiki_toolkit/cli.py
index 0c7e7c3..a384012 100644
--- a/wiki_toolkit/cli.py
+++ b/wiki_toolkit/cli.py
@@ -14,7 +14,7 @@
 from wiki_toolkit.doctor import run_doctor
 from wiki_toolkit.init import run_init
 from wiki_toolkit.log import ALLOWED_LOG_ACTIONS, append_log_entry, build_log_entry
-from wiki_toolkit.settings import resolve_docs_dir
+from wiki_toolkit.settings import Context, build_context
 from wiki_toolkit.sources import (
     ALLOWED_SNAPSHOT_UNITS,
     SourceScanResult,
@@ -29,11 +29,29 @@
 from wiki_toolkit.wiki import build_catalog, find_cross_link_candidates, lint_wiki, search_catalog
 from wiki_toolkit.write_gate import ALLOWED_FRAMES, commit_pages, propose_pr, start_wiki_branch
 
+_SOURCES_META_KEY = "wiki_toolkit.sources"
+
 
 @click.group()
+@click.option(
+    "--docs-dir",
+    type=click.Path(path_type=Path, resolve_path=True),
+    default=None,
+    help="Override the resolved docs/ directory.",
+)
+@click.option(
+    "--repo-root",
+    type=click.Path(path_type=Path, resolve_path=True),
+    default=None,
+    help="Override the resolved repo root.",
+)
 @click.version_option()
-def cli() -> None:
+@click.pass_context
+def cli(ctx: click.Context, docs_dir: Path | None, repo_root: Path | None) -> None:
     """AI skills and helper tools that implement and maintain an LLM Wiki."""
+    context, sources = build_context(docs_dir_flag=docs_dir, repo_root_flag=repo_root)
+    ctx.obj = context
+    ctx.meta[_SOURCES_META_KEY] = sources
 
 
 @cli.group()
@@ -42,23 +60,20 @@ def config() -> None:
 
 
 @config.command("show")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def config_show(docs_dir: Path | None) -> None:
-    """Print the resolved docs_dir and which source (flag/env/pyproject/default) it came from."""
-    resolved = resolve_docs_dir(flag=docs_dir)
-    click.echo(f"docs_dir={resolved.docs_dir} (source: {resolved.source})")
+@click.pass_context
+def config_show(ctx: click.Context) -> None:
+    """Print the resolved settings and which source (flag/env/dedicated_file/pyproject/default) each came from."""
+    context: Context = ctx.obj
+    sources = ctx.meta[_SOURCES_META_KEY]
+    for field in Context.model_fields:
+        click.echo(f"{field}={getattr(context, field)} (source: {sources[field]})")
 
 
 @cli.command()
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def init(docs_dir: Path | None) -> None:
+@click.pass_obj
+def init(context: Context) -> None:
     """Scaffold a docs/ tree: sources/, wiki/, catalog.jsonl, log.jsonl, source-manifest.jsonl, schema.md."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    report = run_init(docs_dir)
+    report = run_init(context.docs_dir)
 
     for name in report.created:
         click.echo(f"  [created] docs/{name}")
@@ -67,13 +82,12 @@ def init(docs_dir: Path | None) -> None:
 
 
 @cli.command()
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def doctor(docs_dir: Path | None) -> None:
+@click.pass_context
+def doctor(ctx: click.Context) -> None:
     """Non-mutating health check of the wiki's docs/ structure and git clone."""
-    resolved = resolve_docs_dir(flag=docs_dir)
-    report = run_doctor(resolved.docs_dir, root=Path.cwd(), docs_dir_source=resolved.source)
+    context: Context = ctx.obj
+    docs_dir_source = ctx.meta[_SOURCES_META_KEY]["docs_dir"]
+    report = run_doctor(context.docs_dir, root=context.repo_root, docs_dir_source=docs_dir_source)
 
     click.echo(f"Python: {report.python_version}")
     click.echo(f"Config: docs_dir={report.docs_dir} (source: {report.docs_dir_source})")
@@ -105,28 +119,22 @@ def doctor(docs_dir: Path | None) -> None:
 
