diff --git a/headroom/cli/learn.py b/headroom/cli/learn.py
index b17a339ec..6ea29f2ad 100644
--- a/headroom/cli/learn.py
+++ b/headroom/cli/learn.py
@@ -225,6 +225,7 @@ def learn(
     total_projects = 0
     total_failures = 0
     total_recommendations = 0
+    total_analysis_failures = 0
     matched_projects = 0
     available_projects: list[tuple[str, Path]] = []
 
@@ -299,6 +300,12 @@ def learn(
                 f"Failures: {result_data.total_failures} ({result_data.failure_rate:.1%})"
             )
 
+            analysis_error = getattr(result_data, "analysis_error", None)
+            if analysis_error:
+                total_analysis_failures += 1
+                click.echo(f"  Analysis failed: {analysis_error}", err=True)
+                continue
+
             if result_data.failure_rate == 0 and not result_data.recommendations:
                 click.echo("  No failures or patterns found.")
                 continue
@@ -350,6 +357,9 @@ def learn(
             f"{total_recommendations} recommendations"
         )
 
+    if total_analysis_failures:
+        raise SystemExit(1)
+
 
 def _make_llm_judge(model: str) -> Any:
     """Build an LLM judge callable for verbosity, or None if unavailable.
diff --git a/headroom/learn/analyzer.py b/headroom/learn/analyzer.py
index 670b5c2b6..5fdb44a0e 100644
--- a/headroom/learn/analyzer.py
+++ b/headroom/learn/analyzer.py
@@ -56,7 +56,7 @@ _MAX_DIGEST_TOKENS = 80_000  # Budget for the digest (leave room for prompt + ou
 _CLI_BACKENDS: list[tuple[str, str, list[str]]] = [
     ("claude", "claude-cli", ["claude", "-p", "--output-format", "stream-json", "--verbose"]),
     ("gemini", "gemini-cli", ["gemini", "-p"]),
-    ("codex", "codex-cli", ["codex", "exec"]),
+    ("codex", "codex-cli", ["codex", "exec", "--skip-git-repo-check"]),
 ]
 
 # Set of valid CLI model identifiers, derived from _CLI_BACKENDS.
@@ -202,7 +202,9 @@ class SessionAnalyzer:
             result.recommendations.sort(key=lambda r: r.estimated_tokens_saved, reverse=True)
         except Exception as e:
             logger.warning("LLM analysis failed: %s", e)
-            # Return result with stats but no recommendations
+            # Preserve the stats so multi-project runs can continue, but retain
+            # the failure so the CLI cannot report an empty result as success.
+            result.analysis_error = str(e) or type(e).__name__
 
         return result
 
diff --git a/headroom/learn/models.py b/headroom/learn/models.py
index 5af68211e..6852f38f8 100644
--- a/headroom/learn/models.py
+++ b/headroom/learn/models.py
@@ -174,6 +174,7 @@ class AnalysisResult:
     total_calls: int = 0
     total_failures: int = 0
     recommendations: list[Recommendation] = field(default_factory=list)
+    analysis_error: str | None = None
 
     @property
     def failure_rate(self) -> float:
diff --git a/tests/test_cli_learn.py b/tests/test_cli_learn.py
index 0142e8fc9..cdb92e123 100644
--- a/tests/test_cli_learn.py
+++ b/tests/test_cli_learn.py
@@ -370,6 +370,35 @@ def test_learn_handles_empty_sessions_and_no_pattern_outputs(
     assert "No actionable patterns found." in result.output
 
 
+def test_learn_surfaces_analysis_failure_and_exits_nonzero(
+    monkeypatch: pytest.MonkeyPatch, runner: CliRunner, tmp_path: Path
+) -> None:
+    project = SimpleNamespace(name="broken", project_path=tmp_path / "broken")
+    plugin = FakePlugin("codex", "Codex", [project])
+
+    class FailingAnalyzer(FakeAnalyzer):
+        def analyze(self, project, sessions):  # noqa: ANN001, ANN201
+            self.calls.append((project, sessions))
+            return SimpleNamespace(
+                total_sessions=1,
+                total_calls=3,
+                total_failures=1,
+                failure_rate=1 / 3,
+                recommendations=[],
+                analysis_error="codex CLI failed (exit 1): Not inside a trusted directory",
+            )
+
+    monkeypatch.setattr("headroom.learn.analyzer._detect_default_model", lambda: "codex-cli")
+    monkeypatch.setattr("headroom.learn.registry.get_plugin", lambda name: plugin)
+    monkeypatch.setattr("headroom.learn.analyzer.SessionAnalyzer", FailingAnalyzer)
+
+    result = runner.invoke(main, ["learn", "--agent", "codex", "--all"])
+
+    assert result.exit_code == 1
+    assert "Analysis failed: codex CLI failed (exit 1)" in result.output
+    assert "No actionable patterns found." not in result.output
+
+
 def test_learn_main_only_flag_threads_to_scanner(
     monkeypatch: pytest.MonkeyPatch, runner: CliRunner, tmp_path: Path
 ) -> None:
diff --git a/tests/test_learn/test_analyzer.py b/tests/test_learn/test_analyzer.py
index e271d2226..69308f4e3 100644
--- a/tests/test_learn/test_analyzer.py
+++ b/tests/test_learn/test_analyzer.py
@@ -473,6 +473,7 @@ class TestSessionAnalyzer:
         assert result.total_calls == 1
         assert result.total_failures == 1
         assert result.recommendations == []
+        assert result.analysis_error == "API key not set"
 
     @patch("headroom.learn.analyzer._call_llm")
     def test_passes_events_to_digest(self, mock_call_llm: MagicMock):
@@ -865,7 +866,7 @@ class TestCallCliLlm:
         result = _call_cli_llm("test digest", "codex-cli")
         assert result == {"context_file_rules": [], "memory_file_rules": []}
         cmd = mock_run.call_args[0][0]
-        assert cmd == ["codex", "exec"]
+        assert cmd == ["codex", "exec", "--skip-git-repo-check"]
 
     @patch("headroom.learn.analyzer.subprocess.run")
     def test_gemini_cli_uses_p_flag(self, mock_run: MagicMock):