diff --git a/gitnexus/src/core/ingestion/languages/python/import-target.ts b/gitnexus/src/core/ingestion/languages/python/import-target.ts
index 3905f3301..677372966 100644
--- a/gitnexus/src/core/ingestion/languages/python/import-target.ts
+++ b/gitnexus/src/core/ingestion/languages/python/import-target.ts
@@ -61,37 +61,81 @@ export function resolvePythonImportTarget(
   const pathLike = parsedImport.targetRaw.replace(/\./g, '/');
   if (pathLike.includes('/')) {
     const [leadingSegment] = pathLike.split('/').filter(Boolean);
-    if (!leadingSegment || !hasRepoCandidate(leadingSegment, ctx.allFilePaths)) {
+    if (!leadingSegment || !hasRepoCandidate(leadingSegment, ctx.allFilePaths, ctx.fromFile)) {
       return null;
     }
   }
 
-  // Multi-segment absolute resolve: try exact paths first, then suffix
-  // match in nested repos. Using direct `Set.has` + `endsWith` instead of
-  // `suffixResolve`'s shared helper because that helper requires a
-  // pre-built `SuffixIndex` to disambiguate ties — without one it falls
-  // back to an O(files) scan that silently picks the wrong file when
-  // the last segment collides across directories (e.g. `accounts.models`
-  // matching `billing/models.py` when both files exist).
-  return resolveAbsoluteFromFiles(pathLike, ctx.allFilePaths);
+  // Multi-segment absolute resolve: try exact paths first, then ancestor
+  // walk (mirrors the single-segment ancestor walk in
+  // `resolvePythonImportInternal`), then a suffix match in nested repos.
+  // Using direct `Set.has` + `endsWith` instead of `suffixResolve`'s shared
+  // helper because that helper requires a pre-built `SuffixIndex` to
+  // disambiguate ties — without one it falls back to an O(files) scan that
+  // silently picks the wrong file when the last segment collides across
+  // directories (e.g. `accounts.models` matching `billing/models.py` when
+  // both files exist).
+  return resolveAbsoluteFromFiles(pathLike, ctx.allFilePaths, ctx.fromFile);
 }
 
 /**
  * Resolve `package/sub/module` style paths (already dot-flattened) to a
- * concrete file in `allFilePaths`. Tries the exact path first, then the
- * `__init__.py` variant, then a suffix match for nested layouts.
+ * concrete file in `allFilePaths`. Tries the exact path first, then walks
+ * ancestors of `fromFile` looking for `<ancestor>/<pathLike>.py` (or
+ * `__init__.py`), then falls back to a suffix match for nested layouts.
  * Returns the original (un-normalized) path from the set.
+ *
+ * Precedence order:
+ *  1. Workspace-root direct hit (`<pathLike>.py`, `<pathLike>/__init__.py`).
+ *  2. Closest-ancestor match walking up from the importer's directory.
+ *  3. Suffix fallback (first match).
+ *
+ * Root wins over ancestor by construction — if both `services/sync.py` and
+ * `backend/services/sync.py` exist, `backend/routers/cron.py`'s
+ * `from services.sync import X` resolves to the root file. This mirrors
+ * Python's `sys.path` semantics where the project root is searched first.
+ *
+ * The ancestor walk mirrors the single-segment behavior in
+ * `resolvePythonImportInternal`. For `from services.sync import X` in
+ * `backend/routers/cron.py`, walk up: `backend/routers/services/sync.py` →
+ * `backend/services/sync.py` ✓.
  */
-function resolveAbsoluteFromFiles(pathLike: string, allFilePaths: Set<string>): string | null {
+function resolveAbsoluteFromFiles(
+  pathLike: string,
+  allFilePaths: Set<string>,
+  fromFile: string,
+): string | null {
   const directFile = `${pathLike}.py`;
   const directPkg = `${pathLike}/__init__.py`;
+
+  // Direct hit at workspace root.