 
 @cli.command()
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def build(docs_dir: Path | None) -> None:
+@click.pass_obj
+def build(context: Context) -> None:
     """Regenerate docs/catalog.jsonl from the current docs/wiki/ notes."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = build_catalog(docs_dir)
+    result = build_catalog(context.docs_dir)
 
-    catalog_path = docs_dir / "catalog.jsonl"
-    write_jsonl(catalog_path, [asdict(entry) for entry in result.entries], stage_root=Path.cwd())
+    catalog_path = context.docs_dir / "catalog.jsonl"
+    write_jsonl(catalog_path, [asdict(entry) for entry in result.entries], stage_root=context.repo_root)
 
     click.echo(f"Wrote {len(result.entries)} entries to docs/catalog.jsonl")
 
 
 @cli.command()
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def lint(docs_dir: Path | None) -> None:
+@click.pass_obj
+def lint(context: Context) -> None:
     """Validate wiki note frontmatter, allowed tags, source links, and source_count."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = lint_wiki(docs_dir)
+    result = lint_wiki(context.docs_dir)
 
     for violation in result.violations:
         click.echo(f"[VIOLATION] {violation.path}: {violation.message}")
@@ -155,15 +163,10 @@ def batch_plan_cmd(vault: Path, source_dir: Path) -> None:
     multiple=True,
     help="Limit --update's write/stage step to this source id (repeatable). Omit to write every classified source.",
 )
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_scan(
-    update_manifest: bool, accept_covered: bool, source_ids: tuple[str, ...], docs_dir: Path | None
-) -> None:
+@click.pass_obj
+def source_scan(context: Context, update_manifest: bool, accept_covered: bool, source_ids: tuple[str, ...]) -> None:
     """Classify docs/sources/ files as new, update, or duplicate."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = scan_sources(docs_dir, accept_covered=accept_covered)
+    result = scan_sources(context.docs_dir, accept_covered=accept_covered)
 
     for entry in result.entries:
         click.echo(f"[{entry.classification.upper()}] {entry.path} ({entry.source})")
@@ -177,7 +180,7 @@ def source_scan(
     if update_manifest:
         scope, unmatched = calculate_scan_scope(result, source_ids)
 
-        apply_result = apply_source_scan(docs_dir, result, source_ids=scope, stage_root=Path.cwd())
+        apply_result = apply_source_scan(context.docs_dir, result, source_ids=scope, stage_root=context.repo_root)
         click.echo(f"Wrote {apply_result.written} entries to docs/source-manifest.jsonl")
 
     if result.needs_attention or unmatched:
@@ -196,13 +199,10 @@ def calculate_scan_scope(result: SourceScanResult, source_ids: tuple[str, ...])
 
 
 @cli.command("source-lint")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_lint(docs_dir: Path | None) -> None:
+@click.pass_obj
+def source_lint(context: Context) -> None:
     """Validate docs/sources/ frontmatter and report processed-but-uncovered sources."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = lint_sources(docs_dir)
+    result = lint_sources(context.docs_dir)
 
     for violation in result.violations:
         click.echo(f"[VIOLATION] {violation.path}: {violation.message}")
@@ -219,13 +219,10 @@ def source_lint(docs_dir: Path | None) -> None:
 
 
 @cli.command("source-coverage")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_coverage_cmd(docs_dir: Path | None) -> None:
+@click.pass_obj
+def source_coverage_cmd(context: Context) -> None:
     """Show which docs/sources/ files are covered by at least one wiki note."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = source_coverage(docs_dir)
+    result = source_coverage(context.docs_dir)
 
     for entry in result.covered:
         click.echo(f"[COVERED] {entry.path} ({entry.source})")
@@ -236,13 +233,10 @@ def source_coverage_cmd(docs_dir: Path | None) -> None:
 
 
 @cli.command("source-dedupe")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_dedupe(docs_dir: Path | None) -> None:
+@click.pass_obj
+def source_dedupe(context: Context) -> None:
     """Suggest which docs/sources/ file to keep per group sharing a source id with a duplicate: true file."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    result = suggest_dedupe(docs_dir)
+    result = suggest_dedupe(context.docs_dir)
 
     for violation in result.violations:
         click.echo(f"[VIOLATION] {violation.path}: {violation.message}")
@@ -261,14 +255,11 @@ def source_dedupe(docs_dir: Path | None) -> None:
 
