diff --git a/routes/model_routes.py b/routes/model_routes.py
index 858c236..47e527c 100644
--- a/routes/model_routes.py
+++ b/routes/model_routes.py
@@ -348,7 +348,24 @@ def _ping_endpoint(base_url: str, api_key: str = None, timeout: float = 1.5) ->
     if api_key:
         headers["Authorization"] = f"Bearer {api_key}"
 
+    # Ollama exposes /v1/models (OpenAI-compatible) AND native /api/version,
+    # /api/tags. The OpenAI-style GET base + "/models" returns 404 when the
+    # base is the host root or the native /api root (e.g. http://localhost:11434,
+    # http://localhost:11434/api) because /models lives under /v1 there. Treat
+    # 4xx on a port-11434 / Ollama-named base as "try the native paths" rather
+    # than as a definitive offline verdict — Ollama is reachable, it just
+    # doesn't speak OpenAI on that prefix. Without this gate the quickstart
+    # marks an alive Ollama as offline whenever cached_models is empty (issue
+    # #1025): _probe_endpoint() falls through to /api/tags on the same 404, but
+    # _ping_endpoint() was returning before that fallback could run.
+    parsed_base = urlparse(base)
+    looks_like_ollama = (
+        parsed_base.port == 11434
+        or "ollama" in (parsed_base.hostname or "").lower()
+    )
+
     url = base + "/models"
+    last_error: Optional[str] = None
     try:
         r = httpx.get(url, headers=headers, timeout=timeout)
         if 300 <= r.status_code < 400:
@@ -360,17 +377,21 @@ def _ping_endpoint(base_url: str, api_key: str = None, timeout: float = 1.5) ->
                     "error": "That is Odysseus, not a model server. Use the Ollama URL, usually http://host.docker.internal:11434/v1 in Docker.",
                 }
             return {"reachable": False, "status_code": r.status_code, "error": f"HTTP {r.status_code} redirect"}
-        if r.status_code < 500:
-            return {"reachable": r.status_code < 400, "status_code": r.status_code, "error": None if r.status_code < 400 else f"HTTP {r.status_code}"}
+        if r.status_code < 400:
+            return {"reachable": True, "status_code": r.status_code, "error": None}
+        if r.status_code < 500 and not looks_like_ollama:
+            return {"reachable": False, "status_code": r.status_code, "error": f"HTTP {r.status_code}"}
+        last_error = f"HTTP {r.status_code}"
     except Exception as e:
         last_error = str(e)[:120]
-    else:
-        last_error = f"HTTP {r.status_code}"
 
     try:
-        parsed = urlparse(base)
-        if parsed.port == 11434 or "ollama" in (parsed.hostname or "").lower():
-            root = base[:-3].rstrip("/") if base.endswith("/v1") else base
+        if looks_like_ollama:
+            root = base
+            for suffix in ("/v1", "/api"):
+                if root.endswith(suffix):
+                    root = root[: -len(suffix)].rstrip("/")
+                    break
             for path in ("/api/version", "/api/tags"):
                 try:
                     r = httpx.get(root + path, timeout=timeout)