diff --git a/src/mcp/server/transport_security.py b/src/mcp/server/transport_security.py
index 91b5fa7edb..b9dfdc540f 100644
--- a/src/mcp/server/transport_security.py
+++ b/src/mcp/server/transport_security.py
@@ -53,17 +53,20 @@ def _validate_host(self, host: str | None) -> bool:
             logger.warning("Missing Host header in request")
             return False
 
+        host_lower = host.lower()
+        allowed_hosts_lower = [h.lower() for h in self.settings.allowed_hosts]
+
         # Check exact match first
-        if host in self.settings.allowed_hosts:
+        if host_lower in allowed_hosts_lower:
             return True
 
         # Check wildcard port patterns
-        for allowed in self.settings.allowed_hosts:
+        for allowed in allowed_hosts_lower:
             if allowed.endswith(":*"):
                 # Extract base host from pattern
                 base_host = allowed[:-2]
                 # Check if the actual host starts with base host and has a port
-                if host.startswith(base_host + ":"):
+                if host_lower.startswith(base_host + ":"):
                     return True
 
         logger.warning(f"Invalid Host header: {host}")
@@ -75,17 +78,20 @@ def _validate_origin(self, origin: str | None) -> bool:
         if not origin:
             return True
 
+        origin_lower = origin.lower()
+        allowed_origins_lower = [o.lower() for o in self.settings.allowed_origins]
+
         # Check exact match first
-        if origin in self.settings.allowed_origins:
+        if origin_lower in allowed_origins_lower:
             return True
 
         # Check wildcard port patterns
-        for allowed in self.settings.allowed_origins:
+        for allowed in allowed_origins_lower:
             if allowed.endswith(":*"):
                 # Extract base origin from pattern
                 base_origin = allowed[:-2]
                 # Check if the actual origin starts with base origin and has a port
-                if origin.startswith(base_origin + ":"):
+                if origin_lower.startswith(base_origin + ":"):
                     return True
 
         logger.warning(f"Invalid Origin header: {origin}")
diff --git a/tests/server/test_transport_security.py b/tests/server/test_transport_security.py
index 67fe4ef1a1..599281ca19 100644
--- a/tests/server/test_transport_security.py
+++ b/tests/server/test_transport_security.py
@@ -45,6 +45,12 @@ def _request(host: str | None, origin: str | None, content_type: str | None = "a
         pytest.param("good.example", "http://evil.example:9000", 403, id="origin-wildcard-base-mismatch"),
         pytest.param("good.example", "http://good.example", None, id="origin-exact"),
         pytest.param("good.example", "http://wild.example:9000", None, id="origin-wildcard-match"),
+        pytest.param("GOOD.EXAMPLE", None, None, id="host-exact-case-insensitive-uppercase-host"),
+        pytest.param("WILD.EXAMPLE:9000", None, None, id="host-wildcard-case-insensitive-uppercase-host"),
+        pytest.param("good.example", "HTTP://GOOD.EXAMPLE", None, id="origin-exact-case-insensitive-uppercase-origin"),
+        pytest.param(
+            "good.example", "http://WILD.EXAMPLE:9000", None, id="origin-wildcard-case-insensitive-uppercase-origin"
+        ),
     ],
 )
 async def test_validate_request_checks_host_then_origin(
@@ -56,6 +62,20 @@ async def test_validate_request_checks_host_then_origin(
     assert (None if response is None else response.status_code) == expected
 
 
+@pytest.mark.anyio
+async def test_validate_request_case_insensitive_uppercase_settings() -> None:
+    """When allowed_hosts is configured in uppercase (e.g. %COMPUTERNAME% on Windows), lowercase clients pass."""
+    settings = TransportSecuritySettings(
+        enable_dns_rebinding_protection=True,
+        allowed_hosts=["MYHOST:*", "EXACTHOST"],
+        allowed_origins=["HTTP://MYHOST:*", "HTTP://EXACTHOST"],
+    )
+    middleware = TransportSecurityMiddleware(settings)
+    # Lowercase host sent by WHATWG fetch / undici client
+    assert await middleware.validate_request(_request("myhost:8000", "http://myhost:8000")) is None
+    assert await middleware.validate_request(_request("exacthost", "http://exacthost")) is None
+
+
 @pytest.mark.anyio
 async def test_validate_request_skips_host_and_origin_when_protection_is_disabled() -> None:
     """With DNS-rebinding protection off, any Host/Origin is accepted."""