+  if (allFilePaths.has(directFile)) return directFile;
+  if (allFilePaths.has(directPkg)) return directPkg;
+
+  // Ancestor walk — match the single-segment resolver's behavior at
+  // multi-segment granularity. Closest match wins. Stop at `i > 0` because
+  // `i === 0` would re-check the workspace-root candidates already covered
+  // by the direct check above.
+  const importerDir = fromFile.replace(/\\/g, '/').split('/').slice(0, -1).join('/');
+  if (importerDir) {
+    const dirParts = importerDir.split('/').filter(Boolean);
+    for (let i = dirParts.length; i > 0; i--) {
+      const ancestor = dirParts.slice(0, i).join('/');
+      const prefix = `${ancestor}/`;
+      const candidateFile = `${prefix}${directFile}`;
+      const candidatePkg = `${prefix}${directPkg}`;
+      if (allFilePaths.has(candidateFile)) return candidateFile;
+      if (allFilePaths.has(candidatePkg)) return candidatePkg;
+    }
+  }
+
+  // Existing suffix-match fallback (preserved for monorepo/nested-repo
+  // layouts that don't share a directory ancestor with the importer).
   const suffixFile = `/${directFile}`;
   const suffixPkg = `/${directPkg}`;
-
   let suffixMatch: string | null = null;
   for (const raw of allFilePaths) {
     const f = raw.replace(/\\/g, '/');
-    if (f === directFile || f === directPkg) return raw;
     if (suffixMatch === null && (f.endsWith(suffixFile) || f.endsWith(suffixPkg))) {
       suffixMatch = raw;
     }
@@ -100,21 +144,54 @@ function resolveAbsoluteFromFiles(pathLike: string, allFilePaths: Set<string>):
 }
 
 /**
- * Does the repo contain a module/package named `leadingSegment` at the top
- * level? Used to guard against false-positive suffix matches on external
- * dotted imports (e.g. `django.apps` matching a local `accounts/apps.py`).
+ * Does the repo contain a module/package named `leadingSegment` somewhere
+ * the importer can plausibly reach?
  *
- * Checks, in order: `<segment>.py` root file, `<segment>/__init__.py`
- * regular package, or any `<segment>/**.py` file (namespace package).
+ * Used to guard against false-positive suffix matches on external dotted
+ * imports (e.g. `django.apps` matching a local `accounts/apps.py`).
+ *
+ * Checks, in order:
+ *  1. `SEGMENT.py` root file or `SEGMENT/__init__.py` regular package.
+ *  2. Any `SEGMENT/...py` file at the workspace root (namespace package).
+ *  3. Any `<importer-ancestor>/SEGMENT/...py` file (nested namespace
+ *     package the importer could reach via an ancestor walk, e.g.
+ *     `backend/services/sync.py` from `backend/routers/cron.py`).
+ *
+ * The nested case is bounded to the importer's own ancestors so a
+ * vendored copy of an external package (e.g. `vendor/django/urls.py`)
+ * does not gate-pass external imports like `from django.urls import path`
+ * issued from `app/main.py`. Files inside the vendored tree itself
+ * (importer under `vendor/django/...`) still resolve correctly because
+ * the ancestor walk includes their own parents.
  */
-function hasRepoCandidate(leadingSegment: string, allFilePaths: Set<string>): boolean {
+function hasRepoCandidate(
+  leadingSegment: string,
+  allFilePaths: Set<string>,
+  fromFile: string,
+): boolean {
   const prefix = `${leadingSegment}/`;
   const rootFile = `${leadingSegment}.py`;
   const initFile = `${leadingSegment}/__init__.py`;
+
+  // Build importer-ancestor prefixes: for `backend/routers/cron.py`,
+  // produces `["backend/routers/services/", "backend/services/"]` for
+  // segment `services` (closest first, root excluded — covered above).