 @cli.command("source-delta")
 @click.argument("source")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_delta(source: str, docs_dir: Path | None) -> None:
+@click.pass_obj
+def source_delta(context: Context, source: str) -> None:
     """Diff a source's current content against its last-known revision on main."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
     try:
-        delta = compute_source_delta(docs_dir, source)
+        delta = compute_source_delta(context.docs_dir, source)
     except ValueError as e:
         raise click.UsageError(str(e)) from e
 
@@ -288,14 +279,11 @@ def source_delta(source: str, docs_dir: Path | None) -> None:
 @click.option(
     "--units", type=click.Choice(ALLOWED_SNAPSHOT_UNITS), required=True, help="Mutation type driving this snapshot."
 )
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def source_snapshot(source: str, units: str, docs_dir: Path | None) -> None:
+@click.pass_obj
+def source_snapshot(context: Context, source: str, units: str) -> None:
     """Write a new Raw snapshot unit for SOURCE, for a comments or fields mutation."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
     try:
-        result = write_source_snapshot(docs_dir, source, units, stage_root=Path.cwd())
+        result = write_source_snapshot(context.docs_dir, source, units, stage_root=context.repo_root)
     except ValueError as e:
         raise click.UsageError(str(e)) from e
 
@@ -304,13 +292,10 @@ def source_snapshot(source: str, units: str, docs_dir: Path | None) -> None:
 
 @cli.command("search-catalog")
 @click.option("--query", required=True, help="Text to search for in catalog entry titles and paths.")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def search_catalog_cmd(query: str, docs_dir: Path | None) -> None:
+@click.pass_obj
+def search_catalog_cmd(context: Context, query: str) -> None:
     """Search docs/catalog.jsonl for entries matching --query."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    entries = read_jsonl(docs_dir / "catalog.jsonl")
+    entries = read_jsonl(context.docs_dir / "catalog.jsonl")
     matches = search_catalog(query, entries)
 
     if not matches:
@@ -323,13 +308,10 @@ def search_catalog_cmd(query: str, docs_dir: Path | None) -> None:
 
 @cli.command("cross-link-candidates")
 @click.argument("page_paths", nargs=-1, required=True)
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def cross_link_candidates_cmd(page_paths: tuple[str, ...], docs_dir: Path | None) -> None:
+@click.pass_obj
+def cross_link_candidates_cmd(context: Context, page_paths: tuple[str, ...]) -> None:
     """Find literal title/alias mentions of other catalog pages inside PAGE_PATHS' bodies (JSONL output)."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
-    candidates = find_cross_link_candidates(docs_dir, list(page_paths))
+    candidates = find_cross_link_candidates(context.docs_dir, list(page_paths))
 
     for candidate in candidates:
         click.echo(orjson.dumps(asdict(candidate)).decode())
@@ -337,10 +319,11 @@ def cross_link_candidates_cmd(page_paths: tuple[str, ...], docs_dir: Path | None
 
 @cli.command("start-branch")
 @click.option("--frame", type=click.Choice(ALLOWED_FRAMES), required=True, help="Reviewer framing for this session.")
-def start_branch_cmd(frame: str) -> None:
+@click.pass_obj
+def start_branch_cmd(context: Context, frame: str) -> None:
     """Open a new local git branch for a batch coordinator session, before any source commits."""
     try:
-        branch = start_wiki_branch(Path.cwd(), frame)
+        branch = start_wiki_branch(context.repo_root, frame)
     except ValueError as e:
         raise click.UsageError(str(e)) from e
 
