diff --git a/headroom/proxy/auth_policy.py b/headroom/proxy/auth_policy.py
index 73f6cf91d..7e55cc95a 100644
--- a/headroom/proxy/auth_policy.py
+++ b/headroom/proxy/auth_policy.py
@@ -71,8 +71,15 @@ def classify_auth_signals(signals: AuthSignals) -> AuthMode:
             return AuthMode.SUBSCRIPTION
 
     auth = signals.authorization
-    if auth.startswith("Bearer "):
-        token = auth[len("Bearer ") :]
+    # The auth-scheme token ("Bearer") is case-insensitive per RFC 7235 §2.1,
+    # so a client sending `Authorization: bearer sk-...` must classify the same
+    # as `Bearer`. A case-sensitive `startswith("Bearer ")` sent such a request
+    # to the `elif auth:` (OAUTH) fallthrough, misclassifying a PAYG API key —
+    # which mis-routes compression policy and mislabels cost/TOIN auth_mode.
+    # Only the scheme is case-folded; the credential itself stays case-sensitive.
+    scheme, sep, credentials = auth.partition(" ")
+    if sep and scheme.lower() == "bearer":
+        token = credentials
         if token.startswith("sk-ant-oat"):
             return AuthMode.OAUTH
         if token.startswith("sk-ant-api") or token.startswith("sk-"):
diff --git a/tests/test_auth_policy.py b/tests/test_auth_policy.py
index e15c3552b..25417fabe 100644
--- a/tests/test_auth_policy.py
+++ b/tests/test_auth_policy.py
@@ -60,3 +60,34 @@ def test_codex_stamp_only_for_unidentified_responses_callers() -> None:
         is False
     )
     assert should_stamp_codex_client_signals("/v1/chat/completions", AuthSignals()) is False
+
+
+def test_bearer_scheme_is_case_insensitive() -> None:
+    # RFC 7235 §2.1: the auth-scheme token is case-insensitive. A lowercase or
+    # mixed-case "bearer" carrying a PAYG key must classify as PAYG, not fall
+    # through to the non-Bearer OAUTH branch.
+    for scheme in ("bearer", "BEARER", "Bearer", "BeArEr"):
+        signals = AuthSignals(authorization=f"{scheme} sk-ant-api03-abc")
+        assert classify_auth_signals(signals) is AuthMode.PAYG, scheme
+
+
+def test_bearer_case_insensitive_preserves_oauth_and_jwt_shapes() -> None:
+    jwt = "eyJhbGciOiJIUzI1NiJ9.eyJzdWIiOiIxMjM0In0.signature"
+    assert classify_auth_signals(AuthSignals(authorization="bearer sk-ant-oat01-abc")) is (
+        AuthMode.OAUTH
+    )
+    assert classify_auth_signals(AuthSignals(authorization=f"bearer {jwt}")) is AuthMode.OAUTH
+
+
+def test_credential_case_is_not_folded() -> None:
+    # Only the scheme is case-folded; the token keeps its case, so a PAYG
+    # `sk-...` prefix still matches exactly (it is lowercase by construction).
+    signals = AuthSignals(authorization="Bearer sk-PROJ-Abc123")
+    assert classify_auth_signals(signals) is AuthMode.PAYG
+
+
+def test_non_bearer_scheme_still_oauth() -> None:
+    # AWS SigV4 (Bedrock) and any other non-Bearer scheme keep the OAUTH
+    # passthrough-prefer classification.
+    signals = AuthSignals(authorization="AWS4-HMAC-SHA256 Credential=AKIA/...")
+    assert classify_auth_signals(signals) is AuthMode.OAUTH