+  const importerDir = fromFile.replace(/\\/g, '/').split('/').slice(0, -1).join('/');
+  const dirParts = importerDir ? importerDir.split('/').filter(Boolean) : [];
+  const ancestorPrefixes: string[] = [];
+  for (let i = dirParts.length; i > 0; i--) {
+    ancestorPrefixes.push(`${dirParts.slice(0, i).join('/')}/${leadingSegment}/`);
+  }
+
   for (const raw of allFilePaths) {
     const f = raw.replace(/\\/g, '/');
     if (f === rootFile || f === initFile) return true;
     if (f.startsWith(prefix) && f.endsWith('.py')) return true;
+    if (f.endsWith('.py')) {
+      for (const ap of ancestorPrefixes) {
+        if (f.startsWith(ap)) return true;
+      }
+    }
   }
   return false;
 }
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/auth_utils.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/auth_utils.py
new file mode 100644
index 000000000..c384c28c6
--- /dev/null
+++ b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/auth_utils.py
@@ -0,0 +1,6 @@
+def verify_cron_secret(token):
+    return token == "expected"
+
+
+def get_org_id_from_header(headers):
+    return headers.get("x-org-id") if headers else None
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/__init__.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/alerts.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/alerts.py
new file mode 100644
index 000000000..997a75a83
--- /dev/null
+++ b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/alerts.py
@@ -0,0 +1,2 @@
+def send_daily_alerts():
+    return "sent"
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/cron.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/cron.py
new file mode 100644
index 000000000..f57dcf73c
--- /dev/null
+++ b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/routers/cron.py
@@ -0,0 +1,24 @@
+from auth_utils import verify_cron_secret, get_org_id_from_header
+from services.sync import _start_cron_run, _complete_cron_run
+from services.alerts import _create_ops_alert
+from routers.alerts import send_daily_alerts
+
+
+def handler_a():
+    if verify_cron_secret("x"):
+        org = get_org_id_from_header(None)
+        _start_cron_run("a")
+        _create_ops_alert("a")
+        send_daily_alerts()
+        _complete_cron_run("a")
+        return org
+
+
+def handler_b():
+    _start_cron_run("b")
+    _create_ops_alert("b")
+    send_daily_alerts()
+
+
+def handler_c():
+    _start_cron_run("c")
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/__init__.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/alerts.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/alerts.py
new file mode 100644
index 000000000..92229fc68
--- /dev/null
+++ b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/alerts.py
@@ -0,0 +1,2 @@
+def _create_ops_alert(name):
+    return f"alert:{name}"
diff --git a/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/sync.py b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/sync.py
new file mode 100644
index 000000000..ea3f1a77f
--- /dev/null
+++ b/gitnexus/test/fixtures/lang-resolution/python-multi-segment-ancestor-import/backend/services/sync.py
@@ -0,0 +1,6 @@
+def _start_cron_run(name):
+    return f"started:{name}"
+
+
+def _complete_cron_run(name):
+    return f"completed:{name}"
diff --git a/gitnexus/test/integration/resolvers/python.test.ts b/gitnexus/test/integration/resolvers/python.test.ts
index 817483849..dd0104a5c 100644
--- a/gitnexus/test/integration/resolvers/python.test.ts
+++ b/gitnexus/test/integration/resolvers/python.test.ts
@@ -416,6 +416,213 @@ describe('Python ancestor directory import resolution (Issue #417)', () => {
   });
 });
 
+// ---------------------------------------------------------------------------
+// Multi-segment ancestor walk: `from services.sync import X` style imports
+// from a sibling sub-package nested under a shared root directory.
+//
+// Before this fix, single-segment ancestor walks worked (`from middleware
+// import X` from `backend/services/auth.py` → `backend/middleware.py`) but
+// multi-segment dotted imports were only resolved against the workspace
+// root. In a `backend/`-prefixed repo, `from services.sync import X` from
+// `backend/routers/cron.py` would silently drop because `services/sync.py`
+// does not exist at the workspace root — only `backend/services/sync.py`
+// does. The fix mirrors the single-segment ancestor walk for multi-segment
+// paths.
