diff --git a/airbyte_cdk/sources/utils/schema_helpers.py b/airbyte_cdk/sources/utils/schema_helpers.py
index ab7fbbf459..9c672edd4b 100644
--- a/airbyte_cdk/sources/utils/schema_helpers.py
+++ b/airbyte_cdk/sources/utils/schema_helpers.py
@@ -11,7 +11,7 @@
 from typing import TYPE_CHECKING, Any, ClassVar, Dict, List, Mapping, MutableMapping, Tuple, cast
 
 import jsonref
-from jsonschema import validate
+from jsonschema import Draft7Validator
 from jsonschema.exceptions import ValidationError
 from pydantic.v1 import BaseModel, Field
 from referencing import Registry, Resource
@@ -185,25 +185,66 @@ def _resolve_schema_references(self, raw_schema: dict[str, Any]) -> dict[str, An
             raise ValueError(f"Expected resolved to be a dict. Got {resolved}")
 
 
+def _format_oneof_error(error: ValidationError) -> str:
+    """Format a oneOf/anyOf validation error with per-branch details."""
+    field_path = ".".join(str(p) for p in error.absolute_path) if error.absolute_path else "root"
+    branch_schemas = error.schema.get(error.validator, [])
+    branch_messages: list[str] = []
+    errors_by_branch: dict[int, list[str]] = {}
+    for sub_error in error.context:
+        branch_index = sub_error.schema_path[0]
+        if isinstance(branch_index, int):
+            errors_by_branch.setdefault(branch_index, []).append(sub_error.message)
+
+    for i, branch_schema in enumerate(branch_schemas):
+        label = branch_schema.get("title", f"option {i + 1}")
+        sub_errors = errors_by_branch.get(i, [])
+        if sub_errors:
+            details = "; ".join(sub_errors)
+            branch_messages.append(f"{label}: {details}")
+        else:
+            branch_messages.append(f"{label}: unknown validation failure")
+
+    joined = " | ".join(branch_messages)
+    return f'Config validation error: the provided configuration for "{field_path}" does not match any supported option. {joined}.'
+
+
 def check_config_against_spec_or_exit(
     config: Mapping[str, Any], spec: ConnectorSpecification
 ) -> None:
-    """
-    Check config object against spec. In case of spec is invalid, throws
-    an exception with validation error description.
+    """Check config object against spec and raise on validation failure.
 
-    :param config - config loaded from file specified over command line
-    :param spec - spec object generated by connector
+    Uses iter_errors to detect oneOf/anyOf failures and produce a message
+    that lists per-branch validation details instead of surfacing a
+    misleading error from the last non-matching branch.
     """
     spec_schema = spec.connectionSpecification
-    try:
-        validate(instance=config, schema=spec_schema)
-    except ValidationError as validation_error:
-        raise AirbyteTracedException(
-            message="Config validation error: " + validation_error.message,
-            internal_message=validation_error.message,
-            failure_type=FailureType.config_error,
-        ) from None  # required to prevent logging config secrets from the ValidationError's stacktrace
+    validator = Draft7Validator(spec_schema)
+    errors = list(validator.iter_errors(config))
+    if not errors:
+        return
+
+    oneof_errors = [e for e in errors if e.validator in ("oneOf", "anyOf") and e.context]
+    if oneof_errors:
+        error = oneof_errors[0]
+        message = _format_oneof_error(error)
+        internal_parts = [
+            f"{sub.message} (path: {list(sub.absolute_path)})" for sub in error.context
+        ]
+        internal_message = (
+            f"oneOf validation failed at path {list(error.absolute_path)}: "
+            + "; ".join(internal_parts)
+        )
+    else:
+        error = errors[0]
+        message = "Config validation error: " + error.message
+        internal_message = error.message
+
+    raise AirbyteTracedException(
+        message=message,
+        internal_message=internal_message,
+        failure_type=FailureType.config_error,
+    ) from None  # required to prevent logging config secrets from the ValidationError's stacktrace
 
 
 class InternalConfig(BaseModel):