@@ -350,10 +333,11 @@ def start_branch_cmd(frame: str) -> None:
 @cli.command("commit-pages")
 @click.option("--pages", required=True, multiple=True, help="Page path to commit. Repeat for multiple pages.")
 @click.option("--message", required=True, help="Commit message, e.g. naming the source that was just ingested.")
-def commit_pages_cmd(pages: tuple[str, ...], message: str) -> None:
+@click.pass_obj
+def commit_pages_cmd(context: Context, pages: tuple[str, ...], message: str) -> None:
     """Commit PAGES onto the currently checked-out branch (a batch coordinator's per-source streaming commit)."""
     try:
-        commit_sha = commit_pages(Path.cwd(), list(pages), message)
+        commit_sha = commit_pages(context.repo_root, list(pages), message)
     except ValueError as e:
         raise click.UsageError(str(e)) from e
 
@@ -365,10 +349,11 @@ def commit_pages_cmd(pages: tuple[str, ...], message: str) -> None:
 @cli.command("propose-pr")
 @click.option("--pages", required=True, multiple=True, help="Page path to stage. Repeat for multiple pages.")
 @click.option("--frame", type=click.Choice(ALLOWED_FRAMES), required=True, help="Reviewer framing for this change.")
-def propose_pr_cmd(pages: tuple[str, ...], frame: str) -> None:
+@click.pass_obj
+def propose_pr_cmd(context: Context, pages: tuple[str, ...], frame: str) -> None:
     """Stage a wiki change as a local git branch + commit. Never pushes or opens a real PR."""
     try:
-        result = propose_pr(Path.cwd(), list(pages), frame)
+        result = propose_pr(context.repo_root, list(pages), frame)
     except ValueError as e:
         raise click.UsageError(str(e)) from e
 
@@ -381,13 +366,10 @@ def propose_pr_cmd(pages: tuple[str, ...], frame: str) -> None:
 @click.option("--title", "message", required=True, help="Short message describing the event.")
 @click.option("--details", required=True, help="Additional detail about the event.")
 @click.option("--action", type=click.Choice(ALLOWED_LOG_ACTIONS), required=True, help="Event category.")
-@click.option(
-    "--docs-dir", type=click.Path(path_type=Path), default=None, help="Override the resolved docs/ directory."
-)
-def log(message: str, details: str, action: str, docs_dir: Path | None) -> None:
+@click.pass_obj
+def log(context: Context, message: str, details: str, action: str) -> None:
     """Append a structured entry to docs/log.jsonl."""
-    docs_dir = resolve_docs_dir(flag=docs_dir).docs_dir
     entry = build_log_entry(action, message, details)
-    append_log_entry(docs_dir, entry, stage_root=Path.cwd())
+    append_log_entry(context.docs_dir, entry, stage_root=context.repo_root)
 
     click.echo(f"Appended {action} entry to docs/log.jsonl")
diff --git a/wiki_toolkit/doctor.py b/wiki_toolkit/doctor.py
index 7ed15c0..ca6b431 100644
--- a/wiki_toolkit/doctor.py
+++ b/wiki_toolkit/doctor.py
@@ -10,7 +10,7 @@
 import orjson
 
 from wiki_toolkit.init import PROVENANCE_FILENAME
-from wiki_toolkit.settings import ConfigSource
+from wiki_toolkit.settings import ContextConfigSource
 from wiki_toolkit.sources import SOURCE_MANIFEST_FILENAME
 
 DOCS_DIRS = ("sources", "wiki")
@@ -25,7 +25,7 @@ class DoctorReport:
 
     python_version: str
     docs_dir: Path
-    docs_dir_source: ConfigSource
+    docs_dir_source: ContextConfigSource
     missing_structure: list[str] = field(default_factory=list)
     present_structure: list[str] = field(default_factory=list)
     note_count: int = 0
@@ -96,7 +96,9 @@ def check_skills_version_drift(docs_dir: Path) -> tuple[str, str] | None:
     return (local_version, installed_version)
 
 
-def run_doctor(docs_dir: Path, root: Path | None = None, docs_dir_source: ConfigSource = "default") -> DoctorReport:
+def run_doctor(
+    docs_dir: Path, root: Path | None = None, docs_dir_source: ContextConfigSource = "default"
+) -> DoctorReport:
     """Run the non-mutating `doctor` health check against `docs_dir`.
 
     `root` is the git repository root used for the shallow-clone check; it