+// ---------------------------------------------------------------------------
+
+describe('Python multi-segment ancestor directory import resolution', () => {
+  let result: PipelineResult;
+
+  beforeAll(async () => {
+    result = await runPipelineFromRepo(
+      path.join(FIXTURES, 'python-multi-segment-ancestor-import'),
+      () => {},
+    );
+  }, 60000);
+
+  it('resolves from services.sync import to backend/services/sync.py via ancestor walk', () => {
+    const imports = getRelationships(result, 'IMPORTS');
+    const syncImport = imports.find(
+      (i) =>
+        i.sourceFilePath === 'backend/routers/cron.py' &&
+        i.targetFilePath === 'backend/services/sync.py',
+    );
+    expect(syncImport).toBeDefined();
+  });
+
+  it('resolves from services.alerts import to backend/services/alerts.py via ancestor walk', () => {
+    const imports = getRelationships(result, 'IMPORTS');
+    const alertsImport = imports.find(
+      (i) =>
+        i.sourceFilePath === 'backend/routers/cron.py' &&
+        i.targetFilePath === 'backend/services/alerts.py',
+    );
+    expect(alertsImport).toBeDefined();
+  });
+
+  it('resolves from routers.alerts import to backend/routers/alerts.py (sibling sub-package)', () => {
+    const imports = getRelationships(result, 'IMPORTS');
+    const routerImport = imports.find(
+      (i) =>
+        i.sourceFilePath === 'backend/routers/cron.py' &&
+        i.targetFilePath === 'backend/routers/alerts.py',
+    );
+    expect(routerImport).toBeDefined();
+  });
+
+  it('emits CALLS edges for every multi-segment-imported callee', () => {
+    const calls = getRelationships(result, 'CALLS').filter(
+      (c) => c.sourceFilePath === 'backend/routers/cron.py',
+    );
+
+    const startCronRunCalls = calls.filter((c) => c.target === '_start_cron_run');
+    expect(startCronRunCalls.length).toBe(3);
+    expect(startCronRunCalls.every((c) => c.targetFilePath === 'backend/services/sync.py')).toBe(
+      true,
+    );
+
+    const completeCronRunCalls = calls.filter((c) => c.target === '_complete_cron_run');
+    expect(completeCronRunCalls.length).toBe(1);
+    expect(completeCronRunCalls[0].targetFilePath).toBe('backend/services/sync.py');
+
+    const opsAlertCalls = calls.filter((c) => c.target === '_create_ops_alert');
+    expect(opsAlertCalls.length).toBe(2);
+    expect(opsAlertCalls.every((c) => c.targetFilePath === 'backend/services/alerts.py')).toBe(
+      true,
+    );
+
+    const sendDailyCalls = calls.filter((c) => c.target === 'send_daily_alerts');
+    expect(sendDailyCalls.length).toBe(2);
+    expect(sendDailyCalls.every((c) => c.targetFilePath === 'backend/routers/alerts.py')).toBe(
+      true,
+    );
+  });
+
+  it('preserves single-segment ancestor walk (regression check for from auth_utils import X)', () => {
+    const calls = getRelationships(result, 'CALLS').filter(
+      (c) => c.sourceFilePath === 'backend/routers/cron.py',
+    );
+
+    const verifyCalls = calls.filter((c) => c.target === 'verify_cron_secret');
+    expect(verifyCalls.length).toBe(1);
+    expect(verifyCalls[0].targetFilePath).toBe('backend/auth_utils.py');
+
+    const orgCalls = calls.filter((c) => c.target === 'get_org_id_from_header');
+    expect(orgCalls.length).toBe(1);
+    expect(orgCalls[0].targetFilePath).toBe('backend/auth_utils.py');
+  });
+});
+
+// ---------------------------------------------------------------------------
+// Negative case for `hasRepoCandidate` widening: a vendored copy of an
+// external package (e.g. `vendor/django/urls.py`) must not cause an external
+// import like `from django.urls import path` issued from an unrelated file
+// (`app/main.py`) to be treated as a local candidate. The ancestor-bounded
+// nested check rejects vendored matches that don't sit on the importer's
+// own ancestor path.
