diff --git a/cli/commands/analyst.py b/cli/commands/analyst.py
index e93bd08..db37ef6 100644
--- a/cli/commands/analyst.py
+++ b/cli/commands/analyst.py
@@ -314,8 +314,17 @@ def _generate_claude_md(workspace: Path, server_url: str, token: str) -> None:
         resp = httpx.get(url, headers=headers, timeout=15.0)
         if resp.status_code == 200:
             rendered = resp.json().get("content")
-    except Exception:
-        pass
+        elif resp.status_code != 404:
+            typer.echo(
+                f"  Warning: server returned {resp.status_code} for /api/welcome; "
+                "using minimal fallback. Tell your admin if this persists.",
+                err=True,
+            )
+    except Exception as e:
+        typer.echo(
+            f"  Warning: couldn't fetch welcome prompt ({e}); using minimal fallback.",
+            err=True,
+        )
 
     if rendered is None:
         # Fallback for older servers — keeps the CLI usable, just less rich.
diff --git a/tests/test_cli_analyst_welcome.py b/tests/test_cli_analyst_welcome.py
index 5c424b7..41edc42 100644
--- a/tests/test_cli_analyst_welcome.py
+++ b/tests/test_cli_analyst_welcome.py
@@ -1,5 +1,6 @@
 """Integration tests for da analyst setup → /api/welcome wiring."""
 
+import json
 from pathlib import Path
 
 import httpx
@@ -19,9 +20,14 @@ class _MockClient:
         return httpx.Response(status_code=status, json=body, request=httpx.Request("GET", url))
 
 
-def test_generate_claude_md_uses_server_render(tmp_path, monkeypatch):
+def _ws(tmp_path: Path) -> Path:
     workspace = tmp_path / "ws"
     (workspace / ".claude").mkdir(parents=True)
+    return workspace
+
+
+def test_generate_claude_md_uses_server_render(tmp_path, monkeypatch):
+    workspace = _ws(tmp_path)
     rendered = "# CUSTOM\n\nFrom server.\n"
     mock = _MockClient({
         "https://example.com/api/welcome?server_url=https%3A%2F%2Fexample.com": (
@@ -30,15 +36,54 @@ def test_generate_claude_md_uses_server_render(tmp_path, monkeypatch):
     })
     monkeypatch.setattr("cli.commands.analyst.httpx", type("_M", (), {"get": mock.get}))
     _generate_claude_md(workspace, server_url="https://example.com", token="t")
+
     assert (workspace / "CLAUDE.md").read_text(encoding="utf-8") == rendered
+    # Workspace side-effects are created on the success path too.
+    assert (workspace / ".claude" / "CLAUDE.local.md").exists()
+    settings = json.loads((workspace / ".claude" / "settings.json").read_text(encoding="utf-8"))
+    assert settings["model"] == "sonnet"
 
 
 def test_generate_claude_md_falls_back_on_404(tmp_path, monkeypatch):
-    workspace = tmp_path / "ws"
-    (workspace / ".claude").mkdir(parents=True)
+    workspace = _ws(tmp_path)
     mock = _MockClient({})  # everything 404s
     monkeypatch.setattr("cli.commands.analyst.httpx", type("_M", (), {"get": mock.get}))
     _generate_claude_md(workspace, server_url="https://example.com", token="t")
     body = (workspace / "CLAUDE.md").read_text(encoding="utf-8")
-    assert "AI Data Analyst" in body  # embedded fallback contains this string
+    assert "AI Data Analyst" in body
     assert "https://example.com" in body
+
+
+def test_generate_claude_md_falls_back_on_null_content(tmp_path, monkeypatch):
+    """Server returns 200 but malformed body (`content: null`). CLI must use fallback."""
+    workspace = _ws(tmp_path)
+    mock = _MockClient({
+        "https://example.com/api/welcome?server_url=https%3A%2F%2Fexample.com": (
+            {"content": None}, 200
+        ),
+    })
+    monkeypatch.setattr("cli.commands.analyst.httpx", type("_M", (), {"get": mock.get}))
+    _generate_claude_md(workspace, server_url="https://example.com", token="t")
+    body = (workspace / "CLAUDE.md").read_text(encoding="utf-8")
+    # Embedded fallback contains these literals
+    assert "AI Data Analyst" in body
+    assert "https://example.com" in body
+
+
+def test_generate_claude_md_warns_on_5xx(tmp_path, monkeypatch, capsys):
+    """500 from server → embedded fallback, with a stderr warning so operators can diagnose."""
+    workspace = _ws(tmp_path)
+    mock = _MockClient({
+        "https://example.com/api/welcome?server_url=https%3A%2F%2Fexample.com": (
+            {"detail": "boom"}, 500
+        ),
+    })
+    monkeypatch.setattr("cli.commands.analyst.httpx", type("_M", (), {"get": mock.get}))
+    _generate_claude_md(workspace, server_url="https://example.com", token="t")
+
+    body = (workspace / "CLAUDE.md").read_text(encoding="utf-8")
+    assert "AI Data Analyst" in body  # fallback used
+
+    captured = capsys.readouterr()
+    assert "500" in captured.err
+    assert "fallback" in captured.err.lower()