diff --git a/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py b/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
index 7c41e21d440..72e2509e484 100644
--- a/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
+++ b/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
@@ -331,6 +331,23 @@ def _deserialize_json_dict(data: Any) -> Optional[Dict[str, str]]:
         return data
 
 
+def _resolve_static_header_env_ref(key: str, value: str) -> str:
+    """Resolve an ``os.environ/NAME`` static header to its environment value.
+
+    Non-references pass through untouched; an unset env var keeps the literal so
+    the misconfiguration stays visible instead of being silently dropped.
+    """
+    if not value.startswith("os.environ/"):
+        return value
+    secret = get_secret_str(value)
+    if secret is not None:
+        return secret
+    verbose_logger.warning(
+        f"MCP static_header {key!r}: env var {value!r} not set; keeping literal value"
+    )
+    return value
+
+
 def _deserialize_json_list(data: Any) -> Optional[List[Dict[str, Any]]]:
     """Deserialize a JSON array stored in the DB (``env_vars`` and friends).
 
@@ -1065,20 +1082,10 @@ class MCPServerManager:
             getattr(mcp_server, "static_headers", None)
         )
         if static_headers_dict:
-            resolved: dict[str, str] = {}
-            for k, v in static_headers_dict.items():
-                if isinstance(v, str) and v.startswith("os.environ/"):
-                    secret = get_secret_str(v)
-                    if secret is None:
-                        verbose_logger.warning(
-                            f"MCP static_header {k!r}: env var {v!r} not set; keeping literal value"
-                        )
-                        resolved[k] = v
-                    else:
-                        resolved[k] = secret
-                else:
-                    resolved[k] = v
-            static_headers_dict = resolved
+            static_headers_dict = {
+                key: _resolve_static_header_env_ref(key, value)
+                for key, value in static_headers_dict.items()
+            }
         env_vars_list = self._resolve_env_vars_list(
             mcp_server,
             env_vars_are_encrypted=(
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_env_vars.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_env_vars.py
index a846ca24739..82a37dc0e74 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_env_vars.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_env_vars.py
@@ -1709,3 +1709,67 @@ async def test_missing_user_env_vars_error_renders_in_mcp_call_tool():
     assert "CorporateDB" in text
     assert "CORP_USERNAME" in text
     assert "fill_env_vars=srv-99" in text
+
+
+@pytest.mark.asyncio
+async def test_build_mcp_server_from_table_resolves_os_environ_static_headers(
+    monkeypatch,
+):
+    """A DB-loaded ``os.environ/NAME`` static header must build into the runtime
+    server carrying the resolved environment value, not the literal reference, so
+    upstream requests send the real secret."""
+    from litellm.proxy._experimental.mcp_server.mcp_server_manager import (
+        MCPServerManager,
+    )
+    from litellm.proxy._types import LiteLLM_MCPServerTable
+
+    monkeypatch.setenv("MCP_STATIC_HEADER_TOKEN", "resolved-secret")
+
+    table = LiteLLM_MCPServerTable(
+        server_id="srv-os-environ",
+        alias="echo",
+        url="https://upstream.example.com/mcp",
+        transport="http",
+        auth_type="none",
+        static_headers={
+            "X-Token": "os.environ/MCP_STATIC_HEADER_TOKEN",
+            "X-Static": "plain-value",
+        },
+    )
+
+    server = await MCPServerManager().build_mcp_server_from_table(table)
+
+    assert server.static_headers == {
+        "X-Token": "resolved-secret",
+        "X-Static": "plain-value",
+    }
+
+
+@pytest.mark.asyncio
+async def test_build_mcp_server_from_table_keeps_literal_when_env_missing(
+    monkeypatch, caplog
+):
+    """When the referenced env var is unset, the literal ``os.environ/NAME`` is
+    preserved and a warning is logged, so the misconfiguration stays visible
+    instead of silently collapsing to an empty header."""
+    from litellm.proxy._experimental.mcp_server.mcp_server_manager import (
+        MCPServerManager,
+    )
+    from litellm.proxy._types import LiteLLM_MCPServerTable
+
+    monkeypatch.delenv("MCP_MISSING_HEADER_TOKEN", raising=False)
+
+    table = LiteLLM_MCPServerTable(
+        server_id="srv-os-environ-missing",
+        alias="echo",
+        url="https://upstream.example.com/mcp",
+        transport="http",
+        auth_type="none",
+        static_headers={"X-Token": "os.environ/MCP_MISSING_HEADER_TOKEN"},
+    )
+
+    with caplog.at_level("WARNING"):
+        server = await MCPServerManager().build_mcp_server_from_table(table)
+
+    assert server.static_headers == {"X-Token": "os.environ/MCP_MISSING_HEADER_TOKEN"}
+    assert "MCP_MISSING_HEADER_TOKEN" in caplog.text