+// ---------------------------------------------------------------------------
+
+describe('Python multi-segment widening: vendored external package false-positive guard', () => {
+  let repoDir: string;
+  let result: PipelineResult;
+
+  beforeAll(async () => {
+    repoDir = fs.mkdtempSync(path.join(os.tmpdir(), 'gn-python-vendored-django-'));
+    writeFixtureRepo(repoDir, {
+      'app/main.py': `from django.urls import path
+
+def boot():
+    path("/")
+`,
+      'vendor/django/__init__.py': '',
+      'vendor/django/urls.py': `def path(p):
+    return p
+`,
+    });
+    result = await runPipelineFromRepo(repoDir, () => {});
+  }, 60000);
+
+  afterAll(() => {
+    if (repoDir !== undefined) fs.rmSync(repoDir, { recursive: true, force: true });
+  });
+
+  it('does not resolve from django.urls to vendor/django/urls.py from an unrelated importer', () => {
+    const imports = getRelationships(result, 'IMPORTS');
+    const stray = imports.find(
+      (i) => i.sourceFilePath === 'app/main.py' && i.targetFilePath === 'vendor/django/urls.py',
+    );
+    expect(stray).toBeUndefined();
+  });
+
+  it('does not emit a CALLS edge from app/main.py:boot to vendor/django/urls.py:path', () => {
+    const calls = getRelationships(result, 'CALLS').filter(
+      (c) => c.sourceFilePath === 'app/main.py',
+    );
+    const stray = calls.find(
+      (c) => c.target === 'path' && c.targetFilePath === 'vendor/django/urls.py',
+    );
+    expect(stray).toBeUndefined();
+  });
+});
+
+// ---------------------------------------------------------------------------
+// Workspace-root precedence: when both `services/sync.py` (root) and
+// `backend/services/sync.py` (ancestor) exist, an importer at
+// `backend/routers/cron.py` doing `from services.sync import X` resolves to
+// the root file. Mirrors Python's `sys.path` semantics where the project
+// root is searched before package-local namespaces.
+// ---------------------------------------------------------------------------
+
+describe('Python multi-segment resolution: workspace root wins over ancestor', () => {
+  let repoDir: string;
+  let result: PipelineResult;
+
+  beforeAll(async () => {
+    repoDir = fs.mkdtempSync(path.join(os.tmpdir(), 'gn-python-root-precedence-'));
+    writeFixtureRepo(repoDir, {
+      'services/__init__.py': '',
+      'services/sync.py': `def root_marker():
+    return "root"
+`,
+      'backend/__init__.py': '',
+      'backend/services/__init__.py': '',
+      'backend/services/sync.py': `def ancestor_marker():
+    return "ancestor"
+`,
+      'backend/routers/__init__.py': '',
+      'backend/routers/cron.py': `from services.sync import root_marker
+
+def handler():
+    return root_marker()
+`,
+    });
+    result = await runPipelineFromRepo(repoDir, () => {});
+  }, 60000);
+
+  afterAll(() => {
+    if (repoDir !== undefined) fs.rmSync(repoDir, { recursive: true, force: true });
+  });
+
+  it('resolves the import edge to the root services/sync.py, not backend/services/sync.py', () => {
+    const imports = getRelationships(result, 'IMPORTS').filter(
+      (i) => i.sourceFilePath === 'backend/routers/cron.py',
+    );
+    const rootEdge = imports.find((i) => i.targetFilePath === 'services/sync.py');
+    expect(rootEdge).toBeDefined();
+
+    const ancestorEdge = imports.find((i) => i.targetFilePath === 'backend/services/sync.py');
+    expect(ancestorEdge).toBeUndefined();
+  });
+
+  it('binds the imported name to the root file, not the ancestor copy', () => {
+    const calls = getRelationships(result, 'CALLS').filter(
+      (c) => c.sourceFilePath === 'backend/routers/cron.py' && c.target === 'root_marker',
+    );
+    expect(calls.length).toBe(1);
+    expect(calls[0].targetFilePath).toBe('services/sync.py');
+  });
+});
+
 // ---------------------------------------------------------------------------
 // Re-export chain: from .base import X barrel pattern via __init__.py
 // ---------------------------------------------------------------------------