diff --git a/routstr/auth.py b/routstr/auth.py
index e74a94a5..3864a506 100644
--- a/routstr/auth.py
+++ b/routstr/auth.py
@@ -91,11 +91,20 @@ def redemption_error_to_http_exception(error: Exception) -> HTTPException:
     status_code = 400
     if "already spent" in lowered:
         message = "Cashu token already spent"
-    elif "insufficient" in lowered or "melt fee" in lowered:
+    elif (
+        "insufficient" in lowered
+        or "melt fee" in lowered
+        or "exceed token amount" in lowered
+        or "estimate fees" in lowered
+    ):
         message = "Token value is too small to cover swap fees"
     elif "failed to melt" in lowered:
         message = "Failed to swap token from foreign mint"
-    elif "invalid" in lowered or "decode" in lowered:
+    elif ("invalid" in lowered or "decode" in lowered) and "token" in lowered:
+        # Anchor the broad buckets to "token" so internal faults whose text
+        # merely contains "invalid"/"decode" (e.g. "invalid literal",
+        # SQLAlchemy "Invalid …") fall through to the generic 500 below
+        # instead of masquerading as a 401 token error.
         message = "Invalid Cashu token"
         status_code = 401
     elif isinstance(error, ValueError):
diff --git a/routstr/upstream/base.py b/routstr/upstream/base.py
index 51afb080..c3d9c5d6 100644
--- a/routstr/upstream/base.py
+++ b/routstr/upstream/base.py
@@ -4049,7 +4049,7 @@ class BaseUpstreamProvider:
             if "mint error" in error_message.lower():
                 return create_error_response(
                     "mint_error",
-                    f"CASHU mint error: {error_message}",
+                    "CASHU mint error while processing token",
                     422,
                     request=request,
                     token=x_cashu_token,
@@ -4057,7 +4057,7 @@ class BaseUpstreamProvider:
 
             return create_error_response(
                 "cashu_error",
-                f"CASHU token processing failed: {error_message}",
+                "CASHU token processing failed",
                 400,
                 request=request,
                 token=x_cashu_token,
@@ -4717,7 +4717,7 @@ class BaseUpstreamProvider:
             if "mint error" in error_message.lower():
                 return create_error_response(
                     "mint_error",
-                    f"CASHU mint error: {error_message}",
+                    "CASHU mint error while processing token",
                     422,
                     request=request,
                     token=x_cashu_token,
@@ -4725,7 +4725,7 @@ class BaseUpstreamProvider:
 
             return create_error_response(
                 "cashu_error",
-                f"CASHU token processing failed: {error_message}",
+                "CASHU token processing failed",
                 400,
                 request=request,
                 token=x_cashu_token,
diff --git a/tests/unit/test_auth_cashu.py b/tests/unit/test_auth_cashu.py
index 61707698..2eff6c40 100644
--- a/tests/unit/test_auth_cashu.py
+++ b/tests/unit/test_auth_cashu.py
@@ -75,6 +75,13 @@ async def test_failed_first_cashu_redemption_rolls_back_empty_api_key(
             400,
             "Token value is too small to cover swap fees",
         ),
+        (
+            ValueError(
+                "Failed to estimate fees: Fees (7 sat) exceed token amount (5 sat)"
+            ),
+            400,
+            "Token value is too small to cover swap fees",
+        ),
         (
             ValueError(
                 "Failed to melt token from foreign mint http://foreign:3338: boom"
@@ -158,3 +165,37 @@ async def test_unexpected_redemption_error_returns_internal_error(
     assert error_detail["code"] == "internal_error"
     assert "/var/lib/secret" not in error_detail["message"]
     assert await session.get(ApiKey, hashed_key) is None
+
+
+@pytest.mark.asyncio
+async def test_internal_error_with_invalid_keyword_does_not_masquerade(
+    session: AsyncSession,
+) -> None:
+    """A non-wallet fault whose text merely contains "invalid" (but not
+    "token") must fall through to a generic 500, not a 401 token error.
+
+    Guards the anchored `"invalid"/"decode"` + `"token"` gate against stdlib/
+    driver strings like "Invalid isoformat string" leaking as token errors."""
+    token = "cashuAinternal_fault_mentions_invalid"
+    hashed_key = hashlib.sha256(token.encode()).hexdigest()
+    token_obj = SimpleNamespace(mint="http://mint:3338", unit="sat")
+
+    from routstr.core.settings import settings
+
+    with (
+        patch.object(settings, "cashu_mints", ["http://mint:3338"]),
+        patch("routstr.auth.deserialize_token_from_string", return_value=token_obj),
+        patch(
+            "routstr.auth.credit_balance",
+            new=AsyncMock(
+                side_effect=RuntimeError("Invalid isoformat string: '2020-13-99'")
+            ),
+        ),
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await validate_bearer_key(token, session)
+
+    assert exc_info.value.status_code == 500
+    detail = cast(dict[str, dict[str, str]], exc_info.value.detail)
+    assert detail["error"]["code"] == "internal_error"
+    assert await session.get(ApiKey, hashed_key) is None